Cyclohexanol Caprolactam Nylon 6

KA oil
Polymerization
w-amino acid
Liquid-phase Oxidation
1. + H2O H2N(CH2)5COOH

Hydrogenation: ΔH = -266
160-220˚C 25-30atm
Ni/alumina or Ni/Pd
2. H2N(CH2)5COOH + [-HN(CH2)5CO-]n
95-120˚C 10atm 95% short contact
Cobalt acetate and orthoboric acid catalyst Nylon 6
250-280˚C
system
*T control is important especially for depolymerization,
which directly proportional to rexn T and water content

Benzene Cyclohexane

Alkylation: Liquid-phase Oxidation

+21/2O2 HOOC(CH2)4COOH + H2O

Cobalt acetate catalyst
40-100˚C 2-8atm AlCl3-HCl
(1st monomer ) (2nd monomer)
Ethylbenzene (Badger Process) Adipic Acid Hexamethylenediamine Nylon 6,6
HOOC(CH2)4COOH H2N(CH2)6NH2
Dehydrogenation
1) Hydrogenation 1,6-hexanediol n HOOC(CH2)4COOH + n H2N(CH2)6NH2
HOOC(CH2)4COOH + 4H2 HO(CH2)6OH + 2H2O
• [OOC(CH2)4COO]n2-+ [H3N(CH2)6NH3]
2) HO(CH2)6OH +2NH3 H2N(CH2)6NH2 + 2H2O • [-CO(CH2)4CONH(CH2)6NH-] +2nH2O
600-700˚C ≤ 1atm Hexamethylenediamine
90%yield@30-40%conversion Hexamethylene diammonium adipate salt

Styrene (Monsanto/Lummus
Crest Process)