Pyrene derivatives of 2,2′-bipyridine as models for asphaltenes: Synthesis, characterization, and supramolecular organization

Energy and Fuels

Volumn 22, Issue 2, 2008, Pages 715-720

  Tan, Xiaoli ^a   Fenniri, Hicham ^a   Gray, Murray R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; AROMATIC COMPOUNDS; ASPHALTENES; GAS ADSORPTION; HYDROSTATIC PRESSURE; MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE; PYRENE; RESONANCE; SINGLE CRYSTALS; SOLUBILITY; TERNARY SYSTEMS; VAPOR PRESSURE;

ADSORPTION BEHAVIORS; AROMATIC SPECIES; AS MODELS; BIPYRIDINE; BIPYRIDYL; BRIDGED STRUCTURES; CHROMATOGRAPHIC PROPERTIES; FUSED AROMATIC RINGS; PETROLEUM ASPHALTENES; PYRENE DERIVATIVES; RAY ANALYSES; STACKING INTERACTIONS; STEADY STATE FLUORESCENCES; SUPRAMOLECULAR ORGANIZATIONS; VAPOR PRESSURE OSMOMETRY;

ASSOCIATION REACTIONS;

EID: 42049111060     PISSN: 08870624     EISSN: None     Source Type: Journal    
DOI: 10.1021/ef700395g     Document Type: Article

References (59)

