Abstract
High-vanadium heavy oil asphaltenes were fractionated by a sequential precipitation method. Using FT-IR spectroscopy, elemental analysis, and optical spectroscopy, the differences in the compositions of the asphaltene fractions were thoroughly investigated. To isolate and purify vanadyl porphyrins (VPs) from the asphaltenes, extraction with N,N-dimethylformamide (DMF) followed by two-step column chromatography on silica gel and sulfocationite was employed. The effects of VPs on the solubility of the asphaltene fractions were evaluated based on optical density variations in the solvent/precipitant system in a kinetic mode. It was found that, in most cases, adding petroleum VPs to toluene solutions of asphaltene fractions decreases the solubility of these fractions. The highest effect of VPs on the solubility of the asphaltene fractions was observed for samples with a high concentration of polar heteroatom groups and low aromaticity.
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REFERENCES
Mitchell, D.L. and Speight, J.G., Fuel, 1973, vol. 52, p. 149. https://doi.org/10.1016/0016-2361(73)90040-9
Miller, J.T., Fisher, R.B., Thiyagarajan, P., Winans, R.E., and Hunt, J.E., Energy Fuels, 1998, vol. 12, pp. 1290–1298. https://doi.org/10.1021/ef9800664
Kohli, K., Prajapati, R., Maity, S.K., Sau, M., and Garg, M.O., Fuel, 2016, vol. 175, pp. 264–273. https://doi.org/10.1016/j.fuel.2016.02.036
Stark, J.L. and Asomaning, S., Pet. Sci. Technol., 2003, vol. 21, pp. 569– 579. https://doi.org/10.1081/LFT-120018539
Wiehe, I.A., Kennedy, R.J., and Dickakian, G., Energy Fuels, 2001, vol. 15, pp. 1057– 1058. https://doi.org/10.1021/ef010063i
Spiecker, P., Gawrys, K.L., and Kilpatrick, P.K., J. Colloid. Interface Sci., 2003, vol. 267, pp. 178–193. https://doi.org/10.1016/S0021-9797(03)00641-6
da Silva Ramos, A.C., Rolemberg, M.P., de Moura, L.G.M., Zilio, E.L., dos Santos, M.D.F.P., and González, G., J. Petrol. Sci. Eng., 2013, vol. 102, pp. 36–40. https://doi.org/10.1016/j.petrol.2013.01.008
Álvarez, P., Menendez, J.L., Berrueco, C., Rostani, K., and Millan, M., Fuel Proc. Technol., 2012, vol. 96, pp. 16–21. https://doi.org/10.1016/j.fuproc.2011.12.007
Mamin, G.V., Gafurov M, R., Yusupov, R.V., Gracheva, I.N., Ganeeva, Y.M., Yusupova, T.N., and Orlinskii, S.B., Energy Fuels, 2016, vol. 30, pp. 6942–6946. https://doi.org/10.1021/acs.energyfuels.6b00983
Trukhan, S.N., Kazarian, S.G., and Martyanov, O.N., Energy Fuels, 2017, vol. 31, pp. 387–394. https://doi.org/10.1021/acs.energyfuels.6b02572
Evdokimov, I.N., Eliseev, N.Y., and Akhmetov, B.R., J. Petrol. Sci. Eng., 2003, vol. 37, pp. 135–143. https://doi.org/10.1016/S0920-4105(02)00350-9
Evdokimov, I.N., Fesan, A.A., and Losev, A.P., Energy Fuels, 2017, vol. 31, pp. 3878–3884. https://doi.org/10.1021/acs.energyfuels.7b00114
Gawrys, K.L., Blankenship, G.A., and Kilpatrick, P.K., Langmuir, 2006, vol. 22, pp. 4487–4497. https://doi.org/10.1021/la052509j
Yang, Y., Chaisoontornyotin, W., and Hoepfner, M.P., Langmuir, 2018, vol. 34, pp. 10371–10380. https://doi.org/10.1021/acs.langmuir.8b01873
Chacón-Patiño, M.L., Moulian, R., Barrère-Mangote, C., Putman, J.C., Weisbrod, C.R., Blakney, G.T., Bouyssiere, B., Rodgers, R., and Giusti, P., Energy Fuels, 2020, vol. 34, pp. 16158–16172. https://doi.org/10.1021/acs.energyfuels.0c03349
Rogel, E., Ovalles, C., Moir, M., and Schabron, J.F., Energy Fuels, 2009, vol. 23, pp. 4515–4521. https://doi.org/10.1021/ef900358q
Zhang, Y., Siskin, M., Gray, M.R., Walters, C.C., and Rodgers, R.P., Energy Fuels, 2020, vol. 34, pp. 9094–9107. https://doi.org/10.1021/acs.energyfuels.0c01564
