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161.Polymers- Biodegradability and Recycling

161.Polymers- Biodegradability and Recycling

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Polymers – Biodegradability and Recycling
Number 161
1
C
 hem
 F
 actsheet
www.curriculum-press.co.uk
To succeed in this topic you need to:-
Be familiar with Factsheet 76 – “Polymers”
Know basic organic nomenclature
Be familiar with hydrolysis reactions of esters and amides
After working through this Factsheet you will:-
Understand the problems associated with disposing of plastics
Be aware of the different types of recycling
Be familiar with the type of plastics that will biodegrade
Know some example of biodegradable plastics
Introduction
Factsheet 76, Polymers, introduced the key distinctions betweenaddition and condensation polymers but this will be covered again inbrief as the distinction is vital as an introduction to the relatedproblems of biodegradability and recycling. The problem boils downto the fact that simple addition polymers are so inert that they taketens, or even hundreds of years, to break down naturally so recyclingis the only way to avoid either filling up landfill sites or risking theproduction of toxic gases by burning the plastic waste.The production of condensation polymers can, however, lead toplastics that are much more readily broken down by moisture, light ormicrobial activity in a relatively short period of time.
Non-Biodegradable Plastics
Addition polymers are produced from alkenes that are, in turn,obtained from crude oil, which means that their production dependson a non-renewable resource (about 4% of the World’s oil is used toprovide the raw materials needed for polymer manufacture and aboutthe same again to provide the energy needed).
CCHH
 
HHnCCHHHHn
The high strength of the carbon-carbon and carbon-hydrogen bondsmeans that such polymers are very useful, as they are inert. Thebenefits include:
Extreme versatility and ability to be tailored to meet very specifictechnical needs.
Lighter weight than competing materials, reducing fuelconsumption during transportation.Polythene
 
monomerrepeat unit of polymerPolypropene
CCH
3
CH
 
HHnCCCH
3
HHHn
 
monomerrepeat unit of polymer
Extreme durability.
Resistance to chemicals, water and impact.
Good safety and hygiene properties for food packaging.
Excellent thermal and electrical insulation properties.
Relatively inexpensive to produce.However, the bond strengths also mean that they are non-biodegradable and will not decompose naturally after disposal.There are three main methods for dealing with the waste: (1) burialin a landfill site, (2) incineration and (3) sorting and recycling.
Landfill
Currently up to 80% of polymers aredisposed of by this method and nearly70% of the waste disposed of in thisway is non-biodegradable. Thenegative issues associated with thismethod of disposal include:
Nuisance to local people from gullsattracted to the site, traffic, smells
Fuel costs for transport of waste to sites
Cost of treating and sorting before disposal
Incineration
This involves burning the waste at hightemperatures in a furnace. The heat energygenerated can be used to generateelectricity. Although this reduces the needfor landfill, the combustion processproduces greenhouse gases and the needto remove any toxic gases (e.g. chlorine and nitrogen compounds)from the waste gases produced adds to the overall cost of theprocess.
Recycling
This can involve simply re-using, mechanical recycling or feedstock recycling.Reusing is preferable to recycling as it uses less energy and fewerresources. However, even if re-used, plastics have a limited lifespanand will eventually need disposing of.Whichever process is chosen, the first stage, that goes hand-in-hand with recycling (
and must be mentioned in any exam answer to meet the needs of the mark scheme
) is
sorting
so that differenttypes and colours are separated. Traditionally this is done byhand (making it slow and costly) but increasingly flotation is beingused to separate the plastics on the basis of differing densities.Mechanical recycling involves themelting, shredding and granulation of waste plastics. Following sorting, theplastic is either melted down directlyand moulded into a new shape, ormelted down after being shredded intoflakes and then processed intogranules.
Typical plastics shredder
 
Chem Factsheet
2
161. Polymers – Biodegradability and Recycling
Feedstock recycling describes a rangeof techniques, which break downpolymers into their constituentmonomers, which in turn can be usedagain in refineries, or petrochemicaland chemical production. A range of feedstock recycling technologies iscurrently being explored. Theseinclude: pyrolysis hydrogenation,gasification and thermal cracking.
Plastics pyrolysis plant
A typical ‘life-cycle’ of a plastic can be summarised as below:
Biodegradable Plastics
Such plastics fall into two broad categories. Some are still based onpetrochemicals but include additives that make them degradablewhilst others are produced from natural, plant-based materials, suchas corn starch, and have the benefit of being virtually carbon-neutralas any carbon dioxide released during their decomposition is matchedby that taken in by the plants, from which the plastics are made,during their growthOne type of degradable plastic involves the addition of a metal saltduring the manufacture of polythene or polypropene, at levels of only between 1% and 3%. The commonly used transition metalcompounds are manganese, iron, cobalt and nickel. None of theseare “heavy metals” and none have been shown to be eco-toxic. Thesalt acts as a catalyst for the breakdown of carbon-carbon bonds.The manufacturing process can be controlled such that the plasticstarts to decompose between about 60 days and 5-6 years aftermanufacture so that it can be adapted to a variety of different uses.A claimed advantage of this process is that the decomposition doesnot require a biologically active environment and the plastic willbecome brittle and break down into small flakes wherever it is.Eventually, when the molecular mass of the polymer falls belowabout 40000, the chains become susceptible to breakdown by micro-organisms.
Poly(lactic acid) (PLA)
Lactic acid can be produced from corn starch or cane sugar and isused to produce the cyclic lactide monomer, for this plastic.
Crudeoilfractionsmonomersplasticsusedisposalland fillincinerationre-usemechanicalrecyclingfeedstock recycling
 
OOOOCH
3
H
3
C
catalyst +heat
CHO
 
COCHCOOCH
3
CH
3
nlactidepolylactide
PLA has become a significant commercialbioplastic. Its clarity makes it useful forpackaging, such as bottles, yogurt cups, andcandy wrappers. It has also been used forwaste bags, coatings for paper and cardboard,and fibres for clothing, carpets, sheets andtowels, and wall coverings. In biomedicalapplications, it is used for sutures, prosthetic materials, and materialsfor drug delivery.The biodegradability of the plastic is due to the relative ease of hydrolysis of the ester links.
Poly(ethenol)
Poly(ethenol) is also called polyvinyl alcohol or PVOH. It issometimes called PVA but this also stands for poly(vinyl acetate)so it is best to use PVOH.It has the repeat unit shown below. It would be expected to beformed from the monomer ethenol.
CCOHHHHH
However, ethenol is highly unstable. Instead the monomer used isethenyl ethanoate
CCOHHHC
 
OCH
3
nCCOHHHC
 
OCH
3
n
The poly (ethenyl ethanoate) is then reacted with methanol toremove the ester groups.
CCOHHHC
 
OCH
3
+ H
3
C
OHCCOHHHH+ H
3
C
C
O
CH
3
 
O
Poly(ethenol) can be used to make plasticbags which dissolve in water. Amongstmany other applications, these are usedfor hospital laundry where the bag can besafely handled to avoid contact with thecontents which may be infected. The bagdissolves in the water and the laundrygets washed!

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