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A Comparative Analysis of Vanadyl Porphyrins Isolated from Heavy Oil Asphaltenes with High and Low Vanadium Content

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Abstract

The paper describes an investigation of the composition of purified vanadyl porphyrins recovered from heavy oil asphaltenes. For this purpose, high-vanadium crude oils from the Smorodinskoye field, Russia, were compared with low-vanadium crude oils from the Varadero field, Cuba. Based on the comparison of the FT-IR spectra of the asphaltenes, the distinctive features of their structural-group composition were identified. The vanadium content in the Smorodinskoye heavy oil asphaltenes was demonstrated to be 19-fold higher than that in the Varadero heavy oil asphaltenes. To recover and purify vanadyl porphyrins from the asphaltenes, extraction with N,N-dimethylformamide (DMF) followed by two-step column chromatography on silica gel and sulfocationite was employed. The compositions of the vanadyl porphyrin concentrates extracted from the heavy oil asphaltenes differing in vanadium content were identified using MALDI mass spectrometry, FT-IR spectroscopy, and UV-Visible spectroscopy.

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REFERENCES

  1. Speight, J.G., Heavy Oil Recovery and Upgrading, Houston, Texas, USA: Gulf Professional Publishing, 2019.

  2. Serebrennikova, O.V., Filippova, T.Yu., and Krasnoyarova, N.A., Petrol. Chem., 2003, vol. 43, no. 3, pp. 145–149.

    Google Scholar 

  3. Izmailova, D.Z., Serebrennikov, V.M., Mozzhelina, T.K., and Serebrennikova, O.V., Petrol. Chem., 1996, vol. 36, no. 1, pp. 111–117.

    Google Scholar 

  4. Zhao, X., Xu, C., and Shi, Q., Structure and Modeling of Complex Petroleum Mixtures, Berlin: Springer International Publishing, 2015, pp. 39−70. https://doi.org/10.1007/430_2015_189

  5. Huang, H., Song, W., Rieffel, J., and Lovell, J.F., Front. Phys., 2015, vol. 3. Article 23. https://doi.org/10.3389/fphy.2015.00023

  6. Ali, M.F., Perzanowski, H., Bukhari, A., and Al-Haji, A.A., Energy Fuels, 1993, vol. 7, pp. 179–184. https://doi.org/10.1021/ef00038a003

    Article  CAS  Google Scholar 

  7. Zheng, F., Zhu, G., Chen, Z., Zhao, Q., and Shi, Q., J. Fuel Chem. Technol., 2020, vol. 48, no. 5, pp. 562–567. https://doi.org/10.1016/s1872-5813(20)30023-2

    Article  CAS  Google Scholar 

  8. Isaji, Y., Kawahata, H., Takano, Y., Ogawa, N.O., Kuroda, J., Yoshimura, T., Lugli, S., Manzi, V., Roveri, M., and Diazotrophy, N.O., Front. Earth Sci., 2019, vol. 7. Article 85. https://doi.org/10.3389/feart.2019.00085

  9. Barona-Castano, J.C., Carmona-Vargas, C.C., Brocksom, T.J., and de Oliveira, K.T., Molecules, 2016, vol. 21, pp. 310. https://doi.org/10.3390/molecules21030310

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Che, Ch.-M. and Huang, J.-S., Chem. Commun., 2009, vol. 27, pp. 3996–4015. https://doi.org/10.1039/B901221D

    Article  Google Scholar 

  11. Nakagaki, S., Ferreira, G., and Ucoski, G., Molecules, 2013, vol. 18, pp. 7279–7308. https://doi.org/10.3390/molecules18067279

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Zhang, J-L. and Che, Ch.-M., Org. Lett., 2002, vol. 4, no.11, pp. 1911–1914. https://doi.org/10.1021/ol0259138

    Article  CAS  PubMed  Google Scholar 

  13. Li, L.L. and Diau, E.W.G., Chem. Soc. Rev., 2013, vol. 42, pp. 291–304. https://doi.org/10.1039/C2CS35257E

    Article  CAS  PubMed  Google Scholar 

  14. Huang, H., Song, W., Rieffel, J., and Lovell, J.F., Front. Phys., 2015, vol. 3. Article 23. https://doi.org/10.3389/fphy.2015.00023

  15. Caron, S., Dugger, R.W., Ruggeri, S.G., Ragan, J.A., and Brown Ripin, D.H., Chem. Rev., 2006, vol. 106, pp. 2943–2989. https://doi.org/10.1021/cr040679f

    Article  CAS  PubMed  Google Scholar 

  16. Srour, H., Jalkh, J., le Maux, P., Chevance, S., Kobeissi, M., and Simonneaux, G., J. Mol. Catal. A: Chem., 2013, vol. 370, pp. 75–79. https://doi.org/10.1016/j.molcata.2012.12.016

