A novel demetalation process for vanadyl- and nickelporphyrins from petroleum residue by photochemical reaction and liquid-liquid extraction

Industrial and Engineering Chemistry Research

Volumn 39, Issue 5, 2000, Pages 1345-1355

  Shiraishi, Yasuhiro ^a   Hirai, Takayuki ^a   Komasawa, Isao ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUEL OILS; HYDROCHLORIC ACID; NICKEL; ORGANIC SOLVENTS; ORGANOMETALLICS; PHOTOCHEMICAL REACTIONS; VANADIUM;

DEMETALATION; LIQUID-LIQUID EXTRACTION; PORPHYRINS;

EXTRACTION;

METAL COMPLEX; METALLOPORPHYRIN; NICKEL; PETROLEUM; PORPHYRIN DERIVATIVE; VANADYL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; ATMOSPHERIC DISPERSION; CATALYSIS; HYDROGENATION; LIQUID LIQUID EXTRACTION; OXIDATION; PHOTOCHEMISTRY; REACTION ANALYSIS; RESIDUE ANALYSIS;

EID: 0034019716     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie990809o     Document Type: Article

References (32)

1. Yen, T. F.; Bougher, L. J.; Dickie, J. P.; Tynan, E. C.; Vaughan, G. B. Vanadium Complexes and Porphyrins in Asphaltenes. J. Inst. Petrol. 1969, 55, 87.
2. Tsai, M.-C.; Chen, Y.-W.; Kang, B.-C.; Wu, J. C.; Leu, L. J. Hydrodesulfurization and Hydrodemetalation Reactions of Residual Oils over CoMo/Alumina Borate Catalysts in a Trickle Bed Reactor. Ind. Eng. Chem. Res. 1991, 30, 1801.
3. Chen, H.-J.; Massoth, F. E. Hydrodemetalation of Vanadium and Nickel Porphyrins over Sulfided Co/Mo Catalyst. Ind. Eng. Chem. Res. 1988, 27, 1629.
4. Chen, Y.-W.; Hsu, W. C. Hydrodemetalation of Residue Oil over CoMo/Alumina-Aluminum Phosphate Catalysts in a Trickle Bed Reactor. Ind. Eng. Chem. Res. 1997, 36, 2526.
5. Barrett, J. Photo-Oxidation of Magnesium Porphyrins and Formation of Protobiliviolin. Nature 1967, 215, 733.
6. Seely, G. R.; Calvin, M. Photochemical Studies of the Porphyrins. III. Photoreduction of a Porphyrin by Benzoin. J. Chem. Phys. 1955, 23, 1068.
7. Jones, A. C.; Dale, M. J.; Keenan, G. A.; Langridge-Smith, P. R. R. Photoionization and Photodissociation of Laser-Vaporised Metallotetraphenylporphyrins. Chem. Phys. Lett. 1994, 219, 174.
8. Shiraishi, Y.; Hirai, T.; Komasawa, I. A Deep Desulfurization Process for Light Oil by Photochemical Reaction in an Organic Two-Phase Liquid-Liquid Extraction System. Ind. Eng. Chem. Res. 1998, 37, 203.
9. Shiraishi, Y.; Taki, Y.; Hirai, T.; Komasawa, I. Visible Light-Induced Deep Desulfurization Process for Light Oils by Photochemical Electron-Transfer Oxidation in an Organic Two-Phase Extraction System. Ind. Eng. Chem. Res. 1999, 38, 3310.
10. Shiraishi, Y.; Taki, Y.; Hirai, T.; Komasawa, I. Visible Light-Induced Desulfurization Process for Catalytic-Cracked Gasoline Using an Organic Two-Phase Extraction System. Ind. Eng. Chem. Res. 1999, 38, 4538.
11. Kameyama, H.; Sugishima, M.; Yamada, M.; Amano, A. Hydrodevanadization of Vanadyl Porphyrin by Tetrarin. J. Jpn. Petrol. Inst. (in Japanese) 1981, 24, 317.
12. Hung, C.-W.; Wei, J. The Kinetics of Porphyrin Hydrodemetalation. 2. Vanadyl Compounds. Ind. Eng. Chem. Process Des. Dev. 1980, 19, 257.
13. Bonnet, R.; Brewer, P.; Noro, K.; Noro, T. Chemistry of Vanadyl Porphyrins. Tetrahedron 1978, 34, 379.
