Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl State Technical University
Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
graduate student
Yaroslavl, Yaroslavl, Russian Federation
UDC 547.572.1
During the research, by alkylation of benzene with hexanol-1 the mixture consisting of 60-65% 2-phenylhexane and 35-40% 3-phenylhexane was synthesised. The paper explores the promising but understudied process of this mixture aerobic liquid phase oxidation to corresponding hydroperoxides for further obtaining of higher ketones. As a result, the use of N-hydroxyphthalimide at this stage allows us to achieve technological conditions for mixture industrial implementation. The conversion of the phenylhexane mixture is more than 30% within 60 minutes of reaction with high selectivity of hydroperoxide formation.
Alkylation, oxidation, 2 phenylhexane, 3 phenylhexane
1. Balakrishnan M., Arab G.E., Kunbargi O.B., Gokhale A.A., Grippo A.M., Toste F.D., Bell A.T. Production of renewable lubricants via self-condensation of methyl ketones. Green Chem., 2016, 18(12), 3577-3581. DOI:https://doi.org/10.1039/C6GC00579A.
2. Lopaschuk G.D., Dyck J.R. Ketones and the cardiovascular system. Nat. Cardiovasc. Res., 2023, 2(5), 425-437. DOI:https://doi.org/10.1038/s44161-023-00259-1. EDN: https://elibrary.ru/YBNJEJ
3. Albarracín Orio A.G., Petras D., Tobares R.A., Aksenov A.A., Wang M., Juncosa F., Sayago P., Moyano A.J., Dorrestein P.C., Smania A.M. Fungal-bacterial interaction selects for quorum sensing mutants with increased production of natural antifungal compounds. Commun. Biol., 2020, 3(1), 670. DOI:https://doi.org/10.1038/s42003-020-01342-0. EDN: https://elibrary.ru/BYZKJV
4. Gehrig R.F., Knight S.G. Formation of ketones from fatty acids by spores of Penicillium roqueforti. Nature, 1958, 182(4644), 1237-1237. DOI:https://doi.org/10.1038/1821237a0.
5. Friedman O.A. Plasticisation of cellulose acetate. Izvestiya VUZov. Chemistry and chemical technology, 2010, 53(3), 82-86 (in Russian). EDN: https://elibrary.ru/OMQSSV
6. Tambovtsev K.A., Yakovleva M.P., Ishmuratova N.M. Synthetic pheromone preparations in beekeeping. Bulletin of the Bashkir University, 2010, 15(2), 265-281 (in Russian). EDN: https://elibrary.ru/MSUBYJ
7. Karakhanov E. A., Narin S. Yu., Filippova T. Yu., Dedov A. G. Pat. SU 1409621 A1, 1988.
8. Ulybin V.B., Efremov S.V., Romantsova O.V. Comparative analysis of various methods for producing hydrogen peroxide. Global energy, 2012, 3-2(154), 267-272 (in Russian). EDN: https://elibrary.ru/PESLKV
9. Knochel P., Molander G.A Comprehensive Organic Synthesis: Second Edition. Elsevier, 2014, 9806 p.
10. Elschenbroich C. Organometallics. Wiley-VCH: Weinheim, 2006, 804 p.
11. Stolyarov V.A. New handbook of chemist and technologist. Raw materials and industrial products of organic and inorganic substances. Part II. St. Petersburg: ANO NPO "Professional", 2005, 1141 p. (in Russian).
12. Rodikova Yu.A., Zhizhina E.G. Catalytic methods for obtaining higher 2-ketones: prospects of the Wacker system in the oxidation reaction of α-olefins. Kin. and cat., 2023, 64(2), 121-138 (in Russian). DOI: https://doi.org/10.31857/S0453881123020065; EDN: https://elibrary.ru/GNRGKD
13. Gogin L.L., Rodikova Yu.A., Zhizhina E.G. Patent of the Russian Federation 2790246 C1, 2023.
14. Shioyama T.K. Pat. USA 4507506, 1985.
15. Alper H., Januszkiewicz K., Smith D.J.H. A facile method for the amination of alkenes and other related reactions catalyzed by aluminum chloride. Tetrahedron Lett., 1985, 26(19), 2263-2266. DOI: https://doi.org/10.1016/S0040-4039(00)95069-X
16. Maksimov A.L., Buchneva T.S., Karakhanov E.A. Oxidation of olefins to ketones, catalyzed by a water-soluble palladium complex with calyx[4]arene modified with benzonitrile groups. Neftekhimia, 2003, 43(3), 173-178 (in Russian).
