Ionic liquids screening for desulfurization of natural gasoline by liquid-liquid extraction

Molecular Diversity

Volumn 14, Issue 4, 2010, Pages 777-787

  Likhanova, Natalya V ^a   Guzmán Lucero, Diego ^a   Flores, Eugenio A ^a   García, Paloma ^a   Domínguez Aguilar, Marco A ^a   Palomeque, Jorge ^a   Martínez Palou, Rafael ^a  

^a INSTITUTO MEXICANO DEL PETRÓLEO   (Mexico)

Author keywords

Desulfurization; Ionic liquids; Liquid liquid extraction; Microwave; Natural gasoline

Indexed keywords

ALUMINUM; AMMONIA; COPPER; GASOLINE; HALOGEN; IMIDAZOLE; INDIUM; IONIC LIQUID; IRON; MOLYBDENUM; PYRIDINIUM DERIVATIVE; SULFATE; SULFUR; TIN; TOLUENESULFONIC ACID DERIVATIVE; ZINC;

ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL STRUCTURE; DESULFURIZATION; LIQUID LIQUID EXTRACTION; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

CHEMICAL FRACTIONATION; CHROMATOGRAPHY, LIQUID; DRUG EVALUATION, PRECLINICAL; EFFICIENCY; GASOLINE; HYDROGEN BONDING; IONIC LIQUIDS; MODELS, BIOLOGICAL; SULFUR; SULFUR COMPOUNDS;

EID: 78650172552     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9217-x     Document Type: Article

References (52)

