Page 596 - Carrahers_Polymer_Chemistry,_Eighth_Edition

Synthesis of Reactants and Intermediates for Polymers 559

Adipic acid can also be made from tetrahydrofurane (THF), obtained from furfural a naturally
derived material (Equation 17.2). It is carbonylated in the presence of nickel carbonyl-nickel iodide
catalyst. Furfural is a chemurgic product obtained by the steam-acid digestion of corn cobs, oat
hulls, bagasse, or rice hulls.
OH

O CO O
O (17.2)
H 2 O
OH
THF Adipic acid

Adiponitrile may be produced from the hydrodimerization of acrylonitrile or from 1,3-butadiene
via 1,4-dicyanobutene-2. Adiponitrile is then hydrogenated forming 1,6-hexanediamine.

N
H C NH 2
2
H N
2
N
N (17.3)
Acrylonitrile Adiponitrile 1,6-Hexanediamine

1,6-Hexanediamine can also be made by the liquid-phase catalytic hydrogenation of adiponitrile
or adipamide, which is made from adipic acid.

NH 2
OH
O H N NH 2
O O 2
O
OH NH 2
Adipic acid Adipamide 1,6-Hexanediamine
(17.4)

Sebacic acid (1,8-octane dicarboxylic acid), which is used to make nylon-610, has been produced
from 1,3-butadiene and by the dry distillation of caster oil (ricinolein). The cleavage of ricinoleic
acid gives 2-octanol and the salt of sebacic acid.

Ricinoleic acid
HO

Caster oil O
H C
3
(17.5)
OH
−
O Na +
OH
C + O
H 3 O
CH 3
−
O Na +
2-Octanol Disodium salt of sebacic acid

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