Chemistry and association of vanadium compounds in heavy oil and bitumen, and implications for their selective removal

Energy and Fuels

Volumn 24, Issue 5, 2010, Pages 2795-2808

  Dechaine, Greg P ^a   Gray, Murray R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORBANCES; ASPHALTENE FRACTIONS; BOUND METALS; CATALYTIC CONVERSION; CHEMICAL FORMS; DEASPHALTING; DIFFERENT SOLVENTS; EXAFS; HEAVY OIL; IN-DEPTH ANALYSIS; LIGHT OIL; MALTENES; METALLOPORPHYRINS; MOLECULAR ASSOCIATIONS; POLAR SOLVENTS; SELECTIVE REMOVAL; SELECTIVE SEPARATION; SPECTROSCOPIC TECHNIQUE; VACUUM RESIDUE; XANES;

ABSORPTION; ABSORPTION SPECTROSCOPY; ASPHALTENES; ASSOCIATION REACTIONS; BITUMINOUS MATERIALS; CHEMICAL BONDS; CHEMICAL COMPOUNDS; FEEDSTOCKS; KETONES; PORPHYRINS; RESINS; SOLVENTS; VACUUM; VANADIUM ALLOYS; X RAY SPECTROSCOPY;

VANADIUM COMPOUNDS;

EID: 77952725105     PISSN: 08870624     EISSN: 15205029     Source Type: Journal    
DOI: 10.1021/ef100173j     Document Type: Article

References (167)

1. Branthaver, J. F. ACS Sym. Ser. 1987, 344, 188-204
2. Zychlinski, L.; Byczkowski, J. Z.; Kulkarni, A. P. Arch. Environ. Con. Tox. 1991, 20, 295-298
3. Cooper, R. G. Indian J. Occup. Environ. Med. 2007, 11, 97-102
4. Occupational Safety & Health Administration, U. S. Occupational Safety and Health Guideline for Vanadium Pentoxide. www.osha.gov (accessed Jan 7, 2010).
5. Drbal, L. F.; Boston, P. G.; Westra, K. L. Power Plant Engineering by Black & Veatch: Springer: New York, 1996.
6. Siskin, M.; Kelemen, S. R.; Eppig, C. P.; Brown, L. D.; Afeworki, M. Energy Fuels 2006, 20, 1227-1234
7. Brons, G.; Yu, J. M. Energy Fuels 1995, 9, 641-647
8. Reynolds, J. G. Liq. Fuels Technol. 1985, 3, 73-105
9. Gray, M. R. Upgrading Petroleum Residues and Heavy Oils; Marcel Dekker, Inc.: New York, 1994.
10. Barwise, A. J. G.; Whitehead, E. V. Prepr. - Am. Chem. Soc., Div. Pet. Chem. 1980, 25, 268-279
11. Pearson, C. D.; Green, J. B. Fuel 1989, 68, 456-464
12. Pearson, C. D.; Green, J. B. Fuel 1989, 68, 465-474
13. Altgelt, K. H.; Boduszynski, M. M. Composition and Analysis of Heavy Petroleum Fractions; Marcel Dekker, Inc.: New York, 1994; Vol. 54
14. Filby, R. H.; Strong, D. AIChE Symp. Ser. 1991, 87, 1-9
15. Pena, M. E.; Manjarréz, A.; Campero, A. Fuel Process. Technol. 1996, 46, 171-182
16. Yang, X.; Hamza, H.; Czarnecki, J. Energy Fuels 2004, 18, 770-777
17. Yen, T. F. Chemical Aspects of Metals in Native Petroleum. In The Role of Trace Metals in Petroleum; Yen, T. F., Ed.; Ann Arbor Science Publichers Inc.: Ann Arbor, MI, 1975; pp 1 - 30.
18. Qian, K.; Mennito, A. S.; Edwards, K. E.; Ferrughelli, D. T. Rapid Commun. Mass Spectrom. 2008, 22, 2153-2160
19. Smith, K. M. General Features of the Structure and Chemistry of Porphyrin Compounds. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier Scientific Publishing Company: New York, 1975; pp 1 - 28.
