Why some plastics last

Section 4 of 4

A fallen leaf rots away in a year or two. A plastic bag in the soil can last for decades. The difference is in the bonds along their chains.

Bacteria and fungi break down dead plants and animals with enzymes. Many of these enzymes cut one kind of link using a water molecule, the way amylase cuts the links in a starch chain and lipase splits the ester links in a fat. The polymers of living things are full of links like these.

A poly(ethene) chain has only C–⁠C and C–⁠H bonds. Carbon and hydrogen share their electrons almost evenly, so the chain carries no charged or partly charged spots for an enzyme to grip. Like oil, the chains keep water out. Microbes' enzymes have nothing easy to break, so poly(ethene) lasts a very long time.

A poly(ethene) chain and a PLA chain Top: part of a poly(ethene) chain, a row of carbon atoms joined by single bonds, each carrying two hydrogen atoms. It has only C–C and C–H bonds. Bottom: part of a PLA chain. An oxygen atom, then a carbon carrying a hydrogen atom and a CH3 group, then a carbon double-bonded to an oxygen atom, and the pattern repeats. Each carbon with its double-bonded oxygen and the chain oxygen next to it are shaded and labelled ester link, with the bond between them in amber: water can split the chain there. poly(ethene): only C–C and C–H bonds CHHCHHCHHCHHCHHCHHCHH PLA: ester links water can split OCCOCCOHCH3HCH3OO ester link ester link
Poly(ethene) has only C–⁠C and C–⁠H bonds. PLA's chain has an ester link (shaded) in every repeat unit, and water can split the chain at each one.

A plastic made to break down

PLA, poly(lactic acid), is a polyester made from plants. Bacteria ferment sugar from maize starch or sugar cane into lactic acid, the same acid that makes yoghurt tangy. Each lactic acid molecule carries both an -⁠OH group and a -⁠COOH group, so lactic acid molecules can join to each other into a polyester. PLA makes cold drinks cups, food packaging and the filament for many 3D printers.

Lactic acid (2-hydroxypropanoic acid), C₃H₆O₃The monomer of PLA. A chain of three carbon atoms; the middle carbon carries an -OH group and the end carbon is a -COOH group.HHOHCCCOHHOH
Lactic acid, C₃H₆O₃, the monomer of PLA. The -⁠OH on the middle carbon of one molecule joins the -⁠COOH of the next through an ester link.

PLA is sold as compostable, and the word means something exact. In an industrial composting plant, heaps of food and garden waste stay hot, around 60 °C, and damp. There, water splits PLA's ester links into short pieces, and microbes digest the pieces to carbon dioxide and water. Items that meet the European standard for compostable packaging, EN 13432, turn at least 90% of their carbon into carbon dioxide within six months in those conditions. In a cool garden compost heap, in soil or in the sea, PLA breaks down very slowly, over years.

Microplastics

Sunlight and waves break plastic left outdoors into smaller and smaller pieces. Pieces smaller than 5 mm across are called microplastics. They also come from fibres shed by clothes made of polyester and nylon in the wash, and from dust worn off car tyres. Scientists have found microplastics in the deep sea, in Arctic snow, in drinking water and in the human body, and they are studying what the pieces do there.

Quick check

Why can a poly(ethene) bag last for decades in soil?

That's the end of lesson 25

In this lesson you found out:

  • What makes a chemical process greener, and how to work out its atom economy
  • How plastics are recycled, and what the codes mean
  • Why some plastics break down and others last