Abstract
The review discusses currently relevant methods for studying petroleum resins. A significant proportion of the research work deals with the study of resins in heavy oils, for which experimental approaches have been systematized and the possibilities and limitations of the mass spectrometric, spectroscopic, X-ray, and chromatographic methods have been discussed. Published data on the effect of resins on the stability of asphaltenes in heavy oils and other petroleum stocks has been analyzed. In addition to experimental approaches, an important factor for understanding the role of resins in the aggregation of asphaltenes is studying their intermolecular interactions using quantum-mechanical calculations. Commonly known approaches to the concentration, fractionation, and purification of heteroatomic petroleum components from heavy oil resins using extraction and chromatographic methods for the isolation of chemical compounds from complex multicomponent mixtures have also been considered.
Similar content being viewed by others
REFERENCES
J. G. Speight, Heavy Oil Recovery and Upgrading (Gulf Professional–Elsevier, Oxford, 2013).
R. G. Santos, W. Loh, A. C. Bannwart, and O. V. Trevisan, Braz. J. Chem. Eng. 31, 571 (2014).
G. P. Kurbskii, Geochemistry of Tatarian Oils (Nauka, Moscow, 1987) [in Russian].
G. Márquez and F. J. Alejandre, and M. R. Bencomo, Mater. Constr. 56, 41 (2006).
M. Ghanavati, M.-J. Shojaei, and S. A. Ramazani, Energy Fuels 27, 7217 (2013).
A. C. Jenifer, P. Sharon, A. Prakash, and P. C. Sande, Energy Fuels 29, 7743 (2015).
K. Kohli, R. Prajapati, S. K. Maity, Met al., Fuel 175, 264 (2016).
H. Liu, Z. Wang, A. Guo, et al., Pet. Sci. Technol. 33, 203 (2015).
M. F. Ali and S. Abbas, Fuel Process. Technol. 87, 573 (2006).
S. R. Sergienko, B. A. Taimanova, and E. I. Talalaev, High-Molecular-Weight Nonhydrocarbon Petroleum Compounds: Resins and Asphaltenes (Nauka, Moscow, 1979) [in Russian].
A. A. Christy, B. Dahl, and O. M. Kvalheim, Fuel 68, 430 (1989).
L. S. Borisova and A. E. Kontorovich, Dokl. Earth Sci. 420, 664 (2008).
A. E. Kontorovich and L. S. Borisova, Geokhimiya, No. 11, 1660 (1994).
B. M. Rybak, Analysis of Petroleum and Petroleum Products (GosTekhIzdat, Moscow, 1962) [in Russian].
E. Rogel, Energy Fuels 22, 3922 (2008).
J. D. McLean and P. K. Kilpatrick, J. Colloid Interface Sci. 189, 242 (1997).
D. S. Khvostichenko and S. I. Andersen, Energy Fuels 24, 2327 (2010).
R. Hamadou, M. Khodja, M. Kartout, and A. Jada, Fuel 87, 2178 (2008).
Y.-J. Lin, P. He, M. Tavakkoli, et al., Energy Fuels 31, 11660 (2017).
