Study on extraction of thiophene from model gasoline with br?nsted acidic ionic liquids

doi:10.1007/s11705-010-0539-0

Front Chem Sci Eng

2011, Vol. 5

Issue (1) : 107-112 https://doi.org/10.1007/s11705-010-0539-0

RESEARCH ARTICLE

Study on extraction of thiophene from model gasoline with br?nsted acidic ionic liquids

Xiaomeng WANG¹, Mingjuan HAN², Hui WAN¹, Cao YANG¹, Guofeng GUAN¹(

)

1. College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing 210009, China; 2. College of Sciences, Nanjing University of Technology, Nanjing 210009, China

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Abstract

Br?nsted acidic ionic liquids (ILs), N-methylimidazole hydrogen sulfate ([HMIm]HSO₄) and N-methylpyrrolidone hydrogen sulfate ([HNMP]HSO₄), are synthesized and employed as extractants to extract thiophene from model gasoline (thiophene dissolved in n-octane). The effect of extraction temperature, extraction time and volume ratio of ILs to model gasoline on desulfurization rates is investigated. Then, the optimal desulfurization conditions are obtained: the ratio of ILs to model gasoline is 1∶1, extraction temperature is 50°C for [HMIm]HSO₄ and 60°C for [HNMP]HSO₄, extraction time is 60 min. Meanwhile, the desulfurization rate of [HNMP]HSO₄ for model gasoline is 62.8%, which is higher than that of [HMIm]HSO₄ (55.5%) under optimal conditions. The reason is discussed on the basis of the interaction energy between thiophene and ILs at the B3LYP/6-311++ G(d,p) level. Furthermore, the total desulfurization rate of [HNMP]HSO₄ and [HMIm]HSO₄ reaches 96.4% and 94.4%, respectively, by multistage extraction. Finally, the used ILs can be reused by vacuum drying, and their desulfurization rates are not significantly decreased after recycling 7 times in single-stage desulfurization.

Keywords br?nsted ionic liquids model gasoline thiophene extraction density functional theory

Corresponding Author(s): GUAN Guofeng,Email:guangf@njut.edu.cn

Issue Date: 05 March 2011

Cite this article:

Xiaomeng WANG,Hui WAN,Cao YANG, et al. Study on extraction of thiophene from model gasoline with br?nsted acidic ionic liquids[J]. Front Chem Sci Eng, 2011, 5(1): 107-112.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-010-0539-0
https://academic.hep.com.cn/fcse/EN/Y2011/V5/I1/107

Fig.1 Chemical structures of the br?nsted acidic ILs: (a) -methyl-imidazole hydrogen sulfate ([HMIm]HSO) and (b) -methyl-pyrrolidone hydrogen sulfate ([HNMP]HSO)

Fig.2 Effects of volume ratios of ILs to model gasoline on desulfurization rates at the optimized conditions for [HMIm]HSO: extraction temperature, 50°C; extraction time, 60 min; [HNMP]HSO: temperature 60°C; extraction time, 60 min

Fig.3 Optimized structures of thiophene (a), [HMIm] (b) and [HNMP] (c)

Fig.4 Optimized structures of T-[HMIm] (a) and T-[HNMP] (b)

Fig.5 Effects of extraction time and temperature on the desulfurization rates of [HMIm]HSO when the volume ratio of IL to model gasoline is 1∶1

Fig.6 Effects of extraction time and temperature on the desulfurization rates with [HNMP]HSO when the volume ratio of IL to model gasoline is 1∶1