20. Senglet, N.; Williams, C.; Faure, D.; Des Courieres, T.; Guilard, R. Fuel 1990, 69, 72-77
21. Sugihara, J. M.; Bean, R. M. J. Chem. Eng. Data 1962, 7, 269-271
22. Czernuszewicz, R. S.; Maes, E. M.; Rankin, J. G. Resonance Raman Spectroscopy of Petroporphyrins. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 7, pp 293 - 335.
23. Goulon, J.; Retournard, A.; Friant, P.; Goulonginet, C.; Berthe, C.; Muller, J. F.; Poncet, J. L.; Guilard, R.; Escalier, J. C.; Neff, B. J. Chem. Soc. Dalton 1984, 1095-1103
24. Goulon, J.; Esselin, C.; Friant, P.; Berthe, C.; Muller, J. F.; Pncet, J. L.; Guilard, R.; Escalier, J. C.; Neff, B. In Structural Characterization by X-Ray Absorption Spectroscopy (EXAFS/XANES) of the Vanadium Chemical Environment in Various Asphaltenes, Characterization of heavy crude oils and petroleum residues. International Symposium on Characterization of Heavy Crude Oils and Petroleum Residues, Lyon, France, June 25-27, 1984; Editions Technip: Paris, pp 158 - 163.
25. Poncet, J. L.; Guilard, R.; Friant, P.; Goulonginet, C.; Goulon, J. New J. Chem. 1984, 8, 583-590
26. Berthe, C.; Muller, J.-F.; Cagniant, D.; Grimblot, J.; Bonnelle, J.-P. In Characterisation des Fractions Lourdes du Pétrole par Spectroscopie IR, UV-Visible, Spectroscopie Photoélectronique ESCA et Spectrométrie LAMMA en Relation avec L'environnement du Vanadium, Characterization of heavy crude oils and petroleum residues: International Symposium on Characterization of Heavy Crude Oils and Petroleum Residues, Lyon, France, June 25-27, 1984; Editions Technip: Paris, pp 164 - 168.
27. Loos, M.; Ascone, I.; Friant, P.; Ruiz-Lopez, M. F.; Goulon, J.; Barbe, J. M.; Senglet, N.; Guilard, R.; Faure, D.; Des Courieres, T. Catal. Today 1990, 7, 497-513
28. Zhang, G.; Boduszynski, M. M. In The Binding Structure of Vanadium in Arabian Heavy Petroleum: An X-Ray Absorption Investigation, International Conference on Petroleum Refining and Petrochemical Processing, Beijing, China, September 11-15, 1990; Xianglin, H., Ed.; International Academic Publishers: Beijing, China, 1991; pp 821 - 826.
29. Miller, J. T.; Fisher, R. B.; Thiyagarajan, P.; Winans, R. E.; Hunt, J. E. Energy Fuels 1998, 12, 1290-1298
30. Miller, J. T.; Fisher, R. B.; van der Eerden, A. M.; Koningsberger, D. C. Energy Fuels 1999, 13, 719-727
31. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 3 rd ed.; Wiley-VCH: Weinheim, Germany, 2003.
32. Jauquet, M.; Laszlo, P. Influence of Solvents on Spectroscopy. In Solutions and Solubilities; Dack, M. R. J., Ed.; John Wiley & Sons: New York, 1975; Vol. VIII, pp 195 - 258.
