Ammonia → Caprolactam

Reaction equation

C1(=[N:7]O)CCCCC1.[S:9](=[O:13])(=[O:12])([OH:11])[OH:10].OS(O)(=O)=O.O=S(=O)=O.S(O)(O)(=O)=O.[C:28]1(=[O:35])[NH:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[NH3:36]>>[C:28]1(=[O:35])[NH:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[S:9]([O-:13])([O-:12])(=[O:11])=[O:10].[NH4+:7].[NH4+:36]

Participants

Reactant 5

HCID 222Ammonia

HCID 1118Sulfuric Acid2×

HCID 7517Cyclohexanone Oxime

HCID 24681Fuming sulfuric acid

HCID 67062907Caprolactam sulfate

Product 2

HCID 7768Caprolactam

HCID 6097028Ammonium Sulfate

Procedure

The Beckmann rearrangement of the cyclohexanone oxime is carried out with sulfuric acid or oleum. The caprolactam sulfate prepared in this case and excess sulfuric acid are reacted with ammonia to give caprolactam and ammonium sulfate.

Sources & evidence

ORD record: ord-01f4839d1f2846ee93e0257eb0d561d9
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841445B2

Reaction notes

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