    Article  CAS  Google Scholar 

  17. Mironov, N.A., Milordov, D.V., Abilova, G.R., Yakubova, S.G., and Yakubova, M.R., Petrol. Chem., 2019, vol. 59, no. 10, pp. 1077–1091. https://doi.org/10.1134/S0965544119100074

    Article  CAS  Google Scholar 

  18. Rytting, B.M., Singh, I.D., Kilpatrick, P.K., Harper, M.R., Mennito, A.S., and Zhang, Y., Energy Fuels, 2018, vol. 32, no. 5, pp. 5711–5724. https://doi.org/10.1021/acs.energyfuels.7b03358

    Article  CAS  Google Scholar 

  19. Milordov, D.V., Mironov, N.A., Abilova, G.R., Tazeeva, E.G., Yakubova, S.G., and Yakubov, M.R., Katal. Khim. Neftekhim. Prom–ti, 2020, vol. 20, no. 5, pp. 352–358 https://doi.org/10.18412/1816-0387-2020-5-352-358

    Article  CAS  Google Scholar 

  20. Mironov, N.A., Sinyashin, K.O., Abilova, G.R., Tazeeva, E.G., Milordov, D.V., Yakubova, S.G., Borisov, D.N., Gryaznov, P.I., Borisova, Yu.Yu., and Yakubov, M.R., Russ. Chem. Bull., Int. Ed., 2017, vol. 66, no. 8, pp. 1450–1455. https://doi.org/10.1007/s11172-017-1907-4

    Article  CAS  Google Scholar 

  21. Mironov, N.A., Abilova, G.R., Sinyashin, K.O., Gryaznov, P.I., Borisova, Y.Y., Milordov, D.V., Tazeeva, E.G., Yakubova, S.G., Borisov, D.N., and Yakubov, M.R., Energy Fuels, 2018, vol. 32, pp. 161–168. https://doi.org/10.1021/acs.energyfuels.7b02816

    Article  CAS  Google Scholar 

  22. Mironov, N.A., Milordov, D.V., Tazeeva, E.G., Abilova, G.R., Tazeev, D.I., Morozov, V.I., Yakubova, S.G., and Yakubov, M.R., Russ. J. Appl. Chem., 2020, vol. 93, no. 6, pp. 888–896 https://doi.org/10.1134/S1070427220060166

    Article  CAS  Google Scholar 

  23. Yakubov, M.R., Gryaznov, P.I., Yakubova, S.G., Tazeeva, E.G., Mironov, N.A., and Milordov, D.V., Petrol. Sci. Technol., 2016, vol. 34, no. 22, pp. 1805–1811. https://doi.org/

    Article  CAS  Google Scholar 

  24. 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, vol. 34, no. 2, pp. 177–183. https://doi.org/10.1080/10916466.2015.1122627

    Article  CAS  Google Scholar 

  25. 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

    Article  CAS  Google Scholar 

  26. Yakubova, S.G., Abilova, G.R., Tazeeva, E.G., Borisova, Yu.Yu., and Yakubov, M.R., Chem. Technol. Fuels and Oils, 2017, vol. 53, no. 6, pp. 862–868. https://doi.org/10.1007/s10553-018-0873-3

    Article  CAS  Google Scholar 

  27. Dolphin, D., The Porphyrins V1: Structure and Synthesis. Part A, Elsevier, 2012, p. 664.

  28. Doukkali, A., Saoiabi, A., Zrineh, A., Hamad, M., Ferhat, M., Barbe, J.M., and Guilard, R., Fuel, 2002, vol. 81, pp. 467–472. https://doi.org/10.1016/s0016-2361(01)00182-x

    Article  CAS  Google Scholar 

  29. Gao, Y.-Y., Shen, B.-X., and Liu, J.-C., Energy Sources, Part A, 2012, vol. 34, no. 24, pp. 2260–2267. https://doi.org/10.1080/15567036.2011.584126

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are grateful to the researchers of the Multiple-Access Spectro-Analytical Center for Physical-Chemical Study of Structure, Properties and Composition of Substances and Materials, KazSC RAS, for their kind cooperation in the examinations conducted for the study.

Funding

The study described here was performed with financial support from the Russian Science Foundation (RSF Grant no. 19-13-00089).

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, Russia

    S. G. Yakubova, G. R. Abilova, E. G. Tazeeva, D. I. Tazeev, N. A. Mironov, D. V. Milordov & M. R. Yakubov

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  1. S. G. Yakubova
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  2. G. R. Abilova
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  3. E. G. Tazeeva
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  4. D. I. Tazeev
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  5. N. A. Mironov
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  6. D. V. Milordov
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  7. M. R. Yakubov
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Correspondence to S. G. Yakubova.

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Yakubova, S.G., Abilova, G.R., Tazeeva, E.G. et al. A Comparative Analysis of Vanadyl Porphyrins Isolated from Heavy Oil Asphaltenes with High and Low Vanadium Content. Pet. Chem. 62, 83–93 (2022). https://doi.org/10.1134/S0965544122010030

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  • DOI: https://doi.org/10.1134/S0965544122010030

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