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JUNE 18, 2018

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Contents VOLUME 96, NUMBER 25

June 18, 2018

Cover story

Recycling needs
a revamp
Chemical and biochemical approaches
take aim at plastic pollution
Page 24

Quote of the week Features

“Trade wars 19 Periodic Graphics:


The chemistry of slime
are very Andy Brunning wrings all the
molecular details out of the
bad, and popular goo

unwinnable.”
—Nariman Behravesh,
chief economist, IHS Markit 20 Good times, bad
Page 20 times for industry
A strong economy is
overshadowed by trade wars and
plastics woes
18 Stretching out the
slime fad 22 Social media 101
The kids’ chemistry activity has for scientists
become a big business Chemjobber on taking your first
dip into online networking

Departments ACS News


2 Editorial 38 C&ENjobs 35 ACS Comment
Illustration by Jesse Lenz 3 Concentrates 40 Newscripts 37 ACS News
CE NEA R 9 6 (25) 1–40 • ISSN 0009 -2347
1155—16th St., N.W., Washington, DC 20036
Editorial
A big deal
(202) 872-4600 or (800) 227-5558

EDITOR-IN-CHIEF: Bibiana Campos Seijo


EDITORIAL DIRECTOR: Amanda Yarnell
OPERATIONS DIRECTOR: Kimberly Bryson

T
SENIOR ADMINISTRATIVE OFFICER: Marvel A. Wills
he news last week was domi- Related to this, ACS Nano just pub-
BUSINESS nated by the historic summit lished an editorial titled “Envisioning
NEW YORK CITY: (212) 608-6306
Michael McCoy, Executive Editor between North Korea’s leader, Scientific Innovation in Korea’s De-
Rick Mullin (Senior Editor), Marc S. Reisch (Senior Correspondent), Alexander
H. Tullo (Senior Correspondent), Rachel Eskenazi (Administrative Assistant).
Kim Jong Un, and U.S. President militarized Zone: A Step toward Eco-
BOSTON: (202) 236-7633 Ryan Cross (Assistant Editor). Donald J. Trump, who met in Singapore on nomic Progress and Global Peace”
CHICAGO: (917) 710-0924 Lisa M. Jarvis (Senior Correspondent).
HONG KONG: 852 9093 8445 Jean‑François Tremblay (Senior June 12. The outcomes of their conversa- (DOI: 10.1021/acsnano.8b04249). The
Correspondent). LONDON: 44 1494 564 316 Alex Scott (Senior Editor). tion are the matter of much debate, and al- editorial focuses on the DMZ (Demili-
WEST COAST: (315) 825-8566 Melody M. Bomgardner (Senior Editor)
though the specifics remain nebulous, the tarized Zone), a narrow corridor—4 km
POLICY
WEST COAST: (925) 519-6681 Jyllian Kemsley, Executive Editor
accepted view is that the U.S. president wide, 250 km long—that extends across
WASHINGTON: Cheryl Hogue (Senior Correspondent) committed to end joint military exercises the peninsula and acts as a physical barri-
Britt E. Erickson (Senior Editor), Andrea L. Widener (Senior Editor)
with South Korea and made other unspec- er between North and South Korea. This
SCIENCE/TECHNOLOGY/EDUCATION
WASHINGTON: Lauren K. Wolf, Executive Editor, Deputy Editorial Director
ified “security guarantees” in exchange natural border, which features wetlands,
Celia Henry Arnaud (Senior Correspondent), Stuart A. Borman (Senior for the North Korean leader’s promise to mountains, valleys, forests, and rich
Correspondent), Matt Davenport (Senior Editor, Multimedia), Carmen Drahl
(Senior Correspondent), Kerri Jansen (Assistant Editor, Multimedia), abandon the nation’s nuclear weapons wildlife, was formed upon the signing of
Tien M. Nguyen (Assistant Editor), Cici Zhang (Editorial Fellow). programs. the armistice agreement in 1953 after the
BOSTON: (973) 922-0175 Bethany Halford (Senior Correspondent).
CHICAGO: (847) 679-1156 Mitch Jacoby (Senior Correspondent). Besides the meeting with Trump and devastating Korean War. It has land mines,
WEST COAST: (626) 765-6767 Michael Torrice (Science News
Editor), (202) 815-6827 Sam Lemonick (Assistant Editor)
recent encounters with the leaders of Chi- barbed-wire fences, and a strong military
JOURNAL NEWS & COMMUNITY na and South Korea, Kim had hinted that presence on both sides.
(510) 768-7657 Corinna Wu (Senior Editor)
(651) 447-6226 Jessica H. Marshall (Associate Editor) change was afoot in an April speech, when The DMZ’s inaccessibility has allowed
he said that North Korea would put an end damaged forests and farmlands to reha-
ACS NEWS & SPECIAL FEATURES
Linda Wang (Senior Correspondent) to nuclear tests and turn its attention to bilitate and return to a natural state, while
PRODUCT MANAGER: Jessica Morrison
economic growth fueled by investments the land to the north has suffered defor-
in science and education. This points at a estation along with environmental degra-
AUDIENCE ENGAGEMENT EDITOR: Dorea I. Reeser
Arminda Downey-Mavromatis (Contributing Editor) new focus on diplomacy for North Korea, dation from military operations, and the
EDITING & PRODUCTION
and it is a big deal—if it indeed becomes land to the south has grown in population
Sabrina J. Ashwell (Assistant Editor), Craig Bettenhausen (Associate Editor), a reality. The international community is and suffered the consequences of that—
Luis A. Carrillo (Web ­Production Manager), Melissa T. Gilden (Assistant
Editor), Taylor C. Hood (Digital Content Producer/Taxonomy Specialist), hopeful that the talks, discussions, and habitat destruction and fragmentation and
Manny I. Fox Morone (Associate Editor), Alexandra A. Taylor (Assistant Editor) shift in focus will bring about the prospect pollution of waterways and farmlands by
C&EN MEDIA PRODUCTION LAB of peace, or at least improved relations, pesticides, fertilizers, and industrial and
Robert Bryson, Creative Director, Head of Media Production Lab
Tchad K. Blair, Head of UI/UX Design
greater openness, and some steps toward municipal waste. The DMZ has become
Ian Bakar (Associate Designer), Robin L. Braverman (Senior Art Director), denuclearization. what the authors of the editorial call an
Ty A. Finocchiaro (Senior Web ­Associate), Yang H. Ku (Art Director),
William A. Ludwig (Art Director), Kay Youn (Art Director) It’s a good thing that Kim sees science ecological sanctuary. They point to the
as key to his country’s future. Besides its field of pollen materials research based on
C&EN BRANDLAB
Rajendrani Mukhopadhyay, Executive Editor potential economic impact, science is a pollen grains present in the DMZ as an ex-
Jeff Lee (Senior Editor), Kirsten Dobson (Marketing Manager)
subject around which one can build rela- ample of an area in which scientific coop-
SALES & MARKETING tionships. Much of the country’s research eration and innovation between North and
Stephanie Holland, Assistant Director, Advertising Sales & Marketing
Natalia Bokhari (Advertising Operations Manager), has been driven by what would be useful South Korea is possible. This small piece
Sondra Hadden (Senior Marketing Manager), Joyleen SanFeliz Parnell
­(Advertising Operations Associate), Quyen Pham (Lead Generation
to its military. Currently, its main research of shared land has the potential to turn
­Associate), Ed Rather (Recruitment Advertising Product Manager), areas, judging by publication output, are a low-value and abundant material into
Kierra Tobiere (Recruitment Sales & Marketing Associate)
engineering, physics, chemistry, and ma- a high-value material with medical and
ADVISORY BOARD terials science. Further investments could pharmaceutical applications, they suggest.
Deborah Blum, Raychelle Burks, Jinwoo Cheon, Kendrew H. Colton,
François-Xavier Coudert, Cathleen Crudden, Gautam R. Desiraju, allow these and other fields to flourish, A small step toward peace.
Luis Carlos Diaz, Paula T. Hammond, Matthew Hartings, Christopher Hill,
Yan Liang, Javier García Martínez, Peter Nagler, Daniel García Rivera,
enriching the scientific fabric of the coun-
Anubhav Saxena, Dan Shine, Michael Sofia, William Tolman, James C. Tung, try. If North Korea is more open, then we
Jill Venton, Helma Wennemers, Geofrey K. Wyatt, Deqing Zhang
should expect an increase in scientific
Published by the AMERICAN CHEMICAL SOCIETY output beyond the tens of papers it pub-
Thomas M. Connelly Jr., Executive Director & CEO
Brian D. Crawford, President, Publications Division lishes each year in international journals.
EDITORIAL BOARD: Nicole S. Sampson (Chair),
We should also expect an increase in the
ACS Board of Directors Chair John E. Adams, number and diversity of its collaborations.
ACS President Peter K. Dorhout, Cynthia J. Burrows,
Jerzy Klosin, Julia Laskin, John Russell North Korea’s biggest collaborators are
Copyright 2018, American Chemical Society
China, followed by Germany and South
Canadian GST Reg. No. R127571347 Korea. Russia has long been a partner on
Volume 96, Number 25
nuclear energy research. Greater openness
is likely to transform the way science is Editor-in-chief
done in North Korea. @BibianaCampos

Views expressed on this page are those of the author and not necessarily those of ACS.

2 C&EN | CEN.ACS.ORG | JUNE 18, 2018


Concentrates
▸ Highlights
Analyzing CO oxidation on Pt 4
Nobel laureates die at 99 5
Transgenic cotton feeds on phosphite 6
Psychedelics forge neuron connections 6
China swoons over cleantech, biotech stocks 12

Chemistry news from the week G7 leaders sign plastics pledge


Ikea, Neste advance biobased polypropylene
Kulinowski to lead Chemical Safety Board
13
13
17

DIVERSITY
Science and sexual
Sexual harassment harassment
pervasive in science Why STEM disciplines are
particularly ripe for harassment,
according to the National Academies
of Sciences, Engineering & Medicine:
Cultural change needed to prevent injury to female ▸▸The dependence on advisers and
faculty and students, National Academies study says mentors for career advancement
▸▸The system of meritocracy that
A widespread culture of sexual harassment important issue. “They offer the findings, does not account for the declines in
drives women away from science careers conclusions, and recommendations in a productivity and morale as a result of
and perpetuates a gender gap, according to spirit of optimism: that addressing sexual sexual harassment.
a new report from the National Academies harassment is everybody’s responsibility,” ▸▸The “macho” culture in some fields.
of Sciences, Engineering & Medicine. she says. “It is going to take all of us to real- ▸▸The informal communication
Large percentages of women in science, ly combat sexual harassment.” network, in which rumors and
technology, engineering, and mathematics A complete culture change is needed to accusations are spread within and
(STEM) fields report being harassed. That address sexual harassment in universities, across specialized programs and fields.
includes 50% of female faculty and staff and the report says. Too often, universities have
20 to 50% of students, the report says. just done what is required by law, but that Key changes needed to stop sexual
“The cumulative effect of sexual harass- isn’t enough. “Sexual harassment is primar- harassment:
ment is a significant and costly loss of tal- ily a problem of organizational culture,” ▸▸Integrate values into the system.
ent in science, engineering, and medicine,” Cortina says. “Academic institutions need ▸▸Change the power dynamic.
says committee member Lilia Cortina, a to move away from a culture of compliance ▸▸Support targets of sexual
University of Michigan psychology profes- and toward a culture of respect.” harassment.
sor who has studied harassment. Sexual harassment doesn’t have to in- ▸▸Improve transparency and

50%
volve propositioning, touching, accountability.
or assault to cause problems.
If pervasive, behaviors often
brushed off as unimportant— support for targets of harassment, decrease
such as offhand comments tolerance for harassment, reduce the power
about someone’s appearance or that faculty have over students, and publi-
capabilities and other actions cize harassment reports and consequences.
Female U.S. faculty and staff who report being harassed labeled as gender harassment— The National Academies report also calls
can do just as much damage, on scientific societies to help change the
Source: National Academies report, “Sexual Harassment of Women”
the report points out. Harass- culture of sexual harassment. For example,
Targets of harassment report lower job ment is especially widespread for minori- the report recommends that societies help
satisfaction and often withdraw from or ties and people who identify as lesbian, gay, support people who are harassed.
quit their jobs, the report says. Others re- bisexual, transgender, or queer, who can David Smorodin, assistant general coun-
port depression or posttraumatic stress. face multiple forms of discrimination. sel for the American Chemical Society, says
STEM fields, including chemistry, are Changing academic culture has to start he appreciates that the report recognizes
particularly vulnerable to sexual harass- with leaders who make it clear sexual ha- that societies can play an important role
ment because men still far outnumber rassment will not be tolerated, the report in making that change. The report “really
women in faculty and leadership positions, says. Universities should set clear, escalat- does present a challenge to all professional
and students usually rely on a single adviser ing consequences for harassment and focus scientific societies,” he says.
to guide their research and promote their their training on what people should do if Changing universities will be a challenge,
careers, the report adds. they are harassed or witness harassment. Boyd says. “Sometimes there needs to be an
Chemist Mary Boyd, provost of Berry Academic institutions should also in- incentive, and so far there has not been a
College, is glad the committee took on this crease diversity at all levels, provide more great incentive.”—ANDREA WIDENER

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 3


Science Concentrates
SURFACE CHEMISTRY

Analyzing CO oxidation on Pt
New surface chemistry method answers mechanistic beam to shoot CO at an O2-bound Pt sur-
face at precise times and then employed
questions that have eluded chemists for 40 years slice-ion imaging to determine the reaction
site, speed, and escape angle for specific
A new surface chemistry technique has terrace sites produced both hyperthermal CO2 molecules flying off the surface. These
allowed researchers to determine the long- and thermal CO2. tools had not been used together before
sought mechanisms of one of the most Theofanis N. Kitsopoulos at Max to measure the speed and direction of sur-
studied reactions in heterogeneous cataly- Planck Institute for Biophysical Chem- face-generated species.
sis: the oxidation of carbon monoxide on a istry and coworkers now provide a more The study shows that the reaction has
platinum surface. nuanced view (Nature 2018, DOI: 10.1038/ three mechanisms. Two produce thermal
Catalytic CO oxidation cleans up emis- s41586-018-0188-x). They used a molecular CO2 and predominate at temperatures
sions from motor vehicles and below about 700 K: Either terrace
industrial smokestacks. Studied CO diffuses to a step and reacts
for about 40 years, it is a textbook there with an oxygen atom, or CO
system for the experimental and already on a step reacts with step
theoretical understanding of het- O. In the third mechanism, pre-
erogeneous oxidations—gaseous dominant at high temperatures,
reactions on catalytic surfaces. terrace CO reacts with terrace O
The CO reaction is complex. Pt to make hyperthermal CO2.
surfaces have two possible active The results “are phenomenal,”
sites. About 99% of each surface says surface chemist Dan Killelea
is flat terraces with moderate cat- of Loyola University Chicago.
alytic activity, and the other 1% is “The ability to experimentally dis-
highly active steps between layers tinguish among different possible
of Pt atoms. The reaction also pro- catalytic reaction sites on a surface
duces two types of CO2 molecules: is a long-sought goal” that the new
hyperthermal, with high energies approach makes possible.
and velocities, and thermal, with The strategy could be applied to
moderate energies and speeds. other heterogeneous surface reac-
Scientists have lacked analytical tions as well. “It has the potential
tools to unpack these complexi- to shift the entire focus of efforts
ties, so the exact mechanisms by to understand mechanisms of het-
which CO gets oxidized have been A timed beam of CO molecules hits a Pt surface, where CO erogeneously catalyzed chemical
a mystery. The consensus view was is oxidized to CO2. Laser slice-ion imaging (vertical blue reactions,” Killelea says.—STU
that a single type of reaction on dashed line) measures properties of the released CO2. BORMAN

