Page 595 - Carrahers_Polymer_Chemistry,_Eighth_Edition

558 Carraher’s Polymer Chemistry

CH 2

NH 2
H N
2

N N
CH 3
CH
HO OH 3
CH 3 O
O
OH
H C CH 3
OH 3 OH OH
O

O
O O
OH
H C CH 3
3
O
O
OH
O

FIGURE 17.5 Monomer synthesis chemical flow diagram based on benzene feedstock.

continue to be dominant factors. Many of these and other monomers are now being produced by
various microbes. Some of these efforts are described here and in Sections 19.15 through 19.17.

17.2 REACTANTS FOR STEP-REACTION POLYMERIZATION

Adipic acid (1,4-butanedicarboxylic acid) is used for the production of nylon-66 and may be pro-
duced from the oxidation of cyclohexane as shown below. Cyclohexane is obtained by the Raney
nickel-catalytic hydrogenation of benzene. Both the cyclohexanol and cyclohexanone are oxidized
to adipic acid by heating with nitric acid.

OH O OH
O
O
OH (17.1)

Benzene Cyclohexane Cyclo- Cyclo- Adipic acid
hexanol hexanone

A new method that emphases green chemistry principles involves oxidizing cyclohexene with
hydrogen peroxide through a tungsten catalyst and a phase-transfer catalyst, producing adipic acid
and water as the byproduct.

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