Co-adsorption behaviors of asphaltenes and different flow improvers and their impacts on the interfacial viscoelasticity

doi:10.1016/j.cjche.2021.08.018

Abstract

Abstract: Commonly used flow improvers in oilfields, such as ethylene–vinyl acetate copolymer (EVA), poly(octadecyl acrylate) (POA), and polymethylsilsesquioxane (PMSQ) are proven to be effective to enhance the flowability of crude oil. However, the addition of these flow improvers may change the stability of the emulsion and make the crude oil treatment process challenging. In this research, the impacts of different flow improvers on the interfacial properties of the emulsions containing asphaltenes are systematically investigated. The co-adsorption behaviors of the flow improvers and asphaltenes are analyzed through dynamic interfacial tension (DIFT). The rheological properties of the interfacial layer after the adsorption are explored via dilational viscoelasticity. Significant difference is observed in the structural properties of the interface adsorbed by different flow improvers, which is attributed to different interactions between the flow improvers and asphaltenes. To investigate these interactions, conductivity, asphaltenes precipitation, dynamic light scattering (DLS), and contact angle experiments are conducted systematically. Results show that EVA and POA can alter the interfacial properties by changing the asphaltene dispersion state. The interaction between EVA and asphaltenes is stronger than that between POA and asphaltenes due to the difference in molecular structures. Unlike EVA and POA, the change of interfacial property with the addition of PMSQ is attributed to the partial adsorption of asphaltenes on PMSQ.

Key words: Asphaltene, Flow improver, Interfacial tension, Interfacial rheology, Emulsions, Adsorption

摘要： Commonly used flow improvers in oilfields, such as ethylene–vinyl acetate copolymer (EVA), poly(octadecyl acrylate) (POA), and polymethylsilsesquioxane (PMSQ) are proven to be effective to enhance the flowability of crude oil. However, the addition of these flow improvers may change the stability of the emulsion and make the crude oil treatment process challenging. In this research, the impacts of different flow improvers on the interfacial properties of the emulsions containing asphaltenes are systematically investigated. The co-adsorption behaviors of the flow improvers and asphaltenes are analyzed through dynamic interfacial tension (DIFT). The rheological properties of the interfacial layer after the adsorption are explored via dilational viscoelasticity. Significant difference is observed in the structural properties of the interface adsorbed by different flow improvers, which is attributed to different interactions between the flow improvers and asphaltenes. To investigate these interactions, conductivity, asphaltenes precipitation, dynamic light scattering (DLS), and contact angle experiments are conducted systematically. Results show that EVA and POA can alter the interfacial properties by changing the asphaltene dispersion state. The interaction between EVA and asphaltenes is stronger than that between POA and asphaltenes due to the difference in molecular structures. Unlike EVA and POA, the change of interfacial property with the addition of PMSQ is attributed to the partial adsorption of asphaltenes on PMSQ.

关键词: Asphaltene, Flow improver, Interfacial tension, Interfacial rheology, Emulsions, Adsorption

Hao Zhang, Daiwei Liu, Jiangbo Wen, Guangyu Sun, Chuanxian Li, Xinya Chen, Huihui Zhang, Ze Duan. Co-adsorption behaviors of asphaltenes and different flow improvers and their impacts on the interfacial viscoelasticity[J]. Chinese Journal of Chemical Engineering, 2022, 48(8): 149-157.