33. Smith, B. C. Quantitative Spectroscopy: Theory and Practice; Academic Press: Amsterdam, 2002.
34. Freeman, D. H.; Swahn, I. D.; Hambright, P. Energy Fuels 1990, 4, 699-704
35. Foster, N. S.; Day, J. W.; Filby, R. H.; Alford, A.; Rogers, D. Org. Geochem. 2002, 33, 907-919
36. Ferrer, E. G.; Baran, E. J. J. Electron Spectrosc. 1991, 57, 189-197
37. Freeman, D. H.; Saint Martin, D. C.; Boreham, C. J. Energy Fuels 1993, 7, 194-199
38. Cantú, R.; Stencel, J. R.; Czernuszewicz, R. S.; Jaffe, P. R.; Lash, T. D. Environ. Sci. Technol. 2000, 34, 192-198
39. Trofimenko, G. M.; Semeikin, A. S.; Berezin, M. B.; Berezin, B. D. Russ. J. Coord. Chem. 1996, 22, 476-480
40. Berezin, D. B.; Andrianov, V. G.; Semeikin, A. S. Opt. Spectrosc. 1996, 80, 554-561
41. Berezin, B. D. Coordination Compounds of Porphyrins and Phthalocyanines; John Wiley & Sons: Chichester, U. K., 1981.
42. Gouterman, M. Optical Spectra and Electronic Structure of Porphyrins and Related Rings. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. III-Physical Chemi, pp 1 - 165.
43. Berezin, B. D. J. Appl. Spectrosc. 1999, 66, 521-527
44. White, W. I. Aggregation of Porphyrins and Metalloporphyrins. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 5, pp 303 - 339.
45. Walker, F. A.; Hui, E.; Walker, J. M. J. Am. Chem. Soc. 1975, 97, 2390-2397
46. Bonnett, R.; Brewer, P.; Noro, K.; Noro, T. Tetrahedron 1978, 34, 379-385
47. Drew, M. G. B.; Mitchell, P. C. H.; Scott, C. E. Inorg. Chim. Acta 1984, 82, 63-68
48. Shelnutt, J. A.; Findsen, E. W.; Ondrias, M. R.; Alston, K. ACS Symp. Ser. 1987, 344, 368-383
49. Bencosme, C. S.; Romero, C.; Simoni, S. Inorg. Chem. 1985, 24, 1603-1604
50. Ozawa, T.; Hanaki, A. Inorg. Chim. Acta 1988, 141, 49-51
51. Boyd, P. D. W.; Smith, T. D.; Price, J. H.; Pilbrow, J. R. J. Chem. Phys. 1972, 56, 1253-1263
52. Banci, L. Inorg. Chem. 1985, 24, 782-786
53. Maiya, G. B.; Krishnan, V. Inorg. Chem. 1985, 24, 3253-3257
54. Lemtur, A.; Chakravorty, B. K.; Dhar, T. K.; Subramanian, J. J. Phys. Chem. 1984, 88, 5603-5608
55. Thanabal, V.; Krishnan, V. Inorg. Chem. 1982, 21, 3606-3613
56. Groennings, S. Anal. Chem. 1953, 25, 938-941
57. Biggs, W. R.; Fetzer, J. C.; Brown, R. J.; Reynolds, J. G. Liq. Fuels Technol. 1985, 3, 397-421
58. Reynolds, J. G.; Biggs, W. R.; Bezman, S. A. ACS Symp. Ser. 1987, 344, 205-219
59. Reynolds, J. G.; Jones, E. L.; Bennett, J. A.; Biggs, W. R. Fuel Sci. Techn. Int. 1989, 7, 625-642
60. Van Berkel, G. J.; Filby, R. H. ACS Symp. Ser. 1987, 344, 110-134
61. Pearson, C. D.; Green, J. B. Energy Fuels 1993, 7, 338-346
62. Freeman, D. H.; O'Haver, T. C. Energy Fuels 1990, 4, 688-694
63. Rao, C. N. R. Ultra-Violet and Visible Spectroscopy: Chemical Applications, 3 rd ed.; Butterworths: London, 1975.
64. Halasinski, T. M.; Weisman, J. L.; Ruiterkamp, R.; Lee, T. J.; Salama, F.; Head-Gordon, M. J. Phys. Chem. A 2003, 107, 3660-3669
65. Yokota, T.; Scriven, F.; Montgomery, D. S.; Strausz, O. P. Fuel 1986, 65, 1142-1149
66. Antipenko, V. R.; Zemtseva, L. I. Petrol. Chem. 1996, 36, 31-42
67. Wertz, J. E.; Bolton, J. R. Electron Spin Resonance: Elementary Theory and Practical Applications; McGraw Hill: New York, 1972.
