Yaroslavl State Technical University
Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Samara, Samara, Russian Federation
Rasschitany energii odnokratno zanyatoy molekulyarnoy orbitali radikala substrata i radikala ftalimidnogo katalizatora kvantovo-himicheskim metodom Hartri-Foka (RM7). Ustanovleno, chto proizvodnye N-gidroksiftalimida, soderzhaschie v svoey strukture elektronodonornye zamestiteli, harakterizuyutsya nizkimi chislennymi znacheniyami ∆Eozmo i obladayut vysokoy kataliticheskoy aktivnost'yu. Primenenie takih soedineniy pozvolyaet suschestvenno intensificirovat' process aerobnogo zhidkofaznogo okisleniya alkilaromaticheskih uglevodorodov s sohraneniem vysokih pokazateley konversii ishodnogo syr'ya i selektivnosti obrazovaniya ego gidroperoksida. Raschetnye dannye horosho soglasuyutsya s eksperimental'no poluchennymi, na osnovanii chego sdelan vyvod o vozmozhnosti primeneniya predlagaemogo metoda dlya ocenki kataliticheskoy aktivnosti ftalimidnyh soedineniy primenitel'no k shirokomu spektru aromaticheskih uglevodorodov.
izopropilbenzol, vtor-butilbenzol, gidroperoksid, N-gidroksiftalimid, ftalimidnye katalizatory, kvantovo-himicheskie raschety
1. Harlampovich G.D., Churkin Yu.V. Fenoly. M.: Himiya, 1974. 376 s.
2. Kurganova E.A., Kabanova V.S., Frolov A.S., Koshel' G.N., Smurova A.A., Baev E.I. Gidroperoksidnyy sposob sinteza fenola i ego alkil'nyh proizvodnyh sovmestno s ketonami alifaticheskogo i aliciklicheskogo ryada // Neftegaz.RU. 2023. T. 137, № 5. S. 34-40.
3. Kurganova E.A., Baev E.I., Frolov A.S., Kabanova V.S., Koshel' G.N., Petuhov A.A. Zakonomernosti aerobnogo okisleniya etilbenzola do gidroperoksida v prisutstvii ftalimidnyh katalizatorov // Ot himii k tehnologii shag za shagom. 2023. T. 4, vyp. 2. S. 8-16. URL: https://doi.org/10.52957/2782-1900-2024-4-2-8-16
4. Serebryakov B.R., Masagutov R.M., Pravdin V.G. Novye processy organicheskogo sinteza. M.: Himiya, 1989. 400 s.
5. Frolov A.S., Kurganova E.A., Yarkina E.M., Lebedeva N.V., Koshel' G.N., Kalenova A.S. Intensifikaciya processa zhidkofaznogo okisleniya ciklogeksana // Tonkie himicheskie tehnologii. 2018. T. 13, № 4. S. 50-57. URL: https://doi.org/10.32362/2410-6593-2018-13-4-50-57
6. Yun Hong, Dalei Sun, Yanxiong Fang. The highly selective oxidation of cyclohexane to cyclohexanone and cyclohexanol over VAlPO4 berlinite by oxygen under atmospheric pressure // Chemistry Central Journal. 2018. Vol. 36, no. 12. URL: https://doi.org/10.1186/s13065-018-0405-6
7. Emanuel' N.M., Denisov E.T., Mayzus Z.K. Cepnye reakcii okisleniya uglevodorodov v zhidkoy faze. M.: Nauka, 1965. 375 s.
8. Nazimok V.F., Ovchinnikov V.I., Potehin V.M. Zhidkofaznoe okislenie alkilaromaticheskih uglevodorodov. M.: Himiya, 1987. 240 s.
