Green Chemistry and the Ten Commandments

Chap. 5. The Wonderful World of Carbon: Organic Chemistry and Biochemicals 125

Table 5.1. Some Typical Polymers and the Monomers from which they are Formed

Monomer
(polymer formed) Monomer formula Polymer formula Polymer uses

Propylene

(polypropylene) C C

H

H

H

H 3 C

n

Applications­requiring

harder­plastic,­luggage,

bottles,­outdoor­carpet

Vinyl­chloride

(polyvinyl­chloride)

n

C C

H

H

H

Cl

Thin­plastic­wrap,­hose,

flooring,­PVC­pipe

n

n

C

H

CN H

H

C

n

C C

H 3 C H

C C

H

H

H

H

Styrene

(polystyrene)

H

H

H

C C

Plastic­furniture,­plastic

cups­and­dishes,­blown

to­produce­Styrofoam

plastic­products

Acrylonitrile

(polyacrylonitrile)

Synthetic­fabrics­

(Orlon,­Acrilan,

Creslan),­acrylic

paints

Isoprene

(polyisoprene)

Natural­rubber

C

H

H

H 3 C

H

C

C

H

Cl H

C

H

C

H

H

C

H

H

H

C

H

C

CN

H

C

H 2 C CH 2

H 3 C

C

are not chemically bound as part of the polymer and they leak from the polymer over a
period of time, which can result in human exposure and environmental contamination.
The most widely used plasticizers are phthalates, esters of phthalic acid as shown by
the example of di(2-ethylhexyl) phthalate below. Though not particularly toxic, these
compounds are environmentally persistent, resistant to treatment processes, and prone
to undergo bioaccumulation. They are found throughout the environment and have been
implicated by some toxicologists as possible estrogenic agents that mimic the action
of female sex hormone and cause premature sexual development in young female
children.