Ammonia → 6-Aminohexanoic Acid

HRID 1281083Notes

Reaction equation

HRID 1281083 reaction equation
C(CCCCC(O)=O)=O.N.[H][H].[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]>O.[Ni].[Co].[Ru].[Zr]>[C:19]1(=[O:21])[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]

Participants

10

Reactant 4

HCID 222AmmoniaHCID 5646-Aminohexanoic AcidHCID 4409186-Oxohexanoic acidHCID 178418361HCID 178418361, compound

Product 2

HCID 5646-Aminohexanoic AcidHCID 7768Caprolactam

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 104730CobaltCatalystHCID 71354948Ruthenium--zirconium (1/1)CatalystHCID 962WaterSolvent

Conditions

Temperature
300 °C

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.

Workup

  1. customAfter separation of ammonia
  2. customthe reaction mixture obtained from the reductive amination

Sources & evidence

ORD record
ord-5391a5edd78a49e794dec2ab84aa4a8b
Source dataset
uspto-grants-2002_09
Patent number
US06452002B2

Reaction notes

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