Abstract
The paper describes a method developed for the oxidation of organosulfur compounds using organic peroxides generated in situ under the action of atmospheric oxygen on gasoline fraction after reforming. Naphtha reformate that contained dibenzothiophene as a model substrate was subjected to oxidative desulfurization by organic peroxides generated in situ under atmospheric oxygen. The study examined various catalytic systems, including immobilized Anderson-type polyoxometalates, and initiators, which, in combination, provided effective generation of alkyl hydroperoxides, selective oxidation of organosulfur compounds in the hydrocarbon feedstock, and a high conversion rate.
REFERENCES
Petrukhina, N.N. and Vostrikova, Yu.V., Nekotorye aspekty prevrashchenii vysokomolekulyarnyh soedinenii neftei v protsesse okislitel’nogo obesserivaniya (Some Aspects of Conversions of High Molecular Weight Compounds of Oil in the Process of Oxidative Desulfurization), Moscow: RGU Nefti i Gaza im. I.M. Gubkina, 2013, p. 3.
Akopyan, A.V., Fedorov, R.A., Anisimov, A.V., Eseva, E.A., and Karakhanov, E.А., Petrol. Chem., 2017, vol. 57, no. 12, pp. 1132–1136. https://doi.org/10.1134/S0965544117060123
Anisimov, A.V. and Tarakanova, A.V., Russ. J. Gen. Chem., 2009, vol. 79, no. 4, p. 1264. https://doi.org/10.1134/S1070363209060437
Rakhmanov, E.V., Akopyan, A.V., Tarakanova, A.V., Lesin, S.V., Vinokurov, V.A., Glotov, A.P., Movsesyan, A.K., and Anisimov, A.V., Khim. Tekhnol., 2016, vol. 17, no. 11, pp. 31–35.
Akopyan, A.V., Polikarpova, P.D., Anisimov, A.V., Lysenko, S.V., Maslova, O.V., Stepanov, N.A., Sen’ko, O.V., and Efremenko, E.N., Khim. Tekhnol., 2020, vol. 21, no. 6, pp. 242–250. https://doi.org/10.31044/1684-5811-2020-21-6-242-250
Xiaoliang, M. and Anning, Z., Catal. Today, 2007, vol. 123, pp. 276–284. https://doi.org/10.1016/j.cattod.2007.02.036
Zhou, X., Li, J., Wang, X., Jin, K., and Ma, W., Fuel Proc. Technol., 2009, vol. 90, pp. 317–323. https://doi.org/10.1016/j.fuproc.2008.09.002
Rao, T.V., Sain, B., Kafola, S., Nautiyal, B.R., Sharma, Y.K., Nanoti, S.M., and Garg, M.O., Energy Fuels, 2007, vol. 21, pp. 3420–3424. https://doi.org/10.1021/ef700245g
Murata, S., Murata, K., Kidena, K., and Nomura, M., Energy Fuels, 2004, vol. 18, pp. 116–121. https://doi.org/10.1021/ef034001z
Minaev, B.F., Russ. Chem. Rev., 2007, vol. 76, no. 11, pp. 989–1012. https://doi.org/10.1070/RC2007v076n11ABEH003720
Ismagilov, Z., Yashnik, S., Kerzhentsev, M., Parmon, V., Bourane, A., Al-Shahrani, F.M., Hajji, A.A., and Koseoglu, O.R., Catal. Rev.-Sci. Eng., 2011, vol. 53, no. 3, pp. 199–255. https://doi.org/10.1080/01614940.2011.596426
Guo, W., Wang, C., Lin, P., and Lu, X., Appl. Energy, 2011, vol. 88, pp. 175–179. https://doi.org/10.1016/j.apenergy.2010.08.003
Sundararaman, R., Ma, X., and Song, C., Ind. Eng. Chem. Res., 2010, vol. 49, pp. 5561–5568. https://doi.org/10.1021/ie901812r
Potekhin, V.M. and Potekhin, V.V., Osnovy teorii khimicheskikh protsessov tekhnologii organicheskikh veshchestv i neftepererabotki (Fundamentals of the Theory of Chemical Processes, Technology of Organic Substances and Oil Refining), St. Petersburg: Khimizdat, 2005, p. 912.
Wang, C., Liu, Z.,Gao, R., Liu, J., An, S., Zhang, R., and Zhao, J., New J. Chem., 2020. https://doi.org/10.1039/C9NJ06271H
Eseva, E., Akopyan, A., Schepina, A., Anisimov, A., and Maximov, A., Cat. Com., 2021, vol. 149, pp. 106256. https://doi.org/10.1016/j.catcom.2020.106256
Khenkin, А. and Neumann, R., ChemSusChem., 2011, vol. 4, pp. 346–348. https://doi.org/10.1002/cssc.201000402
Polikarpova, P., Akopyan, A., Shigapova, A., Glotov, A., Anisimov, A., and Karakhanov, E., Energy Fuels, 2018, vol. 32, no. 10, pp. 10898–10903. https://doi.org/10.1021/acs.energyfuels.8b02583
Nomiya, K., Takahashi, T., Shirai, T., and Miwa, M., Polyhedron, 1987, vol. 6(2), pp. 213–218. https://doi.org/10.1016/S0277-5387(00)80791-3
Safa, M.A. and Ma, X., Fuel, 2016, vol. 171, pp. 238–246. https://doi.org/10.1016/j.fuel.2015.12.050
Petkevich, T.S., Kovalenko, N.A., and Mitskevich, N.I., Izv. Akad. Nauk BSSR, 1986, no. 5, pp. 20–24.
Nedosenko, A.V. and Chervinskii, K.A., Khim. Prom–t’, 1971, no. 7, pp. 25–26.
Rakhmanov, Je.V., Tarakanova, A.V., Valieva, T.U., Akopyan, A.V., Litvinova, V.V., Maksimov, A.L., Anisimov, A.V., Vakarin, S.V., Semerikova, O.L., and Zaikov, Yu.P., Petrol. Chem., 2014, vol. 54, no. 1, pp. 48–50. https://doi.org/10.1134/S0965544114010101
Li, S., Gao, R., Zhang, R., and Zhao, J., Fuel, 2016, vol. 184, pp. 18–27. https://doi.org/10.1016/j.fuel.2016.06.132
Yang, H., Zhang, Q., Zhang, J., Yang, L., Ma, Z., Wang, L., Li, H., Bai, L., Wei, D., Wang, W., and Chen, H., J. Colloid Int. Sci., 2019, vol. 554, pp. 572–579. https://doi.org/10.1016/j.jcis.2019.07.036
Shi, Y., Liu, G., Zhang, B., and Zhang, X., Green Chem., 2016, vol. 18, pp. 5273–5279. https://doi.org/10.1039/C6GC01357K
Funding
The study described here was performed with financial support from the Russian Foundation for Basic Research (research project no. 20-33-90330\20).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest requiring disclosure in this article.
Additional information
Translated from Neftekhimiya, 2021, Vol. 61, No. 3, pp. 367–379 https://doi.org/10.31857/S0028242121030084.
Rights and permissions
About this article
Cite this article
Eseva, E.A., Akopyan, A.V., Sinikova, N.A. et al. In Situ Generated Organic Peroxides in Oxidative Desulfurization of Naphtha Reformate. Pet. Chem. 61, 472–482 (2021). https://doi.org/10.1134/S0965544121050133
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0965544121050133