Ammonia → Methyl 6-aminohexanoate

HRID 1601639Notes

Reaction equation

HRID 1601639 reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=O.[NH3:11].[H][H].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>[Ni]>[NH2:11][CH2:1][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 66225Magnesium orthosilicateHCID 81164Methyl 6-oxohexanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 1810164Methyl 6-aminohexanoate

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

U.S. Pat. Nos. 4,730,041 and 4,731,445 use methyl 5-formylvalerate as a starting material and an alkanol as a solvent to produce caprolactam. First, methyl 5-formylvalerate is reacted with excess ammonia and hydrogen in the presence of an alkanol as a solvent and in the presence of a magnesium silicate-supported nickel catalyst at 40° to 130° C. under superatmospheric pressure to form methyl 6-aminocaproate. After the unreacted ammonia and hydrogen gas are removed, methyl 6-aminocaproate is converted into 6-aminocaproic acid and then formed to caprolactam by dehydrolyzation and cyclization or by direct de-alcoholization and cyclization. Although the process does not involve the hydrolyzation procedure of 5-formylvalerate, it suffers from the disadvantage that the starting material has a very low concentration (only 10%) and a great amount of alkanol should be separated and recycled.

Workup

  1. customat 40° to 130° C.

Sources & evidence

ORD record
ord-b4f3bad7598a4c6ab514db4c849e3487
Source dataset
uspto-grants-1999_11
Patent number
US05977356

Reaction notes

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