9. Aoki Y., Sakaguchi S., Ishii Y. One-pot synthesis of phenol and cyclohexanone from cyclohexylbenzene catalyzed by N-hydroxyphthalimide (NHPI) // Tetrahedron. 2005. Vol. 61, no. 22. R. 5219–5222. URL: https://doi.org/10.1016/j.tet.2005.03.079
10. Orlinska B., Zawadiak J. Aerobic oxidation of isopropylaromatic hydrocarbons to hydroperoxides catalyzed by N-hydroxyphthalimide // Reaction Kinetics, Mechanisms and Catalysis. 2013. Vol. 110, no. 1. R. 15–30. URL: https://doi.org/10.1007/s11144-013-0581-2
11. Sawatari N., Yokota T., Sakaguchi S., Ishii Y. Alkane oxidation with air catalyzed by lipophilic N-hydroxyphthalimides without any solvent // J. Org. Chem. 2001. Vol. 66, no. 23. P. 7889–7891. URL: https://doi.org/10.1021/jo0158276
12. Recupero, F., Punta C. Free Radical Functionalization of Organic Compounds Catalyzed by N Hydroxyphthalimide // Chemical Reviews. 2007. Vol. 107. P. 3800-3842. URL: https://doi.org/10.1021/cr040170k
13. Galli C., Gentili P., Lanzalunga O. Hydrogen Abstraction and Electron Transfer with Aminoxyl Radicals: Synthetic and Mechanistic Issues // Angewandte Chemie International Edition. 2008. Vol. 47, no. 26. P. 4790 4796. URL: https://doi.org/10.1002/anie.200704292
14. Koshel' G.N., Smirnova E.V., Kurganova E.A., Ekimova I.D., Lebedeva N.V., Koshel' S.G., Plahtinskiy V.V. Intensifikaciya processa okisleniya izopropilbenzola // Kataliz v promyshlennosti. 2010. № 3. S. 26-29.
15. Frolov A.S. Gidroperoksidnyy metod polucheniya ksilenolov sovmestno s acetonom: dis. … kand. him. nauk. Yaroslavl'. 2016. 124 s.
16. Yarkina E.M., Kurganova E.A., Frolov A.S., Koshel' G.N., Nesterova T.N., Shakun V.A., Spiridonov S.A. Sintez para-tret-butilkumola // Tonkie himicheskie tehnologii. 2020. T. 16, № 1. S. 26-35. URL: https://doi.org/10.32362/2410-6593-2021-16-1-26-35
17. Kabanova V.S., Frolov A.S., Kurganova E.A., Sapunov V.N., Koshel' G.N., Baev E.I. Issledovanie kineticheskih zakonomernostey processa zhidkofaznogo okisleniya vtor-butilbenzola v prisutstvii N-gidroksiftalimida // Kataliz v promyshlennosti. 2024. T. 24, № 3. S. 39-49. URL: https://doi.org/10.18412/1816-0387-2024-3-39-49
18. Fieser L.F., Fieser M. Reagents for Organic Synthtsis. Wiley: New York, 1967. 1457 p.
19. Frolov A.S., Kurganova E.A., Koshel’ G.N. Nesterova T.N. Liquid-phase oxidation of isopropyl-meta-xylene to tertiary hydroperoxide // European Journal of Analytical and Applied Chemistry. 2015. Vol. 1. P. 16-22. URL: https://doi.org/10.1134/s1070427214070088
20. Antonovskiy V.L., Buzlanova M.M. Analiticheskaya himiya organicheskih peroksidnyh soedineniy. M: Himiya, 1978. 309 s.
21. Koshel' G.N., Solov'ev M.E., Kurganova E.A., Rumyanceva Yu.B., Frolov A.S. Kvantovo-himicheskiy analiz termodinamiki reakcii okisleniya uglevodorodov v prisutstvii N-gidroksiftalimida // Vestnik Kazanskogo tehnologicheskogo universiteta. 2013. T. 16, № 2. S. 302-304.
22. Yufei Yang, Jieyi Ma, Junyan Wu, Weixia Zhu, Yadong Zhang. Experimental and theoretical study on N hydroxyphthalimide and its derivatives catalyzed aerobic oxidation of cyclohexylbenzene // Chinese Journal of Chemical Engineering. 2022. Vol. 44, no. 1. P. 124-130. URL: https://doi.org/10.1016/j.cjche.2021.06.017
23. Novikova K.V., Kompanets M.O., Kushch O.V., Kobzev S.P. Substituted N-hydroxyphthalimides as oxidation catalysts // Reaction Kinetics and Catalysis Letters. 2011. Vol. 103, no. 1. P. 31-40. URL: https://doi.org/10.1007/s11144-011-0289-0
24. MOPAC 2016: [sayt]. URL: http://openmopac.net/MOPAC2016.html .
25. Pat. № 2186767 RF. Sposob polucheniya gidroperoksidov / Macui S., Kuroda H., Hirokane N., Makio H., Takai T., Kato K., Fudzita T., Kamimura Makoto. Opubl. 2002.
26. Matsui S., Fujita T. New cumene-oxidation systems: O2 activator effects and radical stabilizer effects // Catalysis Today. 2001. Vol. 71. P. 145-152.