References

[1] P.K. Kilpatrick, Water-in-crude oil emulsion stabilization: review and unanswered questions, Energy Fuels 26 (7) (2012) 4017–4026
[2] T. Kar, B. Hascakir, The role of resins, asphaltenes, and water in water–oil emulsion breaking with microwave heating, Energy Fuels 29 (6) (2015) 3684–3690
[3] E.B. da Silva, D. Santos, M.P. de Brito, R.C.L. Guimar?es, B.M.S. Ferreira, L.S. Freitas, M.C.V. de Campos, E. Franceschi, C. Dariva, A.F. Santos, M. Fortuny, Microwave demulsification of heavy crude oil emulsions: Analysis of acid species recovered in the aqueous phase, Fuel 128 (2014) 141–147
[4] B. Peng, M. Y. Li, S. Q. Zhao, Z. L. Wu, J. Sjoblom, H. Hoiland, Study of oil/water interfacial tension of vacuum residual fractions from Iranian Light crude oil, Chin. J. Chem. Eng. 11(6) (2003) 681-685
[5] O. C. Mullins, The asphaltenes, Annu. Rev. Anal. Chem. 4 (2011) 393-418
[6] Y. Bai, H. Sui, X.Y. Liu, L. He, X.G. Li, E. Thormann, Effects of the N, O, and S heteroatoms on the adsorption and desorption of asphaltenes on silica surface: a molecular dynamics simulation, Fuel 240 (2019) 252–261
[7] H.S. Silva, A.C.R. Sodero, B. Bouyssiere, H. Carrier, J.P. Korb, A. Alfarra, G. Vallverdu, D. Bégué, I. Baraille, Molecular dynamics study of nanoaggregation in asphaltene mixtures: effects of the N, O, and S heteroatoms, Energy Fuels 30 (7) (2016) 5656–5664
[8] M. Lashkarbolooki, R. Parvizi, S. Ayatollahi, E. Ghaseminejad Raeeni, Effect of salts and their interaction with ingenious surfactants on the interfacial tension of crude oil/ionic solution, Chin. J. Chem. Eng. 28 (1) (2020) 224–235
[9] M.D. Lobato, F. Gámez, S. Lago, J.M. Pedrosa, The influence of the polarity of fractionated asphaltenes on their Langmuir-film properties, Fuel 200 (2017) 162–170
[10] H. Y. Wang, M. Y. Li, Z. L. Wu, M. Q. Lin, Effect of petroleum sulphonate on interfacial property and stability of crude oil emulsions, Chin. J. Chem. Eng. 13(5) (2005) 691-695
[11] M. Lashkarbolooki, S. Ayatollahi, Experimental and modeling investigation of dynamic interfacial tension of asphaltenic-acidic crude oil/aqueous phase containing different ions, Chin. J. Chem. Eng. 25 (12) (2017) 1820–1830
[12] V. Pauchard, J.P. Rane, S. Banerjee, Asphaltene-laden interfaces form soft glassy layers in contraction experiments: a mechanism for coalescence blocking, Langmuir 30 (43) (2014) 12795–12803
[13] F. Yang, Y.S. Zhao, J. Sj?blom, C.X. Li, K.G. Paso, Polymeric wax inhibitors and pour point depressants for waxy crude oils: a critical review, J. Dispers. Sci. Technol. 36 (2) (2015) 213–225
[14] S.Z. Yi, J.J. Zhang, Relationship between waxy crude oil composition and change in the morphology and structure of wax crystals induced by pour-point-depressant beneficiation, Energy Fuels 25 (4) (2011) 1686–1696
[15] B. Yao, C. Li, F. Yang, X. Zhang, Z. Mu, G. Sun, Y. Zhao, Ethylene–vinyl acetate copolymer and resin-stabilized asphaltenes synergistically improve the flow behavior of model waxy oils. 1. Effect of wax content and the synergistic mechanism, Energy Fuels 32(2) (2018) 1567-1578
[16] R.A. Soldi, A.R.S. Oliveira, R.V. Barbosa, M.A.F. César-Oliveira, Polymethacrylates: Pour point depressants in diesel oil, Eur. Polym. J. 43 (8) (2007) 3671–3678
[17] A. Omidi, A.K. Manshad, S. Moradi, J.A. Ali, S.M. Sajadi, A. Keshavarz, Smart- and nano-hybrid chemical EOR flooding using Fe3O4/eggshell nanocomposites, J. Mol. Liq. 316 (2020) 113880
[18] A. Rezaei, M. Riazi, M. Escrochi, R. Elhaei, Integrating surfactant, alkali and nano-fluid flooding for enhanced oil recovery: a mechanistic experimental study of novel chemical combinations, J. Mol. Liq. 308 (2020) 113106
[19] F. Yang, B. Yao, C.X. Li, G.Y. Sun, X.B. Ma, Oil dispersible polymethylsilsesquioxane (PMSQ) microspheres improve the flow behavior of waxy crude oil through spacial hindrance effect, Fuel 199 (2017) 4–13
[20] M. Rondón, P. Bouriat, J. Lachaise, J.L. Salager, Breaking of water-in-crude oil emulsions. 1. physicochemical phenomenology of demulsifier action, Energy Fuels 20 (4) (2006) 1600–1604
[21] P. Bouriat, N. El Kerri, A. Graciaa, J. Lachaise, Properties of a two-dimensional asphaltene network at the water-cyclohexane interface deduced from dynamic tensiometry, Langmuir 20 (18) (2004) 7459–7464
[22] L.Y. Zhang, P. Breen, Z.H. Xu, J.H. Masliyah, Asphaltene films at a toluene/water interface, Energy Fuels 21 (1) (2007) 274–285
[23] D.M. Sztukowski, M. Jafari, H. Alboudwarej, H.W. Yarranton, Asphaltene self-association and water-in-hydrocarbon emulsions, J Colloid Interface Sci 265 (1) (2003) 179–186
