Green Chemistry

Dr. Nguyễn Đăng Khoaa, Dr. Lê Vũ Hàa, Dr. Hồ Hoàng Phướcb

a Faculty of Chemical Engineering, Ho Chi Minh City University of Technology,
Vietnam
b Chemical Engineering, Competence Centre for Catalysis, Chalmers University of
Technology, Sweden
Contact: khoand1989@hcmut.edu.vn, lvha@hcmut.edu.vn, phuoc@chalmers.se
Off-line appointments (applied to the whole course): 9:00 – 10:00 Wednesday, 11:00 – 12:00 Thursday at 211B2
 Time Planned Content

Week 1 Introduction to Green Chemistry

Week 2
Week 3 The 12 principles of green chemistry
Week 4
Week 5
Week 6 Green improvements of chemical production: Catalysis
Week 7
Week 8
Week 9 Green improvements of chemical production: Solvents
Week 10
Week 11
Green improvments of chemical production: Renewable materials
Week 12

Week 13 Green improvements of chemical production: Reactors

Week 14 Green improvement of industrial processes: Some examples
Week 15 Summarization
Texbook
1) P.C. Anastas and J.C. Warner ‘Green Chemistry Theory and Practice’, Oxford University Press, New York, 1998
2) M. Lancaster, GREEN CHEMISTRY: An Introductory Text, University of York, RSC, 2002

2023-08-25 Chalmers University of Technology 2

 The 12 principles of Green Chemistry

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 3
 Outline
• What is a Feedstock?
• Renewable vs. Depleting
• Current feedstock consumption
• Types of Renewable Feedstocks
• CO2
• Biomass
• Agricutural wastes
• Industrial Applications
• Challenges and Opportunities

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 4
 FEEDSTOCKS

Video 11.1: https://www.youtube.com/watch?v=-g-7DIXccpM

Question Short Answer

1) What is the most common feedstock?

2) What is the problem of crude oil?

3) What are the challenges of using crude oil?

4) Some examples of renewable feedstocks?

5) Some examples of biomass?

6) Some bioproducts which can be produced

from biomass?

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 FEEDSTOCKS
Quiz:
1) Can you guess how much global carbon dioxide (CO2) emissions were from fossil fuels and industry in 2021?
(unit billion metric tons GtCO2)
a) 7 b) 17 C) 27 D) 37

2) What is the most widely-used substance on the Earth after water?

a) Plastics b) Cements C) Steels D) Papers
3) What is the most common material to make support core in foam mattresses.
a) PP b) PE C) PVC D) Polyurethane

4) What is the most common material to make CDs and DVDs?

a) PE b) PS C) PET D) Polycarbonate

5) What are the two main components of cements?

a) CaO and Al2O3 b) CaO and SiO2 C) SiO2 and Al2O3 D) MgO and CaO

6) Which sector emits the most CO2 greenhouse gas?

a) Aviations b) Cement industry C) Pulp industry D) Shipping industry

7) How much percentage does the cement industry account for the world’s CO2 carbon dioxide (CO2) emissions?
a) 1-2% b) 4-5% C) 7-8% D) 10-11%

2023-11-12 Chalmers University of Technology 6

 FEEDSTOCKS

Use of Renewable Feedstocks

Principle #7:
A raw material or feedstock should be renewable rather than depleting
whenever technically and economically practical.

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 7
 WHAT IS A FEEDSTOCK?

PLA
Plastic
PET Full name? Paper (not recycled)
Plastic
Full name?

Source: Center for Green Chemistry and Green Engineering at Yale

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 WHAT IS A FEEDSTOCK?

Petroleum

O2
catalyst
bromide source
acetic acid
O
O
OH
OH O
OH HO
O
O
high temperature
high pressure O
OH
catalyst
OH

high temperature
PET Plastic vacuum
catalyst

O
O

O
O
n

PET Plastic

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 9
 WHAT IS A FEEDSTOCK?

