Jianwei Li, Xiang Li, Yan Liu, Jie Zhang
Jianwei Li, Xiang Li, Yan Liu, Jie Zhang
摘要： The application of ionic liquids as alternatives to conventional organic solvents in the extraction process has been investigated. In the present study, fourteen species of imidazolium-based ionic liquids were added into the NaOH (aq) to remove the mercaptans. The influences of anion species and cation alkyl chain length of the imidazolium-based ionic liquids on the performance of mercaptan removal from light oils have been discussed. The efficiency of extraction for mercaptans exhibited the order of [Ac]- > [OH]- ≈[Br]- > [BF4]-. The longer alkyl chain imidazolium-based ionic liquids contributed to enhance desulfurization rate of 1-butyl mercaptan. 100% desulfurization rate of 1-butyl mercaptan was achieved by the anion of Ac- ionic liquids and NaOH (aq) at a volume ratio of 40:1 (V(oil):V(ionic liquid)) and a short equilibrium time within 10 min.
|  Y.W. Gong, H.X. Liu, X.N. Cheng, Experiments of mercaptans removal from FCC gasoline by NaOH aqueous in membrane contactor, Pet. Sci. Technol. 28(2010) 903-910.
 L.N. He, H.M. Li,W.S. Zhu, J.X. Guo, X. Jiang, J.D. Lu, Y.S. Yan, Deep oxidative desulfurization of fuels using peroxophosphomolybdate catalysts in ionic liquids, Ind. Eng. Chem. Res. 47(2008) 6890-6895.
 K. Kedrakrolik, F. Mutelet, J.C. Moïse, J.N. Jaubert, Deep fuels desulfurization and denitrogenation using 1-butyl-3-methylimidazolium trifluoromethanesulfonate, Energy Fuel 25(2011) 1559-1565.
 V. Matsis, D. Georgantas, H. Grigoropoulou, Removal of n-butyl mercaptan using stripping with an inert gas:A nonequilibrium approach via mass balances, Ind. Eng. Chem. Res. 45(2006) 1766-1773.
 M. Mehrpooya, F. Gharagheizi, A molecular approach for the prediction of sulfur compound solubility parameters, Phosphorus Sulfur Silicon Relat. Elem. 185(2010) 204-210.
 J.C. Bricker, L. Laricchia,Advances inMeroxTMprocess and catalysis for thiol oxidation, Top. Catal. 55(2012) 1315-1323.
 R.T. Liu, D.H. Xia, Y.Z. Xiang, Y.L. Tian, Effects of caustic concentration on the LPG sweetening, Pet. Sci. Technol. 23(2005) 711-721.
 Q.H. Li, L.Z. Zhuang, S.X. Chen, J.Q. Xu, H.C. Li, Preparation of carbon-supported zinc ferrite and its performance in the catalytic degradation ofmercaptan, Energy Fuel 26(2012) 7092-7098.
 J.K. Joseph, S.L. Jain, B. Sain, Covalently anchored polymer immobilized Co(II) phthalocyanine as efficient catalyst for oxidation of mercaptans using molecular oxygen as oxidant, Ind. Eng. Chem. Res. 49(2010) 6674-6677.
 Y. Wang, Y.L. Tian, R.T. Liu, Y.Z. Xiang, D.H. Xia, Study on the further desulfurization and stability of catalyst in Merox sweetening process of LPG, Nat. Gas Chem. Ind. 30(2005) 14-18.
 X. Sun, S.P. Li, Y. Yao, Research of extraction of sulfide in FCC gasoline with alkaline solution, Henan Chem. Ind. 23(2006) 17-20.
 B. Basu, S. Satapathy, A.K. Bhatnagar, Merox and related metal phthalocyanine catalyzed oxidation process, Catal. Rev. 35(1993) 571-609.
 R. Abro, A.A. Abdeltawab, S.S. Al-Deyab, G.R. Yu, A.B. Qazi, S.R. Gao, X.C. Chen, A review of extractive desulfurization of fuel oils using ionic liquids, RSC Adv. 4(2014) 35302-35317.
