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Progress in Chemistry DOI: 10.7536/PC121239 Previous Articles   Next Articles

• Review •

Supramolecular Interaction of Petroleum Components and Model Compounds

Bian Yinghui, Dong Xujing, Zhu Lijun, Zhou Yulu, Xiang Yuzhi, Xia Daohong*   

  1. State Key Laboratory of Heavy Oil Processing, College of Chemical Engineering, China University of Petroleum (East China), Qingdao 266580, China
  • Received: Revised: Online: Published:
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Petroleum is commonly described as an extremely complex mixture, the interest on the complex colloidal dispersion and its stability are growing, especially the asphaltene supramolecular aggregate which is closely related to the stability of petroleum. Meanwhile, people have been arguing about the main forces of asphaltene association. Here, the development of the supramolecular interaction in the self-associated process of petroleum components and their model compounds is reviewed. Experimental and theoretical studies have shown that asphaltenes have a strong tendency to form supramolecular aggregates via hydrogen bonding, π-π stacking, polar interactions and other interactions. One method to improve the understanding of liquid-phase association behavior relevant to asphaltenes is to synthesize pure compounds that contain selected chemical structures, and then to examine their behavior in solution. Finally, the prospects are pointed out based on the current development of the system. Contents
1 Introduction
2 Supramolecular interaction of petroleum components
2.1 Interaction type of supramolecular aggregates in petroleum components
2.2 Interaction studies of supramolecular aggregates in petroleum components
3 Interaction of supramolecular aggregates in model compounds of petroleum components
3.1 Intermolecular interaction of supramolecular aggregates in model compounds of petroleum components
3.2 Hydrogen bonding of supramolecular aggregates in model compounds of petroleum components
3.3 Supramolecular interaction of petroporphyrins
3.4 Molecular simulations of supramolecular aggregates of petroleum components model compounds
4 Specific application of supramolecular interaction in petroleum chemistry
5 Conclusion and outlook

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[1] Nellensteyn F J. Journal of the Institute of Petroleum Technology, 1924, 10 (43): 311-325
[2] Pfeiffer J P, Seal R N. Phys. Chem., 1940, 44: 139-149
[3] Gould K A. Fuel, 1983, 62 (2): 370-372
[4] Gray M R, Tykwinski R R, Stryker J M, Tan X L. Energy Fuels, 2011, 25 (7): 3125-3134
[5] Yen T F. Fuel Sci. Technol. Int., 1992, 10 (4/6): 723-733
