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.
Preparation Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine:J. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20.
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.
Reactions The most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding ε-caprolactam, which is used to produce Nylon 6:
This reaction is catalyzed by sulfuric acid, but industrial scale reactions use solid acids.Corma, Avelino; Garcia, Hermenegildo "Organic reactions catalyzed over solid acids" Catalysis Today 1997, volume 38, pp. 257-308.
Typical of oximes, the compound can be reduced by sodium amalgam to produce cyclohexylamine.W. H. Lycan, S. V. Puntambeker, and C. S. Marvel "n-Heptylamine" Org. Synth. 1931, volume 11, pp. 58. It can also be hydrolyzed with acetic acid to give back cyclohexanone.
References