68. Saraceno, A. J.; Coggeshall, N. D.; Fanale, D. T. Anal. Chem. 1961, 33, 500-505
69. Tynan, E. C.; Yen, T. F. Fuel 1969, 48, 191-208
70. Ebbing, D. D.; Gammon, S. D. General Chemistry, 6 th ed.; Houghton Mifflin Company: Boston, MA, 1999.
71. Selyutin, G. E.; Shklyaev, A. A.; Eletskii, N. P.; Anufrienko, V. F.; Titov, V. I. Sov. J. Coord. Chem. 1979, 5, 1041-1046
72. Yen, T. F.; Boucher, L. J.; Dickie, J. P.; Tynan, E. C.; Vaughan, G. B. J. Inst. Petrol 1969, 55, 87-99
73. Dickson, F. E.; Kunesh, C. J.; Mcginnis, E. L.; Petrakis, L. Anal. Chem. 1972, 44, 978-981
74. Dickson, F. E.; Petrakis, L. Anal. Chem. 1974, 46, 1129-1130
75. Reynolds, J. G.; Biggs, W. R.; Fetzer, J. C. Liq. Fuels Technol. 1985, 3, 423-448
76. Reynolds, J. G.; Biggs, W. R.; Fetzer, J. C.; Gallegos, E. J.; Fish, R. H.; Komlenic, J. J.; Wines, B. K. In Molecular Characterization of Vanadyl and Nickel Non-Porphyrin Compounds in Heavy Crude Petroleums and Residua, Characterization of heavy crude oils and petroleum residues: International Symposium on Characterization of Heavy Crude Oils and Petroleum Residues, Lyon, France, June 25-27, 1984; Editions Technip: Paris, pp 153 - 157.
77. Graham, W. R. M. ACS Symp. Ser. 1987, 344, 358-367
78. Reynolds, J. G.; Gallegos, E. J.; Fish, R. H.; Komlenic, J. J. Energy Fuels 1987, 1, 36-44
79. Malhotra, V. M.; Buckmaster, H. A. Fuel 1985, 64, 335-341
80. Malawer, E. G.; Senak, L. Introduction to Size Exclusion Chromatography. In Handbook of Size Exclusion Chromatography and Related Techniques, 2 nd ed.; Wu, C.-s., Ed.; Marcel Dekker, Inc.: New York, 2004; Chapter 1.
81. Skoog, D. A.; Leary, J. J. Principles of Instrumental Analysis, 4 th ed.; Saunders College Publishing: Fort Worth, TX, 1992.
82. Fish, R. H.; Komlenic, J. J. Anal. Chem. 1984, 56, 510-517
83. Fish, R. H.; Komlenic, J. J.; Wines, B. K. Anal. Chem. 1984, 56, 2452-2460
84. Biggs, W. R.; Brown, R. J.; Fetzer, J. C. Energy Fuels 1987, 1, 257-262
85. Fish, R. H.; Reynolds, J. G.; Gallegos, E. J. ACS Symp. Ser. 1987, 344, 332-349
86. Reynolds, J. G.; Biggs, W. R. Prepr. - Am. Chem. Soc., Div. Pet. Chem. 1987, 32, 398-405
87. Sundararaman, P.; Biggs, W. R.; Reynolds, J. G.; Fetzer, J. C. Geochim. Cosmochim. Acta 1988, 52, 2337-2341
88. Davison, R. R.; Glover, C. J.; Burr, B. L.; Bullin, J. A. Size Exclusion Chromatography of Asphalts. In Handbook of Size Exclusion Chromatography and Related Techniques, 2 nd ed.; Wu, C.-s., Ed.; Marcel Dekker, Inc.: New York, 2004; Chapter 8.
89. Nguyen, S. N.; Filby, R. H. ACS Symp. Ser. 1987, 344, 384-401
90. Baker, E. W.; Palmer, S. E. Geochemistry of Porphyrins. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. I, pp 486 - 552.