[6] Rogel E. Energy Fuels, 2000, 14 (3): 566-574
[7] Takanohashi T, Sato S, Tanaka R. Pet. Sci. Technol., 2003, 21 (3/4): 491-505
[8] Lian H, Lin J R, Yen T F. Fuel, 1994, 73 (3): 423-428
[9] Leon O, Contreras E, Rogel G, Dambakli G, Espidel J, Acevedo S. Energy Fuels, 2001, 15 (5): 1028-1032
[10] Dickie J P, Yen T F. Anal. Chem., 1967, 39: 1847-1852
[11] Betancourt S S, Ventura G T, Pomerantz A E, Viloria O, Dubost F X, Zuo J, Monson G, Bustamante D, Purcell J M, Nelson R K, Rodgers R P, Reddy C M, Marshall A G, Mullins O C. Energy Fuels, 2009, 23 (3): 1178-1188
[12] Mostow F, Indo K, Mullins O C, McFarlane R. Energy Fuels, 2009, 23 (3): 1194-1200
[13] Andreatta G, Goncalves C C, Bun G, Bostrom N, Quintella C M, Arteaga-Larios F, Perez E, Mullins O C. Energy Fuels, 2005, 19 (4): 1282-1289
[14] Takanohashi T, Sato S, Tanaka R. Prepr. Pap. -Am. Chem. Soc. Div. Fuel Chem., 2001, 46 (2): 357-358
[15] Hu Y F, Yang L Y, Lin X S, Guo T M. Pet. Explor. Dev., 2000, 27 (5): 109-115
[16] Ibrahim H H, Idem R O. Energy Fuels, 2004, 18 (4): 1038-1048
[17] Zhao F L, Yan J N. Oilfield Chem., 2004, 21 (4): 310-312
[18] He X F, Li S L. Nat. Gas Ind., 2003, 23 (2): 78-81
[19] Pu W F. J. Southwest Pet. Inst., 1999, 21 (4): 38-41
[20] Chang C L, Fogler H S. Langmuir, 1994, 10 (6): 1749-1757
[21] Leon O, Rogel E, Urbina A, Audujar A, Lucas A. Langmuir, 1999, 15 (22): 7653-7657
[22] Carbognani L, Espidel J. Vision Tecnol., 1995, 3 (1): 35-42
[23] Ding F C, Wang Y H, Jin G Z, He G X, Gao J B. J. Petrochem. Univ., 2001, 14 (2): 31-34
[24] Rogel E. Colloids Surf. A, 1995, 104 (1): 85-93
[25] Ding F C, Wei J, Wang Y H, He G X, Jin G Z. J. Petrochem. Univ., 2001, l4 (3): 7-9
[26] Murgich J, Rodriguez J M, Aary Y. Energy Fuels, 1996, 10 (1): 68-76
[27] Wargadalam V J, Norinaga K, Lino M. Fuel, 2002, 8l (11/12): 1403-1407
[28] Alboudware J H, Jakher R K, Syreek W Y, Yarranton H W. Pet. Sci. Technol., 2004, 22 (5/6): 647-664
[29] Sun H. J. Phys. Chem. B, 1998, 102 (38): 7338-7364
[30] Dubey S T, Waxman M H. SPE Reservoir Eng., 1991, 6 (3): 389-395
[31] Wang Z J. Pet. Asphalt, 1996, 10 (3): 36-45
[32] Rao B M L, Serrano J E. Fuel Sci. Technol. Int., 1986, 4 (4): 483-510
[33] Painter P C, Sobokowiak M, Youtcheff J. Fuel, 1987, 66 (10): 973-978
[34] Acevedo S, Mendez B, Rojas A, Layrisse I, Rivas H. Fuel, 1985, 64 (12): 1741-1747
[35] Murgich J. Pet. Sci. Technol., 2002, 20: 983-997
[36] Shattock T R, Arora K K, Vishweshwar P, Michael J Z. Cryst. Growth Des., 2008, 8 (12): 4533-4545
[37] Venkataramanan B, Ning Z, Vittal J J, Valiyaveettil S. Cryst. Eng. Commun., 2005, 7: 108-112
[38] Mohamed S, Tocher D A, Vickers M, Karamertzanis P G, Price S L. Cryst. Growth Des., 2009, 9 (6): 2881-2889
