Skip to main content
SpringerLink
Log in

Oxidation of mesitylene by hydrogen peroxide in AcOH-Ac2O-H2SO4

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

By the oxidation of raesitylene by hydrogen peroxide in AcOH-Ac2O-H2SO4 one can obtain mesitol (2,4,6-trimethylphenol) (with a selectivity of 57–69% at a mesitylene conversion of 22–16% and the acetate of mesitol with a selectivity of 72–85% at 25–22% conversion. The peroxide responsible for the oxidation of mesitylene in this system is in the form of peracetic acid, formedin situ. Over the concentration range studied, the reaction is first order in AcOOH, mesitylene, and H2SO4. Hydroxylation of mesitylene by AcOOH proceeds by an electrophilic substitution mechanism, the limiting step being the formation of the σ-complex.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. A. H. Haines, Methods for the Oxidation of Organic Compounds: Alkanes, Alkenes, Alkynes and Arenes, Academic Press, London (1985).

    Google Scholar 

  2. D. H. Derbyshire and W. A. Waters, Nature,165, 401 (1950).

    Google Scholar 

  3. Y. Ogata, Y. Sawaki, K. Tomizawa, and T. Ohno, Tetrahedron,37, 1485 (1981).

    Google Scholar 

  4. E. S. Rudakov and V. L. Lobachev, Kinet. Katal.,28, No. 6, 1335 (1987).

    Google Scholar 

  5. E. S. Rudakov and V. L. Lobachev, Ukr. Khim. Zh.,51, No. 10, 1061 (1985).

    Google Scholar 

  6. G. P. Miklukhin, Isotopes in Organic Chemistry [in Russian], Izd-vo Akad. Nauk UkrSSR, Kiev (1961), p. 262.

    Google Scholar 

  7. O. A. Kholdeeva, I. V. Kozhevnikov, V. N. Sidel'nikov, and V. A. Utkin, Izv. Akad. Nauk SSSR, Ser. Khim., 2069 (1989).

  8. F. P. Greenspan and D. G. MacKellar, Anal. Chem.,20, 1061 (1948).

    Google Scholar 

  9. Handbook of Chemistry, Khimiya, Moscow-Leningrad, Vol. 2 (1964), p. 775.

  10. T. W. Findly, D. Swern, and I. T. Scanlan, J. Am. Chem. Soc.,67, 412 (1945).

    Google Scholar 

  11. D. Swern (ed.), Organic Peroxides, Wiley-Interscience, New York-London, Vol. 1 (1970), Vol. 2 (1971).

    Google Scholar 

  12. A. A. Akhrem, P. A. Kiselev, and D. E. Metelitza, React. Kinet. Catal. Lett.,2, 177 (1975).

    Google Scholar 

  13. A. K. Yatsimirskii and I. V. Berezin, Doklad. Akad. Nauk SSSR,233, No. 2, 414 (1975).

    Google Scholar 

  14. H. Hart, Acc. Chem. Res.,4, 337 (1971).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Catalysis, Siberian Branch of the Academy of Sciences of the USSR, Novosibirsk

    O. A. Kholdeeva & I. V. Kozhevnikov

Authors
  1. O. A. Kholdeeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Kozhevnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2716–2721, December, 1990.

The authors express their thanks to L. V. Efremova, G. M. Maksimov, and V. D. Chinakov for their assistance in this work.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kholdeeva, O.A., Kozhevnikov, I.V. Oxidation of mesitylene by hydrogen peroxide in AcOH-Ac2O-H2SO4 . Russ Chem Bull 39, 2462–2466 (1990). https://doi.org/10.1007/BF01184518

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01184518

Keywords

Search

Navigation