ОБРАЗОВАНИЕ КАРВАКРОЛА В ХОДЕ ГИДРИРОВАНИЯ КАРВОНА НА Au/Al2O3
Ключевые слова:
каталитическая активность, селективность, нанесенные золотые катализато-ры, карвон, карвакрол, карвоментон, карватанацетон, карвеол, дигидрокарвон
Аннотация
Исследовано жидкофазное гидрирование карвона до карвакрола с использованием катализатора Au/Al2O3 в температурном интервале от 273-323К и давлении до 30 атмо-сфер. Карвон, обладающий тремя различными функциональными группами, является слож-ным объектом для селективного гидрирования, эндо- и экзо- >С=С<-связи и карбонильная группа обладают различной реакционной способностью. Целью исследования являлось увели-чение селективности по карвакролу -химиопротекторному агенту, использующегося в про-тивоопухолевых фармацевтических композициях. Установлены рекомендуемые условия гид-рирования карвона до карвакрола – растворитель толуол, температура 305 К и давление 20 атмосфер. Показано, что селективность по карвакролу под давлением 20 атмосфер дости-гает 42%. Результаты демонстрируют потенциал применения катализатора Au/Al2O3 для эффективного и селективного гидрирования карвона в промышленности. Настоящее иссле-дование может стать основой для разработки новых технологий получения карвакрола с высокими селективностью и выходом, что имеет важное значение для повышения эффек-тивности и устойчивости химических процессов в различных отраслях промышленности.
Литература
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25. Retajczyk M., Wróblewska A. The Isomerization of Lim-onene over the Ti-SBA-15 Catalyst The Influence of Reac-tion Time Temperature
2. Bernas H., Simakova I., Mäki-Arvela P., Prosvirin I., Leino R., Murzin D.Yu. Hydrogenation of citral over carbon support-ed iridium catalysts. Catalysis Letters. 2012. V. 142. P. 690-697. https://doi.org/10.1007/s10562-012-0809-1
3. Deliy I.V., Danilova I.G., Simakova I.L., Zaccheria F., Ravasio N., Psaro R. Chemical Industries. V. 123. Cataly-sis of Organic Reactions / Ed. Prunier, M.L. Boca Raton, USA. 2009. P. 87-92.
4. Mäki-Arvela P., Kuusisto J., Mateos Sevilla E., Simakova I.L., Mikkola J.-P., Myllyoja J., Salmi T., Murzin D.Yu. Catalytic hydrogenation of linoleic acid to stearic acid over various supported Pd and Ru catalysts. Ap-plied Catalysis A: General. 2008. V. 345. N 2. P. 201-212. 5. Simonov M.N., Simakova I.L., Parmon V.N. Hydrogena-tion of lactic acid to propylene glycol over copper-containing catalysts. Reaction Kinetics and Catalysis Let-ters. 2009. V. 97. N 1. P. 157-162.
6. Lefedova O.V., Nemtzeva M.P. Effect of solvent composi-tion on the rate and selectivity of 2-nitro-2'-hydroxy-5'-methylazobenzene hydrogenation on promoted nickel cata-lysts. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2025. Т. 68. N 5. С. 101-111. https:/ /doi.org/10.6060/ivkkt.20256805.7116 (in Russian)7. Bicas J.L., Dionísio A.P., Pastore G.M. Bio-oxidation of terpenes: an approach for the flavor industry. Chem. Rev. 2009. V. 109. N 9. P. 4518-4531. https://doi.org/10.1021/ /cr800190y
8. Schmidt E., Wanner J. Adulteration of essential oils. In: Handbook of essential oils: Science, Technology and Ap-plication. 3rd Ed. Edited by K.H. Can Baser, G. Buchbauer. USA, Boca Raton, CRC Press, 2020. P. 543-580.
9. Demidova Y.S., Suslov E.V., Simakova O.A., Volcho K.P., Salakhutdinov N.F., Simakova I.L., & Murzin D.Y. Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis. J. Mol. Catal. A: Chem. 2016. V. 420. P. 142-148. https:/ /doi.org/10.1016/j.molcata. 2016.04.013