J. Ancheyta, Modeling of Processes and Reactors for Upgrading of Heavy Petroleum (CRC Press, Boca Raton, 2013).
J. G. Speight, Heavy and Extra-Heavy Oil Upgrading Technologies (Gulf Professional–Elsevier, Oxford, 2013).
A. H. Alshareef, A. Scherer, X. Tan, et al., Energy Fuels 25, 2130 (2011).
L. C. Castaneda, J. A. D. Munoz, and J. Ancheyta, Catal. Today 220–222, 248 (2014).
E. Fumoto, A. Matsumura, S. Sato, and T. Takanohashi, Energy Fuels 23, 5308 (2009).
I. P. Kosachev, D. N. Borisov, M. R. Yakubov, et al., Pet. Sci. Technol. 37, 323 (2019).
I. P. Kosachev, D. N. Borisov, S. G. Yakubova, et al., Pet. Sci. Technol. 36, 1683 (2018).
L. O. Alemán-Vázquez, P. Torres-Mancera, J. Ancheyta, and J. Ramirez-Salgado, Energy Fuels 30, 9050 (2016).
B. P. Tumanyan, N. N. Petrukhina, G. P. Kayukova, et al., Russ. Chem. Rev. 84, 1145 (2015).
A. K. Golovko and A. A. Grin’ko, Pet. Chem. 58, 599 (2018).
G. S. Pevneva, N. G. Voronetskaya, D. S. Korneev, and A. K. Golovko, Pet. Chem. 57, 739 (2017).
M. A. Kopytov and A. K. Golovko, Pet. Chem. 57, 39 (2017).
G. S. Pevneva, N. G. Voronetskaya, A. A. Grin’ko, and A. K. Golovko, Pet. Chem. 56, 690 (2016).
A. Boukir, E. Aries, M. Guiliano, et al., Chemosphere 43, 279 (2001).
ASTM D2007-03 (2008): Standard Test Method for Characteristic Groups in Rubber Extender and Processing Oils and Other Petroleum-Derived Oils by the Clay-Gel Absorption Chromatographic Method.
C. A. Islas-Flores, E. Buenrostro-Gonzalez, and C. Lira-Galeana, Energy Fuels 19, 2080 (2005).
A. A. Grin’ko and A. K. Golovko, Pet. Chem. 51, 192 (2011).
J. G. Speight, The Chemistry and Technology of Petroleum (Marcel Dekker, New York, 1999).
J. G. Speight, Oil Gas Sci. Technol. Rev. IFP 59, 467 (2004).
R. P. Rodgers and A. M. McKenna, Anal. Chem. 83, 4665 (2011).
O. C. Mullins, Energy Fuels 24, 179 (2010).
S. I. Andersen and J. G. Speight, Pet. Sci. Technol. 19, 1 (2001).
A. M. Elsharkawy, T. A. Al-Sahhaf, M. A. Fahim, and H. W. Yarranton, Pet. Sci. Technol. 26, 153 (2008).
M. R. Yakubov, K. O. Sinyashin, G. R. Abilova, et al., Pet. Chem. 57, 849 (2017).
Y. Y. Gao, B. X. Shen, and J. C. Liu, Pet. Sci. Technol. 31, 509 (2013).
L. Shenghua, Ch. Liu, G. Que, et al., Fuel 76, 1459 (1997).
T. V. Cheshkova, E. Y. Kovalenko, N. N. Gerasimova, et al., Pet. Chem. 57, 31 (2017).
M. V. Peralta-Martínez, R. Vázquez-Ramírez, G. Blass-Amador, and E. M. Palacios-Lozano, Pet. Sci. Technol. 26, 91 (2008).
T. V. Cheshkova, V. P. Sergun, E. Yu. Kovalenko, et al., Energy Fuels 33, 7971 (2019).
D. J. Porter and P. M. Mayer, Energy Fuels 18, 987 (2004).
M. K. Sudipa, O. C. Mullins, C. Y. Ralston, et al., Appl. Spectrosc. 52, 1522 (1998).
W. E. Rudzinski and T. M. Aminabhavi, Energy Fuels 14, 464 (2000).
J. Zhang, Y. Tian, Y. Qiao, et al., Energy Fuels 31, 8072 (2017).
O. A. Beiko, A. K. Golovko, L. V. Gorbunova, et al., Chemical Composition of Western Siberia Oils (Nauka, Novosibirsk, 1988) [in Russian].
G. D. Gal’pern, Usp. Khim. 45, 1395 (1976).
Yu. M. Abyzgil’din, Yu. I. Mikhailyuk, K. S. Yarullin, and A. A. Ratovskaya, Petroleum Porphyrins and Metalloporphyrin Complexes (Nauka, Moscow, 1977) [in Russian].