 S.A. Dharaskara, K.L.Wasewara, M.N. Varmaa, D.Z. Shendea, C.K. Yoob, Ionic liquids:The novel solvent for removal of dibenzothiophene fromliquid fuel, Procedia Eng. 51(2013) 314-317.
 G.R. Yu, X. Li, X.X. Liu, C. Asumana, X.C. Chen, Deep desulfurization of fuel oils using low-viscosity 1-ethyl-3-methylimidazolium dicyanamide ionic liquid, Ind. Eng. Chem. Res. 50(2011) 2236-2244.
 S.R. Gao, X.C. Chen, R. Abro, A.A. Abdeltawab, S.S. Al-Deyab, G.R. Yu, Desulfurization of fuel oil:Conductor-like screening model for real solvents study on capacity of ionic liquids for thiophene and dibenzothiophene, Ind. Eng. Chem. Res. 54(2015) 9421-9430.
 Q.L.Wang, L.C. Lei, J.K. Zhu, B. Yang, Z.J. Li, Deep desulfurization of fuels by extraction with 4-dimethylaminopyridinium-based ionic liquids, Energy Fuel 27(2013) 4617-4623.
 W. Zhang, K. Xu, Q. Zhang, D.L. Liu, S.Y.Wu, F. Verpoort, X.M. Song, Oxidative desulfurization of dibenzothiophene catalyzed by ionic liquid[BMIm]HSO4, Ind. Eng. Chem. Res. 49(2010) 11760-11763.
 X.X. Lu, L. Yue, M.J. Hu, Q. Cao, L. Xu, Y.S. Guo, S.L. Hu,W.J. Fang, Piperazinium-based ionic liquids with lactate anion for extractive desulfurization of fuels, Energy Fuel 28(2014) 1774-1780.
 J.G. Feng, J.G.Mi, Prediction of solubilities and interfacial tensions of ionic liquids for desulfurization of fuel oil, Ind. Eng. Chem. Res. 53(2014) 20234-20240.
 J.P. Hallett, T. Welton, Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev. 99(1999) 2071-2083.
 J.G. Huddleston, A.E. Visser, W.M. Reichert, H.D. Willauer, G.A. Broker, R.D. Rogers, Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation, Green Chem. 3(2001) 156-164.
 Y. Nie, C.X. Li, A.J. Sun, H. Meng, Z.H. Wang, Extractive desulfurization of gasoline using imidazolium-based phosphoric ionic liquids, Energy Fuel 20(2006) 2083-2087.
 R. Sheldon, Catalytic reactions in ionic liquids, Chem. Commun. 23(2001) 2399-2407.
 L. Green, I. Hemeon, R.D. Singer, 1-Ethyl-3-methylimidazolium halogenoaluminate ionic liquids as reaction media for the acylative cleavage of ethers, Tetrahedron Lett. 41(2000) 1343-1346.
 P.A.Z. Suarez, S. Einloft, J.E.L. Dullius, R.F. de Souza, J. Dupont, J. Chim, Synthesis and physical-chemical properties of ionic liquids based on 1-n-butyl-3-methylimidazolium cation, J. Chim. Phys. 95(1998) 1626-1639.
 W.Z.Wu,W.J. Li, B.X. Han, Z.F. Zhang, T. Jiang, Z.M. Liu, A green and effectivemethod to synthesize ionic liquids:Supercritical CO2 route, Green Chem. 7(2005) 701-704.
 M. Ammamz, J. Fransaer, Ionic liquid-heteropolyacid:Synthesis, characterization, and supercapacitor study of films deposited by electrophoresis, J. Electrochem. Soc. 158(2011) 14-21.
 M. Ammam, J. Fransaer, Synthesis and characterization of hybridmaterials based on 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid and Dawson-type tungstophosphate K7[H4PW18O62]·18H2O and K6[P2W18O62]·13H2O, J. Solid State Chem. 184(2011) 818-824.