CORN (BIO-BASED)

PLA Plastic
HO
HO O
O O O
HO
O
O O
OH
HO O OH
O
OH n n

Starch Lactic Acid PolyLacticAcid PLA

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 10
 RENWABLE vs DEPLETING

Feedstock: raw material to supply or fuel a machine or

industrial process
Renewable or Depleting: A question of Time!
-A renewable resource is determined to be renewable if it can
be replenished in a relevant amount of time.

-Fossil fuels are depleting because they cannot be replenished

in a practical timeframe from vegetation.

Source: Center for Green Chemistry and Green Engineering at Yale

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 Types of RENEWABLE FEEDSTOCK

How Biomass works Video 11.2 https://www.youtube.com/watch?v=-jln6yi7LF0

What are differences between Biomass feedstock and organic feedstock?

▪ Organic → substances that have C atoms as molecular backbone → broad

concept
e.g. Crude oil is an organic feedstock

▪ Biomass materials are organic substances derived directly from plants and
animals.

▪ Biomass feedstocks are included under the organic chemical catogory

▪ Biomass feedstock vs oragnic feedstock → sustainability

▪ Biomass → renewable while organic feedstock generally refers to petroleum-

based products → fossil fuels → non-renewable

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 Types of RENEWABLE FEEDSTOCK

• CO2

• Biomass (sunflower seed, algae, seaweed, corn,

switchgrass, bamboo, saw dust …)
• Agricutural waste (e.g. manure, straw, corn stove …)

Source: Center for Green Chemistry and Green Engineering at Yale

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 Types of RENEWABLE FEEDSTOCK

Sugar cane
Why is CO2
Renewable as a
feedstock??

Pure ethanol, E5, E10 Sugar

Bioethanol

Source: Center for Green Chemistry and Green Engineering at Yale

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 Examples of CO2 as a feedstock

Video 11.3: How to cut carbon from cement industry

https://www.youtube.com/watch?v=kbPDlZKB5os

To know more about cement industry. Watch this

https://www.youtube.com/watch?v=asLWBGtAhZk
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 Types of RENEWABLE FEEDSTOCK

Nature Communications volume 6, Article number: 5933 (2015)

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 Examples of CO2 as a feedstock

Salicylic acid
Aspirin

CO2 → polyol → polyurethane

ACS Omega 2019, 4, 5, 7944–7952

CO2 + H2 → CH3OH + ? What is the second product? And balance the reaction

CO2 → cement
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 Examples of CO2 as a feedstock
Video 11.4: Made of pollution: How CO2 is recycled to make your things
https://www.youtube.com/watch?v=9wESzQ0-ZjQ

Question Short Answer

1) What is the target of CO2 removal by 2025 to meet Paris
climate agreement?
2) Some examples of products that CO2 material can go into?

3) What does CCU term stand for ?

4) What is mattress made from?
5) What is the length if all waste mattressesin Europé (per
year) were stacked up?
6) What is the main bottleneck for green chemical production
from CO2?
7) What is the product that can capture a lot of CO2?
8) What is the amount of CO2 capturing every year?

2023-11-12 Chalmers University of Technology 18

 Examples of CO2 as a feedstock

Video 11.5: What is Power-to-X? The technology explained in a simple and short manner
https://www.youtube.com/watch?v=R5HnlP75Vn4

Question Short Answer

1) What is the method to face with climate change according to
COP21 and 26 conference?

2) What is green H2?

3) Give 5 examples of the products (X) in PtX?

4) What are categories of PtX technologies by usage?

5) What are categories of PtX technologies by energy form?