MATERIALS

‘Green’ coating protects plastics


Devices that can flex and stretch, including loxane coatings on polycarbonate eyeglass colloidal chemistry methods to prepare
wearable electronics, roll-up solar cells, lenses make them scratch resistant. the precursor solutions and then sprayed
and foldable displays, are all the rage these Knowing that manufacturers are always the mixtures onto flexible polymer sub-
days. Engineers design those devices to on the lookout for new types of cost-ef- strates, including poly(ether imide) and
keep working, bend after bend. A tough, fective coatings, a team led by Stanford poly(ethylene terephthalate), and then
transparent, eco-friendly coating applied to University materials scientists Farhan An- cured the films at low temperature. The
the plastic support might help those devic- sari and Reinhold H. Dauskardt looked to results were highly transparent, nanome-
es last even longer, a study suggests (ACS an unusual place for source material—the ter-thick films.
Nano 2018, DOI: 10.1021/acsnano.8b01057). forest. Tests indicate that coatings containing
Many plastic devices have thin coatings The team made hybrid coatings by em- 20 wt % nanocellulose protect the polymer
designed to go unnoticed. Measuring just a bedding various concentrations of nano- substrates by boosting hardness and frac-
C R E D I T: NAT UR E

fraction of a micrometer in thickness, these cellulose fibrils, a tough material derived ture resistance. Microscopy analysis shows
nearly invisible films of organic and inor- from trees, in a glass matrix composed of that even after 20,000 bending cycles, the
ganic materials improve a wide range of zirconium alkoxide and an epoxy-func- films revealed no signs of delamination or
commercial products. For example, polysi- tionalized silane. The team used low-cost cracking.—MITCH JACOBY

4 C&EN | CEN.ACS.ORG | JUNE 18, 2018


OBITUARIES

Nobel laureates die at 99


Jens C. Skou and Paul D. Boyer were two winners of
the 1997 chemistry prize for ATP-related studies
Two laureates who shared the 1997 Nobel Bo Nielsen in an Aarhus University press
Prize in Chemistry, Jens C. Skou and Paul release after Skou died. Skou is survived
D. Boyer, died the same week, on May 28 by his wife, Ellen, their two daughters and
and June 2, respectively, both at age 99. sons-in-law, four grandchildren, and one
Both made key discoveries involving ade- great-grandchild.
nosine triphosphate (ATP), the universal Boyer was born in 1918 in Provo,
energy currency of cells. Utah. He earned a B.S. in chemistry from Boyer Skou
Skou was born in 1918 in Lemvig, Den- Brigham Young University in 1939 and a
mark. He earned an M.D. at the University Ph.D. in biochemistry at the University of adenosine diphosphate and inorganic
of Copenhagen in 1944 and a Ph.D. in Wisconsin in 1943. In 1963, he moved to phosphate into ATP. For this work, Boyer
physiology at Aarhus University in 1954. UCLA, where he became founding direc- shared the other half of the 1997 Nobel
In 1957, while studying anesthetic tor of the university’s Molecular Biology Prize with the researcher who verified his
drugs at Aarhus University, he discovered Institute and managed the construction ATP synthase mechanism experimentally,
CR E DI T: AS SO CI AT E D P R ESS (B OT H )

Na+,K+-adenosine triphosphatase. The of the institute’s building, which was later John E. Walker of the Medical Research
enzyme helps maintain proper salt balance named in his honor. Council Laboratory of Molecular Biology.
across neuronal cell membranes, setting Boyer “had outstanding character,” says Boyer donated a majority of his prize mon-
up voltage differences that cause nerve UCLA colleague David Eisenberg. “Every- ey to fund chemistry postdoctoral fellows
impulses and muscle contractions. He re- one liked him and admired him. He was a at UCLA and two other institutions.
tired in 1988 and was awarded half of the modest and thoughtful leader.” Boyer is survived by his wife Lyda, two
1997 Nobel Prize for his 1957 discovery. In the 1970s, Boyer developed a set daughters, eight grandchildren, and six
He was “a cornerstone and a beacon of mechanistic proposals that described great-grandchildren. A son, Douglas, died
for research,” said dean of health Lars how the enzyme ATP synthase converts in 2001.—STU BORMAN

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 5


Science Concentrates
NEUROSCIENCE

Psychedelics forge
neuron connections
Study in rats and fruit flies could aid Pigweed infests a Texas cotton field.
design of better antidepressants BIOTECHNOLOGY
About one-third of people with depression do not find relief with
current drugs. One possible alternative to those agents is the anes-
thetic ketamine, which often works in patients who don’t respond to
GM cotton feeds
conventional drugs, but it can also lead to hallucinations and abuse.
Scientists hope to understand ketamine’s antidepressant mecha-
nism and design new molecules without those side effects.
on phosphite
Now, a study reports that other psychedelic compounds have Technology may outwit weeds
similar effects on neurons as ketamine does: They promote the
growth of connections between neurons (Cell Rep. 2018, DOI:
and mitigate fertilizer pollution
10.1016/j.celrep.2018.05.022). The work suggests new chemical Wily weeds can develop resistance to herbicides, allow-
scaffolds that could mimic ing them to compete with genetically modified crops
ketamine’s antidepressant Control 5 µm designed to tolerate weed-killing chemicals. Now, a team
properties, says lead au- is proposing another approach to genetically engineering
thor David Olson of the crops to outgrow weeds: cotton that feeds on an alterna-
University of California, tive fertilizer, one that weeds can’t use (Proc. Natl. Acad.
Davis. H3CO I Sci. USA 2018, DOI: 10.1073/pnas.1804862115).
Previous research had DMT “This work is exactly the sort of genetic engineering
shown that ketamine rap- that I would like to see more of, traits that expand the
idly grows synapses—the realm of what farmers can do while protecting the envi-
connections between neu- OCH3 ronment,” says Anastasia Bodnar, a plant geneticist who
rons—in parts of the brain Rat neurons treated with DMT grew was not involved with the work and is the policy director
involved in mood. In this H2Noffshoots)
more connections (yellow for Biology Fortified, a nonprofit organization that fos-
new work, Olson’s team than untreated neurons didDOI
(top). ters discussion on biotechnology and agriculture.
found that psychedelic Regular plants need phosphate to grow, but the new
compounds, including N,N-dimethyltryptamine cotton can survive on phosphite instead because the crop
(DMT), 2,5-dimethoxy-4-iodoamphetamine NH is engineered to contain a bacterial gene that confers the
(DOI), and LSD, can also increase the number ability to convert phosphite to phosphate, explains Luis
of synaptic connections in the brains of rats and Herrera-Estrella of Mexico’s National Laboratory of Ge-
fruit flies, as well as in cultured neurons from nomics for Biodiversity, who co-led the work with Texas
the animals. The team had demonstrated before A&M University’s Keerti Rathore. Their combined teams
that DMT produced antidepressant-like effects H3C N developed transgenic cotton that grows just as well on
in rats (ACS Chem. Neurosci. 2018, DOI: 10.1021/ CH3 phosphite as regular cotton grows on phosphate. In soils

C R E D I T: TEXAS A & M AGR I L I FE ( P I GWE E D ) ; C E L L R EP ORTS ( MI C RO GRAP H )


acschemneuro.8b00134). DMT with varied chemical and nutrient profiles, the plants
In the current study, the scientists deter- outcompeted a bane of cotton farmers’ existence: Palmer
mined that the psychedelics promote synaptic growth through a amaranth, or pigweed, which resists the common herbi-
similar signaling pathway involving the protein mTORN that ket- cide glyphosate. The first trials outside the greenhouse
amine does. Ronald Duman, a neuroscientist at Yale University who CH3 commence later this month in Texas. A spin-off company
O
studies ketamine, says that the findings are “interesting N
and import- cofounded by Herrera-Estrella, StelaGenomics, is devel-
H
ant” because they could explain how these agents might treat mood oping the technology for use with other crops.
disorders. While ketamine activates the mTOR pathway by blocking Phosphite is used to kill fungi in crops, but manu-
N-methyl-d-aspartate receptors on neurons, the psychedelic com- facturers would need to scale up production to accom-
pounds do so by activating a different target, the 5-HT2A receptor, modate fertilizer demands, if this strategy ever reaches
which according to Duman suggests a novel approach for treatingNH widespread use. Farmers might be able to apply less
depression. LSD phosphite than they would phosphate, Bodnar says.
But David Feifel, a professor emeritus of psychiatry at the Univer- Phosphate can run off farmlands into waterways, where
sity of California, San Diego, says more work is needed to connect the compound promotes the growth of toxic and harmful
the reported mechanisms to these drugs’ antidepressant properties. algal blooms. But phosphite should be used carefully,
The next step, he says, would be to block the pathway outlined in Bodnar adds, because long-term use might select for
this study and then see if that prevents the drugs from producing an bacteria in soil and waterways that convert phosphite
antidepressant effect in animals.—CICI ZHANG to phosphate, thus recreating the phosphate prob-
lem.—CARMEN DRAHL

6 C&EN | CEN.ACS.ORG | JUNE 18, 2018


ASTROCHEMISTRY

Mysterious galactic radiation


pinned on diamonds
Spinning nanodiamonds may be source sure events like colli- A map of
of anomalous microwave emission sions or supernovae. microwave
Atomic hydrogen— radiation from
When electrons and protons formed the speeds that could generate the observed abundant in interstellar across the
first hydrogen atoms some 379,000 years wavelengths of microwave emissions. The space—forms a layer on universe.
after the Big Bang, they freed up photons prevailing hypothesis was that the particles their surface, and col-
to travel the universe. We still see those consisted of ring-shaped hydrocarbons lisions with other particles can give them
photons today as microwave emissions. because of the molecules’ abundance in the a dipole moment. That, along with their
Astronomers mapping this cosmic micro- dust that whirls around some young stars. propensity to spin, means they could emit
wave background in the 1990s to better But a 2016 study found that AME and signa- microwave radiation.
understand the universe’s genesis noticed tures of PAHs didn’t originate in the same Clive Dickinson of the University of
other signals coming from our own galaxy places, casting that proposal into doubt. Manchester says the results would be
that they couldn’t explain. This anomalous Jane Greaves of Cardiff University was stronger if they were based on more ob-
microwave emission (AME) has long been studying dust disks around stars when she servations. So astronomers need to collect
CR E DI T: N ASA / W M A P SCI E N CE T EAM

ascribed to polycyclic aromatic hydrocar- spotted AME signals. The three stars the more high-resolution observations to deter-
bons (PAHs). A new study suggests the real signals were coming from were the only mine if diamonds produce AME elsewhere.
source may be nanoscopic diamonds (Na- ones in her sample where astronomers had Greaves says one of her students is
ture 2018, DOI: 10.1038/s41550-018-0495-z). observed signatures of hydrogenated nan- examining published spectra of nanodi-
Charged, rotating particles radiate elec- odiamonds. These tetrahedral diamonds amonds to see if the researchers can nail
tromagnetic energy. Astronomers thought contain just a few hundred carbon atoms down whether nanodiamonds—including
nanoparticles were the most likely source and are about a nanometer or less wide. the ones found in meteorites in our own
of AME because they’re light enough that Their origin isn’t known for certain, but solar system—are produced locally or come
random collisions could spin them at Greaves says they likely form in high-pres- from common sources.—SAM LEMONICK

American Chemical Society

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JUNE 18, 2018 | CEN.ACS.ORG | C&EN 7


Science Concentrates
SYNTHESIS
▸▸ Simplified Birch
reduction skips
the ammonia
To break compounds’ aromaticity, chem-
ists commonly rely on the 74-year-old
This rubber circuit board with embedded liquid metals remains conductive
Birch reduction, which uses sodium metal
even when stretched up to five times its length.
and ammonia. However, the components’
moisture-sensitive nature—requiring
practitioners to trot out potentially haz- ELECTRONIC MATERIALS
ardous ammonia tanks to freshly distill
the reagent—makes running the reaction
a chore. A modified Birch reduction
Liquid-metal circuit can
developed in Jie An’s lab at China Agri-
cultural University lets scientists skip
the arduous set-up (Org. Lett. 2018, DOI:
be printed and peeled
10.1021/acs.orglett.8b00891). The re- A new print-and-peel method for making stretchable electronics is based on
searchers’ first experiences with the Birch liquid metals (iScience 2018, DOI: 10.1016/j.isci.2018.05.013). Gallium-based al-
reduction, attempting to reduce graphite loys are highly conductive and liquid at low temperatures, so they can serve as
to graphene, resulted in long set-up times conductors in soft electronics that must bend and flex. Researchers can print
and a small, but likely still smelly, ammo- custom circuit patterns using liquid-metal inks created by dispersing droplets
of the alloy in a solvent. But droplets of gallium alloys quickly form a thin oxide
Sodium, crown ether skin, inhibiting conductivity in the printed pattern. To overcome that issue, a
R Isopropanol, THF, 0 °C
R
team led by Xingyu Jiang of China’s National Center for Nanoscience & Tech-
nology screen-printed a eutectic gallium-indium alloy onto a plastic substrate,
The new Birch 24 examples then cast a flexible rubber layer on top of the liquid-metal pattern. After the
conditions rubber cured around the pattern, they peeled the rubber off. The oxide layer
reduce aromatic, nia leak, spurring surrounding each droplet tends to stick to the substrate as the pattern is pulled
heteroaromatic, them to try to away, so the oxide skin breaks and the droplets merge to form a conductive
alkenyl and alkynyl simplify things. path embedded in the rubber layer. The liquid-metal circuit remained conduc-
compounds. The new method tive even when stretched to five times its length.—KERRI JANSEN
replaces ammo-
nia with the commercial crown ether
15-crown-5, which can be recovered after
the reaction. The crown ether takes on el, manganese, and other metals. Pure mance-reducing reactions with common
ammonia’s role for the most part; it mix- lithium electrodes provide higher charge battery electrolytes and poses safety haz-
es with a bench-stable sodium dispersion capacity than mixed metal forms. But ards, especially during charging. Aiming
to form the solvated electrons that re- lithium metal’s reactivity leads to perfor- to exploit the metal’s advantages while
duce the substrates and give the reaction bypassing its problems, Stanford Univer-
its signature blue hue. However, tertiary sity scientists searched for a thin film to
amides, typically converted to alcohols protect the electrode surface. The film
under standard Birch conditions, survived had to be electrochemically stable; free

C R E D I T: TA N G E T A L. /iS C I ENC E ( C IRC UI T ) ; J OU L E ( BAT T ERY)


in the team’s reaction, suggesting that the from pinholes that allow dendrites to grow
crown ether reagent switches the mech- and short-circuit the battery, potentially
anism from an inner- to an outer-sphere igniting it; flexible enough to stretch and
electron transfer.—TIEN NGUYEN shrink during charging cycles without
cracking; and able to allow unimpeded
flow of lithium ions to and from the metal
ENERGY STORAGE electrode. The team, which includes Yayu-
▸▸ Diamond may be an Liu, Steven Chu, and Yi Cui, met those
requirements by using a low-cost depo-
sition method to grow a two-layer, nano-
batteries’ best friend meter-thin diamond film (Joule 2018, DOI:
Coating metallic lithium battery 10.1016/j.joule.2018.05.007). The dou-
Lithium-ion batteries, which power most electrodes with two layers of diamond ble-layer design, which effectively blocks
of today’s portable electronics and many (false colored to distinguish between pinholes, led to energy-efficient cells that
vehicles, rely on electrodes that combine them) prevents undesirable reactions and remained stable through more than 400
lithium with the oxides of cobalt, nick- safety hazards. charge cycles.—MITCH JACOBY

