Cyclohexanone oxime is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer.
Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine:[1]
C5H10CO + H2NOH → C5H10C=NOH + H2O
Alternatively, another industrial route involves the reaction of cyclohexane with nitrosyl chloride, which is a free radical reaction. This method is advantageous as cyclohexane is much cheaper than cyclohexanone.
The most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding ε-caprolactam:
This reaction is catalyzed by sulfuric acid,[1] but industrial scale reactions use solid acids.[2]
Typical of oximes, the compound can be reduced by sodium amalgam to produce cyclohexylamine.[3] It can also be hydrolyzed with acetic acid to give back cyclohexanone.