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Mechanism of the alkylation of 2,6-di-tert-butylphenol by methyl acrylate in the presence of potassium 2,6-di-tert-butylphenoxide and alkali

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

A mechanism is proposed for the reaction of 2,6-di-tert-butylphenol with methyl acrylate in the presence of potassium 2,6-di-tert-butylphenoxide and KOH and, based on a computer calculation of the kinetic scheme, the constants have been found for the elementary stages of the reaction, sufficient to interpret the experimental data. The alkylation of 2,6-di-tert-butylphenol by methyl acrylate takes place by an inhibited catalytic chain mechanism involving the participation of ion pairs in the reaction.

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Literature cited

  1. N. M. Emanuel, G. E. Zalkov, and Z. K. Maizus, Oxidation of Organic Compounds, Pergamon Press, Oxford (1984), p. 650.

    Google Scholar 

  2. A. A. Volod'kin, L. K. Popov, F. M. Egidis, et al., Chemicals for Polymeric Materials [in Russian], NIITÉKhIM, Moscow (1987).

    Google Scholar 

  3. G. Stillson and D. Sawyer, J. Am. Chem. Soc.,47, 303 (1945).

    Google Scholar 

  4. USSR Inventor's Certificate No. 1,001,649; Byull. Izobret., No. 23 (1986).

  5. A. A. Volod'kin, V. I. Paramonov, and B. I. Rubinshtein, Abstracts of Papers, 8th All-Union Sci. Techn. Conf. Tambov. Proletarian Torch-Bearers (1986), p. 8.

  6. V. A. Bulgakov, N. N. Gorodetskaya, G. A. Nikiforov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 71 (1983).

    Google Scholar 

  7. C. W. Gear, Numerical Initial Value Problems in Ordinary Differential Equations, Prentice-Hall, N. Y. (1971), p. 158.

    Google Scholar 

  8. E. M. Kosower, Recent Problems in Physical Organic Chemistry [Russian translation], Mir, Moscow (1969), p. 207.

    Google Scholar 

  9. J. M. Mellor, A Comprehensive Treatise on Inorganic and Theoretical Chemistry, Vol. 11, Longmans Green and Co. Ltd., London (1927), p. 502.

    Google Scholar 

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Authors and Affiliations

  1. N. N. Semenov Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow

    A. A. Volod'kin, A. S. Zaitsev, V. L. Rubailo, V. A. Belyakov & G. E. Zaikov

Authors
  1. A. A. Volod'kin
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  2. A. S. Zaitsev
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  3. V. L. Rubailo
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  4. V. A. Belyakov
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  5. G. E. Zaikov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1829–1835, August 1988.

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Volod'kin, A.A., Zaitsev, A.S., Rubailo, V.L. et al. Mechanism of the alkylation of 2,6-di-tert-butylphenol by methyl acrylate in the presence of potassium 2,6-di-tert-butylphenoxide and alkali. Russ Chem Bull 38, 1677–1682 (1989). https://doi.org/10.1007/BF00956955

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  • DOI: https://doi.org/10.1007/BF00956955

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