8 C&EN | CEN.ACS.ORG | JUNE 18, 2018


MEDICINAL CHEMISTRY
NANOMATERIALS
▸▸ Chili pepper
compound made NanoSaturn synthesized
to self-destruct Saturn and its extraordinary rings have captivated scientists since they
first started peering through telescopes. Chemists have now created a
Capsaicin, the compound that gives chili molecular homage to this heavenly body by building a
peppers their heat, soothes pain and itch so-called nanoSaturn out of just carbon and hydro-
by acting on an ion channel called TRPV1 gen (Angew. Chem. Int. Ed. 2018, DOI: 10.1002/
in cells. But along with this relief, capsa- anie.201804430). A team led by Tokyo Institute
icin and some of its derivatives can deliver of Technology’s Shinji Toyota synthesized the
troubling side effects, including a burning supramolecular complex by trapping a C60
sensation and fever spikes. Now research- within a large, hydrocarbon ring composed
ers have developed a modified capsaicin of substituted anthracene units. Scientists
that skin enzymes inactivate within previously captured fullerenes with belt-type
hours, averting some side effects while hydrocarbons or disk-like thiophene-based mac-
demonstrating pain and itch relief in mice rocycles, but this is the first example of a nanoSat-
(J. Med. Chem. 2018, DOI: 10.1021/acs. urn with a disk-type hydrocarbon ring. To make the
jmedchem.8b00109). Asia Fernández-Car- molecular assembly, the chemists simply combine the hydrocarbon ring
vajal of Miguel Hernández University, system with C60, and weak CH–π interactions hold the system together.
Tracey Pirali of the University of Eastern The researchers determined the
Piedmont, and their colleagues made cap- nanoSaturn’s structure using X-ray
saicin derivatives (example shown) with crystallography (shown). Toyota
a built-in self-destruct switch: an ester notes the macrocyclic compounds
bond in the tail of the compounds. Ester- might be useful for extracting or
ase enzymes in skin hydrolyze this bond, sieving fullerenes, but that wasn’t
producing two metabolites that the body his main motivation. “What is most
easily eliminates. The researchers tested exciting for me,” he says, “is that this beautiful and harmonized shape can
the compounds for activity on TRPV1 and arouse the curiosity of any observer as planet Saturn does.”—BETHANY
then assayed the most potent candidates HALFORD
in human skin cells to find those that
were significantly hydrolyzed. In mice, the
O which can cause bad odors and increase maceuticals, and positively charged chi-
CH3O N the chances of tooth decay and gum dis- tosan, derived from crustacean shells, onto
H ease (ACS Appl. Mater. Interfaces 2018, DOI: sheets of poly(ethylene terephthalate)
C R E D I T: A NG EW. CH EM . I N T. ED. ( N A N O SAT U R N ST RUCT UR ES ) ; JAOW FAH / S H U T T E RSTO CK (R E TAI N E RS )

HO 10.1021/acsami.8b04433). Jinkee Hong of (PET), the transparent plastic used to


Capsaicin Yonsei University, Hyo-Wan Anh of Kyung make most dental devices. The resulting
Hee University, and colleagues wanted coating attracted a smooth, ultrathin wa-
antibacterial films for plastics that would ter film that stopped bacteria from stick-
O endure the hodgepodge of enzymes and ing. After 24 hours of exposure to a com-
CH3O O C11H23 pHs the mouth encounters, while being mon oral bacterium, a coated PET sheet
N
H safe for oral use and made from readily had 75% less bacterial growth than an un-
HO O available materials. They electrostatically coated sheet. The coating resisted artificial
I
deposited alternating layers of negatively saliva solutions with varying acidity levels
Ester-containing capsaicin derivative
charged carboxymethylcellulose, a com- and enzymes, and the coated
best-performing molecule reduced sensi- mon thickener used in food and phar- plastic was slightly stron-
tivity to heat, touch, and itch without ger and more fracture-re-
producing body temperature spikes. sistant than uncoated
The effects lasted up to 90 minutes. plastic.—PRACHI
 DEIRDRE LOCKWOOD, special to
— PATEL, special to
C&EN C&EN

Dental
COATINGS retainers,
▸▸ Say good-bye invisible tooth
aligners, and
to retainer scuzz night guards tend
to accumulate
bacteria in their
A new coating could protect retainers, nooks and crannies,
clear tooth aligners, and other plastic even with regular
dental appliances from bacterial growth, cleaning.

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 9


CHEMISTRY Do science, take

IN PICTURES
pictures, win money.
Enter our photo contest at
cen.chempics.org or e-mail
cenchempics@acs.org.
Selections from cen.chempics.org,
where C&EN showcases the beauty of chemistry

Lapus lattice
Rohit Bhargava and colleagues at the University of Illinois, Urbana-
Champaign, used a three-dimensional printer to construct this
rabbit from isomalt, a sugar alcohol often used to make edible cake
decorations, mixed with rhodamine dye. As the team prints with
the mixture, the isomalt hardens into place. The scientists would
like to grow cells and tissues on the resulting lattices and then melt
away the isomalt, leaving behind cylindrical tubes that mimic blood
vessels. These structures could enable researchers to study
tissues or tumors in the lab in a reproducible manner.—
ALEXANDRA TAYLOR

Credit: Troy Comi

Call of Cthulhu
At his day job, Chemistry In Pictures reader
Charles M works in a lab that makes ultrasound
gels for materials science and failure analysis
experiments. But he also applies his scientific
skills around his house. He bought a supply
of the fluorescent dye fluorescein and used
it to detect a leak in his truck’s coolant lines.
Afterward, he suspended the leftovers in
silicone resin to make this custom figurine for a
tabletop role-playing game. “Call of Cthulhu is
a role-playing game like Dungeons & Dragons,
but with a horror theme based on the cosmic
fiction of H.P. Lovecraft,” Charles explains.
“Science plays a huge part in the game, which
takes place in the Prohibition era 1920s, where
science and technology were growing so fast
it genuinely scared people. I often use things
like chemical history to improve the gameplay
setting.”—CRAIG BETTENHAUSEN

Credit: Charles M

10 C&EN | CEN.ACS.ORG | JUNE 18, 2018


Dusty peacock
Jess Wade, a physicist at Imperial College
London, studies polymers and liquid
crystals used in display and light-emitting
diode technologies. This microscope image
(at 10x magnification) shows a polymer and
small chiral molecule blended in a film less
than 100 nm thick. When Wade warmed
the film up to a certain temperature called
the polymer’s glass transition temperature,
the chains became more flexible and,
where there were defects on the underlying
surface, started to form peacock-like
structures. The feathery structures “may
look great through a cross-polarized
microscope, but in reality, any aggregates
aren’t good for displays,” she says. By
studying these transitions in and out of the
liquid crystal state, Wade and her group
can understand how temperature and film
composition affects device performance.—
CRAIG BETTENHAUSEN

Credit: Jess Wade and Li Wan,


@jesswade, Department of Physics and
Centre for Plastic Electronics, Imperial
College London

Faux ice floes


Although they look like sheets of ice floating
on a polar sea, these white chunks of salts and
blue copper sulfate were the by-products of
a reaction run by Anthony Carroll, a graduate
student at the University of Wollongong.
Carroll had reacted xylose with acetone,
adding sulfuric acid and anhydrous copper
sulfate to speed up the reaction. After the
xylose and acetone formed his acetonide
product, Carrol neutralized the sulfuric
acid with a solution of ammonia in water
and vacuum filtered the mixture. These are
the leftover waste solids: The acid-base
neutralization created the white salts and the
copper sulfate turned blue when hydrated.—
MANNY MORONE

Submitted by Anthony Carroll

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 11


Business Concentrates
FINANCE

China eyes cleantech, biotech stocks


Stock market conditions are favorable Auspicious times
for Chinese technology firms Several Chinese technology firms had
successful initial listings in the past year.
Shares in the Chinese lithium-ion battery tion, saw its shares hit their maximum
maker Contemporary Amperex Technolo- allowed price increase for 16 days in a row COMPANY BUSINESS AMOUNT RAISED
gy (CATL) surged 44% on their first day of after it listed in November 2017. The surg- CATL Lithium-ion $850 million
trading on the Shenzhen Stock Exchange ing price of the stock turned one of the batteries
last week. The company’s performance company’s chauffeurs into a U.S.-dollar PharmaBlock Custom drug $32 million
mirrors that of other cleantech and bio- millionaire, CEO Haijun Dong says. ingredients
technology firms that listed in China and WuXi AppTec listed in China recently Ping An Online health care $1.1 billion
Hong Kong over the past year. after delisting from the New York Stock Good Doctor services
CATL, already one of the world’s larg- Exchange in 2015. In a 2016 C&EN inter- WuXi Contract research $900 million
est producers of lithium-ion batteries, view, founder Ge Li said he had been dis- AppTec
raised the funds to finance its expansion appointed that U.S. stock analysts misun-
WuXi Contract $500 million
as demand for electric vehicles grows in derstood his company’s business. Chinese Biologics manufacturing
China, it said in a filing to the Shenzhen investors gave WuXi the warmest welcome
exchange. The company picked a good by oversubscribing to its IPO by almost Sources: Companies, media reports
time for its initial public offering (IPO), 5,000 times.
as the stock issue was priced at a healthy In a recent overview of regional stock nies that are not yet profitable to list.
23 times its annual earnings per share. markets, KPMG predicts that technol- The Chinese drug discovery firm Ascle-
Other Chinese technology firms have ogy firms from China and beyond will tis, which is not profitable but has drug
listed in China and Hong Kong in recent increasingly turn to Hong Kong for their candidates in late stages of the regulatory
months with comparable success. Pharma­ IPOs. The auditing firm notes that the approval process, recently announced it
Block, a custom maker of chemicals used Stock Exchange of Hong Kong recent- has selected Hong Kong for its upcoming
in pharmaceutical research and produc- ly changed its rules to allow compa- IPO.—JEAN-FRANÇOIS TREMBLAY

CRISPR GOES BANANAS RARE DISEASE

CoA Therapeutics launches


BridgeBio Pharma is expanding its ros- kinase-associated neurodegeneration
ter of laser-focused subsidiaries. Last (PKAN), is the focus of CoA Therapeu-
week, it launched CoA Therapeutics tics. A mutation in a gene called PANK2
to develop small-molecule drugs that prevents children from making enough
boost levels of an important biochemi- CoA in the brain, leading to involun-
cal called coenzyme A (CoA) in genetic tary muscle contractions and difficulty
diseases where it is in short supply. speaking and swallowing. People with
Also last week, BridgeBio launched PKAN often die as young adults.
a company called Origin Bioscienc- Suzanne Jackowski and colleagues at
es, which licensed a compound from St. Jude Children’s Research Hospital
Alexion Pharmaceuticals to treat an in Memphis developed allosteric activa-
ultrarare metabolic disease caused by a tors of PANK3, a normally inactive pro-
specific kind of molybdenum cofactor tein that can increase CoA levels, much
deficiency. like PANK2, once it is activated. “It is
U.K.-based start-up Tropic Founded in 2015, BridgeBio now has like a backup system,” Jackowski says.
Biosciences has raised 19 subsidiary companies. “We’ve been In a PKAN mouse model, the group
$10 million from agriculture and moving so fast that it has been difficult showed the compounds readily crossed
biotechnology investors in its first round to keep tabs on how many programs the blood-brain barrier and corrected
of funding. The company is using CRISPR morph into subsidiaries,” Shafique behaviors associated with the disease.
C R E D I T: S H UT T ERSTO C K

and other gene-editing techniques to Virani, CEO of CoA Therapeutics, says. CoA Therapeutics has licensed and
develop traits for warm-region crops. Its BridgeBio’s companies are all focused further refined the St. Jude team’s
scientists hope to develop bananas that on genetically defined cancer targets or compounds. The company plans to test
can resist the devastating fungal pathogen rare genetic diseases. the drug in people with PKAN by the
that causes Panama disease and hope One such disease, pantothenate end of 2019.—RYAN CROSS
to alter the caffeine content in coffee.

12 C&EN | CEN.ACS.ORG | JUNE 18, 2018


Plastic pileups such
as this one on the
CONSUMER PRODUCTS Hong Kong shoreline
are raising alarms.
Ikea, Neste
advance
bioplastics
This fall, Ikea and the Finnish oil
company Neste will start commer-
cial-scale production of polypropyl- POLLUTION
ene and polyethylene made from
renewable feedstocks for use in Ikea
goods. Neste will supply the inputs,
which include vegetable oil and
G7 leaders sign
waste cooking oil.
The two firms first partnered
in 2016 with the goal of producing
plastics pledge
common plastics with renewable
raw materials rather than fossil Ocean Plastics Charter seeks to rein in
fuels. Ikea has vowed to change
all of the plastic used in its iconic
the mounting problem of waste
household goods to biobased or re- Leaders at the G7 summit in Charlevoix, nificant threat to the environment, to liveli-
cycled materials by 2030. Quebec, turned up the heat on the ocean hoods and potentially to human health.”
Neste primarily makes renewable plastics issue by signing an agreement Ocean Conservancy, an environmental
diesel from waste oil but in recent meant to boost recycling and reduce sin- group that has collaborated with industry,
years has been working to make gle-use plastics. The move was met with says the G7 leaders demonstrated a “new
plastics from a leftover fraction of skepticism from some environmentalists, level of leadership” by signing the charter.
the renewable oil. who are hungry for specific policies to The environmental group Greenpeace
To do so, Neste will send several tackle the problem, and with accelerated says the charter doesn’t go far enough.
thousand tons of plant-based crude efforts from the plastics industry, which “Voluntary charters focused on recycling
oil to an unnamed plastics pro- increasingly finds itself on the defensive. and repurposing will not solve the prob-
cessor, which will make batches of Five countries—Canada, France, Ger- lem at the source,” Greenpeace Interna-
plastic containing partially biobased many, Italy, and the U.K.—as well as the tional Executive Director Jennifer Morgan
content. Ikea has targeted 20% European Union signed the Ocean Plastics said in a statement. “Governments must
biobased content for certain prod- Charter. The U.S. and Japan abstained. move beyond voluntary agreements to leg-
uct lines including plastic storage The document calls for working with in- islate binding reduction targets and bans
boxes. As the amount of available dustry to make all plastics reusable, recy- on single-use plastics.”
feedstock increases, the firm says, clable, or recoverable by 2030. Additional- While the U.S. didn’t sign the docu-
more products will follow. ly, the leaders want to recycle or reuse 55% ment, the American Chemistry Council,
While some products, such as of plastic packaging by 2030 and recover a leading trade group, is reacting to the
Coca-Cola’s green-capped soda bot- all plastics by 2040. They also want to sig- mounting pressure on plastics. ACC CEO
tles, are made with cane-sugar-de- nificantly reduce single-use plastics. Cal Dooley has delayed his retirement by
rived polyethylene terephthalate, The agreement seeks to address marine one year to the end of 2019 to lead the in-
the Ikea project will be the first to litter in “global hot spots” by helping such dustry response to the plastic waste issue.
produce renewable polypropylene. places develop waste management infra- “While plastic products provide count-
C R E D I T: O CEA N CO N S E RVA N CY ( P LAST I C ) ; I KEA ( C H A I RS )

