Novel methodology toward deep desulfurization of diesel feed based on the selective elimination of nitrogen compounds

Industrial and Engineering Chemistry Research

Volumn 43, Issue 24, 2004, Pages 7843-7849

  Macaud, Mathieu ^a   Sévignon, Marc ^a   Favre Réguillon, Alain ^a   Lemaire, Marc ^a   Schulz, Emmanuelle ^b   Vrinat, Michel ^c  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ PARIS SUD   (France)

^c INST DE RECHERCHES SUR LA CATALYSE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIESEL FUELS; GAS OILS; HYDROPHILICITY; ION EXCHANGE; NITROGEN COMPOUNDS; POLYMERS; SULFUR DEPOSITS;

DIESEL FEEDS; HETEROCYCLIC COMPOUNDS; HYDRODESULFURIZATION (HDS);

DESULFURIZATION;

DIESEL FUEL; HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; POLYMER; SULFUR;

DESULFURIZATION; DIESEL; NITROGEN; SEPARATION;

ADSORPTION; ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; DESULFURIZATION; HYDROPHILICITY; ION EXCHANGE;

EID: 9244244240     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie049465e     Document Type: Article

References (55)

1. Regulatory Impact Analysis: Heavy-Duty Engine and Vehicle Standards and Highway Diesel Fuel Sulfur Control Requirements; United States Environmental Protection Agency, December 2000; EPA420-R-00-026.
2. Breysse, M.; Djega-Mariadassou, G.; Pessayre, S.; Geantet, C.; Vrinat, M.; Perot, G.; Lemaire, M. Deep desulfurization: reactions, catalysts and technological challenges. Catal. Today 2003, 84, 129-138.
3. Milenkovic, A.; Schulz, E.; Meille, V.; Loffreda, D.; Forissier, M.; Vrinat, M.; Sautet, P.; Lemaire, M. Selective Elimination of Alkyldibenzothiophenes from Gas Oil by Formation of Insoluble Charge-Transfer Complexes. Energy Fuels 1999, 13, 881-887.
4. Shafi, R.; Hutchings, G. J. Hydrodesulfurization of hindered dibenzothiophenes: an overview. Catal. Today 2000, 59, 423-442.
5. Laredo, G.; De los Reyes, A.; Cano, L.; Castillo, J. Inhibition effects of nitrogen compounds on the hydrodesulfurization of dibenzothiophene. Appl. Catal. A 2001, 207, 103-112.
6. Laredo, G.; Altamirano, E.; De los Reyes, A. Inhibition effects of nitrogen compounds on the hydrodesulfurization of dibenzothiophene: Part 2. Appl. Catal. A 2003, 243, 207-214.
7. 3- and MCM-41-supported Co-Mo sulfide catalysts. Catal. Today 2003, 86, 265-275.
8. Koltai, T.; Macaud, M.; Guevara, A.; Schulz, E.; Lemaire, M.; Bacaud, R.; Vrinat, M. Comparative inhibiting effect of polycondensed aromatics and nitrogen compounds on the hydrodesulfurization of alkyldibenzothiophenes. Appl. Catal. A 2002, 231, 253-261.
9. Perot, G. Reactions involved in hydrodenitrogenation. Catal. Today 1991, 10, 447-472.
10. Girgis, M. J.; Gates, B. C. Reactivities, reaction networks, and kinetics in high-pressure catalytic hydroprocessing. Ind. Eng. Chem. Res. 1991, 30, 2021-2058.
11. Kasztelan, S.; Des Courieres, T.; Breysse, M. Hydrodenitrogenation of petroleum distillates: industrial aspects. Catal. Today 1991, 10, 433-445.
12. Furimsky, E.; Massoth, F. E. Deactivation of hydroprocessing catalysts. Catal. Today 1999, 52, 381-495.
13. Satterfield, C. N.; Modell, M.; Wilkens, J. A. Simultaneous catalytic hydrodenitrogenation of pyridine and hydrodesulfurization of thiophene. Ind. Eng. Chem. Process Des. Dev. 1980, 19, 154-160.
14. LaVopa, V.; Satterfield, C. N. Poisoning of thiophene hydrodesulfurization by nitrogen compounds. J. Catal. 1988, 110, 375-387.
15. LaVopa, V.; Satterfield, C. N. Response of dibenzothiophene hydrodesulfurization to presence of nitrogen compounds, Chem. Eng. Commun. 1988, 70, 171-176.
16. Nagai, M.; Sato, T.; Aiba, A. Poisoning effect of nitrogen compounds on dibenzothiophene hydrodesulfurization on sulfided nickel-molybdenum/alumina catalysts and relation to gas-phase basicity. J. Catal. 1986, 97, 52-58.
17. Nagai, M.; Kabe, T. Selectivity of molybdenum catalyst in hydrodesulfurization, hydrodenitrogenation, and hydrodeoxygenation: effect of additives on dibenzothiophene hydrodesulfurization. J. Catal. 1983, 81, 440-449.
