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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

• Reactions

• References

Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine:cite-ref-eck-1-0[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, which is used to produce Nylon 6:

This reaction is catalyzed by sulfuric acid,cite-ref-eck-1-1[1] but industrial scale reactions use solid acids.cite-ref-2[2]

Typical of oximes, the compound can be reduced by sodium amalgam to produce cyclohexylamine.cite-ref-3[3] It can also be hydrolyzed with acetic acid to give back cyclohexanone.

cite-note-eck-11. ↑ J. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20. doi:10.15227/orgsyn.019.0020

cite-note-22. ↑ Corma, Avelino; Garcia, Hermenegildo "Organic reactions catalyzed over solid acids" Catalysis Today 1997, volume 38, pp. 257-308. doi:10.1016/S0920-5861(97)81500-1

cite-note-33. ↑ W. H. Lycan, S. V. Puntambeker, and C. S. Marvel "n-Heptylamine" Org. Synth. 1931, volume 11, pp. 58.doi:10.15227/orgsyn.011.0058