Askarov, K.A., Berezin, B.D., Evstigneeva, R.P., et al., Porphyrins: Structure, Properties, and Synthesis (Nauka, Moscow, 1985).
X. Zhao, Y. Liu, Ch. Xu, et al., Energy Fuels 27, 2874 (2013).
X. Zhao, Ch. Xu, and Q. Shi, Structure and Modeling of Complex Petroleum Mixtures (Springer International, Cham, 2016).
N. A. Mironov, D. V. Milordov, G. R. Abilova, et al., Pet. Chem. 59, 1077 (2019).
W. S. Caughey and A. H. Corwin, J. Am. Chem. Soc. 77, 1509 (1955).
N. A. Mironov, K. O. Sinyashin, G. R. Abilova, et al., Izv. Akad. Nauk, Ser. Khim., No. 8, 1450 (2017).
R. W. Balek and A. Szutka, J. Chromatogr. 17, 127 (1965).
M. F. Ali, H. Perzanowski, A. Bukhari, and A. A. Al-Haji, Energy Fuels 7, 179 (1993).
R. A. Galimov, L. B. Krivonozhkina, V. V. Abushayeva, and G. V. Romanov, Pet. Chem. 33, 539 (1993).
O. V. Serebrennikova, N. I. Shilonosova, V. N. Burkova, et al., Geol. Nefti Gaza, No. 5, 46 (1989).
R. A. Galimov, L. B. Krivonozhkina, V. V. Abushayeva, and G. V. Romanov, Pet. Chem. 30, 55 (1990).
D. Z. Izmailova, V. M. Serebrennikov, T. K. Mozzhelina, and O. V. Serebrennikova, Pet. Chem. 36, 111 (1996).
M. G. R. Vale, M. M. Silva, I. C. F. Damin, et al., Talanta 74, 1385 (2008).
M. R. Yakubov, G. R. Abilova, K. O. Sinyashin, et al., Energy Fuels 30, 8997 (2016).
M. R. Yakubov, G. R. Abilova, K. O. Sinyashin, et al., Phthalocyanines and Some Current Applications, Ed. by Y. Yilmaz (IntechOpen, Rijeka, 2017), ch. 7.
N. A. Mironov, G. R. Abilova, Y. Y. Borisova, et al., Energy Fuels 32, 12435 (2018).
N. A. Mironov, G. R. Abilova, K. O. Sinyashin, et al., Energy Fuels 32, 161 (2018).
X. Zhao, Ch. Xu, and Q. Shi, Structure and Modeling of Complex Petroleum Mixtures, Ed. by C. Xu and Q. Shi (Springer International, Cham, 2016), p. 39.
J. G. Speight, The Chemistry and Technology of Petroleum (Marcel Dekker, New York, 1991).
S. Akmaz, O. Iscan, M. A. Gurkaynak, and M. Yasar, Pet. Sci. Technol. 29, 160 (2011).
D. E. Dmitriev and A. K. Golovko, Chem. Sust. Dev. 18, 171 (2010).
C. A. Franco, M. M. Lozano, S. Acevedo, et al., Energy Fuels 30, 264 (2015).
O. Castellano, R. Gimon, C. Canelon, et al., Energy Fuels 26, 2711 (2012).
W. Daxi, P. Yueqiu, and Zh. Hongye, Pet. Sci. 4 (4), 89 (2007).
F. Alvarez-Ramirez, E. Ramirez-Jaramillo, and Y. Ruiz-Morales, Energy Fuels 20, 195 (2006).
J. G. Speight, Oil Gas Sci. Technol. 59, 467 (2004).
J. Murgich, J. Rodriguez, and Y. Aray, Energy Fuels 10, 68 (1996).
S. Li, C. Liu, G. Que, and W. Liang, J. Pet. Sci. Eng. 22, 37 (1999).
M. Mousavi, T. Abdollahi, F. Pahlavan, and E. H. Fini, Fuel 183, 262 (2016).
D. Merino-Garcia and S. I. Andersen, J. Dispers. Sci. Technol. 26, 217 (2005).
J. S. Buckley, J. Wang, and J. L. Creek, Asphaltenes, Heavy Oils, and Petroleomics, Ed. by O. C. Mullins, E. Y. Sheu, A. Hammami, and A. G. Marshall (Springer, New York, 2007), p. 401.