91. Blumer, M.; Rudrum, M. J. Inst. Petrol. 1970, 57, 99-106
92. Baker, E. W.; Yen, T. F.; Dickie, J. P.; Rhodes, R. E.; Clark, L. F. J. Am. Chem. Soc. 1967, 89, 3631-3639
93. Blumer, T. Geochim. Cosmochim. Acta 1964, 28, 1147-1154
94. Strong, D.; Filby, R. H. ACS Symp. Ser. 1987, 344, 154-172
95. Van Berkel, G. J.; Quinoñes, M. A.; Quirke, M. E. J. Energy Fuels 1993, 7, 411-419
96. Xu, H.; Que, G.; Yu, D.; Lu, J. R. Energy Fuels 2005, 19, 517-524
97. Beato, B. D.; Yost, R. A.; Van Berkel, G. J.; Filby, R. H.; Quirke, J. M. E. Org. Geochem. 1991, 17, 93-105
98. Grigsby, R. D.; Green, J. B. Energy Fuels 1997, 11, 602-609
99. Rodgers, R. P.; Hendrickson, C. L.; Emmett, M. R.; Marshall, A. G.; Greaney, M.; Qian, K. Can. J. Chem. 2001, 79, 546-551
100. Tanaka, R.; Hunt, J. E.; Winans, R. E.; Thiyagarajan, P.; Sato, S.; Takanohashi, T. Energy Fuels 2003, 17, 127-134
101. Spiecker, P. M.; Gawrys, K. L.; Kilpatrick, P. K. J. Colloid Interface Sci. 2003, 267, 178-193
102. Thiyagarajan, P.; Hunt, J. E.; Winans, R. E.; Anderson, K. B.; Miller, J. T. Energy Fuels 1995, 9, 829-833
103. Cosultchi, A.; Bosch, P.; Lara, V. H. Colloid Polym. Sci. 2003, 281, 325-330
104. Savvidis, T. G.; Fenistein, D.; Barre, L.; Behar, E. AIChE J. 2001, 47, 206-211
105. Bardon, C.; Barre, L.; Espinat, D.; Guille, V.; Li, M. H.; Lambard, J.; Ravey, J. C.; Rosenberg, E.; Zemb, T. Fuel Sci. Technol. Int. 1996, 14, 203-242
106. Kim, H.-g.; Long, R. B. Ind. Eng. Chem. Fund. 1979, 18, 60-63
107. Strausz, O. P.; Peng, P.; Murgich, J. Energy Fuels 2002, 16, 809-822
108. Andersen, S. I. Fuel Sci. Techn. Int. 1994, 12, 51-74
109. Yarranton, H. W.; Alboudwarej, H.; Jakher, R. Ind. Eng. Chem. Res. 2000, 39, 2916-2924
110. Agrawala, M.; Yarranton, H. W. Ind. Eng. Chem. Res. 2001, 40, 4664-4672
111. Yarranton, H. W.; Fox, W. A.; Svrcek, W. Y. Can. J. Chem. Eng. 2007, 85, 635-642
112. Wong, G. K.; Yen, T. F. J. Petrol. Sci. Eng. 2000, 28, 55-64
113. Tanaka, R.; Sato, E.; Hunt, J. E.; Winans, R. E.; Sato, S.; Takanohashi, T. Energy Fuels 2004, 18, 1118-1125
114. Mamardashvili, G. M.; Mamardashvili, N. Z.; Golubchicov, O. A.; Berezin, B. D. J. Mol. Liq. 2001, 91, 189-191
115. Mamardashvili, G. M.; Mamardashvili, N. Z.; Golubchikov, O. A.; Berezin, B. D. Russ. J. Phys. Chem. 1999, 73, 894-898
116. Trofimenko, G. M.; Mamardashvili, N. Z.; Golubchikov, O. A.; Berezin, B. D. Russ. J. Phys. Chem. 1997, 71, 240-243
117. Berezin, B. D.; Koifman, O. I.; Nikitina, G. E. Russ. J. Phys. Chem. 1980, 54, 1413-1415
118. Berezin, B. D.; Koifman, O. I.; Zelov, V. V.; Nikitina, G. E. Russ. J. Phys. Chem. 1978, 52, 1281-1282
119. Koifman, O. I.; Berezin, B. D.; Zelov, V. V.; Nikitina, G. E. Russ. J. Phys. Chem. 1978, 52, 1032-1034
120. Salcedo, R.; Zaragoza, I. P.; Martinez-Magadan, J. M.; Garcia-Cruz, I. THEOCHEM 2003, 626, 195-201
121. Pfeiffer, J. P.; Saal, R. N. J. J. Phys. Chem. 1940, 44, 139-149
122. Yen, T. F.; Erdman, J. G.; Pollack, S. S. Anal. Chem. 1961, 33, 1587-1594
123. Speight, J. G. Asphaltenes and the Structure of Petroleum. In Petroleum Chemistry and Refining; Speight, J. G., Ed.; Taylor and Francis: Washington, DC, 1998; pp 103 - 120.
