cyclohexanone

Cyclohexanone is a cyclic ketone with the formula C6H10O. It is a colorless, flammable liquid with a characteristic odor and is miscible with many organic solvents while being only sparingly soluble in water.

Industrially, cyclohexanone is produced as part of KA oil, a mixture of cyclohexanone and cyclohexanol formed during the catalytic oxidation of cyclohexane. The KA oil stream is separated to yield cyclohexanone, which serves as a versatile chemical feedstock for further transformations and as a solvent in various applications. In large-scale Nylon manufacturing, cyclohexanone is converted to cyclohexanone oxime and then subjected to Beckmann rearrangement to produce caprolactam, the monomer for Nylon 6.

Common uses of cyclohexanone include its role as a precursor in the production of adipic acid (via oxidation of KA oil) and caprolactam, as well as a solvent for resins, waxes, oils, and dyes. It also serves as an intermediate in fragrance chemistry and pharmaceutical synthesis.

Reactions of cyclohexanone include oxidation to adipic acid and the formation of cyclohexanone oxime through reaction with hydroxylamine. The oxime can undergo Beckmann rearrangement to give caprolactam, a key step in nylon-6 production.

Safety and handling notes: cyclohexanone is a flammable irritant. Vapors can irritate the eyes, skin, and respiratory tract; avoid inhalation and contact with skin. Store in a cool, well-ventilated area away from heat and oxidizers, in tightly closed containers. It may form peroxides on aging and should be handled with appropriate precautions.