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Synthetic Polymers - Highlight

This document discusses various synthetic polymers including poly(ethene), poly(propene), poly(chloroethene), poly(tetrafluoroethene) and how to deduce their monomers. It also covers condensation polymerization, important reaction types like addition reactions and substitution reactions. Biodegradable polyesters are made from monomers like lactic acid.

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Zhiming
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64 views

Synthetic Polymers - Highlight

This document discusses various synthetic polymers including poly(ethene), poly(propene), poly(chloroethene), poly(tetrafluoroethene) and how to deduce their monomers. It also covers condensation polymerization, important reaction types like addition reactions and substitution reactions. Biodegradable polyesters are made from monomers like lactic acid.

Uploaded by

Zhiming
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Synthetic Polymers

compounds containing –COOH functional group


Addition polymerisation
Monomer、polymer and repeat unit
Use of poly(ethene)
ethene
LDPE: Low density poly(ethene)
- Used as a thin film to make polythene bags
- Very flexible and not very strong

HDPE: High density poly(ethene)


- Used to make plastic bottle, milk bottles
- Very strength and rigidity
How to deduce the polymerization of any alkene

H, CH3, CI, -OH……

3 CH3

CI
• CH3CH=CH2

• CH3CH= CHCH3

• CH3CH=CHBr Br Br
Use of poly(propene) propene

Poly(propene) is stronger than poly(ethene)


- Used to make ropes and crates
- Symbol: PP
chloroethene
Use of poly(chloroethene)
Poly(chloroethene)
- Quite strong and rigid
- Used for water pipes and replacement windows
- Flexible by adding plasticiser, sheet floor covering, clothing
- Not conduct electricity for electrical insulation
- Symbol: PVC (polyvinylchloride)

Chloroethene: vinyl chloride, old name


Use of poly(tetrafluoroethene) tetrafluoroethene
Poly(tetrafluoroethene)
- Used as a non-stick coating for pots and pans
- Very unreactive due to the strong carbon-fluorine bonds
- Lining containers for corrosive chemicals
- Symbol: PTFE
How to work out the monomer from the given polymers?
• Find out the repeated unit from the given polymers
• Remove the 【】n and form C=C bond
Disposal of addition polymers
• Addition polymers will cause a big environment problems
• Unable to biodegrade, microogranisms and bacteria are unable to break
them down
• They are inert/ unable to react, because they have strong covalent bond
• The production of toxic gases when they are burned
• Cardon dioxide is released when burnt, which contribute to global warming
Disposal of addition polymers
Important reaction type
condensation reaction is a type of chemical reaction in which two molecules are combined to
form a single molecule, usually with the loss of a small molecule such as water.
Ethanol + ethanolic acid→ ethyl ethanoate+H2O

decomposition reaction is a type of chemical reaction in which one reactant breaks down
into two or more products
CaCO3→ CaO+CO2

addition reaction is a type of organic reaction where two or more molecules combine to form a
larger one, without taking anything away Ethene+ H O→ ethanol
2

Cracking is a reaction in which larger saturated hydrocarbon molecules are broken


down into smaller, more useful hydrocarbon molecules, some of which are unsaturated
Reaction condition: high temperature (over 500°C ) and catalyst

Hydrogenation reaction is a type of organic reaction where hydrogen is added to unsaturated


compounds CH2=CH2 + H2→ CH3CH3
Important reaction type

substitution reaction is a type of chemical reaction in which an atom or group of atoms is


replaced by different atom or group of atoms

Hydration reaction is a type of organic reaction where H2O is added to unsaturated compounds
CH2=CH2 + H2O→ CH3CH2OH

dehydration reaction is a type of reaction where H2O is removed from molecules


CH3CH2OH→CH2=CH2 + H2O (reaction condition: heating, concentrated H2SO4 as catalyst
Polyester: condensation polymerization

di-carboxylic acid + di-ol to form long chain


Condensation polymerization

Monomers
H2 O

n
Block diagram shows the general condensation polymerization reaction
CH3CH2CH2OH: propan-1-ol

HOCH2CH2CH2OH: propane-1,3-diol

HOCH2CH2OH: ethane-1,2-diol
The blue and red box can be anything
How to deduce the polyester? Just put di-ol and dioic-acid at two ends
Move and repeat the unit in blue and red box

[-COCH2CH2CH2CH2-CO-O-CH2CH2-O-]n
n + n
n
How to deduce the monomer from polyester?

1、find
[-COCH2CH2CH2CH2-CO -O-CH2CH2-O-]n
2、Cut

3、Break into di-ol and dioic-acids


C=O belongs to dioic acid

HO-COCH2CH2CH2CH2-COOH HO-CH2CH2-OH monomer


Self-polymerization 2-hydroxybutanoic acid
The molecule has both alcohol and CH3CHOHCH2COOH
carboxylic acid functional group

n
Self-polymerization (amino acids)
Amino acids has –NH2 and carboxylic acid functional group

- NH2 can react with carboxylic acid very similarly to the –OH
group

- Amino acids self-polymerize to form polypeptides, primary


structure of proteins
Biodegradable polyester

• As with addition polymers, there are environmental issues with the disposal of condensation
polymers.
• More reactive because the ester linkage/bond will be broken eventually, although it could take
hundreds of years
• Biodegradable polyesters can break down much more quickly, biopolyesters
• Biodegradable polymers can be made from lactic acid(obtained from corn starch)
• PLA: polylactic acid
• Usage: Biodegradable plastic bags or surgery for internal stitches

lactic acid
-OH
-COOH

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