124. Merino-Garcia, D.; Andersen, S. I. Langmuir 2004, 20, 4559-4565
125. Merino-Garcia, D.; Andersen, S. I. Langmuir 2004, 20, 1473-1480
126. Merino-Garcia, D.; Murgich, J.; Andersen, S. I. Petrol. Sci. Technol. 2004, 22, 735-758
127. Juyal, P.; Merino-Garcia, D.; Andersen, S. I. Energy Fuels 2005, 19, 1272-1281
128. Merino-Garcia, D.; Andersen, S. I. J. Disper. Sci. Technol. 2005, 26, 217-225
129. Verdier, S.; Plantier, F.; Bessieres, D.; Andersen, S. I.; Stenby, E. H.; Carrier, H. Energy Fuels 2007, 21, 3583-3587
130. Akbarzadeh, K.; Alboudwarej, H.; Svrcek, W. Y.; Yarranton, H. W. Fluid Phase Equilib. 2005, 232, 159-170
131. Akbarzadeh, K.; Dhillon, A.; Svrcek, W. Y.; Yarranton, H. W. Energy Fuels 2004, 18, 1434-1441
132. Alboudwarej, H.; Akbarzadeh, K.; Beck, J.; Svrcek, W. Y.; Yarranton, H. W. AIChE J. 2003, 49, 2948-2956
133. Yarranton, H. W.; Masliyah, J. H. AIChE J. 1996, 42, 3533-3543
134. Cimino, R.; Correra, S.; Sacomani, P. A.; Carniani, C. In Thermodynamic modelling for prediction of asphaltene deposition in live oils. International Symposium on Oilfield Chemistry, Feb 14-17, 1995, San Antonio, TX; Society of Petroleum Engineers (SPE): Richardson, TX, 1995; pp 499 - 512.
135. Cimino, R.; Correra, S.; Del Bianco, A.; Lockhart, T. P. Solubility and Phase behaviour of Asphaltenes in Hydrocarbon Media. In Asphaltenes: Fundamentals and Applications; Sheu, E. Y.; Mullins, O. C., Eds.; Plenum Press: New York, 1995; pp 97 - 130.
136. Akbarzadeh, K.; Ayatollahi, S.; Moshfeghian, M.; Alboudwarej, H.; Yarranton, H. W. J. Can. Petrol. Technol. 2004, 43, 31-39
137. Sabbagh, O.; Akbarzadeh, K.; Badamchi-Zadeh, A.; Svrcek, W. Y.; Yarranton, H. W. Energy Fuels 2006, 20, 625-634
138. Buenrostro-Gonzalez, E.; Lira-Galeana, C.; Gil-Villegas, A.; Wu, J. AIChE J. 2004, 50, 2552-2570
139. Wu, J.; Prausnitz, J. M.; Firoozabadi, A. AIChE J. 2000, 46, 197-209
140. Akbarzadeh, K.; Bressler, D. C.; Wang, J.; Gawrys, K. L.; Gray, M. R.; Kilpatrick, P. K.; Yarranton, H. W. Energy Fuels 2005, 19, 1268-1271
141. Rakotondradany, F.; Fenniri, H.; Rahimi, P.; Gawrys, K. L.; Kilpatrick, P. K.; Gray, M. R. Energy Fuels 2006, 20, 2439-2447
142. Tan, X.; Fenniri, H.; Gray, M. R. Energy Fuels 2008, 22, 715-720
143. Tan, X.; Fenniri, H.; Gray, M. R. Energy Fuels 2009, 23, 3687-3693
144. Yudin, I. K.; Nikolaenko, G. L.; Gorodetskii, E. E.; Markhashov, E. L.; Frot, D.; Briolant, Y.; Agayan, V. A.; Anisimov, M. A. Petrol. Sci. Technol. 1998, 16, 395-414
