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The specific features of the liquid-phase oxidation of saturated esters. Kinetics, reactivity and mechanisms of formation of destruction products

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Abstract

Data on kinetics, reactivity, and mechanisms of formation of destruction products of the liquid-phase oxidation of saturated esters by molecular oxygen have been systematized and discussed. The ester group has both an activating and deactivating effects on the reactivity of the CH bonds of the alkoxyl (α′-, β′-, γ′-, and δ′-) and acyl (α-, β-, and γ-) groups. The activating effect in esters is weaker than in alcohols, ketones, and ethers and extends to the α- and α′-CH bonds. The reactivity of the β-, β′-, and γ′-CH bonds is significantly lower than that of the secondary CH bonds of hydrocarbons. Oxidation of the β-CH bonds of the acyl moieties of esters leads to HOO· radical, α,β-epoxy-, α,β-dihydroxy-, and α,β-unsaturated esters, but not to hydroperoxides. Upon the oxidation of esters, the highly active α-carboxy-alkylperoxy-, α-acyloxyperoxy-, and HOO· -radicals are formed. The recombination reactions involving these radicals occur both with and without chain termination. The specificity of the decomposition of ester hydroperoxides are due to intra- and intermolecular interactions of the hydroperoxide groups with the ester groups. Labile peroxide intermediates (α-hydroxyperoxy-esters, peroxyesters, and peroxylactones) are formed through the corresponding tetrahedral intermediates and decay predominantly by the non-radical pathway. The recombination of the peroxyl radicals and the decay of labile peroxides result in the parallel accumulation of peroxide and non-peroxide products during the oxidation of esters.

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Authors and Affiliations

  1. Institute of Chemical and Oil-Gas Technologies, T. F. Gorbachev Kuzbass State Technical University, 28 ul. Vesennyaya, 650000, Kemerovo, Russian Federation

    A. L. Perkel & S. G. Voronina

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  1. A. L. Perkel
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  2. S. G. Voronina
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Correspondence to A. L. Perkel.

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Dedicated to the blessed memory of Professor Beniamin Grigorievich Freidin, who made a significant contribution to the theory and practice of the liquid-phase oxidation processes, including processes of oxidation of esters, and Professor Vladimir Semenovich Martemyanov, whose ideas continue to encourage the authors of this review to study specific features of the ester oxidation process.

The authors are grateful to Professor S. L. Khursan for valuable comments made during the preparation of this review, which made it possible to improve its quality.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2031—2058, November, 2020.

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Perkel, A.L., Voronina, S.G. The specific features of the liquid-phase oxidation of saturated esters. Kinetics, reactivity and mechanisms of formation of destruction products. Russ Chem Bull 69, 2031–2058 (2020). https://doi.org/10.1007/s11172-020-2999-9

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  • DOI: https://doi.org/10.1007/s11172-020-2999-9

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