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Inhibiting Effect of 4-Hydroxy-2,5-Dimethylfuran-3-one on the Radical Chain Oxidation of Styrene

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Abstract

The O–H bond strength was calculated by the G4 and the M06-2X/MG3S methods for 2‑hydroxy-3-methylcyclopent-2-en-1-one (maple lactone), 4-hydroxy-2,3-dimethyl-2H-furan-5-one (sotolon), 4-hydroxy-5-methylfuran-3-one, 4-hydroxy-2,5-dimethylfuran-3-one (strawberry furanone), (2R)-2-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2H-furan-5-one (ascorbic acid), 5-hydroxy-2-(hydroxymethyl)pyran-4-one (kojic acid), 3-hydroxy-2-methylpyran-4-one (maltol), 3-hydroxy-2-ethylpyran-4-one (ethylmaltol), 4-hydroxy-6-methylpyran-2-one, and 5-hydroxy-6-methyl-3,4-dihydro-2H-pyran-4-one (dihydromaltol). The calculations indicated the presence of a weak O–H bond of less than 82.0 kcal/mol in 4-hydroxyfuran-3-one derivatives. The experimental rate constant of the reaction of the compound with the lowest O–H bond strength, 4-hydroxy-2,5-dimethylfuran-3-one, with peroxyl radicals in chlorobenzene and acetonitrile was comparable to the data for dibutylhydroxytoluene, but the stoichiometric coefficient of inhibition was 0.17 (PhCl) and 0.66 (MeCN), which was significantly smaller than for dibutylhydroxytoluene. The activation enthalpy for hydrogen atom elimination from 4-hydroxy-2,5-dimethylfuran-3-one by peroxyl radicals calculated by the SMD(PhCl)-M05/MG3S method correlated well with the data for 5-hydroxy and 5-aminouracil derivatives, which is indicative of the common mechanism of interaction of these compounds with peroxyl radicals.

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ACKNOWLEDGMENTS

This study was performed using the equipment of the “Chemistry” Multiaccess Center, Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

This study was performed under the research program at the Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences (state registration no. AAAA-A20-120012090025-2).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, 450054, Ufa, Russia

    S. A. Grabovskii, Y. S. Grabovskaya, A. V. Antipin & N. N. Kabal’nova

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  1. S. A. Grabovskii
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  2. Y. S. Grabovskaya
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  3. A. V. Antipin
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  4. N. N. Kabal’nova
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Correspondence to S. A. Grabovskii.

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Translated by L. Smolina

Abbreviations: AIBN, 2,2'-azo-bis-isobutyronitrile; St, styrene; α-TP, α-tocopherol; HPLC, high-performance liquid chromatography; wi, initiation rate; w0, oxygen absorption rate during the oxidation without inhibitor; w, oxygen absorption rate in inhibited oxidation at the initial moment of time; wt, oxygen absorption rate in inhibited oxidation at a moment of time t; f, stoichiometric coefficient of inhibition; F, degree of inhibition; tind induction period; k7, rate constant of the reaction of the peroxyl radical with inhibitor; k6, rate constant of recombination of peroxyl radicals; ν, oxidation chain length.

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Grabovskii, S.A., Grabovskaya, Y.S., Antipin, A.V. et al. Inhibiting Effect of 4-Hydroxy-2,5-Dimethylfuran-3-one on the Radical Chain Oxidation of Styrene. Kinet Catal 62, 43–48 (2021). https://doi.org/10.1134/S002315842101002X

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