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Tocopherol- and Ascorbic Acid–Inhibited Radical Chain Oxidation of Tetrahydrofuran

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Abstract

The role of ascorbic acid and α-tocopherol in the radical chain oxidation of tetrahydrofuran at 309 K was studied. The reaction was initiated by \(2,2{\kern 1pt} '\)-azobisisobutyronitrile. The rate of the process was monitored by oxygen consumption. The rate constant of the reaction of the tetrahydrofuran peroxyl radical with α-tocopherol was measured to be k7 = (2.9 ± 0.6) × 105 L mol–1 s–1. The effect of an aqueous solution of ascorbic acid on the rate of tetrahydrofuran oxidation was studied. The rate constant of the reaction of the tetrahydrofuran peroxyl radical with ascorbic acid was measured to be k7 = (10.2 ± 1.0) × 104 L mol–1 s–1. The effect of ascorbic acid on the α-tocopherol-inhibited oxidation of tetrahydrofuran was examined. It was shown that, when both inhibitors are used together, the induction period is equal to the sum of the induction periods of the individual compounds. The effective inhibition rate constant in this case is k7 = (2.5 ± 0.5) × 105 L mol–1 s–1.

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Funding

The work was carried out in accordance with the plan of scientific research work of the Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia, on the subject “Reactivity of molecules containing reactive oxygen in processes of oxidation of organic compounds,” reg. no. NIOKTR 122031400201-0.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Bashkortostan, Russia

    L. R. Yakupova, A. R. Migranov, R. A. Nasibullina & R. L. Safiullin

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  1. L. R. Yakupova
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  2. A. R. Migranov
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  3. R. A. Nasibullina
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  4. R. L. Safiullin
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Correspondence to L. R. Yakupova.

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Translated by V. Glyanchenko

Abbreviations and notation: ki, initiation rate constant; k1 and k2, chain propagation rate constants; k6, rate constant of oxidation chain termination by recombination of peroxyl radicals; k7, inhibition rate constant; τ, induction period; f, stoichiometric inhibition coefficient; RH, substrate to be oxidized (tetrahydrofuran); THF, tetrahydrofuran; \({\text{R}}_{{}}^{ \bullet }\) and \({\text{RO}}_{2}^{ \bullet }\), alkyl and peroxyl radicals formed from tetrahydrofuran, respectively; AIBN, 2,2'-azobisisobutyronitrile; AscH, ascorbic acid (vitamin C); As\({\text{c}}_{{}}^{ \bullet }\), radical formed by the interaction of ascorbic acid with \({\text{RO}}_{2}^{ \bullet }\) TocH, α-tocopherol (vitamin E); HPLC, high-performance liquid chromatography.

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Yakupova, L.R., Migranov, A.R., Nasibullina, R.A. et al. Tocopherol- and Ascorbic Acid–Inhibited Radical Chain Oxidation of Tetrahydrofuran. Kinet Catal 64, 759–764 (2023). https://doi.org/10.1134/S0023158423060198

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  • DOI: https://doi.org/10.1134/S0023158423060198

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