M. Sedghi, L. Goual, W. Welch, and J. Kubelka, J. Phys. Chem. 117, 5765 (2013).
H. W. Yarranton, H. Alboudrone, and R. Jakher, Ind. Eng. Chem. Res. 39, 2916 (2000).
P. M. Spiecker, K. L. Gawrys, Ch. B. Trail, and P. K. Kilpatrick, Colloids Surf., A 220, 9 (2003).
D. Merino-Garcia, J. Murgich, and S. I. Andersen, Pet. Sci. Technol. 22, 735 (2004).
M. Agrawala and H. W. Yarranton, Ind. Eng. Chem. Res. 40, 4664 (2001).
S. Acevedo, K. Guzman, and O. Ocanto, Energy Fuels 24, 1809 (2010).
J. C. Pereira, I. Lopez, R. Salas, et al., Energy Fuels 21, 1317 (2007).
L. B. Gutierrez, M. A. Ranaudo, B. Mendez, and S. Acevedo, Energy Fuels 15, 624 (2001).
Z. Hosseini-Dastgerdi, S. A. R. Tabatabaei-Nejad, E. Khodapanah, and E. Sahraei, Asia-Pacif. J. Chem. Eng. 10, 1 (2015).
D. D. Li and M. L. Greenfield, Fuel 115, 347 (2014).
O. Castellano, R. Gimon, and H. Soscun, Energy Fuels 25, 2526 (2011).
J. Murgich, Pet. Sci. Technol. 20, 983 (2002).
Asphaltenes, Heavy Oils, and Petroleomics, Ed. by O. C. Mullins, E. Y. Sheu, A. Hammami, and A. G. Marshall (Springer, New York, 2006).
K. Akbarzadeh, A. Hammami, A. Kharrat, et al., Oilfield Rev. 19, 22 (2007).
M. M. Amro, J. Pet. Sci. Eng. 46, 243 (2005).
M. D. C. Garcia, H. Magaly, and O. Jose, in Proceedings of SPE International Symposium on Oilfield Chemistry (2003).
C. L. Chang and H. Foglel, Proceedings of SPE International Symposium on Oilfield Chemistry (1993).
K. Kraiwattanawong, H. S. Fogler, S. G. Gharfeh, et al., Energy Fuels 23, 1575 (2009).
E. Rogel, Energy Fuels 25, 472 (2011).
F. Soorghali, A. Zolghadr, and Sh. Ayatollahi, Energy Fuels 29, 5487 (2015).
O. Leon, E. Contreras, E. Rogel, et al., Langmuir 18, 5106 (2002).
T. Ren, Y. Wang, and G. Zhang, Pet. Sci. Technol. 35, 1481 (2017).
L. A. Alcazar-Vara, L. S. Zamudio-Rivera, and E. Buenrostro-Gonzalez. J. Dispers. Sci. Technol. 37, 1544 (2016).
H. Liu, Zh. Liu, A. Guo, et al., Energy Fuels 32, 3380 (2018).
L. C. C. Marques, J. O. Pereira, A. D. Bueno, et al., J. Braz. Chem. Soc. 23, 1880 (2012).
L. Goual and A. Firoozabadi, AIChE J. 50, 470 (2004).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by S. Zatonsky
Rights and permissions
About this article
Cite this article
Yakubov, M.R., Abilova, G.R., Yakubova, S.G. et al. Composition and Properties of Heavy Oil Resins. Pet. Chem. 60, 637–647 (2020). https://doi.org/10.1134/S0965544120060109
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0965544120060109