Skip to main content
SpringerLink
Log in

Synthesis and inhibitory activity of alkyl(hydroxyaryl)amines

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The reaction of ω-(4-hydroxyaryl)haloalkanes with various nitrogen-containing agents afforded primary, secondary, and tertiary amino derivatives of 2,6-dialkylphenols. For the compounds synthesized, the reaction rate constants with peroxide radicals were measured for cumene and methyl oleate oxidation. The total inhibitory activity in the model reactions of thermal autooxidation of lard and hexadecane was studied. The rate constants of alkyl(hydroxylaryl)amines are the same as those of the corresponding alkylphenols, whereas the total inhibitory activity of some alkyl(hydroxylaryl)amines exceeds substantially that for alkylphenols.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. US Pat. 2003040594; Chem. Abstrs, 2003, 138, 189241.

    Google Scholar 

  2. US Pat. 2003031507; Chem. Abstrs, 2003, 138, 305086.

    Google Scholar 

  3. US Pat. 5814695; Chem. Abstrs, 1998, 129, 162267.

    Google Scholar 

  4. US Pat. 4863999; Chem. Abstrs, 1989, 112, 159707.

    Google Scholar 

  5. EP Pat. 474403; Chem. Abstrs, 1991, 116, 248431.

    Google Scholar 

  6. EP Pat. 500336; Chem. Abstrs, 1992, 117, 239832.

    Google Scholar 

  7. N. P. Konovalova, G. N. Bogdanov, L. S. Vasil’eva, L. M. Dronova, and A. A. Matveeva, Dokl. Akad. Nauk SSSR, 1966, 168, 1419 [Dokl. Chem., 1966 (Engl. Transl.)].

    CAS  Google Scholar 

  8. E. B. Burlakova and N. G. Khrapova, in Teoriya i praktika zhidkofaznogo okisleniya [Theory and Practice of Liquid-Phase Oxidation], Ed. N. M. Emanuel, Nauka, Moscow, 1974, 244 (in Russian).

    Google Scholar 

  9. S. B. Bilalov, M. M. Movsumzade, and F. D. Alieva, Neftekhimiya, 1992, 32, 554 [Petroleum Chemistry, 1992, 32, 221 (Engl. Transl.)].

    CAS  Google Scholar 

  10. F. Yu. Rachinskii, G. F. Bol’shakov, Yu. A. Bruk, M. Z. Kremen’, L. V. Pavlova, T. G. Potapenko, and N. M. Slavachevskaya, in Khimiya seraorganicheskikh soedinenii, soderzhashchikhsya v neftyakh i nefteproduktakh [Chemistry of Sulfur-Containing Organic Compounds of Petroleum and Petrochemicals], Ed. R. D. Obolentsev, Khimiya, Moscow, 1964, Vol. 7, 47 (in Russian).

    Google Scholar 

  11. O. I. Dyubchenko, V. V. Nikulina, E. I. Terakh, A. E. Prosenko, and I. A. Grigor’ev, Zh. Prikl. Khim., 2005, 78, 796 [Russ. J. Appl. Chem., 2005, 78, 781 (Engl. Transl.)].

    Google Scholar 

  12. O. I. Dyubchenko, V. V. Nikulina, E. I. Terakh, N. V. Kandalintseva, A. F. Markov, I. A. Grigor’ev, and A. E. Prosenko, Neftekhimiya, 2005, 45, 359 [Petroleum Chemistry, 2005, 45, 330 (Engl. Transl.)].

    CAS  Google Scholar 

  13. G. A. Kovtun and A. L. Aleksandrov, Izv. Akad. Nauk SSSR, Ser. Khim., 1974, 1274 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1974, 23 (Engl. Transl.)].

  14. V. A. Roginskii, Fenol’nye antioksidanty: reaktsionnaya sposobnost’ i effektivnost’ [Phenol Antioxidants: Reactivity and Efficiency], Nauka, Moscow, 1988, 247 pp. (in Russian).

    Google Scholar 

  15. V. F. Tsepalov, in Issledovanie sinteticheskikh i prirodnykh antioksidantov in vivo i in vitro [Investigation of Synthetic and Natural Antioxidants in vivo and in vitro], Ed. E. B. Burlakova, Nauka, Moscow, 1992, 16 (in Russian).

    Google Scholar 

  16. G. D. Kadochnikova, in Svobodnoradikal’noe okislenie lipidov v eksperimente i klinike [Free Radical Oxidation of Lipids in Experiment and Clinic], Ed. V. N. Ushkalova, Izd. Tyumen Gos. Univ., Tyumen, 1997, 21 (in Russian).

    Google Scholar 

  17. V. A. Roginskii, Kinet. Katal., 1990, 31, 546 [Kinet. Catal., 1990, 31, 475 (Engl. Transl.)].

    CAS  Google Scholar 

  18. RF Pat. 1376511; Chem. Abstrs, 1993, 124, 316743.

    Google Scholar 

  19. RF Pat. 1370952; Chem. Abstrs, 1993, 125, 10363.

    Google Scholar 

  20. A. E. Prosenko, O. I. Dyubchenko, and A. P. Krysin, Tez. dokl. region. konf. “Perspektivy razvitiya malotonnazhnoi khimii” [Proc. Regional Conf. xxx201CxChallenges of Low-Tonnage Chemistry], Krasnoyarsk, 1989, 22 (in Russian).

  21. O. I. Dyubchenko, V. V. Nikulina, A. F. Markov, N. V. Kandalintseva, A. E. Prosenko, O. M. Khoshchenko, Ya. Sh. Shvarts, and M. I. Dushkin, Khim.-Farm. Zh., 2006, 40, 117 [Pharm. Chem. J., 2006, 40 (Engl. Transl.)].

    Google Scholar 

  22. I. S. Belostotskaya and V. V. Ershov, Izv. Akad. Nauk SSSR, Ser. Khim., 1964, 765 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1964, 13, 715 (Engl. Transl.)].

  23. Ya. B. Kozlikovskii, V. A. Koshchii, S. A. Butov, and A. V. Sokolova, Zh. Org. Khim., 1987, 23, 1918 [J. Org. Chem. USSR, 1987, 23 (Engl. Transl.)].

    CAS  Google Scholar 

  24. N. M. Emanuel and Yu. N. Lyasovskaya, Tormozhenie protsessov okisleniya zhirov [Inhibition of Fat Oxidation], Pishchepromizdat, Moscow, 1961, 385 pp. (in Russian).

    Google Scholar 

  25. A. A. Zinov’ev, Khimiya zhirov [Chemistry of Fats], Pishchepromizdat, Moscow, 1952, 372 pp. (in Russian).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Institute of Antioxidant Chemistry, Novosibirsk State Pedagogical University, 28 ul. Vilyuiskaya, 630126, Novosibirsk, Russian Federation

    O. I. Dyubchenko, V. V. Nikulina, E. I. Terakh & A. E. Prosenko

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    I. A. Grigor’ev

Authors
  1. O. I. Dyubchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. V. Nikulina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. I. Terakh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. E. Prosenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. A. Grigor’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. I. Dyubchenko.

Additional information

Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1107–1112, June, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dyubchenko, O.I., Nikulina, V.V., Terakh, E.I. et al. Synthesis and inhibitory activity of alkyl(hydroxyaryl)amines. Russ Chem Bull 56, 1149–1155 (2007). https://doi.org/10.1007/s11172-007-0174-1

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-007-0174-1

Key words

Search

Navigation