[39] Kato T, Fukumasa M, Frechet J M. Chem. Mater., 1995, 7 (2): 368-372
[40] Tan X L, Fenniri H, Gray M R. Energy Fuels, 2009, 23 (7): 3687-3693
[41] Stoyanov S R, Yin C X, Gray M R, Stryker J M, Gusarov S, Kovalenko A. J. Phys. Chem. B, 2010, 114 (6): 2180-2188
[42] Hunter C A, Lawson K R, Perkins J, Urch C J. J. Chem. Soc. Perkin Trans. 2, 2001, 5: 651-669
[43] Cockroft S L, Perkins J, Zonta C, Adams H, Spey S E, Low C M R, Vinter J G, Lawson K R, Urch C J, Hunter C A. Org. Biomol. Chem., 2007, 5 (7): 1062-1080
[44] Barbour R V, Petersen J C. Analytical Chemistry, 1974, 46 (2): 273-277
[45] 李生华(Li S H). 石油大学(北京)博士学位论文(Doctoral Dissertation of University of Petroleum(Beijing)), 1991
[46] Speight J G, Moschopedis S E. Petroleum. Chem. ACS, 1979, 24 (4): 910-923
[47] 刘东(Liu D), 王宗贤(Wang Z X), 阙国和(Que G H). 燃料化学学报(Journal of Fuel Chemistry and Technology), 2002, 30 (3): 281-284
[48] Liu D, Kong X, Li M Y, Wang Z X. Energy Fuels, 2010, 24 (5): 3624-3627
[49] Kawashima H, Takanohashi T, Iino M, Matsukawa S. Energy Fuels, 2008, 22 (6): 3989-3993
[50] Tanaka R, Sato E, Hunt J E, Winans R E, Sato S, Takanohashi T. Energy Fuels, 2004, 18 (4): 1118-1125
[51] Espinat D, Rosenberg E, Scarsella M, Barre L, Feinstein D, Broseta D. Structures and Dynamics of Asphaltene (Eds. Mullins O C, Sheu E Y). New York: Plenum Press, 1998, Chapter V
[52] Albina R, Mutina A R, Hurlimann M D. J. Phys. Chem. A, 2008, 112 (15): 3291-3301
[53] Zielinski L, Saha I, Freed D E, Hüurlimann M D. Langmuir, 2010, 26 (7): 5014-5021
[54] Bloembergen N, Purcell E M, Pound R V. Phys. Rev., 1948, 73: 679-712
[55] Kowalewski J, Mäler L. Nuclear Spin Relaxation in Liquids, Theory Experiments, and Applications. New York/London: Taylor & Francis, 2006, 195-197
[56] Kimmich R, Fatkullin N. Adv. Polym. Sci., 2004, 170: 1-113
[57] Zhang S H, Sun L L, Xu J B, Wu H, Wen H. Energy Fuels, 2010, 24(8): 4312-4326
[58] Merdrignac I, Espinat D. Oil Gas Sci. Technol., 2007, 62 (1): 7-32
[59] Kharrat A M, Zacharia J, Cherian V J, Anyatonwu A. Energy Fuels, 2007, 21 (6): 3618-3621
[60] Zhang L, Greeneld M L. Energy Fuels, 2007, 21 (3): 1712-1716
[61] Murgich J, Rodríguez M J, Aray Y. Energy Fuels, 1996, 10 (1): 68-76
[62] Gavezzotti A. Acta Crystallogr., 1990, B46: 275-283
[63] Israelachvili J N. Intermolecular and Surface Forces, 2nd. New York: Academic, 1991, 380-382
[64] Sieffert B, Kuczinski J, Papirer E. J. Colloid Interface Sci., 1990, 135: 107-117
[65] Aray Y, Hernández-Bravo R, Parra J G, Rodríguez J, David S. J. Phys. Chem. A, 2011, 115 (42): 11495-11507
[66] Quintella C M, Arteaga-Larios F, Perez E, Mullins O C. Energy Fuels, 2005, 19 (4): 1282-1289
[67] Castellano O, Gimon R, Canelon C, Aray Y, Soscun H. Energy Fuels, 2012, 26 (5): 2711-2720
