On the origin of the byproducts in the autoxidation of cyclohexane to cyclohexanol and cyclohexanone

Abstract Tracer experiments involving autoxidation of dilute solutions of inactive cyclohexanol and inactive cyclohexanone in 14C‐labeled cyclohexane have shown that a number of byproducts such as butanol, pentanol, butyric acid, valeric acid, caproic acid, and ϵ‐hydroxycaproic acid are to a large part formed directly from cyclohexane and not via cyclohexanol and cyclohexanone. The label distribution in ϵ‐cyclohexyloxycaproic acid, hitherto unknown as a byproduct in the cyclohexane oxidation, clearly indicated that this acid is formed from the addition product of cyclohexyl hydroperoxide and cyclohexanone.