Abstract
The inhibition activity of hydroxy-and alkoxysubstituted 2,2,4-trimethyl-1,2,3,4-tetrahydroquinolines (HQs) was studied in R(+) limonene autooxidation and oxidation catalyzed by cationic surfactants and transition metal compounds. It was shown that HQs exhibit a high antioxidant activity in limonene autooxidation. In oxidation catalyzed by cationic surfactants and Fe(III), Co(II), or Mn(II) acetylacetonates, HQs also show a relatively high antioxidant activity and, additionally, react with hydroperoxides along with the reactions with peroxyl radicals in the presence of these catalysts. In the presence of Cu(II) compounds, HQs significantly accelerate the oxidation. It was found that HQs form complexes with Cu(II), which catalyze hydroperoxide degradation into free radicals.
Similar content being viewed by others
References
V. G. Kondratovich, T. V. Lobanova, I. F. Rusina, et al., Neftekhimiya 44, 226 (2004) [Pet. Chem. 44, 200 (2004)].
A. M. Kashkai and O. T. Kasaikina, Polyfunctional Antioxidants: Reactivity, Mechanism of Inhibition (Viking, Moscow, 2001) [in Russian].
O. T. Kasaikina, A. M. Kashkay, and T. V. Maximova, Oxid. Commun. 23, 383 (2000).
J. Pospishil, Polym. Degrad. Stab. 34, 85 (1991).
A. P. Zhedek, Doctoral Dissertation in Chemistry (Kharkov, 1971).
G. M. Kuznetsova, T. V. Lobanova, I. F. Rusina, and O. T. Kasaikina, Izv. Akad. Nauk, Ser. Khim., No. 7, 1676 (1996).
L. M. Pisarenko, V. G. Kondratovich, and O. T. Kasaikina, Izv. Akad. Nauk, Ser. Khim., No. 10, 29 (2004).
M. M. Mogilevich and E. M. Pliss, Oxidation and Oxidative Polymerization of Unsaturated Compounds (Khimiya, Moscow, 1990) [in Russian].
E. N. Frankel, Lipid Oxidation (The Oily, Dundee, 1998).
D. A. Krugovov, Zh. V. Shmyreva, L. F. Ponomoreva, et al., Vestn. Voronezh. Gos. Univ., Ser. Khim., Biol. Farm., No. 1, 64 (2004).
N. M. Emanuel, E. T. Denisov, and Z. K. Maizus, Liquid-Phase Oxidation of Hydrocarbons (Nauka, Moscow, 1965; Plenum, New York, 1967).
E. T. Denisov and I. B. Afanas’ev, Oxidation and Antioxidants in Organic Chemistry and Biology, (CRC, Boca Raton, 2005).
D. V. Fentsov, O. T. Kasaikina, L. M. Baider, and Yu. A. Ivanov, Dokl. Akad. Nauk SSSR 280, 435 (1985).
D. V. Fentsov, O. T. Kasaikina, and N. M. Emanuel’, Dokl. Akad. Nauk SSSR 280, 678 (1985).
V. A. Roginskii, Phenolic Antioxidants: Reactivity and Efficiency (Nauka, Moscow, 1988) [in Russian].
A. L. Buchachenko and A. M. Vasserman, Stable Radicals: Electron Structure, Reactivity and Application (Khimiya, Moscow, 1973) [in Russian].
E. Denisov and T. Denisova, in Handbook of Antioxidants: Bond Dissociation Energies, Rate Constants, Activation Energies and Enthalpies of Reactions (CRC, Boca Raton, 2000).
E. T. Denisov, T. G. Denisova, and T. S. Pokidova, in Handbook of Free Radical Initiators (Wiley, Chichester, 2003).
G. Para, E. Jarek, and P. Warszynski, Colloids Surf., A 261, 65 (2005).
O. T. Kasaikina, in Oxidation, Oxidative Stress, Antioxidants (RUDN, Moscow, 2006), p. 48.
L. M. Pisarenko, T. V. Maksimova, and O. T. Kasaikina, Izv. Ross. Akad. Nauk, Ser. Khim., No. 8, 1802 (2005).
E. T. Denisov, O. M. Sarkisov, and G. I. Likhtenshtein, A Textbook on Chemical Kinetics (Khimiya, Moscow, 2000) [in Russian].
V. V. Davydov, V. I. Sokol, E. V. Balebanova, et al., Koord. Khim. 20, 311 (1994).
Author information
Authors and Affiliations
Additional information
Original Russian Text © D.A. Krugovov, V.G. Kondratovich, O.T. Kasaikina, 2007, published in Neftekhimiya, 2007, Vol. 47, No. 3, pp. 213–220.
Rights and permissions
About this article
Cite this article
Krugovov, D.A., Kondratovich, V.G. & Kasaikina, O.T. Effect of the conditions of liquid-phase oxidation of unsaturated compounds on the behavior of hydroquinoline antioxidants. Pet. Chem. 47, 193–200 (2007). https://doi.org/10.1134/S0965544107030073
Received:
Issue Date:
DOI: https://doi.org/10.1134/S0965544107030073