1. Kidnay AJ, Parrish WR (2006) Fundamentals of natural gas processing. CRC Press, Boca Raton
2. Zaczepinski S (1996) Exxon diesel oil deep desulfurization (DODD). In: Meyer RA (eds) Handbook of petroleum refining processes, Chapter 8.7. McGraw-Hill, New York
3. Kabe T, Ishihara A, Qian W (1999) Hydrodesulfurization and hydrodenitrogenation: chemistry and engineering. Willey-VCH, Weinheim
4. P Wasserscheid T Welton 2003 Ionic liquids in synthesis Willey-VCH Weinheim 10.1002/3527600701
5. Wasserscheid P, Welton T (2003) Ionic liquids in synthesis. Willey-VCH, Weinheim. doi: 10.1002/3527600701
6. H Zhao SV Malhotra 2002 Applications of ionic liquids in organic synthesis Aldrichim Acta 35 75 83 1:CAS:528:DC%2BD3sXhslGhs70%3D 10.1016/S0003-2670(01)01543-4 (Pubitemid 34159196)
7. Martínez-Palou R (2009) Microwave-assisted synthesis using ionic liquids. Mol Divers. doi: 10.1007/s11030-009-9159-3 (in press)
8. Rogers RD, Seddon KR (eds) (2003) Ionic liquids as green solvent: progress and prospects. ACS symposium series, vol 856. American Chemical Society, Washington, DC
9. Rogers RD, Seddon K (ed) (2005) Ionic liquids IIIB: fundamentals, progress, challenges, and opportunities: transformations and processes. ACS Symposium Series, vol 902. American Chemical Society, Washington, DC
10. Roger, RD, Seddon, KR, Volkov, S (eds) (2002) Green industrial applications of ionic liquids. NATO Science Series. Kluwer, Netherlands
11. E Ito JAR van Veen 2006 On novel processes for removing sulphur from refinery streams Catal Today 116 446 460 10.1016/j.cattod.2006.06.040 1:CAS:528:DC%2BD28XotlWmtLc%3D 10.1016/j.cattod.2006.06.040 (Pubitemid 44234029)
12. S Brunet D Mey G Perot C Bouchy F Diehl 2005 On the hydrodesulfurization of FCC gasoline a review Appl Catal A 278 143 172 10.1016/j.apcata.2004.10.012 1:CAS:528:DC%2BD2MXhvF2nuw%3D%3D 10.1016/j.apcata.2004.10.012
13. CS Song 2003 An overview of new approaches to deep desulfurization for ultra-clean gasoline diesel fuel and jet fuel Catal Today 86 211 263 10.1016/s0920-5861(03)00412-7 1:CAS:528:DC%2BD3sXotVCnsLc%3D 10.1016/S0920-5861(03)00412-7
14. Bosmann A, Datsevich L, Jess A, Lauter A, Schmitz C, Wasserscheid P (2001) Deep desulfurization of diesel fuel by extraction with ionic liquids. Chem Commun 2494-2495. doi: 10.1039/b108411a
15. SG Zhang ZC Zhang 2002 Novel properties of ionic liquids in selective sulfur removal from fuels at room temperature Green Chem 4 376 379 10.1039/b205170m 1:CAS:528:DC%2BD38XlvFSqsro%3D 10.1039/b205170m
16. J Eer P Wasserscheid A Jess 2004 Deep desulfurization of oil refinery streams by extraction with ionic liquids Green Chem 6 316 322 10.1039/b407028c 10.1039/b407028c (Pubitemid 39163787)
17. SG Zhang QL Zhang ZC Zhang 2004 Extractive desulfurization and denitrogenation of fuels using ionic liquids Ind Eng Chem Res 43 614 622 10.1021/ie030561+ 1:CAS:528:DC%2BD3sXpvVCitbs%3D 10.1021/ie030561+
18. CP Huang BH Chen J Zhang ZC Liu YX Li 2004 Desulfurization of gasoline by extraction with new ionic liquids Energy Fuels 18 1862 1864 10.1021/ef049879k 1:CAS:528:DC%2BD2cXnslartL0%3D 10.1021/ef049879k
19. Y Nie CX Li AJ Sun H Meng ZH Wang 2006 Extractive desulfurization of gasoline using imidazolium-based phosphoric ionic liquids Energy Fuels 20 2083 2087 10.1021/ef060170i 1:CAS:528:DC%2BD28XnvFOrtbk%3D 10.1021/ef060170i (Pubitemid 44541301)
20. Y Nie CX Li ZH Wang 2007 Extractive desulfurization of fuel oil using alkylimidazole and its mixture with dialkylphosphate ionic liquids Ind Eng Chem Res 46 5108 5112 10.1021/ie070385v 1:CAS:528:DC%2BD2sXmslyqsr8%3D 10.1021/ie070385v (Pubitemid 47172890)
21. JD Holbrey I Lopez-Martin G Rothenberg KR Seddon G Silvero X Zheng 2008 Desulfurisation of oils using ionic liquids: selection of cationic and anionic components to enhance extraction efficiency Green Chem 10 87 92 10.1039/b710651c 1:CAS:528:DC%2BD1cXhtlCrsg%3D%3D 10.1039/b710651c