6) Write reaction for NH3 synthesis from green H2

7) Write reaction for methane synthesis from green H2 and CO2

8) Write reaction for methanol synthesis from green H2 and CO2

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 Examples of CO2 as a feedstock

Power to X (PtX or P2X) and Carbon Capture & Utilisation (CCU)

o Renewable energy → 22% of energy consumption in 2020

o Fluctuation of renewable energy → a smart way for utilisation
o PtX: convert renewable electricity into other forms of energy
o Combine with CCU → reduction of CO2 emissions
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 BIOMASS PLATFORMS

https://www.dreamstime.com/illustration/biomass.html
Source: Center for Green Chemistry and Green Engineering at Yale
2023-11-12 Chalmers University of Technology 21
 Four generation of BIOMASS based for Biofuel production

Singh, V., Tiwari, R., Chaturvedi, V.K., Singh, N., Mishra, V. (2021). Microbiological Aspects of Bioenergy Production: Recent Update and Future Directions.
In: Srivastava, M., Srivastava, N., Singh, R. (eds) Bioenergy Research: Revisiting Latest Development. Clean Energy Production Technologies. Springer,
Singapore. https://doi.org/10.1007/978-981-33-4615-4_2

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 Lignocellulose Biomass

Lignin

Cellulose a polysaccharide consisting of a

linear chain of several hundred to
many thousands of β(1→4) linked
D-glucose units

Hemicellulose Heteropolymers of C5 C6 sugars units

https://doi.org/10.1002/bbb.2048
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 Some examples of biomass conversions
Bioplastic
Celluose
Hemicellulose Sugars Bioethanol Bio C2H4
Starch Various
monomers

Lignin Chemicals

Biomass Oil seeds Biofuels

Algae/Seaweed O

CO2
Food wastes Levulinic acid HO

Waste wood O

Agricutural residues
Manures Biogas

Biosolvent CO2
Peels of citrus fruit Polycarbonate
(e.g. limonene)
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 Lignin as a byproduct from pulp industry

Video 12.1 Lignin to chemicals https://www.youtube.com/watch?v=wb5aEVfee6s

Question Short Answer

1) Lignin is the second most abundant biopolymer in
trees. What is the first most abundant biopolymer in
trees?
2) Name of three main composition in the plant cell walls
and their percentages?
3) Lignin is a byproduct from which industry? What is the
use of lignin in that industry?
4) What is the main monomer which can be obtained
after breaking lignin molecules? And what are its
applications?
5) What are the challenges to make chemicals from lignin
in industrial scale?

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 Lignin as a byproduct from pulp industry

Lignin powder

Burnt or Discarded

Source: Center for Green Chemistry and Green Engineering at Yale

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 Lignin – Very Abundant

Lignin = 30% of all non-fossil Carbon on the planet

= 20-35% of wood by weight
= 300 billion tons bioavailability (+ 20 billion tons per year)
= 50 million tons extracted from pulp and paper industry

BUT…..

= 1.1 million tons utilized (~ 2%)

= 409 $/ton in 2006 → 660$/ton in 2013
= 730 million dollar market
= considered supply constrained
→ Most produced lignin not of a high enough purity to sell

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 27
 Petroleum source Phenols

Petroleum

Nylon

Phenols
Polycarbonates
Pharmaceuticals
(Including
Salicylic Acid)

Yellow Dye #6
Polyurethane Foams

Source: Center for Green Chemistry and Green Engineering at Yale

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 Lignin – Source of Renewable ‘Drop-in’ Platform Chemicals
O

HO O
O

OH
O HO

HO O
Lignin HO
Plant Cell Wall O
O OH

OH
HO
O
Needs of New Nylon
O
O O
Methodology:
O
O

O
O
HO OH
Economical
O
Sustainable
HO OH O OH Selective
HO Efficient Polyurethane Foams
O OH O
O
O
O
HO O
O OH
HO
O Pharmaceuticals
(Including
Source: Center for Green Chemistry and Green Engineering at Yale Salicylic Acid)
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Lignin – Source of Renewable ‘Drop-in’ Platform Chemicals

Major challenges
• Lignin – Structure is very complex, depends on
plant material & isolation method

• Difficult to obtain products selectively because of

lignin complexity → purification difficult and costly

• Lignin solubility (insoluble)

• Lignin from pulp & paper industry deactivates

most catalysts….

