Caprolactam → 6-Oxohexanoic acid

HRID 1281082Notes

Reaction equation

HRID 1281082 reaction equation
C1(=O)NCCCCC1.[CH:9]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[O:10]>O>[CH:9]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:10]

Participants

4

Reactant 2

HCID 7768CaprolactamHCID 81164Methyl 6-oxohexanoate

Product 1

HCID 4409186-Oxohexanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A process for preparing ε-caprolactam is described in U.S. Pat. No. 4,730,040. In this process, methyl 5-formylvalerate is first hydrolyzed (step a) in the presence of water and an acidic agent to yield 5-formylvaleric acid. In this process, the 5-formylvaleric acid is reductively aminated in water through contact with ammonia and hydrogen using a ruthenium/zirconium on alumina catalyst, a Raney Nickel catalyst or a Raney Cobalt catalyst to obtain a 6-aminocaproic acid containing reaction mixture. After separation of ammonia, the reaction mixture obtained from the reductive amination is heated to 300° C. to form ε-caprolactam by cyclization of the 6-aminocaproic acid.

Sources & evidence

ORD record
ord-7cb4340ed15c4f578086267a4bba5010
Source dataset
uspto-grants-2002_09
Patent number
US06452002B2

Reaction notes

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