14. Erdman, J. G.; Ramsey, V. G.; Kalenda, N. W.; Hanson, W. E. Synthesis and Properties of Porphyrin Vanadium Complex. J. Am. Chem. Soc. 1956, 78, 5844.
15. Taylor, S. E. Investigations into the Electrical and Coalescence Behaviour of Water-in-Crude Oil Emulsions in High Voltage Gradients. Colloid Surf. 1988, 29, 29.
16. Ono, T. Rapid Method for Determination of Asphaltene Content in Residual Fuel Oils. J. Jpn. Petrol. Inst. (in Japanese) 1971, 14, 504.
17. Saraceno, A. J.; Fanale, D. T.; Coggeshell, N. D. An Electron Paramagnetic Resonance Investigation of Vanadium in Petroleum Oils. Anal. Chem. 1961, 33, 500.
18. Jeoung, S. C.; Kim, D.; Hahn, S. J.; Ryu, S. Y.; Yoon, M. Lowest Excited State of Oxovanadyl(IV)Tetraphenylporphyrin. J. Phys. Chem. A 1998, 102, 315.
19. Selbin, J. The Chemistry of Oxovanadium(IV). Chem. Rev. 1965, 65, 2.
20. Freeman, D. H.; Swahn, I. D.; Hambright, P. Spectrophotometry and Solubility Properties of Nickel and Vanadyl Porphyrin Complexes. Energy Fuels 1990, 4, 699.
21. Harriman, A. Luminescence of Porphyrins and Metallo Porphyrins. Part 1. -Zinc(II), Nickel(II) and Manganese(II) Porphyrins. J. Chem. Soc., Faraday Trans. 1 1980, 76, 1978.
22. Drain, C. M.; Gentemann, S.; Roberts, J. A.; Nelson, N. Y.; Medforth, C. J.; Jia, S.; Simpson, M. C.; Smith, K. M.; Fajer, J.; Shelnutt, J. A.; Holten, D. Picosecond to Microsecond Photodynamics of a Nonplanar Nickel Porphyrin: Solvent Dielectric and Temperature Effects. J. Am. Chem. Soc. 1998, 120, 3781.
23. Dickie, J. P.; Yen, T. F. Macrostructure of the Asphaltic Fractions by Various Instrumental Methods. Anal. Chem. 1967, 39, 1847.
24. Tynan, E. C.; Yen, T. F. Association of Vanadium Chelates in Petroleum Asphaltenes as Studied by ESR. Fuel 1969, 43, 191.
25. Yamada, Y.; Koinuma, Y. Behavior of Vanadyl Chelate Complexes in GPC Fractionated Asphaltenes. J. Jpn. Petrol. Inst. (in Japanese) 1989, 32, 7.
26. Reynolds, J. G.; Gallegos, E. J.; Fish, R. H.; Komlenic, J. J. Characterization of the Binding Sites of Vanadium Compounds in Heavy Crude Petroleum Extracts by Electron Paramagnetic Spectroscopy. Energy Fuels 1987, 1, 36.
27. Verne-Mismer, R.; Ocampo, R.; Bauder, C.; Callot, H. J.; Albrecht, P. Structural Comparison of Nickel, Vanadyl, Copper, and Free Base Porphyrins from Oulad Abdoum Oil Shale (Maastrichtian, Morocco). Energy Fuels 1990, 4, 639.
28. Didik, B. M.; Alturki, Y. I. A.; Pillingger, C. T.; Eglinton, G. Petroporphyrins as Indicators of Geochemical Maturation. Nature 1975, 256, 563.
29. Dunning, H. N.; Moore, J. W.; Denekas, M. O. Interfacial Activities and Porphyrin Contents of Petroleum Extracts. Ind. Eng. Chem. 1953, 45, 1759.
30. Boukir, A.; Guiliano, M.; Asia, L.; Hallaoui, A. El.; Mille, G. A Fraction to Fraction Study of Photo-oxidation of BAL 150 Crude Oil Asphaltenes. Analysis 1998, 26, 358.
31. Fujishiro, M.; Ohta, K.; Iwai, S. Influence of Light Irradiation on Asphalt Components. J. Jpn. Petrol. Inst. 1979, 22, 319.
32. Shiraishi, Y.; Hirai, T.; Komasawa, I. Photochemical Desulfurization of Light Oils Using Oil/Hydrogen Peroxide Aqueous Solution Two-Phase System: Application for High Sulfur Content Straight-Run Light Gas Oil and Aromatic Rich Light Cycle Oil. J. Chem. Eng. Jpn. 1999, 32, 158.