Degradable polymers

Chemistry A2 · Polymerisation. The idea in plain words, the rules to remember, the mistake to avoid and a worked example, written and checked by Mega Lecture.

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The idea

Poly(alkenes) such as poly(ethene) contain only strong, non-polar C–C and C–H bonds. Water, acids, alkalis and the enzymes of microorganisms cannot attack them, so they are chemically inert and very slow to biodegrade. They stay in landfill for a very long time.

Some polymers are photodegradable: they absorb light, often through C=O groups in the chain, and the energy breaks bonds so the chain falls into small pieces. This only works where light reaches the polymer.

Polyesters and polyamides have polar ester and amide links. These links can be broken by hydrolysis with acid or alkali, so these polymers are biodegradable.

Rules to remember

Common mistake

Students give the same products for acid and alkaline hydrolysis. In alkali the carboxylic acid appears as its salt, –COO−Na+; in acid the amine appears as its salt, –NH3+.

Worked example

Poly(lactic acid) has the repeat unit –O–CH(CH3)–CO– (Mr 72). What mass of NaOH (Mr 40) is needed to hydrolyse 7.2 g of the polymer completely, and what is the organic product?

  1. Each repeat unit has one ester link, so it needs one NaOH: the product is CH3CH(OH)COO−Na+.
  2. Moles of repeat units = 7.2 ÷ 72 = 0.10 mol.
  3. Moles of NaOH = 0.10 mol, so mass = 0.10 × 40 = 4.0 g.

Answer: 4.0 g of NaOH; the product is sodium 2-hydroxypropanoate

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