Cyclohexanone Production and use

Cyclohexanone is produced commercially in several major ways. One widely used process yields cyclohexanol and cyclohexanone by the catalytic oxidation of cyclohexane. The cyclohexanol/Cyclohexanone product mixture, also called KA oil, is further reacted to produce adipic acid and hexamethylene diamine, intermediates in the manufacture of nylon 66. Pure cyclohexanone can be produced in high yields by this process either by distillation or by catalytic dehydrogenation of the cyclohexanol (Considine, 1974).

Another important and very efficient process is based on the hydrogenation of phenol. The cyclohexanone produced is further reacted to produce cyclohexanone oxime, an intermediate which then can undergo a Beckmann rearrangement to yield caprolactam (see IARC, 1986; Considine, 1974; Fisher & Van Peppen, 1979), the important intermediate for nylon 6 (see IARC, 1979).

Cyclohexanone production and consumption are determined by the demand for raw materials for nylon. Other uses are minor and have little effect on overall production.

In 1979, approximately 318 000 tonnes of cyclohexanone were produced in the USA (Mannsville Chemical Products Corp., 1979). The US International Trade Commission (1985),1986,1987) reported production of approximately 360 000 tonnes each year in 1984 and 1985 and 404 000 tonnes in 1986.

Production of Cyclohexanone elsewhere in the world has not been documented.

Cyclohexanone is used predominantly (about 95% of production in the USA) for the synthesis of raw materials used in the production of nylon. The remainder is used as a chemical intermediate in other processes, as an additive or as a high-boiling, slow-drying solvent. Cyclohexanone is used as a solvent in insecticides, wood stains, paint and varnish removers, spot removers, cellulosics, and natural and synthetic resins and lacquers. Additive uses include detergents, degreasing of metals, mould release agent for paints or varnishes, levelling agent in dyeing and delustering silk, and lube oil additive, especially for aircraft piston-type engines. Cyclohexanone is also used as a monomer in the synthesis of cyclohexanone resins, polyvinyl chloride and its copolymers (see IARC, 1979), and methacrylate ester polymers (International Technical Information Institute, 1979; Hawley, 1981; Windholz, 1983; Sittig, 1985; American Chemical Society, 1987).

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