“Together with Neste, we are structure. A lack of infrastructure makes less health, safety, lifestyle, and sustainabil-
ensuring that there is an opportu- some developing countries—namely, Chi- ity benefits, those benefits cannot be fully
nity to scale up the production of na, Indonesia, the Philippines, Thailand, realized unless we take swift and aggressive
this material,” says Erik Ljungblad, and Vietnam—the source of a majority of actions to ... dramatically increase rates of
Ikea’s manager of plastic the plastics that wind up in the sea. reuse, recycling, and recovery,” Dooley says.
products.—MELODY BOMGARDNER Additionally, Canadian Prime Minis- The Ellen MacArthur Foundation,
ter Justin Trudeau pledged $100 million which advocates for a circular economy,
toward reducing marine litter and plastic says it will form a coalition of govern-
pollution. ments and businesses aimed at eliminating
“Plastics are one of the most revolu- plastic waste. It says the effort will build
tionary inventions of the past century and on its New Plastics Economy initiative,
play an important role in our economy and which involves consumer product com-
daily lives,” the charter says. “However, the panies like Coca-Cola, Danone, and Pepsi,
current approach to producing, using, man- as well as chemical makers such as BASF,
aging and disposing of plastics poses a sig- DuPont, and Novamont.—ALEX TULLO

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 13


Business Concentrates
RESEARCH FUNDING
BIOFUELS
▸▸ BASF backs the Europe proposes big new
expanding LanzaTech innovation program
The venture capital arm of BASF has made The European Commission says Horizon 2020, its program to fund research
an undisclosed investment in LanzaTech, and innovation from 2014 to 2020, is a success. So much so that the EC wants
the Chicago-based firm that uses gas-fer- to up the ante for its next program. It is proposing a new program, Horizon
menting microbes to make ethanol and Europe, to fund research in the European Union from 2021 to 2027. The EC
other chemicals from industrial waste wants to devote 100 billion euros (about $117 billion) to research through
emissions. A LanzaTech facility, with an Horizon Europe, up 25% from Horizon 2020. Making the case for Horizon
annual capacity of 58,000 L, is now pro- Europe, the EC points to achievements from the current program, such as
ducing ethanol from emissions at the Jing- graphene-based supercapacitors from the Estonian company Skeleton and a
tang steel mill in China’s Hebei province. project by the Italian chemical companies Novamont and Matrica to turn this-
Meanwhile, steelmaker ArcelorMittal has tle into biobased monomers for plastics and cosmetics.—MICHAEL MCCOY
begun construction of a LanzaTech facility
at its site in Ghent, Belgium, which will be
able to produce up to 80,000 L per year of
the biofuel.—MELODY BOMGARDNER next five years. The company says it will certificates
expand aromatic derivatives, phenol, and to 1,019
olefins. It will also invest in its R&D center. castor bean
ENERGY STORAGE Orlen says the expansion will help Poland farmers for
▸▸ Clariant partners with transition from being a net importer of
chemicals to a net exporter.—ALEX TULLO
sustainability improvements relating to
productivity, social impact, environment,
health, and safety. The nylon 11 precursor
hydrogen storage firm 11-aminoundecanoic acid is derived from
BIOLOGICS castor oil.—MELODY BOMGARDNER
Clariant will put its catalysis expertise to
work improving a hydrogen storage tech- ▸▸ WuXi invests in
nology developed by the German start-up PHARMACEUTICALS
Massachusetts
Hydrogenious Technologies. The technol-
ogy uses Clariant’s ▸▸ Cambrex expanding
EleMax H catalyst Chinese contract manufacturer WuXi
to bind the element Biologics is spending $60 million in
generics R&D in Italy
to liquid diben- Worcester, Mass., to build a plant that will
zyltoluene. The produce biologics and employ as many as Cambrex will expand R&D capabilities for
hydrogen-bound 150 people. With a total bioreactor capacity generic active pharmaceutical ingredients
compound, which of 4,500 L, the site will primarily employ (APIs) at its Paullo, Italy, facility. The
like diesel can single-use bioreactors but will also im- project will add a 150-m2 laboratory space
be transported plement a continuous process that WuXi as well as a research staff expansion. The
easily, releases claims to have developed. WuXi has been company currently manufactures more
One trailer contains its hydrogen with busily expanding commercial production than 70 generic APIs to the FDA’s current
enough hydrogen another catalyst, in recent months with investments total- Good Manufacturing Practice quality
to fill 350 cars. EleMax D. Clariant ing hundreds of millions of dollars in new standard. Generics account for approx-
says it will work plants in Ireland, Singapore, and China.— imately 20% of Cambrex’s sales. Earlier
to broaden the efficiency of its catalysts, JEAN-FRANÇOIS TREMBLAY this year the company invested $5 million
thus enabling widespread use of renewable in an expansion of its laboratory facili-
hydrogen.—MARC REISCH ties in Karlskoga, Sweden, augmenting
BIOBASED CHEMICALS process development, handling of highly

PETROCHEMICALS ▸▸ Indian castor bean potent substances, and crystallization


studies.—RICK MULLIN
C R E D I T: H YD RO GE N IO U S T ECH NO LO G I ES

▸▸ PKN Orlen in massive program a success


BIOBASED CHEMICALS
Polish expansion Arkema and BASF, along with castor oil
firm Jayant Agro-Organics and the civil ▸▸ DuPont biosciences
Petrochemical maker and refiner PKN society organization Solidaridad, have
Orlen will spend $2.3 billion, a record wrapped up an initiative to put a sus-
headquarters debuts
amount for the Polish firm, to expand its tainable castor oil supply chain in place
petrochemical capacity by 30% at its plants in Gujarat, India. Project Pragati, named DuPont Industrial Biosciences has opened
in Płock and Włocławek, Poland, over the for the Hindi word for progress, awarded its newly revitalized headquarters in

14 C&EN | CEN.ACS.ORG | JUNE 18, 2018


therapy could be useful for many neuro- Alzheimer’s treatment lanabecestat.
degenerative conditions. Complement will An early look at data from two trials
receive up to $17 million in milestone pay- showed the drug was safe but unlikely
ments as it tests the compound in a Phase I to slow down the cognitive decline in
clinical trial. Alexion also has an option to people with early or mild forms of the
acquire Complement.—RYAN CROSS disease. In 2014, Lilly had agreed to pay
AstraZeneca up to $500 million to code-
velop lanabecestat, a small molecule that
VACCINES blocks the activity of BACE, an enzyme

DuPont Industrial Wilmington, ▸▸ Sanofi, Translate Bio that snips down ­amyloid-β. Lanabecestat
adds to Lilly’s list of failed Alzheimer’s
Del. The facility, treatments, which include the internally
Biosciences
headquarters housed in one of
to make mRNA vaccines developed BACE inhibitor LY2886721,
the 50 buildings the γ-secretase inhibitor semagaces-
at DuPont’s more than 100-year-old Ex- Sanofi Pasteur is paying $45 million up tat, and the anti-amyloid-β antibody
perimental Station, supports business front to Lexington, Mass.-based Translate solanezumab.—LISA JARVIS
teams and researchers whose labs include Bio, formerly known as RaNA Therapeu-
high-throughput equipment as well as tics, to develop messenger RNA (mRNA)
bioinformatics and genomics capabilities. vaccines for up to five infectious diseases. RESEARCH FUNDING
Renovations were part of a $200 million
upgrade of the station first announced
The vaccines could allow the body to use
its own protein-making machinery to de- ▸▸ Editas may give
in 2017.—MARC REISCH velop an immune response to the proteins
translated from the mRNA. Translate could
Broad $125 million
receive up to $760 million in additional
NEUROSCIENCE milestone payments. Sanofi also has an The CRISPR gene-editing company Editas
▸▸ Alexion partners with ongoing partnership with BioNTech to de-
velop cancer immunotherapies based on a
Medicine has signed a sponsored research
agreement with Broad Institute of MIT
similar mRNA technology.—RYAN CROSS and Harvard. The deal stipulates that the
Complement Pharma institute could receive up to $125 million
and Editas will have the first right to li-
Alexion Pharmaceuticals is teaming up NEUROSCIENCE cense Broad inventions arising from the
with Amsterdam-based Complement
Pharma to test its antibody that inhibits ▸▸ Lilly, AstraZeneca sponsored research. Editas currently owes
Broad two payments totaling $12.5 million.
an immune-system protein called C6, The agreement comes after Broad scien-
which forms pores in cells, causing them
drop BACE inhibitor tists Feng Zhang and David Liu, who are
to lyse. C6 inhibition in animal models also cofounders of Editas, launched three
for nerve injury, traumatic brain injury, Eli Lilly & Co. and AstraZeneca are new companies this year based on their
and Guillain-Barré syndrome suggests the shutting down Phase III studies of the CRISPR inventions.—­RYAN CROSS

Business Roundup vestor and has been investing


heavily in chemicals.
coverage will provide most of
the funds.

▸▸ The European Com- ▸▸ Polystyvert, a Montre- ▸▸ Dow Chemical says it will ▸▸ Pfizer will put $600 million
mission has conducted al-based start-up developing build an alkoxylation facility into its investment arm, Pfiz-
unannounced inspections a process that recycles poly- on the Gulf Coast by the end er Ventures. The venture fund
of companies involved in styrene by dissolving it in a of 2021 to support home and will devote roughly $150 mil-
purchasing styrene, used to solvent, has raised $11 million personal care businesses. In- lion of the fund to early-stage
make polymers and elasto- in a financing round, largely eos recently announced a sim- companies focused on neu-
mers. The EC is investigating from local investors. The ilar plan. Separately, Dow says roscience, a therapeutic area
possible cartel and restric- company also has a collabo- it will nearly double glycol where in January Pfizer made
tive business practices. ration with French oil giant ether capacity with a series of deep cuts.
Total. projects around the globe.
▸▸ Haldor Topsoe, a fami- ▸▸ Juvenescence, an antiag-
ly-owned Danish chemical ▸▸ Siluria, a San Francis- ▸▸ Daiichi Sankyo will pay up ing drug company based on
process and catalyst firm, co-based start-up that has to $358 million in compen- the Isle of Man, has raised
is looking for an investor developed a technology to sation to U.S. patients for $50 million in series A fi-
to buy a minority stake in make ethylene via the oxida- failing to warn them about nancing. The firm has already
the company. The investor tive coupling of methane, has the possible gastrointestinal made investments in multiple
would have the option of signed a multiplant technolo- illnesses that its blood pres- artificial intelligence and
C R E D I T: D UP O N T

floating its shares in an ini- gy license with Saudi Aramco. sure drug olmesartan—trade regenerative medicine compa-
tial public offering in five to The Saudi national oil com- name Benicar—can cause. nies, including Insilico Medi-
seven years. pany is already a Siluria in- The company’s insurance cine and LyGenesis.

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 15


Policy Concentrates
CHEMICAL REGULATION
INDUSTRIAL SAFETY
▸▸ Kulinowski to lead Reporting required
Chemical Safety Board for U.S. releases of
Kristen Kulinowski will head the Chemi-
cal Safety Board as its “interim executive nonylphenol ethoxylates
authority” following the resignation of
chair Vanessa Allen Sutherland, according Makers and users of a group of widely used nonionic surfactants found in
to a CSB statement. The board will now some cleaning products and paints will have to report U.S. releases of these
be down to three members, two short of chemicals to EPA each year. The requirement applies to 13 nonylphenol
the number set by law. “I am committed ethoxylates (NPEs), says an EPA regulation released June 7. Short-chain
to ensuring that the CSB’s current inves- NPEs are highly toxic to water-dwelling organisms, according to EPA.
tigations are completed in a timely and Longer-chain NPEs aren’t as hazardous, but they can degrade in the envi-
efficient manner and that the lessons ronment to short-chain NPEs and to nonylphenols, which are also highly
learned are avail- toxic to aquatic life
able to industry, and suspected of
workers, and mem- disrupting hormones. O
bers of the public,” The regulation di- HO O
Kulinowski said. rects companies to
4-Nonylphenol diethoxylate
The board current- report their annual
ly has 10 investiga- quantities of NPE releases. That information will be made public under the
tions under way. A nation’s right-to-know law starting in 2020. NPEs are used in industrial
longtime American applications and consumer products as wetting agents, emulsifiers, sur-
Chemical Society factants, stabilizers, dispersants, and defoamers. EPA has not curtailed the
member, Kulinows- use of NPEs, but retailers are forging ahead. Walmart and Target have told
Kulinowski ki was a research their suppliers to eliminate NPEs, among a handful of other substances,
staff member in the from household and personal care products they sell.—CHERYL HOGUE
Science & Technology Policy Institute of
the Institute for Defense Analyses before
being appointed to CSB in 2015. Earlier,
she spent 13 years at Rice University as ex- lier this year amid concerns and environment. She also
ecutive director of the Center for Biologi- about her views on climate served as deputy counsel for
cal & Environmental Nanotechnology and change and renewable energy. environment and nuclear pro-
director of the International Council on White is an outspoken skeptic grams at the U.S. Department
Nanotechnology. At CSB, she has focused of climate change. Neumayr is of Energy under the George
her outreach efforts on laboratory safety a much less controversial pick W. Bush administration and as
and safe practices for welding and other to lead CEQ and likely to win counsel to the assistant attor-
“hot work” in the chemical industry. The Senate confirmation. Before ney general for environment
U.S. president nominates and the Senate joining CEQ, she spent nearly and natural resources at the
confirms CSB members and the chair. a decade on Capitol Hill in U.S. Department of Justice.
President Donald J. Trump has twice pro- various positions with the Neumayr Neumayr received her J.D.
posed eliminating CSB.—JEFF JOHNSON, Energy & Commerce Com- from the University of Califor-
special to C&EN mittee in the House of Representatives, nia Hastings College of the Law.—BRITT
C R E D I T: CBS ( KUL I NOWS KI ) ; @ EC _MI N I STE R /T W I T TE R ( N E U MAYR )

including deputy chief counsel, energy ERICKSON


PEOPLE
▸▸ White House picks BY THE NUMBERS

3 trillion
environmental adviser
President Donald J. Trump nominat-
ed Mary Neumayr on June 12 for a key
environmental position in the White
House—chair of the Council on Envi-
ronmental Quality (CEQ). Neumayr has
been serving as the top official at CEQ
since joining as chief of staff in March Metric tons of ice lost from the Antarctic ice sheet from 1992 to 2017, according
2017. Trump withdrew his first pick to to an analysis in Nature (2018, DOI: 10.1038/s41586-018-0179-y). This amount of ice
head CEQ, Kathleen Hartnett White, ear- corresponds to an 8-mm rise in sea level.

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 17


Features
The reporter’s
POLYMERS daughter

Stretching
demonstrates slime
made out of glue,
contact lens solution,
food coloring, and

out the slime fad baking soda.