Fig.7 Deep desulfurization properties of ILs

Fig.8 Recycling of two ILs

1	Zhu W S, Li H M, Jiang X, Yan Y S, Lu J D, Xia J X. Oxidative desulfurization of fuels catalyzed by peroxotungsten and peroxomolybdenum complexes in ionic liquids. Energy & Fuels , 2007, 21(5): 2514–2516 doi: 10.1021/ef700310r
2	Hernández-Maldonado A J, Yang R T. Desulfurization of diesel fuels by adsorption via π-complexation with vapor-phase exchanged Cu(I)-Y zeolites. Journal of the American Chemical Society , 2004, 126(4): 992–993 doi: 10.1021/ja039304m
3	Shan G B, Xing J M, Zhang H Y, Liu H Z. Biodesulfurization of dibenzothiophene by microbial cells coated with magnetite nanoparticles. Applied and Environmental Microbiology , 2005, 71(8): 4497–4502 doi: 10.1128/AEM.71.8.4497-4502.2005
4	Otsuki S, Nonaka T, Taksshima N, Qian W, Ishihara A, Imai T, Kabe T. Oxidative desulfurization of light gas oil and vacuum gas oil by oxidation and solvent extraction. Energy & Fuels , 2000, 14(6): 1232–1239 doi: 10.1021/ef000096i
5	Yu G X, Chen H, Lu S X, Zhu Z N. Deep desulfurization of diesel fuels by catalytic oxidation. Frontiers of Chemical Engineering in China , 2007, 1(2): 162–166 doi: 10.1007/s11705-007-0030-8
6	Shiraishi Y, Hirai Y, Komasawa I. Photochemical desulfurization and denitrogenation process for vacuum gas oil using an organic two-phase extraction system. Industrial & Engineering Chemistry Research , 2001, 40(1): 293–303 doi: 10.1021/ie000707u
7	Welton T. Room-temperature ionic liquids: solvents for synthesis and catalysis. Chemical Reviews , 1999, 99(8): 2071–2084 doi: 10.1021/cr980032t
8	Wasserscheid P, Keim W. Ionic liquids—new “solutions” for transition metal catalysis. Angewandte Chemie International Edition , 2000, 39(21): 3772–3789 doi: 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
9	Zhou B L, Fang Y X, Gu H, Huang B H. Ionic liquid mediated esterification of alcohol with acetic acid. Frontiers of Chemical Engineering in China , 2009, 3(2): 211–214 doi: 10.1007/s11705-009-0054-3
10	Wang Y, Yang H. Synthesis of CoPt nanorods in ionic liquids. Journal of the American Chemical Society , 2005, 127(15): 5316–5317 doi: 10.1021/ja043625w
11	Fan Q M, Liu Y X, Zheng Y F. Yan W. Preparation of Ni/SiO₂ catalyst in ionic liquids for hydrogenation. Frontiers of Chemical Engineering in China , 2008, 2(1): 63–68 doi: 10.1007/s11705-008-0013-4
12	Wang J J, Pei Y C, Zhao Y, Hu Z G. Recovery of amino acids by imidazolium based ionic liquids from aqueous media. Green Chemistry , 2005, 7(4): 196–202 doi: 10.1039/b415842c
13	Machida H, Taguchi R, Sato Y, Florusse L J, Peters C J, Smith R L. Measurement and correlation of supercritical CO₂ and ionic liquid systems for design of advanced unit operations. Frontiers of Chemical Engineering in China , 2009, 3(1): 12–19 doi: 10.1007/s11705-009-0151-3
14	B?smann A, Datsevich L, Jess A, Lauter A, Schmitz C, Wasserscheid P. Deep desulfurization of diesel fuel by extraction with ionic liquids. Chemical Communications (Cambridge) , 2001, (23): 2494–2495 doi: 10.1039/b108411a
15	Zhang S G, Zhang Z C. Novel properties of ionic liquids in selective sulfur removal from fuels at room temperature. Green Chemistry , 2002, 4(4): 376–379 doi: 10.1039/b205170m
16	Huang C P, Chen B H, Zhang J, Liu Z C, Li Y X. Desulfurization of gasoline by extraction with new ionic liquids. Energy & Fuels , 2004, 18(6): 1862–1864
17	Zhang S G, Zhang Q L, Zhang Z C. Extractive desulfurization and denitrogenation of fuels using ionic liquids. Industrial & Engineering Chemistry Research , 2004, 43(2): 614–622
18	Esser J, Wasserscheid P, Jess A. Desulfurization of oil refinery streams by extraction with ionic liquids. Green Chemistry , 2004, 6: 316–322 doi: 10.1039/b407028c
19	Nie Y, Li C X, Wang Z H. Extractive Desulfurization of fuel oil using alkylimidazole and its mixture with dialkylphosphate ionic liquids. Industrial & Engineering Chemistry Research , 2007, 46(15): 5108–5112 doi: 10.1021/ie070385v
20	Wang J L, Zhao D S, Zhou E P, Dong Z. Desulfurization of gasoline by extraction with N-alkylpyridinium-based ionic liquids. J Fuel Chem Technol , 2007, 35(3): 293–296 doi: 10.1016/S1872-5813(07)60022-X
21	Gao H S, Li Y G, Liu Q F, Li W L, Liu H Z. Desulfurization of fuel by extraction with pyridinium-based ionic liquids. Industrial & Engineering Chemistry Research , 2008, 47(21): 8384–8388 doi: 10.1021/ie800739w
22	Liu D, Gui J Z, Song L, Zhang X, Sun Z L. Deep desulfurization of diesel fuel by extraction with task-specific ionic liquids. J Pet Sci Technol , 2008, 26(9): 973–982 doi: 10.1080/10916460600695496
23	Holbrey J D, Reichert W M, Nieuwenhuyzen M, Sheppard O, Hardacre C, Rogers R D. Liquid clathrate formation in ionic liquid-aromatic mixtures. Chemical Communications (Cambridge) , 2003, (4): 476–477 doi: 10.1039/b212726a
24	Qian T B. Liu W l, Li J H. Polymeric adsorbent and application. Beijing: Chemical Industry Press, 1990. 197–198
25	Alexandra M, Emmanuelle S, Valerie M, David L, Michel F, Michel V, Marc L. Selective elimination of alkyldibenzothiophenes from gas oil by formation of insoluble charge-transfer complexes. Energy & Fuels , 1999, 13(4): 881–887 doi: 10.1021/ef980262a
26	Zhou J X, Mao J B, Zhang S G. Ab initio calculations of the interaction between thiophene and ionic liquids. Fuel Processing Technology , 2008, 89(12): 1456–1514 doi: 10.1016/j.fuproc.2008.07.006

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