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Russian Chemical Bulletin

, Volume 68, Issue 8, pp 1478–1498 | Cite as

Mechanisms of the formation of carboxylic acids and their anhydrides during the liquid-phase oxidation of cyclohexane

  • A. L. PerkelEmail author
  • S. G. Voronina
Review
  • 4 Downloads

Abstract

The channels of formation and transformation of bifunctional (C5, C6) and monofunctional acids (C1, C5, C6) and their anhydrides during the liquid-phase oxidation of cyclohexane are reviewed. Adipic acid and adipic anhydride are predominantly formed by the radical-chain oxidation of 2-hydroxycyclohexanone. Destructive transformations of 1-hydroxycyclohexyloxyl and cyclohexyloxyl (at a low conversion of cyclohexane) radicals, which are formed by the homolytic decomposition of 1-hydroperoxy-1-hydroxy- or 1-hydroxy-1-alkylperoxy-, and hydroperoxycyclohexane, respectively, afford 6-hydroxyhexanoic and caproic acids. 6-Oxohexanoic acid can be formed by the decomposition of 2-hydroperoxycyclohexanone via the nonradical and radical routes, as well as by the oxidation of 2-hydroxycyclohexanone with peroxide compounds. Valeric and 5-hydroxypentanoic acids are predominantly resulted from the destructive transformations of the 2-oxocyclohexyloxyl radical. The shortening of carbon chain is explained by decarboxylation, decarbonylation, and elimination of formic acid. The ring closure of 5-hydroxypentanoic acid to 8-valerolactone prevents its further oxidation. The schemes for the formation of 5-oxopentanoic and glutaric acids by the oxidation of 6-oxohexanoic acid at the C(5)-H bonds were proposed. The transacylation of the initially formed anhydrides with carboxylic acids leads to mixed anhydrides, and their alcoholysis by cyclohexanol affords all cyclohexyl esters of mono- and dicarboxylic acids.

Key words

cyclohexane cyclohexanol cyclohexanone 2-hydroxycyclohexanone liquid-phase oxidation caproic acid 6-hydroxyhexanoic acid 6-oxohexanoic acid adipic acid adipic anhydride valeric acid 5-hydroxypentanoic acid 5-oxopentanoic acid glutaric acid cyclohexyl esters 

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© Springer Science+Business Media, Inc. 2019

Authors and Affiliations

  1. 1.Institute of Chemical and Oil-Gas TechnologiesKuzbass State Technical University named after T. F. GorbachevKemerovoRussian Federation

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