The kids’ chemistry activity


has become a big business
ALEXANDER H. TULLO, C&EN NEW YORK CITY

O
ver the past year, every parent,
guardian, educator—or anyone who
spends time around children—has no
doubt heard a lot about slime, a viscous
concoction made with household ingredients.
Dozens of slime recipes circulate the internet. A Google search
for “slime” nabs more than 117 million hits. A query on YouTube
yields more than 24 million results. Scores of these videos have
10 million-plus views.
Most of the slime recipes making the rounds have important Audrey Bridgstock, assistant product development manager
ingredients in common. They normally call for white glue, the for Pure Organic Ingredients, says slime aligns with the broader
kind that children use in school to make Thanksgiving turkeys out trend of parents and children scouring Pinterest and other social
of construction paper. Many also use a solution made with borax media sites for how-tos on activities such as making kinetic sand,
powder. Some call for alternatives such as contact lens solution weaving rubber bands, and concocting homemade play dough.
or Tide liquid laundry detergent, which also contain borax. The Hobbies are Pure Organic’s bread and butter. The Utah-based
substitutions come partially out of concern that children would company buys high-purity chemicals in bulk and repackages them
get skin irritation from handling undiluted borax powder. Kids will for sale through online retailers to the do-it-yourself market. For
add other ingredients such as baking soda, food coloring, shaving instance, it sells titanium dioxide for homemade sunscreen and
cream, glitter—even iron filings so the slime responds to magnets. aluminum oxide for glass etching. “Slime is incredibly popular
These recipes are a variant of a decades-old chemistry demon- right now, and borax has been one of our better-selling products
stration: making slime from polyvinyl alcohol and borax (sodium as a result,” Bridgstock says.
tetraborate decahydrate). Borate ions cross-link the hydroxyl People buying glue by the gallon have been great for the school
groups on the polyvinyl alcohol. The result is a shear-thickening glue trade, a business whose rush used to be the back-to-school
non-Newtonian fluid, a viscous substance that will flow like any season. Michael B. Polk, CEO of Elmer’s owner Newell Brands,
other fluid but break apart if yanked hard enough. boasted about slime when he spoke to Jim Cramer, host of
The mixtures that kids are making at home undergo a similar CNBC’s “Mad Money,” in May 2017, just as the fad was peaking.
transformation. The key ingredient in glue is polyvinyl acetate, “Every serving of slime uses a bottle of Elmer’s glue, so this was a
which has ester groups instead of hydroxyl groups. Additionally, huge opportunity,” he said.
glue often contains some polyvinyl alcohol as a stabilizer. In a conference call with analysts around that time, Polk re-
John Fellenstein makes a lot of slime. He is a content specialist ported that glue sales had climbed by 40%.
at the Akron Global Polymer Academy, an outreach program sup- Seeking to capitalize on the craze, Elmer’s has come out with
ported by the University of Akron’s College of Polymer Science & slime-targeted products such as glue in glow-in-the-dark colors,
Polymer Engineering. He travels around Ohio conducting science as well as a slime activator, probably containing borax. Other
demonstrations at schools and special events. firms that specialize in kids’ activities, such as Crayola and Cra-
Fellenstein orders five gallon jugs of glue every two or three Z-Art, also have full lines of slime-making materials. Craft stores
weeks. “Some schools that I know of have outlawed slime, so like Michaels and A.C. Moore have shelves devoted to the stuff.
my way of getting around that is that I don’t call it slime; I call it In the conference call, Polk said he considers slime to be more
cross-linked polymer putty,” he says, explaining that slime can get than a fad. “There is a surge in slime making that is going on
messy. Slime caused such a sensation at one recent event—STEM now,” he said. “But I think that this has a much longer half-life
C R E D I T: A LEX T UL LO/C & EN

Day at the local minor league baseball affiliate, the Akron Rubber- than most of these types of activities.”
Ducks—that Fellenstein used up 4 jugs of glue in 40 minutes. Polk may be right. According to Google Trends data, “slime”
To Fellenstein, the chemical transformation that happens still has 70% of the Google searches it did when it peaked last May.
when a kid mixes the ingredients together is a big part of slime’s Bridgstock agrees that slime should have legs. “Caregivers are
appeal. “If a kid has never done it before and they see that home with the kids and are aware of activities that are very edu-
change, that look they have when they pull the stick out and it is cational and tactile,” she says. “All that created the perfect wave
covered in the putty—it is this look of wonderment,” he says. for people to be interested in slime.” ◾

18 C&EN | CEN.ACS.ORG | JUNE 18, 2018


Periodic Graphics
A collaboration between C&EN and
More
online
To see more of
Brunning’s work, go to
compoundchem.com.
To see all of C&EN’s
Andy Brunning, author of the popular Periodic Graphics,
visit cenm.ag/
graphics blog Compound Interest periodicgraphics.

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 19


Features

Chemical makers are


worried about the
impact of Trump’s
trade policies on
chemical exports.

BUSINESS

Good times, bad times for industry


A strong economy is overshadowed by trade wars and plastics woes
MICHAEL MCCOY, C&EN NEW YORK CITY

T
he opening lines of Charles administration actions on immigration IHS forecasts that the tariffs, if allowed
Dickens’s “A Tale of Two Cit- and trade. For starters, he bemoaned the to go into full effect, will shave a few
ies” have become a cliché; still, impact of U.S. restrictions on H-1A and tenths of a percent from U.S. economic
sometimes the words ring true. H-2B visas for foreign workers, given that growth, which it forecasts will be 2.8%
Many in the audience at the American IHS expects U.S. unemployment to soon this year. More insidious is the effect they
Chemistry Council’s recent annual meet- reach 3.5%, the lowest rate in 50 years. could have on industry supply chains and
ing could nod in agreement when Nariman “We’re scraping the bottom of the bar- on business sentiment in general.
Behravesh, chief economist at the consult- rel,” he said about U.S. employers. “We Frustration over trade policy also
ing firm IHS Markit, began a keynote talk need skilled workers; we need unskilled pervaded a press conference held by Cal
by explaining the current economic situa- workers.” Dooley, the trade association’s CEO, and
tion with Dickens’s words: “It was the best Behravesh also slammed what he sees three of its top officers: Bhavesh V. Patel,
of times, it was the worst of times.” as the Trump administration’s misguid- CEO of LyondellBasell Industries; Mark
Behravesh was describing a world with ed actions on trade. Playing on Trump’s P. Vergnano, CEO of Chemours; and Jerry
a bright economic outlook but also a high contention in a March 2 tweet that “trade MacCleary, the North American CEO of
dose of uncertainty; much of that uncer- wars are good, and easy to win,” Behravesh the German firm Covestro.
tainty, he said, is being created by the quipped that “trade wars are very bad, and A year ago at the same event, executives
Trump administration. unwinnable.” avoided direct criticism of Trump’s eco-
That dichotomy is especially sharp for The administration’s planned 25% tariff nomic policies; this year they took off the
the chemical companies that were at the on $150 billion worth of Chinese imports gloves.
meeting, held from June 4 to 6 in Colorado is basically a $40 billion tax on the Amer- Dooley did point out a number of ways
Springs. Thanks to the strong economy ican public, he said. That’s almost one- the industry is happy with the Trump
and low-cost raw materials, the U.S. third of the impact of Trump’s tax cut. administration. For example, last year’s
chemical industry is doing great. Demand And Behravesh questioned the admin- corporate tax cut helped level the playing
is strong and investment is booming. But istration’s efforts to protect the U.S. steel field for U.S. companies in the global mar-
C R E D I T: S H UT T ERSTO C K

Trump’s actions on trade and tariffs are and aluminum industries with tariffs, in- ketplace. And a “rebalancing” of certain
giving executives agita at a time when they cluding ones against allies in Europe, Can- regulations that were enacted during the
should be feeling good. Public dismay over ada, and Mexico. “What’s unfathomable to Obama administration has removed oner-
the impact of plastics on the environment me is why we are protecting old industries ous provisions without compromising en-
isn’t helping either. and not doing enough to protect new vironmental protections, he said.
In his talk, Behravesh criticized Trump ones,” he said. But on the subject of trade, Dooley and

20 C&EN | CEN.ACS.ORG | JUNE 18, 2018


the company executives were as unsparing providing local customers with customized
as Behravesh. Dooley pointed out that tar- products. Bjacek pointed to the Speedfacto-
iffs like the ones Trump wants to impose ries that Adidas has set up in Germany and
beget retaliatory tariffs. In fact, he added, Atlanta to build personalized athletic shoes.
40% of the tariffs that China said it will In addition to potential trade wars, ACC
impose in response to the U.S. action tar- executives were on high alert about plastic
get chemicals. “That wasn’t an accident,” waste, particularly waste in the marine
Dooley said. “Retaliation will always be environment. More than one attendee
targeted at sectors of the economy that pointed to the sad images appearing in
have a global competitive advantage.” magazines and on social media of sea ani-
The U.S. chemical industry had a mals that died after ingesting or becoming
$33 billion trade surplus with the rest of entangled in plastic waste.
the world last year; in normal circum- At an otherwise festive closing dinner,
stances, the surplus would Dooley acknowledged that
reach $71 billion by 2023,
according to ACC. Aiding
“Trade wars the issue of plastic waste is
“of concern to every man,
chemical exports should
be 325 investments valued
are very woman, and child.” And he
called solving the problem
at more than $194 billion
that firms have announced
bad, and “an imperative for our in-
dustry, a condition of our
in the U.S. to take advan-
tage of low-cost raw mate-
unwinnable.” license to operate.”
Some potential solu-
rials extracted from shale —Nariman Behravesh, tions are market based.
oil and gas. chief economist, IHS Markit Bucking the traditional
But those projects were reluctance of polymer
predicated on free access to international producers to invest in recycling, Lyon-
markets. “We’re building enormous capac- dellBasell recently acquired the Dutch
ity in the U.S.,” Patel said of the industry, recycler Quality Circular Polymers in
“and to the extent that tariffs impede our partnership with the waste management
ability to do that, then that’s an issue.” firm Suez. Patel said the new owners are
Industry executives acknowledged that looking to expand QCP to new locations
Trump has some legitimate gripes about across Europe.
the trade practices of China and other But other initiatives are necessary as
countries. But they want the administra- well, executives said. Steve Russell, ACC’s
tion to seek a negotiated resolution in vice president for plastics, pointed to the
collaboration with its international allies. association’s recently announced goal to
“This is ultimately about job creation in make all plastic packaging used in the U.S.
America,” Patel said. recyclable or recoverable by 2030 and all
The consulting firms trying to drum of it actually reused, recycled, or recovered
up business at the ACC meeting took the by 2040.
opportunity to advise attendees about Soon after the meeting, leaders at the
how to succeed in today’s high-growth, G7 summit in Canada signed a pledge to
high-anxiety environment. reduce plastic waste. Two days later, ACC
Chris Cardinal, a director at Pricewater- announced that Dooley would stay on past
houseCoopers, talked about the challenge his planned retirement to work on the
of deglobalization—the retrenchment of plastic waste issue (see page 13).
open borders and free trade as economic Between trade issues and plastics woes,
nationalism rises. In this new environ- it was easy to forget that attendees were
ment, companies that once freely set up enjoying some of their best economic
international operations may now have to times in decades. In a briefing for C&EN,
cooperate more with local suppliers to get Accenture’s Bjacek noted that profits for
their products to market, Cardinal said. the 57 firms he tracks are their highest in
Likewise, sending technology devel- more than 10 years. And at the closing din-
oped in a central R&D center straight to ner, Dooley pointed out that almost half
far-away countries doesn’t always work in of all U.S. manufacturing investment last
a deglobalizing world. “You need the re- year was made by the chemical industry.
search center out in the market,” Cardinal In this spirit, meeting organizers es-
said. “You need to be local.” chewed the usual pundit or political vet-
Paul Bjacek, research lead for Accen- eran as dinner entertainment and instead
ture’s chemical practice, talked about local- hired Martina McBride, a country music
ization as a third phase of Western indus- singer. The goal, one official said, was to
trial evolution after deindustrialization and, forget politics for a while. By the end of
more recently, reindustrialization. Although the dinner, many normally staid executives
trade barriers are a reason to localize, so is were dancing between the tables. ◾

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 21


Musings
Musings
Bench cubic
cubicee
Bench&&cubice
Musingson
ononworking
workingininthe
thechemistry
the chemistryenterprise
chemistry enterprise
enterprise
BY CHEMJOBBER

Social media 101 for scientists


It’s never too late to start getting connected online

Y
our children or younger col- (seen and unseen) that they have
leagues have been gently prod- surmounted. Despite what you
ding you for years to join Face- might imagine about Twitter,
book, Twitter, Instagram, and I have found encour-
other social media platforms. They want agement, humor, and
to stay in touch with you, and they want friendship on the plat-
you to participate in the fun. You’ve always form. For me, Twitter
said, “I’ll join later,” if you haven’t scorned has been endlessly
virtual networking altogether. fun, engaging, and
Now, perhaps prompted by a job loss, useful for discuss-
or a change in attitude, the time has come. ing ideas, sharing job
You’re staring at your computer screen opportunities, and
wondering where you should start. Will staying in touch with
joining social media help you, or will this people.
end up being a waste of time and effort? The most important
I think social media is useful and can aspect of social media is that
offer returns far greater than you might it needs to be something that
imagine. you enjoy and can sustain over a
If this is your initial for- long period of time. I have been blogging
ay into social media, I Overwhelmed since late 2008 and posting daily since the
suggest starting with by social media? fall of 2010. Of course, it’s partly about
a professional net- There’s help. “keeping the streak going,” but more im-
working community portant, I enjoy the online engagement
like LinkedIn. Most and their contact information enough to keep doing it at a sustainable
of your colleagues can be easy. pace. This has often led to valuable real-life
are probably already After LinkedIn, what next? interactions at scientific conferences and
using the network, and It’s up to you. These days, other meetings.
they would be thrilled there are so many different When I see advice for people who want
to add you to their list of places where you can express to get started in social media, it’s “you
connections. yourself and your professional iden- need a Twitter account” or “you need
Setting up your initial profile tity online. If you have always wanted to be on Instagram!” I feel that’s wrong.
might take a couple of hours at most, to practice writing, you might consider Rather, you need to find something that
and a lot of it can be accomplished by past- starting a blog. Your blog will be slow to you enjoy and that will allow you to build
ing your résumé into your profile. (Here’s attract readers, but that shouldn’t be your community, help people whom you’d like
a great chance to update your résumé, if end goal. Rather, your blog is a space to tell to help, and have fun. The adage “Do what
you haven’t recently!) While that’s proba- the world about your career path and ex- you love and it will never feel like work” is
bly not how you want your profile to look plore your thoughts about work. too simplistic, but I think it’s true for so-
permanently, it’s always easier to change If staying up late and writing about your cial media. Find the social media platform
things later. Also, don’t forget to add a pro- job doesn’t sound like fun, you could use that suits your personality and that you
C R E D I T: YA N G H . KU/C& E N /S H UT TE RSTO CK

fessional-looking photo of yourself. Instagram or Facebook to post (nonpro- can navigate with ease. Do that, and the
Now people will be able to find you prietary) pictures of your work. Or you journey will be a joy.
quickly, learn about your remarkable could try my favorite social media platform:
career, and get a sense of your interests. Twitter. Twitter is a microblogging service Chemjobber is an industrial chemist who
Connecting with people (by inviting people that allows you to broadcast short mes- blogs about the chemistry job market at
to connect or by accepting their invitations sages (280 characters), links, pictures, and chemjobber.blogspot.com. Find all his
to connect) seems like collecting people videos. I have thoroughly enjoyed getting columns for C&EN and suggest future topics
as if they’re baseball cards, but I think of to know chemists all over the world, seeing at cenm.ag/benchandcubicle.
LinkedIn as a Rolodex that can’t get lost or and hearing about their triumphs in the
soaked in coffee. Once you’ve connected laboratory, the different ways that people Views expressed are those of the author and
with someone on LinkedIn, finding people learn chemistry, and the different barriers not necessarily those of C&EN or ACS.