Prakoso, A., Punase, A., Rogel, E., Ovalles, C., and Hascakir, B., Energy Fuels, 2018, vol. 32, pp. 6482–6487. https://doi.org/10.1021/acs.energyfuels.8b00324
Chacón-Patiño, M.L., Smith, D.F., Hendrickson, C.L., Marshall, A.G., and Rodgers, R.P., Energy Fuels, 2020, vol. 34, pp. 3013–3030. https://doi.org/10.1021/acs.energyfuels.9b04288
Mullins, O.C., Energy Fuels, 2010, vol. 24, pp. 2179–2207. https://doi.org/10.1021/ef900975e
Dechaine, G.P. and Gray, M.R., Energy Fuels, 2010, vol. 24, pp. 2795–2808. https://doi.org/10.1021/ef100173j
Branthaver, J.F., ACS Sym. Ser., 1987, vol. 344, pp. 188–204. https://doi.org/10.1021/bk-1987-0344.ch012
Bryers, R.W., Fuel Proc. Technol., 1995, vol. 44, pp. 121–141. https://doi.org/10.1016/0378-3820(94)00118-D
Zhao, X., Xu, C., and Shi, Q., Struct. Model. Compl. Petrol. Mixtures, 2015, vol. 119, pp. 39–70. https://doi.org/10.1007/430_2015_189
Zhao, X., Liu, Y., Xu, C., Yan, Y., Zhang, Y., Zhang, Q., Zhao, S., Chung, K., Gray, M.R., and Shi, Q., Energy Fuels, 2013, vol. 27, pp. 2874–2882. https://doi.org/10.1021/ef400161p
Yakubov, M.R., Milordov, D.V., Yakubova, S.G., Borisov, D.N., Gryaznov, P.I., Mironov, N.A., Abilova, G.R., Borisova, Y.Y., and Tazeeva, E.G., Petrol. Sci. Technol., 2016. 34, pp. 177–183. https://doi.org/10.1080/10916466.2015.1122627
Mironov, N.A., Abilova, G.R., Sinyashin, K.O., Gryaznov, P.I., Borisova, Y.Y., Milordov, D.V., Tazeeva, E.G., Yakubova, S.G., and Yakubov, M.R., Energy Fuels, 2018, vol. 32, pp. 161–168. https://doi.org/10.1021/acs.energyfuels.7b02816
Mironov, N.A., Milordov, D.V., Abilova, G., Tazeeva, E.G., Yakubova, S.G., and Yakubov, M.R., J. Porphyrin. Phthalocyan., 2020, vol. 24, pp. 528–537. https://doi.org/10.1142/S1088424619501979
Yakubov, M.R., Abilova, G.R., Sinyashin, K.O., Milordov, D.V., Tazeeva, E.G., Yakubova, S.G., Borisov, D.N., Gryaznov, P.I., Mironov, N.A., and Borisova, Y.Y., Energy Fuels, 2016, vol. 30, pp. 8997–9002. https://doi.org/10.1021/acs.energyfuels.6b01503
Borisova, Y.Y., Tazeeva, E.G., Mironov, N.A., Borisov, D.N., Yakubova, S.G., Abilova, G.R., Sinyashin, K.O., and Yakubov, M.R., Energy Fuels, 2017, vol. 31, pp. 13382–13391. https://doi.org/10.1021/acs.energyfuels.7b02544
Rytting, B.M., Harper, M.R., Edmond, K.V., Zhang, Y., and Kilpatrick, P.K., Energy Fuels, 2019, vol. 34, pp. 164–178. https://doi.org/10.1021/acs.energyfuels.9b03237
Taherian, Z., Dehaghani, A.S., Ayatollahi, S., and Kharrat, R., J. Petrol. Sci. Eng., 2021, vol. 205, p. 108824. https://doi.org/10.1016/j.petrol.2021.108824
Yakubova, S.G., Abilova, G.R., Tazeeva, E.G., Borisova, Yu.Yu., and Yakubov, M.R., Chem. Technol. Fuel. Oils, 2017, vol. 53. № 6, pp. 862–868. https://doi.org/10.1007/s10553-018-0873-3
Buenrostro-Gonzalez, E., Groenzin, H., LiraGaleana, C., and Mullins, O.C., Energy Fuels, 2001, vol. 15, pp. 972–978. https://doi.org/10.1021/ef0100449
Xu, H., Yu, D., and Que, G., Fuel, 2005, vol. 84, pp. 647–652. https://doi.org/10.1016/j.fuel.2004.06.034
Gray, M.R., Tykwinski, R.R., Stryker, J.M., and Tan, X., Energy Fuels, 2011, vol. 25, pp. 3125–3134. https://doi.org/10.1021/ef200654p
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The study described here was performed with financial support from the Russian Science Foundation (RSF Grant no. 19-13-00089).
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Milordov, D.V., Abilova, G.R., Mironov, N.A. et al. A Comparative Analysis of the Solubility of Asphaltene Fractions with Addition of Petroleum Vanadyl Porphyrins. Pet. Chem. 62, 240–249 (2022). https://doi.org/10.1134/S0965544122060123
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DOI: https://doi.org/10.1134/S0965544122060123