Alcohols
DETAIL
Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:This process co-forms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C6H11O2H. Alternatively, cyclohexanol can be produced by the hydrogenation of phenol:
Basic reactions
Cyclohexanol undergoes the main reactions expected for a secondary alcohol. Oxidation gives cyclohexanone, which is converted on a large scale in industry to the oxime, a precursor to caprolactam. As a laboratory exercise, this oxidation can be effected with chromic acid. Esterification affords the commercially useful derivatives dicyclohexyladipate and dicyclohexylphthalate, which are used as plasticizers. Heating in the presence of acid catalysts converts cyclohexanol to cyclohexene.
Structure
Cyclohexanol has at least two solid phases. One of them is a plastic crystal.
Applications
As indicated above, cyclohexanol is an important feedstock in the polymer industry, firstly as a precursor to nylons, but also to various plasticizers. Small amounts are used as a solvent.