22 C&EN | CEN.ACS.ORG | JUNE 18, 2018


Cover story

W
hat could be easier than recycling?
Almost everywhere you go these
days, there’s a convenient bin for
your empty water bottle.
Yet plastic trash continues to accumulate in the A mere 2% of the plastic that starts out in a drinking
environment. A 2015 study in Science estimated that water bottle will be recycled into a new plastic bottle.
the oceans may hold 155 million metric tons of plastic The rest of the plastic that gets recycled typically ends
by 2025, double the current amount (DOI: 10.1126/ up as carpet fibers or outdoor furniture.
science.1260352). Turns out those convenient recy- Other factors are exacerbating the plastic pollu-
cling bins aren’t always being used. Americans are tion problem, particularly in the U.S. China, which
doing better than ever but still submit only about one- has for decades collected and processed recyclable
third of their plastic waste for recycling. waste from around the world, announced in 2017 that
An even more fundamental problem with plastics it would limit imports of foreign trash. Now some

RECYCLING
becomes apparent if you look past the recycling bin. U.S. waste management facilities have to send recy-
Only about 10% of plastic packaging worldwide—as clable plastic straight to the landfill because there’s
well as in the U.S.—ends up getting remade into a not enough domestic recycling capacity. Reflecting
new product, according to a 2016 World Economic a growing awareness of the plastic trash problem, in
Forum report. Another 14% from around the globe is May the American Chemistry Council announced its
burned, sometimes to generate energy. And the rest goal that by 2040 all plastic packaging used in the U.S.
ends up in a landfill or the environment. will be recycled or made into other products.
And it stays there, preserved. Plastic’s durability is As the mountains of discarded plastic continue to
one reason it has become so widely used. When it be- grow, science has begun to offer some solutions. Chem-

NEEDS
comes trash, however, that durability is a curse. Most ists, including Robertson, are working on new chemical
plastics are made from fossil-fuel-derived polymers, methods to break down current plastics to their build-
made of molecular chains that can reach thousands of ing blocks for reuse, and they’re designing new plastics
covalently bonded repeating units. that could be easier to recycle (see page 26). Research-
Of the plastic that does get recycled and reborn, ers are also working slowly toward biocatalyzed plastics
a majority of it ends up in a lower-quality product recycling, using microbes or enzymes to degrade poly-
because the most widespread, popular recycling mers. In the excitement about Mother Nature playing a
technology involves mechanically shredding, melting, possible role in solving the plastics problem, however,
and re-forming plastics. “Polymers tend to degrade at some news reports about plastic-munching critters

A REVAMP
high temperature,” says Megan Robertson, a chemi- have oversold progress (see page 30).
cal engineer at the University of Houston. “So we’re Read on for a few visions of what the future of plas-
essentially downgrading the material as it’s recycled.” tics recycling might—or might not—look like.

Broken cycle
8% Downgraded Eighty-six percent of plastic
recycling
4% Process packaging produced globally is
losses never collected for recycling,
according to a 2016 World
Chemical and biochemical 14% Recycling
Economic Forum report. Another
4% is lost during the recycling
approaches take aim at 2% Closed-loop
process, 8% is recycled into
lower-quality products like carpet
plastic pollution recycling fiber or plastic lumber, and just
2% is recycled into equivalent
products.
SAM LEMONICK, C&EN WEST COAST
14% Incineration and/or energy recovery

98% 32% Environment


Virgin 78 million metric tons of plastic
feedstock (Annual global production)
C R E D I T: JES S E LE N Z

40% Landfill

Sources: World Economic Forum; Ellen MacArthur Foundation

24 C&EN | CEN.ACS.ORG | JUNE 18, 2018 JUNE 18, 2018 | CEN.ACS.ORG | C&EN 25
POLLUTION

Chemical solutions for


a chemical problem
Researchers explore ways to convert plastics into valuable
products and to develop intrinsically recyclable polymers
SAM LEMONICK, C&EN WEST COAST

T
he world’s mounting plastic
trash crisis is hard to
solve because it has many
dimensions: social, technical,
and economic. But because chemistry
brought the problem into the world, it
doesn’t seem unreasonable to look to
chemistry for a solution.
Such a solution will require that today’s chemists
figure out how to undo the hard work of their prede-
cessors. The polymers we use as plastics were de-
signed to be durable and stable. They’re difficult to
break down on purpose.
Now, as the need for finding better ways to han-
dle plastic waste grows, some researchers are finding
ways to take plastics apart. Several companies have
started up in the past decade to capitalize on these
processes. Some methods return plastics to their
monomeric form in the hope that the re-
claimed building blocks might replace fossil
fuels as the feedstock for new materials.
Other processes yield fuels or additives
for other products.
Developing new recycling meth-
ods is especially important as

CR E D I T: J ES S E LE N Z
the kinds of polymers we use
have started to change. A
growing number of prod-
ucts and applications, such
as cars and wind tur-
bines, are relying on the
strength of composite
materials made with
fiberglass and carbon
fiber. These mate-
rials use polymer
resins that cannot
simply be melted
and re-formed
like other plastics,
and chemists are
just starting to develop

26 C&EN | CEN.ACS.ORG | JUNE 18, 2018


methods for recycling them in re- U.S. recycling status temperature, and pressure of the
search labs. While existing methods can recycle some pyrolysis process.
But other researchers are think- polymers, like poly(ethylene terephthalate), at Pyrolysis can address the poly-
ing about recycling as they develop relatively high rates, new technology is needed for styrene contaminant problem.
new materials that might not be other types. Faulkner says that because the
as difficult to deal with as today’s desired products vaporize as the
plastics. These projects could yield polymer breaks down, the valuable
Key: Mass-produced Percentage recycled
resins and plastics that are intrin- compounds can be separated from
sically easy to recycle. Poly(ethylene terephthalate) some of the dyes, processing aids,
With such developments, it’s pesticides, and food contaminants
conceivable that, one day, chem- 4.5 billion kg 19.5% during the reaction. Later separa-
ists might deliver a plastic bottle O O tion steps are still needed, though,
that can be reincarnated infinitely. 1 he says.
O O Agilyx started out with a more
PET generalized process for turn-
Trash to treasure n
ing plastic waste into valuable
All plastics are not equal when High-density polyethylene products. In 2004, then called
it comes to recycling. Polyethylene Plas2Fuel, the company built reac-
polymers are the easy-to-handle 5.5 billion kg 10.3% tors to convert mixed plastic waste
favorites. Poly(ethylene tere- into a mixed hydrocarbon product
phthalate) (PET) and high-density 2 called Agilyx Synthetic Crude Oil.
polyethylene are the most com- HDPE This mixture can be refined like
n
monly recycled plastics in the U.S. natural crude oil. Agilyx had built
Products made with these plastics and sold several of these systems
are stamped with a recycling sym- Poly(vinyl chloride) to waste management companies
bol encircling the numbers “1” and 0.9 billion kg 0.0% across the country before the price
“2,” respectively. When embla- of oil dropped in 2015, making the
zoned with these numbers, called
Cl crude alternative less competi-
3
resin identification codes (RICs), tive with what comes out of the
plastics can be shredded, cleaned, PVC n ground. That’s when the company
and remade into new bottles or started getting its polystyrene re-
lower-quality materials like carpet cycling plant on-line. But Faulkner
fiber.
Low-density polyethylene says with oil prices climbing again
On the other end of the scale, 7.4 billion kg 5.3% and China limiting how much
many curbside recycling programs plastic waste it will accept from
don’t even accept polystyrene (RIC 4 the U.S. and other countries, Agi-
6), used in food packaging, packing lyx is seeing renewed interest in
LDPE n
peanuts, and disposable cutlery. its oil production process.
Like polyethylene plastics, polysty- Other companies are hoping to
rene waste can be processed and Polypropylene turn waste plastics into valuable
reused to make new products. It 7.2 billion kg 0.6% chemical products or feedstocks. A
just doesn’t happen often. lot of the attention has focused on
“Plastic foam is troublesome for 5 polyethylene.
most material recovery facilities in GreenMantra Technologies
the country,” says Chris Faulkner, PP n in Brantford, Ontario, employs a
C R E D I T: A DA PT ED F RO M P ER I O D IC G RA P H I CS /A N DY BRUN N I N G FO R C& E N

vice president of technology and thermocatalytic process to turn


project management at Agilyx, Polystyrene plastic into waxes for asphalt
which has developed a chemical 2.2 billion kg 0.9% roads and roofs, as well as addi-
process to recycle polystyrene. tives for plastics, adhesives, and
A big challenge in recycling coatings. Domenic Di Mondo,
polystyrene is contamination. Ac- vice president of technology and
tually, it’s a problem for all plastics business development, says those
recycling; if oily molecules, water, 6 products haven’t typically come
and other contaminants make it PS from recycled materials. “We’re
n
into recycled materials, the sub- driving a circular economy and in
stances can disrupt and weaken Note: These data, from EPA, are for the U.S. in 2012 and were most cases creating products with
the polymers. Polystyrene clam- published in 2014. even higher value than the virgin
shell containers and coffee cups starting material,” he says.
are especially likely to be dirty, adding to company can revert polystyrene back to When the company started in 2010, its
the cost of processing them for recycling. monomeric styrene, toluene, and ethyl- first target was polyethylene. GreenMan-
Agilyx uses pyrolysis to break down benzene, which is a precursor to styrene. tra uses a heterogeneous thermocatalytic
polystyrene at its Tigard, Ore., facility, Faulkner wouldn’t share the exact details process to turn the plastic into different
heating it in an oxygen-deprived envi- of Agilyx’s process but says it can select specialty chemical products. Di Mondo says
ronment so the plastics don’t burn. The for different products by tuning the time, the process requires lower temperatures

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 27


than pyrolysis and gives the company a high ty that the polymers alone don’t have. mostly undamaged by the process (Green
degree of control over what gets produced. The makers of cars, planes, and wind Chem. 2017, DOI: 10.1039/c7gc01737e).
Di Mondo wouldn’t specify what catalysts turbine blades rely on these composite Although Zhang says he has licensed
GreenMantra uses, but patent documents materials because of their high strength- some of his technology to a Chinese com-
related to the polyethylene process de- to-weight ratio. Unlike plastic bottles, pany and has had interest from others,
scribe it as using an iron- and copper-based these products don’t get thrown away these methods are a long way from com-
catalyst. Di Mondo says that because the every day. But when their lifetimes do end, mercial applications. As a result, Zhang
method uses a solid catalyst and no sol- a lot of thermoset-polymer-based compos- and others are working on a possibly easi-
vents and has a small physical footprint, the ites get sent to landfills. er path to recycling thermosets: designing
process can be easily scaled up. “We really have no way of dealing with new polymers with recycling in mind.
The company now processes polyeth- those polymers,” says Megan Robertson, Such research could save the chemists a
ylene and polypropyl-
ene at its Brantford
facility, and it plans
to open a polystyrene O O
pilot plant in 2019. But B B B B
it hasn’t targeted all O O O O
B + HO B + HO
types of plastic. Chlo- B B
rine in poly(vinyl chlo-
ride) poses too many OH OH
health and environ-
mental risks for most
recyclers, even the
ones using mechanical
recycling, and Di Mondo says GreenMantra Boroxine rings can break and easily re-form throughout this thermoset, enabling it to be
has not focused on PET because existing reshaped (shown). With boiling water, the thermoset can even revert to its monomers.
recycling processes are sufficient to keep
large amounts of it out of the landfill. a chemical engineer at the University of lot of trouble trying to break down the ma-
Houston. terials when they’re thrown away.
Jinwen Zhang, a polymer scientist at To create these new recycling-ready
The trouble with Washington State University, is one per- materials, Zhang has zeroed in on the
thermosets son trying to change that. He’s developed source of thermoset stability—the cross-
Another class of polymers called ther- mild catalytic processes to break down es- linkers. The materials he’s making are
mosets presents a unique set of recycling ter linkages in amine-cured epoxy resins, a known as vitrimers, a subset of thermo-
challenges. Unlike thermoplastics, such as type of thermoset that is common in com- sets with cross-linking bonds that form
polyethylene, polystyrene, and polypropyl- posite materials. Zhang showed he could and break depending on temperature. In
ene that can be melted and molded into dissolve resin in carbon-fiber scraps from a way, they act like a glass, malleable at
new forms, thermoset polymers harden a major aircraft maker using a ZnCl2-etha- high temperatures and hardening when
irreversibly thanks to covalent cross-linkers nol catalyst at 250 ºC. His group recovered they cool. If manufacturers used such vit-
that bridge polymer strands. These poly- carbon fibers and un-cross-linked oligo- rimers as resins in composite materials,
mers are increasingly used as resins and mers from the resin. A scanning electron the resulting products could be recycled
combined with carbon fiber or other mate- microscope showed that the fibers were through mechanical processes similar to
rials to achieve tensile strength and elastici- still smooth, indicating that they were those used for thermoplastics.
OH
O O Polymers like the vitrimer
shown could be used
as recyclable resins in
OH CH3 composite materials.
O When heated at 12 atm
O O + OH
O HO OH with ethanol and zinc
O catalyst left over from the
O O
O + Residual zinc
O polymerization process,
O this particular vitrimer
CH3 breaks down at its ester
linkages, making it
recycling ready.
12 atm 1 atm
160 °C 190 °C
CH3
O
OH O OH OH
HO O
HO OH
O O O
O
O
O O O
O
CH3

