Cyclohexanone Oxime → Laurolactam

HRID 2206962Notes

Reaction equation

[C:1]1(=[N:7]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1(=[O:16])N[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1(=NO)CCCCCCCCCCC1>>[C:9]1(=[O:16])[NH:7][CH2:1][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Reactant 3

HCID 7517Cyclohexanone Oxime

HCID 7768Caprolactam

HCID 136762Cyclododecanone, oxime

Product 1

HCID 13690Laurolactam

Procedure

An oxime can be converted into an amide compound by Beckmann rearrangement reaction, particularly an oxime derived from a cyclic ketone can be converted into a lactam. For example, cyclohexanone oxime gives ε-caprolactam which is a starting material for Nylon 6 and cyclododecanone oxime gives laurolactam which is a starting material for Nylon 12.

Sources & evidence

ORD record: ord-ed521d42fbe74f65b2239ad9b8c43268
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376375B2

Reaction notes

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