[68] Rogel E. Energy Fuels, 2000, 14 (3): 566-574
[69] Ortega-Rodriguez A, Lira-Galeana C, Ruiz-Morales Y, Cruz S A. Pet. Sci. Technol., 2001, 19 (1): 245-256
[70] Freund H, Matturo M G, Olmstead W N, Reynolds R P, Upton T H. Energy Fuels, 1991, 6(5): 840-846
[71] Schabron J F, Speight J G. Pet. Sci. Technol., 1998, 16: 361-375
[72] Akbarzadeh K, Bressler D C, Wang J N, Gawrys K L, Gray M R, Kilpatrick P K. Energy Fuels, 2005, 19 (4): 1268-1271
[73] Watson M D, Fechtenkötter A, Müllen K. Chem. Rev., 2001, 101: 1267-1300
[74] Ito S, Wehmeier M, Brand J D, Kübel C, Epsch R, Rabe J P, Müllen K. Chem. Eur. J., 2000, 6 (23): 4327-4342
[75] Tchebotareva N, Yin X M, Watson M D, Samori P, Rabe J, Müllen K. J. Am. Chem. Soc., 2003, 125 (32): 9734-9739
[76] Rakotondradany F, Fenniri H, Rahimi P, Gawrys K L, Kilpatrick P K, Gray M R. Energy Fuels, 2006, 20(6): 2439-2447
[77] Kastler M, Pisula W, Wasserfallen D, Pakula T, Müllen K. J. Am. Chem. Soc., 2005, 127(12): 4286-4296
[78] Tan X L, Fenniri H, Gray M R. Energy Fuels, 2008, 22 (2): 715-720
[79] Groenzin H, Mullins O C, Eser S, Mathews J, Yang M G, Jones D. Energy Fuels, 2003, 17 (2): 498-503
[80] Ruiz-Morales Y, Mullins O C. Energy Fuels, 2007, 21 (1): 256-265
[81] Hunter C A, Sanders J K M. J. Am. Chem. Soc., 1990, 112: 5525-5534
[82] Murgich J. Mol. Simul., 2003, 29: 451-461
[83] Zhang L Y, Lawrence S, Xu Z, Masliyah J H. J. Colloid Interface Sci., 2003, 264: 128-140
[84] (a)Fossen M, Kallevik H, Knudsen K D, Sjöblom J. Energy Fuels, 2007, 21 (2): 1030-1037. (b) Fossen M, Sjöblom J, Kallevik H, Jakobsson J. J. Dispersion Sci. Technol., 2007, 28 (1): 193-197
[85] Wattana P, Fogler H S, Yen A, Garcìa M D C, Carbognani L. Energy Fuels, 2005, 19 (1): 101-110
[86] Horváth-Szabó G, Masliyah J H, Elliott J A W, Yarranton H W, Czarnecki J. J. Colloid Interface Sci., 2005, 283: 5-17
[87] Fordedal H, Schildberg Y, Sjöblom J, Volle J L. Colloids Surf. A: Phys. Chem. Eng. Aspects, 1996, 106: 33-47
[88] Zhang L Y, Lopetinsky R, Xu Z, Masliyah J H. Energy Fuels, 2005, 19 (4): 1330-1336
[89] Zhang L Y, Lawrence S, Xu Z, Masliyah J H. Ind. Eng. Chem. Res., 2005, 44: 1160-1174
[90] Zhang L Y, Breen P, Xu Z, Masliyah J H. Energy Fuels, 2007, 21 (1): 274-285
[91] Andersen S I, del Rio J M, Khvostitchenko D, Shakir S, Lira-Galeana C. Langmuir, 2001, 17 (10): 307-313
[92] Murgich J, Merino-Garcia D, Andersen S I, del Rio J M, Lira-Galeana C. Langmuir, 2002, 23 (18): 9080-9086
[93] Khvostitchenko D, Andersen S I. Energy Fuels, 2008, 22: 3096-3103
[94] Nordgrd E, Sjöblom J. J. Dispersion Sci. Technol., 2008, 29 (8): 1114-1122
[95] Bellamy L J, Pace R J. Spectrochim. Acta Part A, 1972, 28: 1869-1876