28 C&EN | CEN.ACS.ORG | JUNE 18, 2018


Zhang developed a vitrimer based on or so-called self-immolative, polymers to plastics on the market right now (Science
eugenol, a renewable phenylpropene found develop new thermoplastics. Pioneered 2018, DOI: 10.1126/science.aar5498).
in nutmeg, cinnamon, and other plants by chemist Doron Shabat of Tel Aviv Uni- Chen has long focused on ring-open-
(Macromolecules 2017, DOI: 10.1021/acs.mac- versity, self-immolative polymers are in- ing reactions to synthesize polymers.
romol.7b01889). When heated with ethanol herently unstable but have an endcap that “Ring-opening polymerization is a highly
and some zinc catalyst left over from the prevents their depolymerization. When effective way of making high-molecu-
polymerization process, the vitrimer breaks triggered by light or a specific chemical, lar-weight polymers in a short period of
down at its ester linkages. Zhang says he’s the endcap releases and triggers depo- time,” he says. He recently reported po-
also experimented with lignin, which can be lymerization. “Self-immolative polymers lymerization of a strained, two-ring mono-
extracted from plants, as a vitrimer. embody that ideal notion of how we could mer called 3,4-T6GBL into either a linear
University of Houston’s Robertson has potentially recycle plastics,” says Eliza- or cyclic polymer, depending on the metal
also developed recyclable thermosets by beth Gillies, a chemist at the University of catalyst used. Using heat and a ZnCl2
finding renewable chemicals to replace Western Ontario. catalyst, Chen and his team can return
some or all of bisphenol A (BPA), which is Gillies developed an ethyl glyoxylate the polymer to 3,4-T6GBL, a process they
used as an epoxy precursor in many resins. polymer that reverts to its monomer, ethyl think can be repeated infinitely.
The BPA alternatives she’s identified in- glyoxylate, when the polymer’s endcap is “The design of the monomer is the key
clude epoxidized soybean oil, salicylic acid, removed via light, hydrogen peroxide, or for developing chemically recyclable poly-
and other plant derivatives. Rob-
ertson says key features she looks O
for in these biobased molecules O
n Lanthanum catalyst Yttrium or zinc catalyst
are convenient functional groups
for conversion to epoxides and O O O
aromatic rings to provide strength, O
mimicking the chemical structure
O O
O n
of BPA (ACS Sustainable Chem. O
Eng. 2016, DOI: 10.1021/acssusche- ZnCl2, heat ZnCl2, heat
meng.6b01343). Because many of
3,4-T6GBL
O
these molecules contain esters, O
Robertson says, chemical recycling
methods under development for Eugene Y.-X. Chen of Colorado State University calls this polymer, in its linear (right)
polyesters could be applied to her or cyclical (left) form, infinitely recyclable, capable of repeatedly breaking down to its
thermoset polymers. monomer (center).
A research group at the Universi-
ty of California, Irvine, led by Zhibin Guan mild acid (J. Am. Chem. Soc. 2014, DOI: mers with high depolymerization selectivity
has turned to boroxine rings to produce re- 10.1021/ja504727u). In theory, that’s an ideal and useful materials properties,” he says.
cyclable thermosets (J. Am. Chem. Soc. 2018, system for a recyclable polymer. In reality, Ensuring that its core structure can be
DOI: 10.1021/jacs.8b03257). These rings she says, the current versions of these poly- chemically recycled is the first step, accord-
form through reversible reactions between mers can’t compete with the properties or ing to Chen. Then adding functional groups
boronic acid groups on the monomers, a cost of PET and other commercial plastics. can achieve desirable physical properties.
property that also allows the thermoset Scott Phillips, a chemist at Boise State One of Chen’s former postdocs, Miao
to be reshaped and re-formed. In boiling University, has designed self-immolative Hong, now developing her own recyclable
water, the polymer breaks down to its polymers with responsive endcaps, in- polymers at the Shanghai Institute of Or-
monomers. cluding phenoxides and alkoxides (Green ganic Chemistry, says chemically recyclable
Researchers at IBM are also interested Chem. 2015, DOI: 10.1039/c5gc01090j). polymers are the best solution to the prob-
in chemically recyclable thermoset poly- When these molecules get cleaved off the lem of plastic trash. Such materials could
mers because computers use the materials polymer, they liberate two electrons that not only make possible the infinitely recy-
in many ways, including as insulators for then cascade down the polymer, selective- clable plastic bottle but also avoid issues
electronics and in the cases that house ly breaking off monomers. of quality loss, seen with mechanical recy-
them. Jeannette Garcia, a chemist at IBM, But not all recyclable thermoplastics cling, and the inability to recover valuable
created poly(hexahydrotriazine), which can need to rely on self-immolation. Eugene products from biodegradable polymers.
be converted back into its monomer with Y.-X. Chen, a chemist at Colorado State Still, intrinsically recyclable plastics
an acid catalyst that selectively hydrolyzes University, recently described a fully recy- are a long way from commercial reality.
the hexahydrotriazine linkers (Science 2014, clable polymer with properties on par with Besides technical hurdles, there are also
DOI: 10.1126/science.1251484). economic ones. For manufac-
turers, it’s usually easier to
O O H O HO OH use a tried-and-true material
Rethinking n UV light H2O than a brand-new one, Garcia
thermoplastics O O Depolymerization O O O O says. Although the barrier
Thermoset polymers to adoption is high, it isn’t
aren’t the only materials insurmountable. So she and
that chemists are designing = UV-responsive endcap other chemists continue to
to be easily recycled. Some work on chemical solutions
researchers have turned to Two-electron reactions can degrade self-immolative polymers to the rapidly growing prob-
the field of self-destructive, linearly when a trigger removes the endcap. lem of plastic trash.

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 29


SUSTAINABILITY

The truth about plastic eaters


Headlines about plastic-munching microbes and worms
belie tough, competitive road to recycling processes
CARMEN DRAHL, C&EN WASHINGTON

“C
ould Nature Rid the Planet of Its Plastic Waste?” Over the past few
years, worms, bacteria, and enzymes that chow down on polymers
have inspired headlines somewhat like this one. The idea that biology
may succeed where humans have so far failed is tantalizing.
Except dealing with the staggering amount of critter is biochemically degrading the polymer rather
plastic waste polluting the earth is more complicat- than simply shredding it. The gold-standard test for
ed than some coverage has let on. Most reported confirming the fate of plastic in an organism involves
cases of an enzyme or critter degrading plastic are feeding isotopically labeled plastic to animals of in-
incomplete and slow. Making these processes faster terest and tracking whether the labels appear later in
and more efficient is not trivial. And even if scien- monomers or other compounds. Scientists who don’t
tists manage to improve polymer biodegradation see this test in a new study are likely to ask for it and to
technologies, they must also bring down the cost ask more questions.
to compete in a marketplace that includes chemical In 2017, biologist Federica Bertocchini at the In-
recycling methods (see page 26) and virgin mono- stitute of Biomedicine & Biotechnology of Cantabria
mers—brand-new materials that have never been reported that wax worm caterpillars could break
polymerized. down polyethylene. After their initial observation,
Media circus notwithstanding, biodepolymer- they exposed a paste made from mashed-up cat-
ization research is slowly moving forward, and an erpillars to a sample of polyethylene film, which
enzyme-based process to break down one common generated new peaks during a scan with an infrared
plastic is making gradual advances to market, which spectrometer. Bertocchini and her team attributed
suggests biocatalysis could someday make up a share the peaks to a breakdown product, ethylene glycol,
of—although certainly not the entire—recycling likely generated by a caterpillar enzyme or an enzyme
landscape. in its gut microbes (Curr. Biol. 2017, DOI: 10.1016/j.
Knowing some polymer chemistry can help put cub.2017.02.060). Many outlets, including C&EN, cov-
glowing headlines in context. Breaking apart poly- ered the work.
esters such as poly(ethylene terephthalate) (PET), Four months later, however, Till Opatz and his
which was the subject of some studies that made coworkers at Johannes Gutenberg University Mainz
headlines, is relatively easy because these plastics published a report disputing the findings (Curr. Biol.
contain the ester bonds that enzymes already degrade 2017, DOI: 10.1016/j.cub.2017.07.004). Bertocchini’s
in nature. But plastics with an all-carbon backbone, infrared spectra lacked characteristic peaks for eth-
such as the polyethylene in shopping bags or the ylene glycol, Opatz argues. He suspected that instead
polystyrene in carryout food containers, are more of coming from ethylene glycol, the spectral peaks
challenging. News about breaking down those kinds of came from ground-up caterpillar proteins that stuck
plastics tends to be greeted with more excitement, but to the polyethylene film after washing. So his team
it also merits more skepticism. smeared ground pork, which would also contain pro-
In addition, the more neatly a polymer’s molecular teins, on polyethylene film and obtained a spectrum
chains are arranged, which is measured by a property that Opatz says matched Bertocchini’s. This con-
called crystallinity, the harder they are for enzymes clusion doesn’t rule out that caterpillars are capable
and organisms to break down. Polymers are never of biodegrading plastic, but it is a simpler explana-
100% crystalline, but some plastics are more crystal- tion for what Bertocchini’s team observed, Opatz
line than others. For instance, some studies reported contends.
breakdown of flexible PET films, but these films tend Bertocchini stands by her work (Curr. Biol. 2017,
to have lower crystallinity, and tend to be easier to DOI: 10.1016/j.cub.2017.07.005). “We do need to better
chomp on, than plastic bottles. check what the by-products of this degradation are,”
she says. Funding challenges in Spain have delayed
follow-up studies, but her team plans to begin experi-
The very hungry grubs ments soon.
When an organism appears to be eating plastic, sci- Some studies do use the gold standard of isotopic
entists and reporters should look for evidence that the labeling to make conclusions about plastic eaters,

30 C&EN | CEN.ACS.ORG | JUNE 18, 2018


These polyethylene-
eating caterpillars
launched a media
feeding frenzy,
but it’s not certain
they biochemically
degrade the plastic.

but scientists may point out other lim- (Environ. Sci. Technol. 2014, DOI: 10.1021/ ethylene breakdown with other tech-
itations. Jun Yang of Beihang University es504038a). But as with Bertocchini’s niques, including mass measurements,
and his team conducted isotope-labeling caterpillar study, no isotope-labeling gel permeation chromatography, and
studies to determine that a gut bacterium work was performed. Yang contends it’s infrared and nuclear magnetic resonance
from mealworms consumes polysty- possible to confirm biochemical poly- spectroscopy.
rene (Environ. Sci. Technol. 2015, DOI: Opatz disagrees because contamination
10.1021/acs.est.5b02661 and 10.1021/acs. could look like degradation products in
est.5b02663). Work with collaborators some of those techniques.
such as Wei-Min Wu at Stanford Univer- Ordered Narayan notes that those
sity suggests that the organisms convert crystalline methods are indirect, and
about half the polystyrene carbon they region any degradation spotted by
ingest to CO2 rather than to styrene them could be attributable
monomers. to degradation that wasn’t performed
But the rest of the products— by the organism. Moreover, Narayan
monomers or otherwise—haven’t argues, it’s not enough to show
been identified. And the bacteria that organisms are biochemically
C R E D I T: S PA N I S H N AT IO N A L R ES EA RC H CO U N C IL

don’t completely digest their plastic breaking down polymers. Without


meals, even after several demonstrating complete degradation,
weeks. Disordered whether to CO2 or recovered mono-
“There appears to amorphous mers, there’s a chance that leftover
region
be some utilization of plastic fragments could wreak havoc
polystyrene carbon, but I would still like on the environment. Microplastics can
others to reproduce the results,” says harm aquatic life that mistakes them for
Ramani Narayan, a specialist in biodegrad- food and transport pollution into the food
able polymer systems at Michigan State chain.
University. The more orderly the arrangement of It remains to be seen whether enzymes
Yang’s team has also reported that polymer chains, the more crystalline the isolated from Yang’s microbes can con-
Indian meal moth larvae and bacteria polymer is said to be, and the harder it is sume plastic quickly and completely. Yang
within those larvae degrade polyethylene to break down with microbes or enzymes. and his team have sequenced the genome

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 31


of one of the polyeth- This microbe contains PETase National Renewable
ylene-munching bacte- and MHETase, two enzymes that O O Energy Laboratory,
rial strains they iden- depolymerize PET to its monomers PET H. Lee Woodcock
tified (J. Biotechnol. (scheme shown). O O of the University of
n
2015, DOI: 10.1016/j. H O PETase South Florida, and
300 nm 2
jbiotec.2015.02.034), their colleagues en-
and Yang says work is countered a pleasant
under way to identify O O surprise when solving
relevant enzymes and HO MHET their structure (Proc.
to produce greater O OH Natl. Acad. Sci. USA
quantities of them. H2O MHETase 2018, DOI: 10.1073/
pnas.1718804115).
They set out to deter-
Proteins O O mine how the PET-de-
attacking Ideonella sakaiensis OH + grading enzyme
HO HO OH
plastic evolved, and in the
Ethylene glycol process, they acciden-
Terephthalic acid
Any enzyme that tally made a mutant
can break up plastic enzyme that could
will be judged by whether it can degrade 02255-z; Nat. Commun. 2018, DOI: 10.1038/ erode more-highly-crystalline PET than
real-world plastic waste and do so ef- s41467-018-02881-1; Biophys. J. 2018, DOI: before. Beckham says the current version
ficiently. In 2016, researchers in Japan 10.1016/j.bpj.2018.02.005; ChemBioChem of the enzyme would still take months to
tested sludge from a recycling plant and 2018, DOI: 10.1002/cbic.201800097). But break down a soft-drink bottle. “We’re do-
uncovered a microbe that could complete- John E. McGeehan of the University of ing a lot of protein engineering to improve
ly break down films of PET to CO2 and Portsmouth, Gregg T. Beckham of the the activity further,” McGeehan says.
H2O, a feat that was a step above partial
degradations reported previously. From
that microbe, the scientists plucked two
enzymes that degraded PET to its mono-
Are microbes evolving to eat plastic?
mers of terephthalic acid and ethylene Some bacteria can degrade plastic, which might be nature’s way of adapting to
glycol (Science 2016, DOI: 10.1126/science. a new food source or just coincidence. We asked sources to weigh in.
aad6359).
Some headlines claimed the microbe
could help with recycling, but breakdown “I hope so, but we would definitely need to
took six weeks on a small plastic sample,
too slow for immediate applications. Yang, control them!”
who wasn’t involved with the work, point- —Federica Bertocchini, Institute of Biomedicine & Biotechnology of
ed out another caveat of the study in a Cantabria
technical comment in Science: The team in
Japan worked with low-crystallinity PET “It would only be natural that microbes
film, which worked better for screening
purposes but is relatively easy to degrade have and will continue to evolve to
compared with the higher-crystallinity
PET in water bottles and other common consume plastics, since they are
products (2016, DOI: 10.1126/science.
aaf8305).
increasingly abundant in nature.”
Kohei Oda of Kyoto Institute of Tech- —Richard Gross, Rensselaer Polytechnic Institute
nology, who co-led the original study,
says his colleagues set out to screen for
microbes that could use PET as a nutrient
“Whether they’d evolve where there
for growth, regardless of crystallinity (Sci-
ence 2016, DOI: 10.1126/science.aaf8625).
are other things to eat besides
Optimizing enzymes can always come plastic is questionable.”
later, he contends. He thinks some news
outlets exaggerated the immediate impact
—Emily Flashman, University of Oxford
of the work, and as a result, he and his
coworkers now monitor coverage “very “This has not yet been demonstrated.”
C R E D I T: S CI E NC E ( M I CRO BE )

carefully.” —Wolfgang Zimmermann, Leipzig University


Multiple groups have since solved
the X-ray crystal structure of one of the
Japanese team’s enzymes, which con-
“We need more examples to
verts PET to an intermediate called mo-
no-(2-hydroxyethyl) terephthalic acid (Nat.
answer this question.”
Commun. 2017, DOI: 10.1038/s41467-017- —Kohei Oda, Kyoto Institute of Technology

32 C&EN | CEN.ACS.ORG | JUNE 18, 2018


Optimization game that depolymerizes 97% of PET starting
materials into monomers in 24 hours.
Richard A. Gross has been doing that “There’s a real gap between what’s been
kind of engineering since 2011. His group published in the press and what we do,”
at Rensselaer Polytechnic Institute works says spokesperson Benjamin Audebert,
with cutinases, so named because they referring to news reports about studies
degrade cutin, a waxy coating on plants. in the academic literature. Before expos-
Many of these enzymes also degrade PET, ing PET to its enzyme, Carbios uses a
which, like cutin, is a polyester. proprietary pretreatment that converts
Gross says teams will want to maximize crystalline PET to an amorphous form,
enzyme binding affinity for PET. To boost facilitating breakdown. Audebert declined
activity, they’ll also have to make sure the Woodcock and colleagues developed a to disclose the enzyme Carbios uses, but
enzyme is stable at or above PET’s glass computational model to show how PET a company patent mentions bacterial
transition temperature of 75 °C. At the (gray and red) docks inside their mutant and fungal cutinase and lipase enzymes.
glass transition temperature, polymer PET-degrading enzyme (space fill). Earlier this year, Carbios started scaling
chains have higher mobility, which you up its process to enable treatment of up
can think of as having more elbow room, there’s still the matter of cost. Engineered to 200 kg of PET waste in 24 hours. By
Gross explains, improving an enzyme’s enzymes tend to be more expensive than year’s end, the goal is to produce a new
access to the bonds it breaks. And finally, commodity chemicals, and scaling up a plastic product, such as a bottle, from re-
adjustments should be made to block biotechnological process takes yet more covered monomers and to test the result-
enzyme aggregation, which can reduce investment. “We already have mature, ing product with corporate partners such
performance. Gross’s team showed earlier scalable, cost-effective technologies to re- as L’Oréal, Audebert says. A 10,000-met-
this year that strategically placed carbo- cycle PET,” such as metal-catalyzed depo- ric-ton plant is in the works for 2021, he
hydrate groups largely prevent cutinases lymerizations, Narayan says. What’s more, adds. “Our business model is built on
from aggregating (Biochemistry 2018, DOI: it’s tough to compete with the low price of the fact that we will be competitive with
10.1021/acs.biochem.7b01189). virgin monomers, he adds. “Nobody wants virgin PET.”
Weighing in on McGeehan and Beck- to face that reality.” As exciting as PET biorecycling could
ham’s work, Emily Flashman, a specialist Wolfgang Zimmermann, an expert in be, PET is only one plastic, says Nick
in enzyme mechanisms at the University biocatalysis for plastics recycling at Leipzig Wierckx of RWTH Aachen University.
of Oxford, adds that to be successful, any University, is more optimistic. “The plas- The next step would be processes that can
biorecycling process must find a produc- tics manufacturing industry hasn’t been degrade plastics with different types of
tive way to harvest and reuse monomer conscious of the waste problem, and this is chemical bonds and cocktails of enzymes
products. McGeehan says he and his changing now,” he says. Changing attitudes that could handle mixtures of plastics, he
collaborators are “keen to develop” a and changing demands from consumers says.
monomer isolation process, and they are could tip the balance in favor of recycling It’s not entirely a hypothetical for
also working to make the enzyme stable at methods that use biocatalysts rather than Wierckx. He and Zimmermann are two
higher temperatures. chemical catalysts, if costs can be some- members of a European consortium
what competitive, he adds. called P4SB, which aims to convert waste
The researchers at Carbios aim to PET and polyurethane to high-value
The elephant in the room capitalize on that sentiment. The French chemical feedstocks (Microb. Biotechnol.
C R E D I T: H . L E E WOO D CO C K/ UN I V E RS I TY O F S O UT H FLO R I DA ( MO D E L) ; CAR B I O S (R EACTO R )

