Kinetic Study of para-tert-Butylcumene Oxidation in the Presence of N-Hydroxyphthalimide

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Abstract

The kinetics of the oxidation of para-tert-butylcumene to hydroperoxide by molecular oxygen in the presence of N-hydroxyphthalimide has been studied. Based on the study of the regularities in the formation of hydroperoxide and non-target reaction products, a mathematical model of the process was obtained that adequately describes the change in the main components of the reaction concentration over time. The main role of N-hydroxyphthalimide is that it converts peroxide radicals into the corresponding hydroperoxides, thereby reducing the formation of non-target reaction products by reducing the quadratic termination rate. Simultaneously formed N-oxyphthalimide radicals increase the rate of hydrocarbon oxidation. Thus, the use of N-hydroxyphthalimide in hydrocarbon oxidation processes results in an increase in the rate and selectivity of hydroperoxide formation.

About the authors

А. S. Frolov

Yaroslavl State Technical University

Email: koshelgn@ystu.ru
Russia, 150023, Yaroslavl, Moskovskiy prosp., 88

E. A. Kurganova

Yaroslavl State Technical University

Email: koshelgn@ystu.ru
Russia, 150023, Yaroslavl, Moskovskiy prosp., 88

V. N. Sapunov

Mendeleev University of Chemical Technology of Russia

Email: koshelgn@ystu.ru
Russia, 125047, Moscow, Miusskaya square, 9, build. 6

R. A. Kozlovskiy

Mendeleev University of Chemical Technology of Russia

Email: koshelgn@ystu.ru
Russia, 125047, Moscow, Miusskaya square, 9, build. 6

G. N. Koshel

Yaroslavl State Technical University

Author for correspondence.
Email: koshelgn@ystu.ru
Russia, 150023, Yaroslavl, Moskovskiy prosp., 88

E. M. Yarkina

Yaroslavl State Technical University

Email: koshelgn@ystu.ru
Russia, 150023, Yaroslavl, Moskovskiy prosp., 88

References

  1. Fukuda O., Sakaguchi S., Ishi Y. // Adv. Synth. Catal. 2001. V. 343. № 8. P. 809.
  2. Koshino N., Cai Y., Espenson J.H. // J. Phys. Chem. A. 2003. V. 107. P. 4262.
  3. Hermans I., Vereecken L., Jacobs P.A., Peeters J. // Chem. Commun. 2004. P. 1140.
  4. Ishii Y., Sakaguchi S. // Catal. Surv. Jpn. 1999. V. 3. P. 27.
  5. Курганова Е.А., Румянцева Ю.Б., Кошель Г.Н., Иванова А.А., Смирнова Е.В. // Химическая промышленность сегодня. 2012. № 4. С. 20.
  6. Recupero F., Punta C. // Chem. Rev. 2007. V. 107. P. 3800.
  7. Кузнецова Л.И., Кузнецова Н.И., Яковина О.А., Зудин В.Н., Бальжинимаев Б.С. // Кинетика и катализ. 2018. № 6. С. 694.
  8. Sheldon R.A., Arends I.W.C.E. // J. Mol. Catal. A: Chem. 2006. V. 251. P. 200.
  9. Yan-ping W.D., Jiang W.H., Luo W.-P., Tan Z., Jiang Q., Guo C.-C. // Catal. Lett. 2014. V. 144. № 2. P. 333.
  10. Kurganova E.A., Frolov A.S., Korshunova A.I., Koshel´ G.N., Yarkina E.M. // Russ. Chem. Bull. Int. Ed. V. 70. № 10. P. 1951.
  11. Saha M., Hossain M.K., Ashaduzzama M., Afroza S.T., Galib M., Sharif N. // Bangladesh J. Sci. Ind. Res. 2009. V. 44. № 1. P. 131.
  12. Sapunov V.N., Kurganova E.A., Koshel G.N. // Int. J. Chem. Kinet. 2018. V. 50. № 1. P. 3.
  13. Sapunov V.N., Koshel’ G.N., Rumyantseva Yu.B., Kurganova E.A., Kukushkina N.D. // Petrol. Chem. 2013. V. 53. № 3. P. 171.
  14. Yarkina E.M., Kurganova E.A., Frolov A.S., Koshel G.N., Nesterova T.N., Shakun V.A., Spiridonov S.A. // Fine Chem. Technol. 2021. V. 16. № 1. P. 26.
  15. Антоновский В.Л., Бузланова М.М. Аналитическая химия органических пероксидных соединений. Москва: Химия, 1978. 309 с.
  16. Bhattacharya A. // Chem. Eng. J. 2008. V. 137. P. 308.
  17. Hattori K., Tanaka Y., Suzuki H., Ikawa T., Kubota H. // J. Chem. Eng. Jpn. 1971. V. 3. № 1. P. 72.
  18. Makgwanea P.R., Harmsea N.I., Fergb E.E., Zeeli B. // Chem. Eng. J. 2010. V. 162. P. 341.
  19. Chianese A. // Chem. Eng. Commun. 1982. V. 17. P. 261.
  20. Schmid R., Sapunov V.N. // Monographs in Modern Chemistry. 1982. V. 14. P. 65.
  21. Denisov E.T., Afanas’ev I.B. Oxidation and Antioxdants in Organic Chemistry and Biology. Boca Raton: CRC Press, Taylor and Francis Group, 2005. 992 c.
  22. Hermans I., Jacobs P., Peeters J. // Phys. Chem. Chem. Phys. 2008. V. 10. P. 1125.
  23. Benderskii V.A., Goldanskii V.I. // Int. Rev. Phys. Chem. 1992. V. 11. P. 1.
  24. Hermans I., Jacobs P., Peeters J. // Phys. Chem. Chem. Phys. 2007. V. 9. P. 686.
  25. Opeida I., Litvinov Yu.E., Kushch O.V., Kompanets M.O., Shendrik O.M. // Int. J. Chem. Kinet. 2013. V. 45. № 9. P. 514.

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Copyright (c) 2023 А.С. Фролов, Е.А. Курганова, В.Н. Сапунов, Р.А. Козловский, Г.Н. Кошель, Е.М. Яркина