Chem. Soc. Rev., 2020, 49, 5510-5560

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 OH O Lignin HO
HO OH
HO HO
Plant Cell Wall O
O OH
Lignocellulose to cellulosic Ethanol
OH n

Hemicellulose OH O
HO
Plant Cell Wall O
O O
OH
HO
OH Hydrolysis
O Fermentation
O
O O O
HO O (Enzyme) O
HO OH
OH OH n
O
Sugars
O
HO
Cellulose O O
Plant Tissue
OH O
HO
Bioethanol
OH
OH O
HO OH O OH
OH O HO O
O
OH
O O
O Lignin
HO
HO
HO
Byproduct: Ligin
BURNT ORHODISCARDED OH Plant Cell Wall O
HO HO O
n OH
OH
Chemicals O OH O
Hemicellulose
Plant Cell Wall
OH O
HO Burning
O
O for boiler
BIOFUEL O
O O
O
PLATFORM CHEMICALS OH HO O
Video 12.2 How it Works DuPont Process
HO
OH for Converting Biomass
O toO Cellulosic Ethanol
O OH
O O O
HO O HO
O
https://www.youtube.com/watch?v=fCvlaXLisAw HO OH
OH OH n O
Question Cellulose Short Answer O
Plant Tissue
1) What is capacity of ethanol production of the O
HO OH O OH

biorefinery developed by Dupont?

HO

2) What is the starting material of the process? O

O OH

3) Describe main steps in the process for ethanol O

O
O
production? HO O
O OH
4) What is the byproduct in the process? What to do HO
O

with it?
2023-11-12 Chalmers University of Technology 31
 Lignocellulose to cellulosic Ethanol

1) 2)

3)
4)

5) Which of the following is not a biomass resource? 5) Which country is the largest producer of biofuels in
a) Animal wastes Europe?
b) Forestry residue
c) Agricultural residue a) France b) Germany c) Italy d) Sweden
d) Sunlight

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 Sugars as a platform chemical

Step 1:
Glucose is produced by the
hydrolysis of cellulosic
materials. Glucose is then
transformed into various furan
derivatives.

Source: Center for Green Chemistry and Green Engineering at Yale

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 Sugars as a platform chemical

Step 2:
The furan compounds undergo
Diels-Alder cycloaddition
reactions with additional
substrate compounds that yield
desired aromatic chemicals.
Reaction examples

Source: Center for Green Chemistry and Green Engineering at Yale

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 Oils and fats to Renewable Diesel

Video 12.3 Renewable Energy Group Renewable Diesel Biorefinery Tour

https://www.youtube.com/watch?v=qlgdlBkDBo4

Question Short Answer

1) What are the feedstocks used in the
renewable diesel biorefinery develop by
Chevron?
2) Describe main steps in the process for
ethanol production?
3) What are the main products in the
process?
4) Compare to ULSD, what are the advantages
of renewable diesel in enevironmental
impact?

2023-11-12 Chalmers University of Technology 35

 Food waste Biomass availability
Green Chem., 2013, 15, 307

• The European Union alone produces

each year just under 90 million tonnes
of food waste
• 38% of which is directly produced by
the food manufacturing sector
• The Americas produces around 250
million tonnes of food waste. A large
portion is due to Brazil’s large usage of
sugarcane.
• Globally, an estimated 973 million
tonnes of waste is generated from
various food supply chains
Source: Center for Green Chemistry and Green Engineering at Yale
2023-11-12 Chalmers University of Technology 36
 Food waste applications

Video 12.4. From Food Waste To Biofuel

https://www.youtube.com/watch?v=XASFGA8O68E
Question Short Answer
1) What is the amount of food waste in
Europe every year?
2) How many steps are there in the process?
What are they?
3) What is a biorefinery? What are their
possible products?
4) How many kg of food waste does it need to
produce 1 L of renewable diesel in the
process?