Even if optimization goes swimmingly, firm says it has optimized an enzyme 2015, DOI: 10.1111/1751-7915.12312). The
consortium’s efforts are largely at the
gram scale so far, Wierckx says, but the
long-term goal is to create a system simi-
lar to what exists for converting biomass
to biofuels.
Although plastics biorecycling holds
promise, the field has its share of challeng-
es, so the media should be cautious, urges
Opatz, the caterpillar skeptic. A step for-
ward shouldn’t be billed as a planet-sav-
ing breakthrough. “If you tell the public
that this problem has been solved when
it hasn’t,” he explains, “people will be
waiting for practical solutions, and they’ll
In a 5-L reactor at be annoyed if in 10 years’ time there’s
Carbios, enzymes still polyethylene debris lying around or
depolymerize a floating in the oceans. They’ll say, ‘What’s
solution of PET. wrong with you scientists? You solved the
problem 10 years ago, and we still have
this mess.’ ”
At the end of the day, Opatz adds, cava-
lier coverage “undermines the relationship
between science and society.” ◾

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 33


COMMENT
ACS
NEWS
Supporting ACS’s volunteers
CAROLYN RIBES, CHAIR, ACS COMMITTEE ON COMMITTEES

E
very year, thousands of dedicated hance their communications, networking, generation, and ACS has volunteers across
and talented volunteers channel and collaborations. Activities include multiple generations (traditional, baby
their passion for chemistry, ed- sponsoring interactive sessions for com- boomer, Generation X, Generation Y, and
ucation, advocacy, diversity, and mittee chairs, sharing committee goals Generation Z). Our committee system
other issues into tangible deliverables that and activities among ACS committees, and needs to embrace each generation’s val-
make an impact on the American Chemi- organizing “speed networking for commit- ues, needs, and styles.
cal Society, the chemistry profession, and tees” events. These differences include a likelihood
society as a whole. ▸▸Identify, assess, and recommend en- to volunteer on an ongoing basis ver-
ACS volunteers ded- hancements to improve sus a tendency to volunteer for discrete
icate their time and the effectiveness and projects; a willingness to travel for their
talents to realizing the
ACS vision of “improving
people’s lives through
ConC needs to ensure
the transforming power
of chemistry.” Some of that we have a committee
these volunteers have
been contributing their system that encourages the
efforts to local and na-
tional projects for ACS
for decades.
participation of all members
ACS’s committee sys-
tem, which is made up
and all generations.
of more than 40 council sustainability of the com- efforts versus a preference for working
and/or board-related mittee system. from home; and a reliance on face-to-
committees, provides a framework for Given ConC’s vision of effective and face interaction versus a comfort with
volunteer engagement at the national dynamic committees, our committee telecommunication.
level. Many volunteers report that they system should provide a meaningful ConC needs to ensure that we have a
have benefited from opportunities to get volunteer experience; facilitate excel- committee system that encourages the
involved though local section, commit- lent collaboration, communication, and participation of all members and all gen-
tee, division, and governance activities. coordination among committees; drive erations. We have to ask ourselves if our
Because ACS is a membership society, impactful decision-making; provide paradigm of assigning 750-plus members
strong engagement of members at multi- transparency; connect individual mem- to committees that meet twice a year in
ple levels is a key factor in the success of bers to national governance; and, above person (typically at national meetings) is
the organization. all, achieve the purpose of ACS as defined the best way to achieve our purpose and
The mission of the ACS Committee in our congressional charter. Although we provide meaningful volunteer experiences
on Committees (ConC) is to ensure that have a strong system now, we also have to for all our members.
ACS committees are optimally organized, consider what the future may bring and We have to consider if our current sys-
resourced, and engaged. ConC has defined how the committee system can best sup- tem encourages or constrains volunteers
four strategic goals to reach our vision port the changing demographics of our and what options exist for engaging more
of an effective and dynamic committee membership. members in reaching our goals of provid-
system: ACS has enjoyed decades of success ing information solutions, empowering
▸▸Develop strategies to best match the with volunteers who are willing and able members and member communities,
needs and demands of committees with to attend the two national meetings each supporting excellence in education, and
member expertise and perspectives. year and work to achieve committee goals communicating chemistry’s value.
ConC is working with each committee to between meetings. However, we miss ConC wants to hear the thoughts
identify the skills, experience, and exper- the contributions of members who are of ACS members as we seek input on
C R E D I T: CO URT ESY O F CA RO LY N R I BES

tise the committee needs and is estab- not able to commit to attending those ways to sustain and enhance the effec-
lishing ways to identify volunteers to fill meetings and yet would like to engage at tiveness, collaborations, and commu-
those needs. the national level. Today’s technologies nications of the committee system and
▸▸Increase the number of qualified and provide opportunities for changing the ­improve the volunteer experience for all
committed volunteers from diverse com- way volunteers contribute, and we need to its participants. Please send your com-
munities by developing ways to expand take full advantage of those technologies ments, ideas, and thoughts to secretary@
the reach of committee preference forms to find ways to involve more members and acs.org.
to include a more diverse pool of potential minimize some of the present require-
volunteers. ments, such as travel. Views expressed are those of the author and
▸▸Partner with ACS committees to en- Volunteerism is evolving with each not necessarily those of C&EN or ACS.

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 35


▸▸ ACS Board actions
ACS
NEWS
from the June Willie May recognized
executive meeting for public service
The ACS Board of Directors met on On May 31, Willie May received the
June 1–2 in Baltimore and took several ac- 2017 ACS Award for Public Service
tions. The following are highlights: from ACS Board Chair John Adams
On the recommendation of the Commit- at a dinner preceding the ACS Board
tee on Pensions & Investments, the board of Directors meeting in Baltimore.
approved an amendment to the ACS De- It is the highest award the American
fined Contribution Retirement Plan. Chemical Society can convey to rec-
On the recommendation of the Commit- ognize exceptional public service.
tee on Professional & Member Relations, May, former director of the National
the board approved a nominee for the 2019 Institute of Standards & Technology,
Othmer Gold Medal, reestablished the was nominated for the award by the
Henry H. Storch Award in Energy Chem- ACS Committee on Chemistry &
istry for presentation beginning in 2020, Public Affairs in recognition of his
and authorized ACS financial support for leadership of NIST and for his life-
several awards for 2020 presentation unless time accomplishments as a chemist,
sponsors are found to support them. administrator, and leader supporting
The board confirmed council appoval of U.S. science and technology pro- Willie May (left) receives the ACS
the continuation of the Joint Board-Council grams.—GLENN RUSKIN, ACS staff Award for Public Service.
Committee on Publications, as well as the
Younger Chemists Committee.
The board also approved the estab-
lishment of new international chemical City; Yutong Dai, Princeton International symposium in Uyo, Nigeria, with the theme
sciences chapters in Jordan and Qatar, School of Math & Science in Princeton, “Sustainable Chemistry: Eco-Innovation for
confirmed the Petition on the Composi- N.J.; Aniket Dehadrai, Oklahoma School Equitable Societies & Industries.”
tion of Society Committees, and approved of Science & Mathematics in Oklahoma Nearly 350 people participated in the
the list of Petroleum Research Fund grant City; Allen Ding, Stevenson High School conference, which featured 56 oral and 16
recommendations submitted by the PRF in Lincolnshire, Ill.; Edward Jin, Arnold poster presentations. Discussions focused
Advisory Board. O. Beckman High School in Irvine, Calif.; on economic and social development
The board agreed that a distribution Omar Khan, Oklahoma School of Science through sustainable management of natural
of $750,000 received from the board of & Mathematics; Chanseo Lee, Lexington resources, as well as how to achieve cleaner
trustees for the Group Insurance Plans High School in Lexington, Mass.; Alex energy through cost-effective processes.
should be used to establish a scholarship Li, Lexington High School; Albert Liu, Technical sessions covered chemical
fund for Project SEED. Also, after 39 years North Hollywood High School in North monitoring and risk assessment for a safer
of service to the society, ACS Treasurer and Hollywood, Calif.; David Liu, West Wind- environment; materials for cleaner energy
Chief Financial Officer Brian Bernstein an- sor-Plainsboro High School South in Princ- and environment; sustainable industrial
nounced his plans to retire at the end of the eton Junction, N.J.; Michelle Lu, Pomper- processes through green synthetic chem-
year. The search for his successor is under aug High School in Southbury, Conn.; istry and catalysis; waste valorization for
way.—LINDA WANG Anton Ni, University High School in Irvine, energy and nutrient recovery; and new
Calif.; Yajvan Ravan, Churchill High School phyto- and agrochemicals for sustainable
in Livonia, Mich.; Jeffrey Shi, Marcellus agriculture and health.
▸▸ Chemistry Olympiad High School in Marcellus, N.Y.; Matthew
Wang, Troy High School in Troy, Mich.;
Keynote speaker Augustine Igbuku,
corporate environment manager of Shell
Study Camp begins Andrew Wu, Park Tudor School; David Petroleum Development Company of Nige-
Wu, Westview High School in San Diego; ria, spoke of the role of chemistry in the oil
From June 10 to 25, 20 students selected by Iris Yan, Carmel High School in Carmel, and gas exploration and production sector
the ACS-sponsored U.S. National Chem- Ind.; and Albert Zhu, Solon High School in in Nigeria. Anthony I. Okoh, director of the
istry Olympiad program are attending the Solon, Ohio. South African Medical Research Council’s
Chemistry Olympiad Study Camp at the For more information, visit the U.S. Microbial Water Quality Monitoring Unit
U.S. Air Force Academy in Colorado. National Chemistry Olympiad website at at the University of Fort Hare, encouraged
The students are vying for a spot on the www.acs.org/olympiad.—LINDA WANG younger researchers to apply for research
four-member team representing the U.S. at scholarships from their institutions.
the 50th International Chemistry Olympi- Participating organizations included
▸▸ ACS Nigeria Chapter
C R E D I T: GLE N N RUS K IN

ad, which will start in Bratislava, Slovakia, the Chemical Society of Nigeria, Acad-
on July 19 and end in Prague on July 29. emy of Science of South Africa, Science
Representing 13 ACS local sections and hosts symposium in Uyo Teachers Association of Nigeria, and
10 states, the students are Jenny Cai, Park the University of Uyo’s department of
Tudor School in Indianapolis; Andrew On March 4–7, the ACS Nigeria Interna- chemistry.—SHAIBU ENEOJO SOLOMON,
Chen, Stuyvesant High School in New York tional Chemical Sciences Chapter hosted a special to ACS

JUNE 18, 2018 | CEN.ACS.ORG | C&EN 37


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Newscripts
stones in biopsy samples, King explains. It can also be
used to identify chemicals that have a fixed refractive
index by taking a sample of a known thickness and
comparing the colors to known values.
“I get the prettiest results out of amino acid com-
binations,” he says. “I really like to make compounds
that we see in our everyday lives stimulating or inspir-

Curating quirky science since 1943 ing for people to look at who maybe aren’t as familiar
with chemistry as we are.”

Masterpiece Magic angle art


microscopy
S
peaking of scientific work that is hard to
explain at a party, consider the challenge for
John Muntean, a solid-state nuclear magnetic

C
hris King is a histology technician at the resonance spectroscopist at Argonne Nation-
National Institutes of Health, near Washing- al Laboratory.
ton, D.C. He enjoys his work, which features NMR is normally done in the solution phase, where
heavy use of microscopy, but used to find molecular motion averages out the orientation of the
it hard to explain what he does to friends and family. molecules being studied. In
“So I started taking pictures of some of the tissue an amorphous solid, every
stains and other things at work, and they seemed to orientation is present, he
get it better,” he says. explains. But by spinning
Soon he was doing experiments to see how he samples at what’s known as
could manipulate various substances to produce in- the magic angle, researchers
teresting colors and shapes. His family was interested can get a single value for all
in what he was doing, so they helped him get his own those different directions.
microscope at home. He picked up other used lab It may sound mystical,
equipment on eBay. Now his lab-studio dominates his but Muntean notes that it’s
just geometry. “Some people
struggle with understanding
the importance of the magic
angle,” he tells Newscripts.

Teaching tool: John


Muntean’s sculpture casts
three different shadows.

“So as a means of demon-


strating it, I created the first
magic angle sculpture.”
Muntean’s sculptures
spin at the same magic angle
as his molecules. At each of
three iterations of that spin,
the pieces cast a different

C R E D I T: CH R I S K I NG ( MI C ROS CO PY ) ; JO H N MU N TEA N ( S H A D OWS )


shadow. He says the math he
uses to create his artwork is
exactly the same as what he
uses in his science. The art
Feathery: Chris King apartment. “It’s in part of my is “a way to explain to peo-
combined amino acids β- bedroom, and then most of the ple, without any math, with-
alanine and l-glutamine under kitchen, and the dining room is out any understanding of
a polarized light microscope. pretty much dedicated to it.” chemical shift tensors, what
King tells Newscripts that it is that we’re doing.”
most of his time outside work is spent on microscope His artwork has taken him to some unexpected
art. “Usually Thursdays I kinda dedicate places. “I’m in museums, I have a patent pending on
the whole night to it. I’ll spend an hour or Craig Bettenhausen the design methods, and I’ve been featured in national
two every day, including editing.” wrote this week’s ad campaigns,” he says. An advertising firm asked if
But polarized light microscopy is not column. Please he could do his sculptures in Lego. For an artist, “the
just pretty colors. The technique is used send comments answer is always yes, even if you can’t. So I said, ‘Sure,
to spot defects in transparent materials, and suggestions to why not?’ That’s the kind of confidence that chemists
visualize tissue features, and spot kidney newscripts@acs.org. bring to problems all the time,” he says.

40 C&EN | CEN.ACS.ORG | JUNE 18, 2018


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