Cyclohexanone

The compound was discovered by in 1888 among the products of AC electrolysis of slightly acidified water solutions of phenol. He named it hydrophenoketone and correctly suggested that phenol was first hydrogenated by electrolytic hydrogen to cyclohexanol, which he wasn't able to isolate, and then oxidized by electrolytic oxygen. Laboratory synthesis Cyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide (Jones oxidation). An alternative method utilizes the safer and more readily available oxidant sodium hypochlorite. Industrial production Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: Therefore, this newer process without producing the acetone by-product appears attractive and is similar to the cumene process as a hydroperoxide is formed and then decomposed to yield two key products. ==Uses==

The great majority of cyclohexanone is consumed in the production of precursors to Nylon 6,6 and Nylon 6. About half of the world's supply is converted to adipic acid, one of two precursors for nylon 6,6. For this application, the KA oil (see above) is oxidized with nitric acid. The other half of the cyclohexanone supply is converted to cyclohexanone oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6: It forms a trimethylsilylenol ether upon treatment with trimethylsilylchloride in the presence of base. It forms an enamine with pyrrolidine. Self condensation of cyclohexanone gives cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol. Treatment with nitrosyl chloride and ethanol in sulfur dioxide gives the oximinecarboxylic ester: : Illicit use Cyclohexanone has been used in the illicit production of phencyclidine and its analogs and is often subject to purchase restrictions, such as being listed on the Special Surveillance List in the US. ==Safety==

Like cyclohexanol, cyclohexanone is not carcinogenic and is moderately toxic, with a TLV of 25 ppm for the vapor. It is an irritant. ==References==