[96] Joseten M D, Schaad I L. Hydrogen Bonding. New York: Marcel Dekker Inc., 1974, 182-183
[97] Samanta U, Chakrabarti P, Chandrasekhar J. J Phys. Chem. A, 1998, 102 (45): 8964-8969
[98] Graton J, Berthelot M, Gal J F, Laurence C, Lebreton J, Le Questel R. J. Org. Chem., 2003, 68 (21): 8208-8221
[99] Tan X L, Fenniri H, Gray M R. Energy Fuels, 2009, 23: 3687-3693
[100] Nordgrd E L, Landsem E, Sjöblom J. Langmuir, 2008, 24 (16): 8742-8751. (b) Nordgrd E L, Srland G, Sjöblom J. Langmiur, 2010, 26 (4): 2352-2360
[101] 刘海洋(Liu H Y), 胡希明(Hu X M), 应晓(Ying X), 刘义(Liu Y), 黄锦汪(Huang J W), 计亮年(Ji L N). 无机化学学报(Chinese Journal of Inorganic Chemistry), 1998, 24: 371-387
[102] 李迪(Li D). 吉林大学博士学位论文(Doctoral Dissertation of Jilin University), 2009
[103] 高颖宁(Gao Y N). 山东大学博士学位论文(Doctoral Dissertation of Shandong University), 2010
[104] Drain C M, Lehn J M. J. Chem. Soc. Chem. Commun., 1994, 2313-2314. (b) Drain C M, Nifiatis F, Vasenko A, Batteas J D. Angew. Chem. Int. Ed., 1998, 37: 2344-2347
[105] Shirakawa M, Fujita N, Shinkai S. J. Am. Chem. Soc., 2005, 127: 4164-4165
[106] Kishida T, Fujita N, Sada K, Shinkai S. J. Am. Chem. Soc., 2005, 127: 7298-7299
[107] Shirakawa M, Fujita N, Shinkai S. J. Am. Chem. Soc., 2003, 125: 9902-9903
[108] Hu J S, Guo Y G, Liang H P, Wan L J, Jiang L. J. Am. Chem. Soc., 2005, 127: 17090-17095
[109] 徐海(Xu H), 于道永(Yu D Y), 王宗贤(Wang Z X), 阙国和(Que G H). 化学研究与应用(Chemical Research and Application), 2001, 13 (4): 347-352
[110] Nguyen S N, Filby R H. Metal Complexes in Fossil Fuels(Eds.Filby R H, Branthaver J F). Washington, D C: ACS, 1987. 384-401
[111] Fish R H, Komlenic J J. Anal. Chem., 1984, 56: 510-517
[112] Fish R H, Komlenic J J, Wines B K. Anal. Chem., 1984, 56: 2452-2460
[113] Yin C X, Tan X L, Müllen K, Stryker J M, Gray M R. Energy Fuels, 2008, 22: 2465-2469
[114] da Costa L M, Stoyanov S R, Gusarov S, Tan X L, Gray M R, Stryker J M, Tykwinski R, Seidl P R, Kovalenko A. Energy Fuels, 2012, 26: 2727-2735
[115] da Costa L M, Hayaki S, Gray M R, Stryker J M, Tykwinski R, Carneiro J W, Sato H, Seidl P R, Kovalenko A. Phys. Chem. Chem. Phys., 2012, 14: 3922-3934
[116] 孙燕(Sun Y), 夏道宏(Xia D H), 项玉芝(Xiang Y Z). 应用化学(Chinese Journal of Applied Chemistry), 2007, 24 (6): 703-706
[117] 孙燕(Sun Y), 夏道宏(Xia D H), 项玉芝(Xiang Y Z). 应用化学(Chinese Journal of Applied Chemistry), 2007, 24 (10): 1201-1204
[118] Sun Y, Xia D H, Xiang Y Z. Petroleum Science & Tech., 2008, 26 (17): 2023-2032
[119] 孙小明(Sun X M), 江胜娟(Jiang S J), 许 艳(Xu Y), 周玉路(Zhou Y L), 项玉芝(Xiang Y Z), 夏道宏(Xia D H). 石油化工(Petrochemical Technology), 2011, 40 (11): 1145-1154
[120] 常运兴(Chang Y X), 张新军(Zhang X J). 油气田地面工程(Oil-Gasfield Surface Engineering), 2006, 25 (4): 8-9
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