22. NH Ko JS Lee ES Huh H Lee KD Jung HS Kim M Cheong 2008 Extractive desulfurization using Fe-containing ionic liquids Energy Fuels 22 1687 1690 10.1021/ef7007369 1:CAS:528:DC%2BD1cXkvVyhur0%3D 10.1021/ef7007369
23. H Gao J Xing Y Li W Li Q Liu H Liu 2009 Desulfurization of diesel fuel by extraction with lewis-acidic ionic liquid Sep Sci Technol 44 971 982 10.1080/01496390802691232 1:CAS:528:DC%2BD1MXivFyqsr0%3D 10.1080/ 01496390802691232
24. H Gao M Luo J Xing Y Wu Y Li W Li Q Liu H Liu 2008 Desulfurization of fuel by extraction with pyridinium-based ionic liquids Ind Eng Chem Res 47 8384 8388 10.1021/ie800739w 1:CAS:528:DC%2BD1cXhtFOqt7nJ 10.1021/ie800739w
25. D Liu J Gui L Song X Zhang Z Sun 2008 Deep desulfurization of diesel fuel by extraction with task-specific ionic liquids Pet Sci Technol 26 973 982 10.1080/10916460600695496 1:CAS:528:DC%2BD1cXnsVSqu78%3D 10.1080/ 10916460600695496
26. 4 ionic liquid for deep desulfurization of real fuels Energy Fuel 22 1774 1778 10.1021/ef7007216 1:CAS:528:DC%2BD1cXktlKjs7w%3D 10.1021/ef7007216
27. 4] ionic liquid AIChE J 53 3108 3115 10.1002/aic.11337 1:CAS:528:DC%2BD2sXhtlyhtLrL 10.1002/aic.11337
28. X Jiang Y Nie C Li Z. Wang 2008 Imidazolium-based alkylphosphate ionic liquids-a potential solvent for extractive desulfurization of fuel Fuel 87 79 84 10.1016/j.fuel.2007.03.045 1:CAS:528:DC%2BD2sXhtlWmsbbL 10.1016/j.fuel.2007.03. 045 (Pubitemid 350087935)
29. Y Shiraishi T Hirai I Komasawa 1999 Identification of desulfurization products in the photochemical desulfurization process for benzothiophenes and dibenzothiophenes from light oil using an organic two-phase extraction system Ind Eng Chem Res 38 3300 3309 10.1021/ie990134p 1:CAS:528:DyaK1MXkvF2ktbw%3D 10.1021/ie990134p (Pubitemid 29454750)
30. NE Leadbeater HM Torenius H Tye 2003 Ionic liquids as reagents and solvents in conjunction with microwave heating: rapid synthesis of alkyl halides from alcohols and nitriles from aryl halides Tetrahedron 59 2253 2258 10.1016/s0040-4020(03)00214-x 1:CAS:528:DC%2BD3sXitFKhtLY%3D 10.1016/S0040-4020(03)00214-X (Pubitemid 36331900)
31. S Csihony C Fischmeister C Bruneau IT Horvath PH Dixneuf 2002 First ring-opening metathesis polymerization in an ionic liquid. Efficient recycling of a catalyst generated from a cationic ruthenium allenylidene complex New J Chem 26 1667 1670 10.1039/b205920g 1:CAS:528:DC%2BD38XosFensLY%3D 10.1039/b205920g (Pubitemid 35346260)
32. Varma RS, Namboodiri VV (2001) An expeditious solvent-free route to ionic liquids using microwaves. Chem Commun 643-644 doi: 10.1039/b101375k
33. M Deetlefs KR Seddon 2003 Improved preparations of ionic liquids using microwave irradiation Green Chem 5 181 186 10.1039/b300071k 1:CAS:528: DC%2BD3sXislCgs7k%3D 10.1039/b300071k (Pubitemid 37487476)
34. J Weng C Wang HR Li Y Wang 2006 Novel quaternary ammonium ionic liquids and their use as dual solvent-catalysts in the hydrolytic reaction Green Chem 8 96 99 10.1039/b508325g 1:CAS:528:DC%2BD28XhsF2gtQ%3D%3D 10.1039/b508325g (Pubitemid 43485031)
35. M Yoshizawa M Hirao K Ito-Akita H Ohno 2001 Ion conduction in zwitterionic-type molten salts and their polymers J Mater Chem 11 1057 1062 10.1039/b101079o 1:CAS:528:DC%2BD3MXit1GjurY%3D 10.1039/b101079o (Pubitemid 32322760)
36. AC Cole JL Jensen I Ntai KLT Tran KJ Weaver DC Forbes JH Davis 2002 Novel Brønsted acidic ionic liquids and their use as dual solvent-catalysts J Am Chem Soc 124 5962 5963 10.1021/ja026290w 1:CAS:528:DC%2BD38XjtlOgs7w%3D 10.1021/ja026290w 12022828 (Pubitemid 34552840)