145. Yin, C.-X.; Tan, X.; Mullen, K.; Stryker, J. M.; Gray, M. R. Energy Fuels 2008, 22, 2465-2469
146. Sirota, E. B. Energy Fuels 2005, 19, 1290-1296
147. Lerner, B. J. Removing metals with a 2-pyrrolidone-alcohol mixture. Patent 3052627, 09/04/1962.
148. Kimberlin, C. N. J.; Mattox, W. J. Butyrolactone solvent extraction process for removal of metal contaminants. Patent 2913394, 11/17/1959.
149. Overfield, R. E. Integrated method for extracting nickel and vanadium compounds from oils. Patent 4643821, 02/17/1987.
150. Galimov, R. A.; Krivonozhkina, L. B.; Abushayeva, V. V.; Romanov, G. V. Petrol. Chem. 1993, 33, 539-543
151. Yin, C.-X.; Stryker, J. M.; Gray, M. R. Energy Fuels 2009, 23, 2600-2605
152. Speronello, B. K.; Reagan, W. J. Oil Gas J. 1984, 82, 139-143
153. Tsiatouras, V. A.; Evmiridis, N. P.; AF Tsiatouras, V. A.; Evmiridis, N. P. Ind. Eng. Chem. Res. 2008, 47, 9288-9296
154. Kimberlin, C. N. J.; Ellert, H. G.; Adams, C. E.; Hamner, G. P. Demetallization with Hydrofluoric Acid. Patent 3,203,892, 08/31/1965.
155. Sugihara, J. M.; Branthaver, J. F.; Willcox, K. W. Oxidative demetallation of oxovanadium(IV) porphyrins. In The Role of Trace Metals in Petroleum; Yen, T. F., Ed.; Ann Arbor Science Publichers Inc.: Ann Arbor, MI, 1975; pp 183 - 193.
156. Gould, K. A. Fuel 1980, 59, 733-736
157. Mann, D. P.; Kukes, S. G.; Coombs, D. M. Metals Removal with a Light Hydrocarbon and an Organophosphorous Compound. Patent 4,518,484, 05/21/1985.
158. Fedorak, P. M.; Semple, K. M.; Vazquez-Duhalt, R.; Westlake, D. W. S. Enzyme Microb. Tech. 1993, 15, 429-437
159. Xu, G.-W.; Mitchell, K. W.; Monticello, D. J. Fuel Product Produced by Demetalizing a Fossil Fuel with an Enzyme. Patent 5,726,056, 03/10/1998.
160. Dedeles, G. R.; Abe, A.; Saito, K.; Asano, K.; Saito, K.; Yokota, A.; Tomita, F. J. Biosci. Bioeng. 2000, 90, 515-521
161. Greaney, M. A.; Kerby, M. C., Jr.; Olmstead, W. N.; Wiehe, I. A. Method for Demetallating Refinrey Feedstreams. Patent 5,529,684, 06/25/1996.
162. Ovalles, C.; Rojas, I.; Acevedo, S.; Escobar, G.; Jorge, G.; Gutierrez, L. B.; Rincon, A.; Scharifker, B. Fuel Process. Technol. 1996, 48, 159-172
163. Sakanishi, K.; Yamashita, N.; Whitehurst, D. D.; Mochida, I. Catal. Today 1998, 43, 241-247
164. Shiraishi, Y.; Hirai, T.; Komasawa, I. Ind. Eng. Chem. Res. 2000, 39, 1345-1355
165. Sakanishi, K.; Saito, I.; Watanabe, I.; Mochida, I. Fuel 2004, 83, 1889-1893
166. Hansen, C. M. Ind. Eng. Chem. Prod. Res. Dev. 1969, 8, 2-11
167. Wiehe, I. A. Process Chemistry of Petroleum Macromolecules; CRC Press: Boca Raton, FL, 2008.