2023-11-12 Chalmers University of Technology 37

 Algae to Biofuel
Video 12.5. Algae CO2 Capture at the University of Kentucky: Part 1

https://www.youtube.com/watch?v=QI3Al1dpuUY

Part 2 https://www.youtube.com/watch?v=2JguLRn5v38

Question Short Answer

1) What is a feasible option of dealing with

CO2 that is captured at the present?

2) What is a new technology for CO2 capture

at University of Kentucky?

3) How to collect algae?

4) What are the possible products produced

from algae? Try to summarize by a scheme

2023-11-12 Chalmers University of Technology 38

 Terpenes: Applications

Biosolvents

Bioplastics

Limonene

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 39
 Terpenes: Applications

• Degreasers typically contain high volatile organic compounds in the

formulation. Leading to high flash times and limiting the application
times.
• Limonene as an active degreaser is an environmentally friendly
alternative with comparable performance. Not to mention better smell.
• Commercially available
Source: Center for Green Chemistry and Green Engineering at Yale
2023-11-12 Chalmers University of Technology 40
 Limonene: Polycarbonate Materials

• Polycarbonates are a thermoplastics that are strong and tough materials

• They can be easily worked, molded, and thermoformed into rigid materials
• Contain application is electronics, construction, and automotive industries

Source: Green Chem., 2016, 18, 760–770

Image: Wikipedia, public domain

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 41
 Advantages
Environmental:
• Improved management of waste
• Lowering the environmental burden of the food supply chain
• Renewable material
• Encompasses the cradle-to-grave platform
• Reduces carbon footprint

Economic:
• Reduction in the dependence of fossil resources
• Provides an additional value stream for both business and the food supply chain.
• Reduction in the production of waste, which can reduce the cost of waste disposal annually on a company bottom line
• Provides opportunities to shift toward more energy efficient processes.

Social:
• Satisfy public and customer demand for more environmentally responsible products.
• Increases the opportunity for a new and skilled workforce in the renewables technology sector
• Increase the positive reputation and image of a company/business.
• Increase the opportunity for more stakeholder engagement.

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 42
 Challenges

• Terpenes, D-Limonene, production is

dependent on the orange growth season.
• A poor growing season can limit supply
and thus making the supply chain
inconsistent from year to year.
• Logistical challenges exist for capturing
large volumes of orange peel waste.
• This can yield to economic challenges in
the commercialization of future products

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 43
 Industrial applications

Platform Chemical

Bioethanol Bio-ethylene/
Bioplastics
polyethylene

Monomer for various

biopolymers
Sugarcane

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 44
 Industrial applications

Video 12.6 https://www.youtube.com/watch?v=UOPhqlx0f6Y&t=204s

Source: Center for Green Chemistry and Green Engineering at Yale
2023-11-12 Chalmers University of Technology 45
 Commercial Properties of Green PE

Braskem’s Polyethylene has the

same technical properties,
appearance and versatility of
applications of polyethylene
from fossil source. The
replacement of fossil source
polyethylene for Braskem’s green
Polyethylene does not require
investment in new machines in
plastics converters.

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 46
 Commercial Properties of Green PE

Allbird Sugar footwear line:

• Developed in partnership with Braskem in
2018.
• Contains a bio-based EVA resin polymer made
from Braskem’s bioethylene.
• Commercially available

Ethylene Vinyl Acetate

Ethylene-Vinyl Acetate

Image Source: https://www.allbirds.com/products/mens-wool-runners

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 47
 The BioFine Process

Paper mill
sludge O

HO
Agricultural
residues,
O
Waste wood
Levulinic acid
one-ton-per-day

Municipal solid waste

and waste paper

Image Source: Masx Pixel, Pixbay, Flickr

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 48
 Levulinic Acid

• Green Chemistry Challenge Award

1999 Small Business Award
C e llu lo s e

H 2S O 4 > 2 0 0 C

OH

O OH O
O
200 C CHO
HO + H C O 2H
C O 2H
HO OH

OH

• > 70% yields

• Product is removed from medium as it is formed (preventing tar formation)

