Cyclohexanone

[11] The compound was discovered by Edmund Drechsel [de] in 1888 among the products of AC electrolysis of slightly acidified water solutions of phenol.

[14][15] Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:[11] This process forms cyclohexanol as a by-product, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid.

Alternatively, cyclohexanone can be produced by the partial hydrogenation of phenol: This process can also be adjusted to favor the formation of cyclohexanol.

In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6:[11] In addition to the large scale reactions conducted in service of the polymer industry, many reactions have been developed for cyclohexanone.

[20] Treatment with nitrosyl chloride and ethanol in sulfur dioxide gives the oximinecarboxylic ester:[21] Cyclohexanone has been used in the illicit production of phencyclidine and its analogs[22] and is often subject to purchase restrictions, such as being listed on the Special Surveillance List in the US.

Skeletal formula of cyclohexanone
Skeletal formula of cyclohexanone
Ball-and-stick model of cyclohexanone
Ball-and-stick model of cyclohexanone
Skeletal formula viewed side-on, showing the non-planar conformation
Skeletal formula viewed side-on, showing the non-planar conformation
Ball-and-stick model of cyclohexanone viewed side-on, showing the non-planar conformation
Ball-and-stick model of cyclohexanone viewed side-on, showing the non-planar conformation
NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code