18. Gutberlet, L. C.; Bertolacini, R. J. Inhibition of hydrodesulfurization by nitrogen compounds. Ind. Eng. Chem. Prod. Res. Dev. 1983, 22, 246-250.
19. Batts, B. D.; Fathoni, A. Z. A literature review on fuel stability studies with particular emphasis on diesel oil. Energy Fuels 1991, 5, 2-21.
20. Mushrush, G. W.; Beal, E. J.; Hardy, D. R.; Hughes, J. M. Nitrogen compound distribution in middle distillate fuels derived from petroleum, oil shale, and tar sand sources. Fuel Process. Technol. 1999, 61, 197-210.
21. Schmitter, J. M.; Ignatiadis, I.; Dorbon, M.; Arpino, P.; Guiochon, G.; Toulhoat, H.; Huc, A. Identification of nitrogen bases in a coker gas oil and influence of catalytic hydrotreatment on their composition. Fuel 1984, 63, 557-564.
22. Dorbon, M.; Bernasconi, C. Nitrogen compounds in light cycle oils: identification and consequences of aging. Fuel 1989, 68, 1067-1074.
23. Merdrignac, I.; Behar, F.; Albrecht, P.; Briot, P.; Vandenbroucke, M. Quantitative Extraction of Nitrogen Compounds in Oils: Atomic Balance and Molecular Composition. Energy Fuels 1998, 12, 1342-1355.
24. Li, M.; Larter, S. R.; Stoddart, D.; Bjoroey, M. Liquid chromatographic separation schemes for pyrrole and pyridine nitrogen aromatic heterocycle fractions from crude oils suitable for rapid characterization of geochemical samples. Anal. Chem. 1992, 64, 1337-1344.
25. Mao, J.; Pacheco, C. R.; Traficante, D. D.; Rosen, W. Analysis of neutral nitrogen compounds in diesel oil by direct injection high-performance liquid chromatography-mass spectrometry-ultraviolet spectrometry methods. J. Chromatogr. A 1994, 684, 103-111.
26. Mao, J.; Pacheco, C. R.; Traficante, D. D.; Rosen, W. Identification and characterization of nitrogen compounds in Brazilian diesel oil by particle beam l.c.-m.s. Fuel 1995, 74, 880-887.
27. Shin, S.; Sakanishi, K; Mochida, I.; Grudoski, D. A.; Shinn, J. H. Identification and reactivity of nitrogen molecular species in gas oils. Energy Fuels 2000, 14, 539-544.
28. Kabe, T.; Qian, W.; Ishihara, A. Hydrodesulfurization and hydrodenitrogenation: chemistry and engineering; Wiley-VCH: Weinheim, 1999.
29. Cronauer, D. C.; Young, D. C.; Solash, J.; Seshadri, K. S.; Danner, D. A. Shale oil denitrogenation with ion exchange. 3. Characterization of hydrotreated and ion-exchange isolated products. Ind. Eng. Chem. Process Des. Dev. 1986, 25, 756-762.
30. Marcelin, G.; Cronauer, D. C.; Vogel, R. F.; Prudich, M. E.; Solash, J. Shale oil denitrogenation with ion exchange. 2. Evaluation of ion-exchange adsorbents and resin treatment procedures. Ind. Eng. Chem. Process Des. Dev. 1986, 25, 747-756.
31. Prudich, M. E.; Cronauer, D. C.; Vogel, R. F.; Solash, J. Shale oil denitrogenation with ion exchange. 1. Process concept and modeling. Ind. Eng. Chem. Process Des. Dev. 1986, 25, 742-746.
32. Qi, J.; Yan, Y.; Su, Y.; Qu, F.; Dai, Y. Extraction of nitrogen compounds from catalytically cracked diesel oil with a volatile carboxylic acid based on reversible chemical complexation. Energy Fuels 1998, 12, 788-791.
33. Qi, J.; Yan, Y.; Fei, W.; Su, Y.; Dai, Y. Solvent extraction of nitrogen compounds from catalytically-cracked diesel oil by metal ion complexation. Fuel 1998, 77, 255-258.
34. Shiraishi, Y.; Taki, Y.; Hirai, T.; Komasawa, I. A novel desulfurization process for fuel oils based on the formation and subsequent precipitation of S-alkylsulfonium salts. 1. Light oil feedstocks. Ind. Eng. Chem. Res. 2001, 40, 1213-1224.
35. Shiraishi, Y.; Tachibana, K.; Taki, Y.; Hirai, T.; Komasawa, I. A novel desulfurization process for fuel oils based on the formation and subsequent precipitation of S-alkylsulfonium salts. 2. Catalytically cracked gasoline. Ind. Eng. Chem. Res. 2001, 40, 1225-1233.