17. Michel B.W., Sigman M.S. Peroxide-Mediated Wacker Oxidations for Organic Synthesis. Aldrichimica Acta, 2011, 44(3), 55-62.
18. Lai L., Pang H.W., Green W.H. Formation of two-ring aromatics in hexylbenzene pyrolysis. Energy Fuel, 2020, 34(2), 1365-1377. DOI:https://doi.org/10.1021/acs.energyfuels.9b03223. EDN: https://elibrary.ru/TQIAQW
19. Yarkina E.M., Kurganova E.A., Frolov A.S., Koshel G.N., Nesterova T.N., Shakun V.A., Spiridonov S.A. Synthesis of para-tert-butylcumol. Fine chemical technologies, 2021, 16(1), 26-35. DOI: https://doi.org/10.32362/2410-6593-2020-16-1-26-35; EDN: https://elibrary.ru/NALYVK
20. Kabanova V.S., Kurganova E.A., Frolov A.S., Plakhtinsky V.V., Shakun V.A. Forecasting of catalytic activity of phthalimide compounds in the process of liquid-phase aerobic oxidation of alkylaromatic hydrocarbons. From Chemistry Towards Technology Step-by-Step, 2024, 5(2), 8-16. DOI:https://doi.org/10.52957/2782-1900-2024-5-2-8-16 (in Russian). EDN: https://elibrary.ru/KIUKGS
21. Antonovsky V.L., Buzlanova M.M. Analytical chemistry of organic peroxide compounds. M.: Khimiya [Chemistry], 1978. 309 p. (in Russian).
22. Fox M.A., Whitesell J.K. Organic Chemistry. Sudbury, Mass.: Jones and Bartlett Publishers, 2003, 1140 p.
23. Song C.E., Shim W.H., Roh E.J., Choi J.H. Scandium(III) triflate immobilised in ionic liquids: a novel and recyclable catalytic system for Friedel-Crafts alkylation of aromatic compounds with alkenes. Chem. Commun., 2000, 17, 1695-1696. DOI:https://doi.org/10.1039/b005335j. EDN: https://elibrary.ru/AUKEAZ
24. Nel R.J., de Klerk A. Selectivity differences of hexene isomers in the alkylation of benzene over solid phosphoric acid. Ind. Eng. Chem. Res., 2007, 46(9), 2902-2906. DOI:https://doi.org/10.1021/ie061545q. EDN: https://elibrary.ru/XVAMUA
25. Bykov V.I., Belyaev B.A. A new method for preparing alkylation catalysts based on heterogenised AlCl3. Kin. and Cat., 2021, 62(2), 277-280 (in Russian). DOI: https://doi.org/10.31857/S0453881121020027; EDN: https://elibrary.ru/JYGANN
26. Danilina N., Payrer E.L., Troussard E., van Bokhoven J.A. Selective Production of 2-Phenylhexane from Benzene and n-Hexane Over Pt- and Ga-Modified Zeolites. Catal. Lett., 2011, 141(3), 391-399. DOI:https://doi.org/10.1007/s10562-010-0511-0.
27. Alfa Aesar Research Chemical Metals and Materials. A Johnson Matthey Company, 2008, 2741 p.
28. Kurganova E.A., Baev E.I., Kabanova V.S., Frolov A.S., Koshel G.N., Smurova A.A. Catalysts for the oxidation of N-hydroxyphthalimide and its analogues. Neftegaz.ru, 2024, 5, 22-31 (in Russian). EDN: https://elibrary.ru/RHLOBO




