Skip to main content
Log in

Synthesis and antioxidant activity of alkyl 3-(4-hydroxyaryl)propyl sulfides

  • Published:
Petroleum Chemistry Aims and scope Submit manuscript

Abstract

4-Alkylthiopropylphenols were synthesized from corresponding 2,6-dialkylphenols via the allyl derivative. A comparative study of the antioxidant activity of the prepared compounds was carried out in five model systems. The rate constants for the reactions of the test compounds with cumene, styrene, and methyl oleate peroxide radicals were measured. It was shown that 4-thioalkylphenols with methyl and cyclohexyl ortho-substituents are powerful inhibitors in the oxidation of mineral oil.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. V. M. Demidova, L. I. Lugova, A. E. Prosenko, et al., USSR Inventor’s Certificate No. 979428, 1982.

  2. G. P. Makarova, L. I. Lugova, A. E. Prosenko, et al., USSR Inventor’s Certificate No. 988840, 1982.

  3. A. E. Prosenko, E. I. Terakh, E. A. Gorokh, et al., Zh. Prikl. Khim. (St.-Petersburg) 76, 256 (2003).

    Google Scholar 

  4. A. E. Prosenko, E. I. Terakh, E. A. Gorokh, et al., Neftekhimiya 43, 190 (2003) [Pet. Chem. 43, 197 (2003)].

    Google Scholar 

  5. I. A. Bakhtina, E. V. Antip’eva, A. E. Prosenko, et al., Byull. Sib. Otd. Akad. Med. Nauk 97/98 24 (2000).

    Google Scholar 

  6. M. I. Dushkin, A. E. Prosenko, N. V. Kandalintseva, and V. V. Lyakhovich, Nauchn. Vestn. Tyumen. Med. Akad. 23, 11 (2003).

    Google Scholar 

  7. N. K. Zenkov, N. V. Kandalintseva, V. Z. Lankin, et al., Phenolic Bioantioxidants (SO RAMN, Novosibirsk, 2003) [in Russian].

    Google Scholar 

  8. E. I. Terakh, P. I. Pinko, O. V. Zaitseva, and A. E. Prosenko, Zh. Prikl. Khim. (St. Petersburg) 76, 1533 (2003).

    Google Scholar 

  9. P. I. Pinko, E. I. Terakh, E. A. Gorokh, et al., Zh. Prikl. Khim. (St. Petersburg) 75, 1694 (2002).

    Google Scholar 

  10. H. Lind, US Patent 4 021 468, 1977; Chem. Abstr. 87:39108.

  11. V. A. Roginskii, Phenolic Antioxidants: Reactivity and Performance (Nauka, Moscow, 1988) [in Russian].

    Google Scholar 

  12. V. F. Tsepalov, in In Vivo and in Vitro Studies of Synthetic and Naturally Occurring Antioxidants (Nauka, Moscow, 1992), p. 16 [in Russian].

    Google Scholar 

  13. E. T. Denisov and T. G. Denisova, Handbook of Antioxidants: Bond Dissociation Energies, Rate Constants, Activation Energies and Enthalpies of Reactions 2nd ed. (CRC, Boca Raton, 2000).

    Google Scholar 

  14. L. N. Shishkina, in In Vivo and in Vitro Studies of Synthetic and Naturally Occurring Antioxidants (Nauka, Moscow, 1992), p. 26 [in Russian].

    Google Scholar 

  15. A. A. Zinov’ev, Chemistry of Fats (Pishchepromizdat, Moscow, 1952) [in Russian].

    Google Scholar 

  16. R. Stroh, R. Seydel, and W. Hahz, Angew. Chem. 22, 699 (1957).

    Google Scholar 

  17. E. I. Terakh, A. E. Prosenko, V. V. Nikulina, and O. V. Zaitseva, Zh. Prikl. Khim. (St. Petersburg) 76, 261 (2003).

    Google Scholar 

  18. V. A. Roginskii, Kinet. Katal. 31, 546 (1990).

    CAS  Google Scholar 

  19. D. S. Terbell and J. F. Kincald, J. Am. Chem. Soc. 62, 728 (1940).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Original Russian Text © A.E. Prosenko, A.F. Markov, A.S. Khomchenko, M.A. Boiko, E.I. Terakh, N.V. Kandalintseva, 2006, published in Neftekhimiya, 2006, Vol. 46, No. 6, pp. 471–475.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Prosenko, A.E., Markov, A.F., Khomchenko, A.S. et al. Synthesis and antioxidant activity of alkyl 3-(4-hydroxyaryl)propyl sulfides. Pet. Chem. 46, 442–446 (2006). https://doi.org/10.1134/S0965544106060119

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0965544106060119

Keywords

Navigation