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The oxidation of primary alcohols to carboxylic acids can be carried out using a variety of reagents, but O 2 /air and nitric acid dominate as the oxidants on a commercial scale. Large scale oxidations of this type are used for the conversion of cyclohexanol alone or as a mixture with cyclohexanone to adipic acid. Similarly cyclododecanol is ...
Adipic acid is produced by oxidation of a mixture of cyclohexanone and cyclohexanol, which is called KA oil, an abbreviation of ketone-alcohol oil. Nitric acid is the oxidant. The pathway is multistep. Early in the reaction, the cyclohexanol is converted to the ketone, releasing nitrous acid: HOCH(CH 2) 5 + HNO 3 → O=C(CH 2) 5 + HNO 2 + H 2 O
Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: [11]. C 6 H 12 + O 2 → (CH 2) 5 CO + H 2 O. 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.
This process coforms 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 C 6 H 11 O 2 H. Alternatively, cyclohexanol can be produced by the hydrogenation of phenol: C 6 H 5 OH + 3 H 2 → C 6 H 11 OH
Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene. [6] Cyclohexylbenzene is a precursor to both phenol and cyclohexanone. [7] Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam. [8] The oxidative cleavage of cyclohexene gives adipic acid.
Although rather unreactive, cyclohexane undergoes autoxidation to give a mixture of cyclohexanone and cyclohexanol. The cyclohexanone–cyclohexanol mixture, called "KA oil", is a raw material for adipic acid and caprolactam, precursors to nylon. Several million kilograms of cyclohexanone and cyclohexanol are produced annually. [9]
This species decomposes to adipic acid and nitrous oxide: HO 2 C(CH 2) 4 C(NO 2)=NOH → HO 2 C(CH 2) 4 CO 2 H + N 2 O. This conversion is thought to be the largest anthropogenic route to N 2 O, which, on a molecule-to-molecule basis, has 298 times the atmospheric heat-trapping ability of carbon dioxide. [4] Adipic acid is a precursor to many ...
This reaction has been used to convert cyclohexanone to the methyl ester of cyclopropanecarboxylic acid. A generalized mechanism of the Favorskii rearrangement to give a ring contracted product. Note that anion formation has been omitted.