10. Murzin D.Yu., Simakova I.L. Catalysis in biomass pro-cessing. Catalysis in industry. 2011. N 3. P. 8-40.
11. Yakovleva M.P., Khasanova E.F., Talipov R.F., Ishmuratov G.Yu. Monoterpenoids in the synthesis of op-tically active insect pheromones. Bulletin of Bashkir Uni-versity. 2009. V 14 N 3-1. P. 1072-1098. (in Russian)
12. Ishmuratov G.Yu., Yakovleva M.P., Valeeva E.F., Vydrina V.A., Tolstikov G.A. Monoterpene ketones in the synthesis of optically active insect pheromones. Chemistry of plant raw materials. 2011. V. 2. P. 5-26. (in Russian)
13. Fahlbusch K.-G., Hammerschmidt F.-J., Panten J., Pickenhagen W., Schatkowski D., Bauer K., Surburg H. Flavors and fragrances Ullmann’s Encyclopedia of Industri-al Chemistry. Wiley-VCH Verlag GmbH & Co KGaA, Weinheim. 2003. V. 15. P. 73-198.
14. Ishmuratov G.Y., Yakovleva M.P., Valeeva E.F., Vydrina V.A., Tolstikov G.A. Monoterpene ketones in the synthesis of optically active insect pheromones. Russian Journal of Bioorganic Chemistry. 2012. V. 38. P. 667-688.
15. Volcho K.P., Rogoza L.N., Salakhutdinov N.F., Tolstikov G.A. Preparative chemistry of terpenoids: In 5 parts. Part 2. Monocyclic monoterpenoids: limonene, carvone and their derivatives. Novosibirsk: ART-AVENU, 2008. 231 p. (in Russian)
16. Montero G.E.R., Stassi J.P., de Miguel S.R., Zgolicz P.D. Hydrogenation of Citral and Carvone on Pt-Based Support-ed Metallic Catalysts. A Comparative Study on the Regioselectivity and Chemoselectivity. React. Chem.& Eng. 2023. V. 8. N 12. Р. 3133-3149. https://doi.org/ 10.1039/ /D3RE00259D 17. Benavente P., Cárdenas-Lizana F., Keane M.A. Selective Production of Carvacrol from Carvone over Supported Pd Catalysts. Cat. Comm. 2017. V. 96. P. 37-40. https://doi. org/ 10.1016/j.catcom.2017.03.026
18. Bhatia S.P., McGinty D., Letizia C.S., Api A.M. Fra-grance material review of carveol. Food Chem. Toxicol. 2008. V. 46. N 11. P. S85-S87. https://doi.org/ 10.1016/ j.fct.2008.06.074
19. Klabunovsky E.I., Godunova L.F., Maslova L.K. On the catalytic hydrogenation of (+)-carvone on palladium and platinum catalysts. Bulletin of the USSR Academy of Sci-ences, Chemical Series. 1972. V. 5. P. 1063-1068.
20. Yuan Y., Yao S., Wang M., Lou S., Yan N. Recent pro-gress in chemoselective hydrogenation of α, β-unsaturated aldehyde to unsaturated alcohol over nanomaterials. Curr. Org. Chem. 17 (2013) 400-413. 21. Petrier C., Luche J.-L. Ultrasonically improved reductive properties of an aqueous Zn-NiCl2 system-2. Regiose-lectivity in the reduction of (−)-carvone. Tetrahedron lett. 1987. V. 28. N 21. P. 2351-2352. https://doi.org/10.1016/ S0040-4039(00)96120-322. Lefedova O.V., Nemtseva M.P. Rate and selectivity of hydrogenation of 2-nitro-2'-hydroxy-5'-methylazobenzene on a nickel catalyst in aqueous solutions of aliphatic alco-hols. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2024. V. 67. N 3. P. 53-62. (in Russian)
23. Bond G.C. The Chemisorption of Hydrocarbons, in: Metal-Catalysed Reactions of Hydrocarbons, Springer, Boston, MA, 2005. Р. 153-207.
24. Keane M.A., Patterson P.M. The Role of Hydrogen Partial Pressure in the Gas-Phase Hydrogenation of Aromatics over Supported Nickel// Ind. Eng. Chem. Res. 1999. V. 38. P. 1295-1305.
25. Retajczyk M., Wróblewska A. The Isomerization of Lim-onene over the Ti-SBA-15 Catalyst The Influence of Reac-tion Time Temperature
Опубликован
2026-04-08
Как цитировать
Осадчая, Т., Афинеевский, А., & Никитин, К. (2026). ОБРАЗОВАНИЕ КАРВАКРОЛА В ХОДЕ ГИДРИРОВАНИЯ КАРВОНА НА Au/Al2O3. Современные наукоёмкие технологии. Региональное приложение, 1(85), 158-164. извлечено от https://snt-isuct.ru/article/view/7209
Выпуск
Раздел
Инженерно-технически науки, машиностроение и технологии