1. Yen T. F.; Chilingarian, G. V.; Eds. Asphaltene and Asphalts, 2. Developments in Petroleum Science; Elsevier Science: Amsterdam, The Netherlands, 2000.
2. Mitchell, D. L.; Speight, J. G. Fuel 1973, 52, 149-152.
3. Gawrys, K. L.; Spiecker, P. M.; Kilpatrick, P. K. Pet. Sci. Technol. 2003, 21, 461-489.
4. Sheu, E. Y.; Liang, K. S.; Sinha, S. K.; Overfield, R. E. J. Colloid Interface Sci. 1992, 153, 399-410.
5. Andersen, S. I.; Keul, A.; Stenby, E. Pet. Sci. Technol. 1997, 15, 611-646.
6. Wiehe, I. A.; Liang, K. S. Fluid Phase Equilib. 1996, 117, 201-210.
7. (a) Yarranton, H. W.; Alboudwarej, H.; Jakher, R Ind. Eng. Chem. Res. 2006, 39, 2916-2924.
8. (b) Agrawala, M.; Yarranton, H. W. Ind. Eng. Chem. Res. 2001, 40, 4664-4672.
9. Merino-Garcia, D.; Andersen, S. I. Pet. Sci. Technol. 2003, 21, 507-525.
10. Moschopedis, S. E.; Speight, J. Fuel 1976, 55, 187-192.
11. Gutiérrez, L. B.; Ranaudo, M. A.; Mendez, B.; Acevedo, S. Energy Fuels 2001, 15, 624-628.
12. Spiecker, M. P.; Gawrys, K. L.; Kilpatrick, P. K. J. Colloid Interface Sci. 2003, 267, 178-193.
13. Buckley, J. S. Fuel Sci. Technol. Int. 1996, 14, 55-74.
14. Buckley, J. S. Energy Fuels 1999, 13, 328-332.
15. Groenzin, H.; Mullins, O. C. Energy Fuels 2000, 14, 677-684.
16. Rogel, E.; Carbognani, L. Energy Fuels 2003, 17, 378-386.
17. Murgich, J. Mol. Simul. 2003, 29, 451-461.
18. Groenzin, H.; Mullins, O. C.; Eser, S.; Mathews, J.; Yang, M.-G.; Jones, D. Energy Fuels 2003, 17, 498-503.
19. Ruiz-Morales, Y.; Mullins, O. C. Energy Fuels 2007, 21, 256-265.
20. Yen, T. F.; Erdman, J. G.; Pollack, S. S. Anal. Chem. 1961, 33, 1587-1594.
21. Murgich, J.; Abanero, J. A.; Strausz, O. P. Energy Fuels 1999, 13, 278-286.
22. Sharma, A.; Groenzin, H.; Tomita, A.; Mullins, O. C. Energy Fuels 2002, 16, 490-496.
23. Sheremata, J. M.; Gray, M. R.; Dettman, H. D.; McCaffrey, W. C. Energy Fuels 2004, 18, 1377-1384.
24. Gray, M. R. Energy Fuels 2003, 17, 1566-1569.
25. Calemma, V.; Iwanski, P.; Nali, M.; Scotti, R.; Montanari, L. Energy Fuels 1995, 9, 225-230.
26. Strausz, O. P.; Mojelsky, T. W.; Lown, E. M. Fuel 1992, 71, 1355-1363.
27. Müller, H.; Andersson, J. T.; Schrader, W. Anal. Chem. 2005, 77, 2536-2543.
28. Panda, S. K.; Schrader, W.; Al-Hajji, A.; Andersson, J. T. Energy Fuels 2007, 21, 1071-1077.
29. Akbarzadeh, K.; Bressler, D. C.; Wang, J.; Gawrys, K. L.; Gray, M. R.; Kilpatrick, P. K.; Yarraton, H. W. Energy Fuels 2005, 19, 1268-1271.
30. Rakotondradany, F.; Fenniri, H.; Rahimi, P.; Gawrys, K. L.; Kilpatrick, P. K.; Gray, M. R. Energy Fuels 2006, 20, 2439-2447.
31. Bair, K. W.; Tuttle, R. L.; Knick, V. C.; Cory, M.; McKee, D. D. J. Med. Chem. 1990, 33, 2385-2393.
32. McClenghan, N. D.; Barigelletti, F.; Maubert, B.; Campagna, S. Chem. Commun. 2002, 602-603.
33. Castillo, J.; Fernández, A.; Ranaudo, M. A.; Acevedo, S. Pet. Sci. Technol. 2001, 19, 75-106.
34. Selucky, M. L.; Kim, S. S.; Skinner, F.; Strausz, O. P. Chemistry of Asphaltenes; Advances in Chemistry Series, 195; ACS: Washington, D.C., 1981; pp 83-118..
35. The detailed properties of PB will be published elsewhere.
36. (a) Watson, M. D.; Jackel, F.; Severin, N.; Rabe, J. P.; Müllen, K. J. Am. Chem. Soc. 2004, 126, 1402-1407.
37. (b) Fechtenkötter, A.; Saalwächter, K.; Harbison, M. A.; Müllen, K.; Spiess, H. W. Angew. Chem., Int. Ed. 1999, 38, 3039-3042.
38. (c) Shetty, A. S.; Fischer, P. R.; Storck, K. F.; Bohn, P. W.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 9409-9414.
39. (d) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027.
40. (e) Kastler, M.; Pisula, W.; Wasserfallen, D.; Pakula, T.; Müllen, K. J. Am. Chem. Soc. 2005, 127, 4286-4296.
41. (f) Prince, R. B.; Saven, J. G.; Wolynes, P. G.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 3114-3121. 42 Goncalves, S.; Castillo, J.; Fernandez, A.; Hung, J. Fuel 2004, 83, 1823-1828.
42. Sheu, E. Y. Energy Fuels 2002, 16, 74-82.
43. Ghosh, A. K. Fuel 2005, 84, 153-157.
44. Liao, Z.; Zhou, H.; Graciaa, A.; Chrostowska, A.; Creux, P.; Geng, A. Energy Fuels 2005, 19, 180-186.
45. Badre, S.; Goncalves, C. C.; Norinaga, K.; Gustavson, G.; Mullins O. C. Fuel 2006, 85, 1-11.
46. Murgich, J. Pet. Sci. Technol. 2002, 20, 983-997.
47. Venkataramana, G.; Sankararaman, S. Org. Lett. 2006, 8, 2739-2742.
48. Winnik, F. M. Chem. Rev. 1993, 93, 587-614.
49. Lakowicz, J. R.; Ed. Principles of Fluorescence Spectroscopy, 3rd ed.; Springer Science: New York, 2006.
50. Cho, D. W.; Fujitsuka, M.; Choi, K. H.; Park, M. J.; Yoon, U. C.; Majima, T. J. Phys. Chem. B 2006, 110, 4576-4582.
51. (a) Sanders, G. M.; van Dijk, M.; van Veldhuizen, A.; van der Plas, H. C.; Hofstra, U.; Schaafsma, T. J. J. Org. Chem. 1988, 53, 5272-5281.
52. (b) Bryant, J. A.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1990, 112, 1254-1255.
53. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
54. Khulbe, K. C.; Sachdev, A. K.; Mann, R. S.; Davis, S. TGA studies of asphaltenes derived from Cold-Lake (Canada) Bitumen. Fuel Process. Technol. 1984, 8, 259-266.
55. Ambalae, A.; Mahinpey, N.; Freitag, N. Energy Fuels 2006, 20, 560-565.
56. Dong, X.-G.; Lei, Q.-F.; Fang, W.-J.; Yu, Q.-S. Thermochim. Acta 2005, 427, 149-153.
57. Karacan, O.; Kok, M. V. Energy Fuels 1997, 11, 385-391.
58. Calemman, V.; Rausa, R. J. Anal. Appl. Pyrolysis 1997, 40-41, 568-584.
59. Japanwala, S.; Chung, K. H.; Dettman, H. D.; Gray, M. R. Energy Fuels 2002, 16, 477-484.