IB Chemistry on Addition and Condensation Polymerization

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Prepared by Lawrence Kok

Tutorial on Addition and Condensation Polymerization Reaction.

• Monomers with double bonds (unsaturated)• Addition reaction • Repeating units joined together by covalent bonds without loss of any molecule

Polymerization

Polymerization• Polymers are long chains molecules • Joining large number of repeating units called monomers• Known as plastics• Addition and condensation polymerization

http://www.fimmtech.com/index.php?id=6&subid=30

• Monomers with different functional gps.• Condensation reaction • Repeating units joined together by covalent bonds with a loss of water/HCI molecule• Polyester – carboxyl and hydroxyl gp join together (ester link)• Polyamide - carboxyl and amine gp join together (amide link)

Addition polymerization Condensation polymerization

Polymerization

Examples Addition Polymers• Polyethene (polythene), (PE)• Polyvinyl chloride,

poly(chloroethene), (PVC)• Polypropene (PP)• Poly (tetrafluoroethene) , PTFE• Polystyrene (PS)

Examples Condensation Polymers• Polyamide, Nylon 6.6• Polyester, Terylene, PET

Ethene monomers - addition polymerization- polyethene, (PE)

http://www.impexgp.com/product.htmlhttp://www.ehow.com/facts_6935785_difference-ldpe-hdpe.htmlhttp://recyclecare.com.au/en/Grade_PP.html

Addition Polymerization

High pressure 1200atm

High Temp 200C

Ethene monomers - addition polymerization- polyethene, (PE)

http://www.impexgp.com/product.htmlhttp://www.ehow.com/facts_6935785_difference-ldpe-hdpe.htmlhttp://recyclecare.com.au/en/Grade_PP.html

Propene monomers - addition polymerization – polypropene, (PP)

High pressure 1200atm

High Temp 200C

http://www.impexgp.com/product.htmlhttp://businessbarbados.com/green-business/the-dangers-of-polystyrene/http://shop.ch.interapp.net/index.php?cat=KAT01&lang=ENG

http://www.ehow.com/facts_6935785_difference-ldpe-hdpe.htmlhttp://recyclecare.com.au/en/Grade_PP.html

Chloroethene monomers - addition polymerization – poly(chloroethene), (PVC)

Styrene/phenylethene monomers - addition polymerization – polystyrene, (PS)

Tetrafluoroethene monomers – poly(tetrafluoroethene), Teflon, (PTFE)

H H | |C = C | |H H

H H | |C = C | |H CI

H H | |C = C | |H CH3

F F | |C = C | |F F

H H | |C = C | |H H

H H | |C = C | |H CI

H H | |C = C | |H CH3

F F | |C = C | |F F

+ + + +

Ethene EtheneEtheneEtheneEthene

PropenePropene PropenePropenePropene

ChloroetheneChloroetheneChloroetheneChloroetheneChloroethene

TetrafluoroetheneTetrafluoroethene Tetrafluoroethene Tetrafluoroethene Tetrafluoroethene

H H | |C = C | |H H

H H | |C = C | |H CI

H H | |C = C | |H CH3

F F | |C = C | |F F

H H | |C = C | |H H

H H | |C = C | |H CI

H H | |C = C | |H CH3

F F | |C = C | |F F

+ + + +

Polyethene

Polychloroethene

Polypropene

Polytetrafluoroethene

H H | |C = C | |H H

H H | |C = C | |H CI

H H | |C = C | |H CH3

F F | |C = C | |F F

H H | |C = C | |H H

H H | |C = C | |H CI

H H | |C = C | |H CH3

F F | |C = C | |F F

Addition Polymerization - No loss of molecule, long chain formed, Unsaturated monomer to Saturated polymer

+ + + +

Polyethene

Polychloroethene

Polypropene

Polytetrafluoroethene

Condensation Reaction

• Monomer having different functional groups on both ends• Different functional groups react together• Forming a covalent bond with removal/loss of a molecule

Monocarboxylic Acid + Monoalcohol → Ester

Monocarboxylic Acid + Monoamine → Amide

Ester bond

Amide bond

Condensation Reaction

Condensation Reaction and Polymerization

• Monomer having different functional groups on both ends• Different functional groups react together• Forming a covalent bond with removal/loss of a molecule

Monocarboxylic Acid + Monoalcohol → Ester

Monocarboxylic Acid + Monoamine → Amide

Ester bond

Amide bond

Dicarboxylic Acid + Diamine → Polyamide

Dihydric Alcohol + Dicarboxylic Acid → Polyester

Condensation Reaction Polymerization Polyester

Polyester bond

Condensation Reaction Polymerization Polyamide

Polyamide bond

http://faculty.uscupstate.edu/llever/Polymer%20Resources/Synthesis.htmhttp://www.pslc.ws/macrog/nylon.htm

Ethane 1, 2 diol + Benzene 1, 4 Dicarboxylic acid → Ethene terephthalate

Condensation Polymerization Polyester

Both ends same functional gps Both ends same functional gps Both ends different functional gps

Monomer Monomer Monomer Monomer

Polymer (Polyester)

Both ends same functional gps

Polyester formation• Monomer with Carboxyl (COOH) and hydroxyl (OH) functional gp join together (Ester link)• Ethane 1, 2 diol + Benzene 1, 4 Dicarboxylic acid → Terylene, PET, (Polyethene terephthalate)• Loss of water molecule (condensation)• Repeating unit

Advantages of polymers• Cheap, Light, insoluble in water - low toxicity• Strong covalent bonds –unreactive, resistant to chemicals, heat or organic solvents• High Strength and electrical insulators• Flexible, easily moulded to form other shapes, sheets, rods or tubes.• Production of fibres – garments and clothes

Both ends same functional gps Both ends different functional gps

Polymer (Polyester)

Hexane 1,6 dioic acid + Hexane 1,6 diamine → Nylon 6.6

Condensation Polymerization Polyamide

Polymer (Polyamide)

Polyamide formation• Monomer with Carboxyl (COOH) and Amine (NH2) functional gp join together (Amide link)• Hexane 1,6 dioic acid + Hexane 1,6 diamine → Nylon 6.6 • Loss of water molecule (condensation)• Polypeptide chains have amide link• Repeating unit

Advantages of polymers• Cheap, Light, insoluble in water - low toxicity• Strong covalent bonds –unreactive, resistant to chemicals, heat or organic solvents• High Strength and electrical insulators• Flexible, easily moulded to form other shapes, sheets, rods or tubes.• Production of fibres – garments and clothes

Acknowledgements

Thanks to source of pictures and video used in this presentation

Thanks to Creative Commons for excellent contribution on licenseshttp://creativecommons.org/licenses/

Prepared by Lawrence Kok

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IB Chemistry on Addition and Condensation Polymerization

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