[24] J.D. McLean, P.K. Kilpatrick, Effects of asphaltene solvency on stability of water-in-crude-oil emulsions, J. Colloid Interface Sci. 189 (2) (1997) 242–253
[25] Xia L, Lu S, Cao G, Stability and demulsification of emulsions stabilized by asphaltenes or resins, J Colloid Interface Sci 271 (2) (2004) 504–506
[26] B. Yao, C. Li, F. Yang, X. Zhang, Z. Mu, G. Sun, G. Liu, Y. Zhao, Ethylene–vinyl acetate copolymer and resin-stabilized asphaltenes synergistically improve the flow behavior of model waxy oils. 2. Effect of asphaltene content, Energy Fuels 32(5) (2018) 5834-5845
[27] B. Yao, C.X. Li, Z.H. Mu, X.P. Zhang, F. Yang, G.Y. Sun, Y.S. Zhao, Ethylene-vinyl acetate copolymer (EVA) and resin-stabilized asphaltenes synergistically improve the flow behavior of model waxy oils. 3. effect of vinyl acetate content, Energy Fuels 32 (8) (2018) 8374–8382
[28] C.L. Chang, H.S. Fogler, Stabilization of asphaltenes in aliphatic solvents using alkylbenzene-derived amphiphiles. 2. study of the asphaltene-amphiphile interactions and structures using Fourier transform infrared spectroscopy and small-angle X-ray scattering techniques, Langmuir 10 (6) (1994) 1758–1766
[29] Y.M. Wu, G.D. Ni, F. Yang, C.X. Li, G.L. Dong, Modified maleic anhydride Co-polymers as pour-point depressants and their effects on waxy crude oil rheology, Energy Fuels 26 (2) (2012) 995–1001
[30] T. Kuznicki, J.H. Masliyah, S. Bhattacharjee, Molecular dynamics study of model molecules resembling asphaltene-like structures in aqueous organic solvent systems, Energy Fuels 22 (4) (2008) 2379–2389
[31] T. Kuznicki, J.H. Masliyah, S. Bhattacharjee, Aggregation and partitioning of model asphaltenes at toluene-water interfaces: Molecular dynamics simulations, Energy Fuels 23 (10) (2009) 5027–5035
[32] F. Fallah, F. Khabaz, Y.R. Kim, S.R. Kommidi, H.F. Haghshenas, Molecular dynamics modeling and simulation of bituminous binder chemical aging due to variation of oxidation level and saturate-aromatic-resin-asphaltene fraction, Fuel 237 (2019) 71–80
[33] X.P. Zhang, F. Yang, B. Yao, C.X. Li, D.W. Liu, G.Y. Sun, Synergistic effect of asphaltenes and octadecyl acrylate-maleic anhydride copolymers modified by aromatic pendants on the flow behavior of model waxy oils, Fuel 260 (2020) 116381
[34] X.L. Zhang, D.J. Taylor, R.K. Thomas, J. Penfold, Adsorption of polyelectrolyte/surfactant mixtures at the air-water interface: modified poly(ethyleneimine) and sodium dodecyl sulfate, Langmuir 27 (6) (2011) 2601–2612
[35] X.M. Luo, H.Y. Gong, Z.L. He, P. Zhang, L.M. He, Research on mechanism and characteristics of oil recovery from oily sludge in ultrasonic fields, J Hazard Mater 399 (2020) 123137
[36] D. Dudá?ová, S. Simon, P.V. Hemmingsen, J. Sj?blom, Study of asphaltenes adsorption onto different minerals and clays: Part 1. Experimental adsorption with UV depletion detection, Colloids Surfaces A: Physicochem. Eng. Aspects 317 (1–3) (2008) 1–9
[37] N.X. Yan, J.H. Masliyah, Characterization and demulsification of solids-stabilized oil-in-water emulsions Part 1. Partitioning of clay particles and preparation of emulsions, Colloids Surfaces A: Physicochem. Eng. Aspects 96 (3) (1995) 229–242
[38] A.L.C. Machado, E.F. Lucas, G. González, Poly(ethylene-co-vinyl acetate) (EVA) as wax inhibitor of a Brazilian crude oil: oil viscosity, pour point and phase behavior of organic solutions, J. Petroleum Sci. Eng. 32 (2–4) (2001) 159–165
[39] C.J. Wu, J.L. Zhang, W. Li, N. Wu, Molecular dynamics simulation guiding the improvement of EVA-type pour point depressant, Fuel 84 (16) (2005) 2039–2047
[40] C.W. Angle, Y.J. Hua, Dilational interfacial rheology for increasingly deasphalted bitumens and n-C5 asphaltenes in toluene/NaHCO3 solution, Energy Fuels 26 (10) (2012) 6228–6239
[41] S. Subramanian, S. Simon, J. Sj?blom, Interfacial dilational rheology properties of films formed at the oil/water interface by reaction between tetrameric acid and calcium ion, J. Dispers. Sci. Technol. 38 (8) (2017) 1110–1116
[42] D.W. Liu, C.X. Li, X.P. Zhang, F. Yang, G.Y. Sun, B. Yao, H. Zhang, Polarity effects of asphaltene subfractions on the stability and interfacial properties of water-in-model oil emulsions, Fuel 269 (2020) 117450
[43] J. Moncada, D. Schartung, N. Stephens, T.S. Oh, C.A. Carrero, Determining the flocculation point of asphaltenes combining ultrasound and electrochemical impedance spectroscopy, Fuel 241 (2019) 870–875
[44] R. Pichot, F. Spyropoulos, I.T. Norton, Competitive adsorption of surfactants and hydrophilic silica particles at the oil-water interface: interfacial tension and contact angle studies, J Colloid Interface Sci 377 (1) (2012) 396–405