36. Shiraishi, Y.; Tachibana, K.; Hirai, T.; Komasawa, I. A novel desulfurization process for fuel oils based on the formation and subsequent precipitation of S-alkylsulfonium salts. 3. Denitrogenation behavior of light oil feedstocks. Ind. Eng. Chem. Res. 2001, 40, 3390-3397.
37. Shiraishi, Y.; Hirai, T.; Komasawa, I. A novel desulfurization process for fuel oils based on the formation and subsequent precipitation of S-alkylsulfonium salts. 4. Desulfurization and simultaneous denitrogenation of vacuum gas oil. Ind. Eng. Chem. Res. 2001, 40, 3398-3405.
38. Shiraishi, Y.; Tachibana, K; Hirai, T.; Komasawa, I. A novel desulfurization process for fuel oils based on the formation and subsequent precipitation of S-alkylsulfonium salts. 5. Denitrogenation reactivity of basic and neutral nitrogen compounds. Ind. Eng. Chem. Res. 2001, 40, 4919-4924.
39. Shiraishi, Y.; Hirai, T.; Komasawa, I. Photochemical denitrogenation processes for light oils effected by a combination of UV irradiation and liquid-liquid extraction. Ind. Eng. Chem. Res. 2000, 39, 2826-2836.
40. Shiraishi, Y.; Hirai, T.; Komasawa, I. Photochemical Desulfurization and Denitrogenation Process for Vacuum Gas Oil Using an Organic Two-Phase Extraction System. Ind. Eng. Chem. Res. 2001, 40, 293-303.
41. Shiraishi, Y.; Tachibana, K.; Hirai, T.; Komasawa, I. Desulfurization and Denitrogenation Process for Light Oils Based on Chemical Oxidation followed by Liquid-Liquid Extraction. Ind. Eng. Chem. Res. 2002, 41, 4362-4375.
42. Vazquez-Duhalt, R.; Torres, E.; Valderrama, B.; Le Borgne, S. Will Biochemical Catalysis Impact the Petroleum Refining Industry? Energy Fuels 2002, 16, 1239-1250.
43. Song, C.; Ma, X. New design approaches to ultra-clean diesel fuels by deep desulfurization and deep dearomatization. Appl. Catal. B 2003, 41, 207-238.
44. Bressler, D. C.; Gray, M. R. Hydrotreating Chemistry of Model Products from Bioprocessing of Carbazoles. Energy Fuels 2002, 16, 1076-1086.
45. Meille, V.; Schulz, E.; Lemaire, M.; Faure, R.; Vrinat, M. An Efficient Synthesis of Pure 4,6-Dimethyldibenzothiophene. Tetrahedron 1996, 52, 3953-3960.
46. Macaud, M.; Schulz, E.; Vrinat, M.; Lemaire, M. A new material for selective removal of nitrogen compounds from gas oils towards more efficient HDS processes. Chem. Commun. 2002, 2340-2341.
47. Lemaire, M.; Schulz, E.; Sevignon, M.; Macaud, M.; Favre-Reguillon, A.; Thomas, M.; Loutaty, R. Polymer-supported π-electron acceptors for charge-transfer-based denitrogenation-desulfurization of petroleum fractions. PCT Int. Appl. 2002024836, 2002.
48. Koltai, T.; Macaud, M.; Milenkovic, A.; Schultz, E.; Lemaire, M.; Vrinat, M. Hydrodesulfurization of diesel fuels by association of a catalytic process and a separation process by using charge-transfer complexes. Catal. Lett. 2002, 83, 143-148.
49. Letourneur, D.; Bacaud, R.; Vrinat, M.; Schweich, D.; Pitault, I. Hydrodesulfurization Catalyst Evaluation in a Upflow Three-Phase Microreactor. Ind. Eng. Chem. Res. 1998,37, 2662-2667.
50. Foster, R.; Fyfe, C. A. Electron-donor-acceptor complex formation by compounds of biological interest. III. Indole complexes. J. Chem. Soc. [Sect.] B: Phys. Org. 1966, 926-929.
51. Orchin, M.; Woolfolk, E. O. Molecular complexes with 2,4,7- trinitrofluorenone. J. Am. Chem. Soc. 1946, 68, 1727-1729.
52. Milenkovic, A.; Loffreda, D.; Schulz, E.; Chermette, H.; Lemaire, M.; Sautet, P. Charge transfer complexes between tetranitrofluorenone and polyaromatic compounds from gasoil: a combined DFT and experimental study. Phys. Chem. Chem. Phys. 2004, 6, 1169-1180.
53. Meille, V.; Schulz, E.; Vrinat, M.; Lemaire, M. A new route towards deep desulfurization: selective charge transfer complex formation. Chem. Commun. 1998, 305-306.
54. Rekker, R. F.; Mannhold, R. Calculation of Drug Lipophilicity. The Hydrophobic Fragmental Constant Approach; VCH: Weinheim, 1992.
55. Min, W. S.; Choi, K., II; Khang, S. Y.; Min, D. S.; Ryu, J. W.; Yoo, K. S.; Kim, J. H. Method for manufacturing cleaner fuels. PCT Int. Appl. 9967345, 1999.