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 49
 Levulinic Acid as a platform chemical
O

OH O
H O
H
O
HO butanediol
HO

O
Acrylic acid
Succinic acid
O

O
O

HO
MTHF THF
(fuel additive)
O
CH3 O
O

HO C C C C OH
H2 H2 O H
O
O H 2 N

O
Diphenolic acid
gamma DALA (-amino levulinic acid)
butyrolactone (non-toxic, biodegradable herbicide)
Source: Center for Green Chemistry and Green Engineering at Yale
2023-11-12 Chalmers University of Technology 50
 Challenges with Renewables
• Feedstock cultivation
• Competition with food supply
• Land demand
• Nutritional needs
• Diseases
• Initial investment
⚫ Harvesting method to maximise yields and minimise

degradation of product
⚫ Post harvest processing

⚫ Product extraction and purification

⚫ Product standardization

⚫ Complexity

⚫ Product storage, packing and distribution

⚫ New methodologies for alternative feedstocks

⚫ Choice of feedstock determines your process

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 51
 Why use Renewable Feedstocks?
Economics

• Inherent long-term tendency for petroleum price increases

(finite resources)

• A fluctuation of a few cents in crude oil price can result in

massive price swings for downstream products

• Decreasing cost of renewable resources

• Lack of petroleum infrastructure

Environment
• Biological compatibility
Scientific Opportunities: (to an extent)
• Better quality renewable feedstocks • Use of waste streams
(wood pulping,
• Modern plant breeding
agriculture, etc.)
• Genetic manipulation

• Breakthroughs in catalysis (enzymes, etc.)

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 52
 Use Renewable Feedstocks?

Ideal Benefits:
1. Renewable
2. Doesn’t compete with food sources
3. Commercial and Industrial Waste
4. Poses no intrinsic hazards to humans and the environment
5. Can be converted into desired products with minimal steps.
6. Conversion process uses minimal energy
7. 100 % yield
8. 100% atom economy

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 53
 Summary

• A renewable feedstock should be renewable rather than depleting

whenever technically and economically practical.

• A renewable resource is determined to be renewable if it can be

replenished in a relevant amount of time.

• Biomass valorization is the process of reusing, recycling or

composting waste materials and converting them into more useful
products

Source: Center for Green Chemistry and Green Engineering at Yale

2023-11-12 Chalmers University of Technology 54
 Some questions
1) Define a renewable resource/feedstock.
2) What has to be satisfied to ensure a resource/feedstock as a viable renewable resource?
3) Provide a list of 3 types of renewable resources used a to make platform materials.
4) How to produce green PE (polyethylene) from sugar cane?
5) What are examples of Biomass?
A) Electricity, Trees, Wind B) Food waste, Sugar cane, Lignin
C) Plastic waste, corn, solar D) Rice straw, Orange peel, Cement
6) Which example is NOT a renewable resource?
A) Trees B) Wind C) Solar D) Uranium (Nuclear)
7) What is one disadvantage of coal?
A) There is not a lot of coal left which makes it expensive
B) The world is not using a lot of coal which makes it an undesirable feedstock
C) Coal produces air pollution
D) Combustion efficiency of coal is low
8) Which product is NOT produced from petroleum?
A) Aluminum cans B) Plastic bags C) Gasoline D) Wax
9) When compared to gasoline and coal, natural gas is the cleanest fuel we can burn.
A) True B) False
10) Consider the following statements (1) and (2):
(1): Renewable resources are unlimited and are not affected by human activities
(2): Renewable resources get replenished quickly as compared to non-renewable resources
Choose the correct answer:
A) Both (1) and (2) are true B) Both (1) and (2) are false
C) (1) is true but (2) is false D) (1) is false but (2) is true
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2023-11-12 Chalmers University of Technology 56