37. JD Holbrey WM Reichert RP Swatloski GA Broker WR Pitner KR Seddon RD Rogers 2002 Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl- and ethyl-sulfate anions Green Chem 4 407 413 10.1039/b204469b 1:CAS:528:DC%2BD38XnsFequ7o%3D 10.1039/b204469b
38. Liu Q, Janseen MHA, Van Rantwijk F, Sheldon RA (2005) Room-temperature ionic liquids that dissolve carbohydrates in high concentration. Green Chem 39-42. doi: 10.1039/b412848f (Pubitemid 40179326)
39. RS Varma VV Namboodiri 2001 Solvent-free preparation of ionic liquids using household microwave Pure Appl Chem 73 1309 1313 1:CAS:528: DC%2BD3MXovVSqurc%3D 10.1351/pac200173081309
40. AP Abbott G Capper DL Davies R Rasheed 2004 Ionic liquids based upon metal halide/substituted quaternary ammonium salt mixtures Inorganic Chem 43 3447 3452 10.1021/ic049931s 1:CAS:528:DC%2BD2cXjs12nt7w%3D 10.1021/ic049931s
41. T Fischer A Sethi T Welton J Woolf 1999 Diels-Alder reactions in room-temperature ionic liquids Tetrahedron Lett 40 793 796 10.1016/S0040- 4039(98)02415-0 1:CAS:528:DyaK1MXntFGltQ%3D%3D 10.1016/S0040-4039(98)02415-0 (Pubitemid 29059464)
42. AA Fannin DA Floreani LA King, et al. 1984 Properties of 1,3-dialkylimidazolium chloride aluminium-chloride ionic liquids. 2. Phase-transitions, densities, electrical conductivities, and viscosities J Phys Chem 88 2614 2621 10.1021/j150656a038 1:CAS:528:DyaL2cXitFKltLY%3D 10.1021/j150656a038
43. S Csihony C Fischmeister C Bruneau, et al. 2002 First ring-opening metathesis polymerization in an ionic liquid. Efficient recycling of a catalyst generated from a cationic ruthenium allenylidene complex New J Chem 26 1667 1670 10.1039/b205920g 1:CAS:528:DC%2BD38XosFensLY%3D 10.1039/b205920g (Pubitemid 35346260)
44. J Robinson RA Osteryoung 1979 An electrochemical and spectroscopic study of some aromatic hydrocarbons in the room temperature molten salt system aluminum chloride-n-butylpyridinium chloride J Am Chem Soc 101 323 327 10.1021/ja00496a008 1:CAS:528:DyaE1MXpsVeksw%3D%3D 10.1021/ja00496a008
45. YJ Kim RS Varma 2005 Tetrahaloindate (III)-based ionic liquids in the coupling reaction of carbon dioxide and epoxides to generate cyclic carbonates: H-bonding and mechanistic studies J Org Chem 70 7882 7891 10.1021/jo050699x 1:CAS:528:DC%2BD2MXpslWrsbk%3D 10.1021/jo050699x 16277307 (Pubitemid 41377492)
46. VV Namboodiri RS Varma 2002 Solvent-free sonochemical preparation of ionic liquids Org Lett 4 3161 3163 10.1021/ol026608p 1:CAS:528: DC%2BD38XmtVylsLg%3D 10.1021/ol026608p 12201742
47. Dzyuba SV, Bartsch RA (2001) New room-temperature ionic liquids with C-2-symmetrical imidazolium cations. Chem Commun:1466-1467 doi: 10.1039/b104512c
48. GW Meindersma A Podt AB de Haan 2005 Selection of ionic liquids for the extraction of aromatic hydrocarbons from aromatic/aliphatic mixtures Fuel Process Technol 87 59 70 10.1016/j.fuproc.2005.06.002 10.1016/j.fuproc.2005.06. 002
49. J Zhang C Huang B Chen, et al. 2007 Extraction of aromatic hydrocarbons from aromatic/aliphatic mixtures using chloroaluminate room-temperature ionic liquids as extractants Energy Fuels 21 1724 1730 10.1021/ef060604+ 1:CAS:528:DC%2BD2sXjslWhtb0%3D 10.1021/ef060604+ (Pubitemid 46929394)
50. O Acevedo WL Jorgensen JD Evanseck 2007 Elucidation of rate variations for a diels-alder reaction in ionic liquids from QM/MM simulations J Chem Theory Comput 3 132 138 10.1021/ct6002753 1:CAS:528:DC%2BD28XhtF2ntbzE 10.1021/ct6002753
51. K Qiao YQ Deng 2002 The first example of alkane carbonylation in superacidic chloroaluminate ionic liquids A Chim Sinica 60 1520 1523 1:CAS:528:DC%2BD38Xms1Churc%3D
52. X Hu J Yu H Liu 2006 Liquid-liquid equilibria of the system 1-(2-hydroxyethyl)-3-methylimidozolium Tetrafluoroborate or 1-(2-hydroxyethyl)- 2,3-dimethylimidozolium tetrafluoroborate + water + 1-butanol at 293.15 K J Chem Eng Data 51 691 695 10.1021/je050382u 1:CAS:528:DC%2BD28XhsVSqtLk%3D 10.1021/je050455+