 F.T. Li, C.G. Kou, Z.M. Sun, Y.J. Hao, R.H. Liu, D.S. Zhao, Deep extractive and oxidative desulfurization of dibenzothiophene with C5H9NO·SnCl2 coordinated ionic liquid, J. Hazard. Mater. 205(2012) 164-170.
|||Huifang Li, Lijuan Li, Xiaowu Peng, Lianmin Ji, Wu Li. Selective recovery of lithium from simulated brine using different organic synergist[J]. Chinese Journal of Chemical Engineering, 2019, 27(2): 335-340.|
|||Ali Taghvaie Nakhjiri, Amir Heydarinasab, Omid Bakhtiari, Toraj Mohammadi. The effect of membrane pores wettability on CO2 removal from CO2/CH4 gaseous mixture using NaOH, MEA and TEA liquid absorbents in hollow fiber membrane contactor[J]. Chinese Journal of Chemical Engineering, 2018, 26(9): 1845-1861.|
|||Pan Sun, Kun Huang, Xiaoqin Wang, Na Sui, Jieyuan Lin, Wenjuan Cao, Huizhou Liu. Three-liquid-phase extraction and separation of V(V) and Cr(VI) from acidic leach solutions of high-chromium vanadium-titanium magnetite[J]. Chinese Journal of Chemical Engineering, 2018, 26(7): 1451-1457.|
|||Xiaoming Gao, Jiao Fei, Yanyan Shang, Feng Fu. Desulfurization of liquid hydrocarbon fuels via Cu2O catalyzed photo-oxidation coupled with liquid-liquid extraction[J]. Chinese Journal of Chemical Engineering, 2018, 26(7): 1508-1512.|
|||Jingxian Qi, Qingfen Liu, Huizhou Liu. Stability of penicillin G in ionic liquid [Bmim]PF6[J]. Chinese Journal of Chemical Engineering, 2018, 26(6): 1430-1434.|
|||Chuanxu Xiao, Kun Huang, Huizhou Liu. A novel constant interfacial area cell for determining the extraction kinetics of Er(III) from chloride medium[J]. Chinese Journal of Chemical Engineering, 2018, 26(6): 1435-1441.|
|||Chunxi Qin, Jie Tang, Fenglei Bi, Zhenhao Xi, Ling Zhao. Experimental and simulation study of nylon 6 solid-liquid extraction process[J]. Chinese Journal of Chemical Engineering, 2018, 26(5): 1022-1030.|
|||Weifeng Xu, Guilin Dai, Kewen Tang, Panliang Zhang, Biquan Xiong, Yu Liu. Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model[J]. Chinese Journal of Chemical Engineering, 2018, 26(4): 708-714.|
|||Pouria Amani, Elham Mohammadi, Sahar Akhgar. Design aspect of a novel L-shaped pulsed column for liquid-liquid extraction applications: Energy consumption and the characteristics velocity concept[J]. Chinese Journal of Chemical Engineering, 2018, 26(4): 723-730.|
|||Li Lü, Chun Li, Guoquan Zhang, Xiaowei Hu, Bin Liang. Decomposition behavior of CaSO4 during potassium extraction from a potash feldspar-CaSO4 binary system by calcination[J]. Chinese Journal of Chemical Engineering, 2018, 26(4): 838-844.|
|||Zhao Wang, Quanyou Zhang, Ying Yao, Yongzhong Jia, Bingjun Xie. The extraction of potassium from K-feldspar ore by low temperature molten salt method[J]. Chinese Journal of Chemical Engineering, 2018, 26(4): 845-851.|
|||Jierong Yang, Wangliang Li, Qingfen Liu, Huizhou Liu. Dissolution of antibiotics mycelium in ionic liquids: Performance and mechanism[J]. Chinese Journal of Chemical Engineering, 2018, 26(2): 252-258.|
|||Zhuo Chen, Yundong Wang. Solvent extraction kinetics of Sm(Ⅲ), Eu(Ⅲ) and Gd(Ⅲ) with 2-ethylhexyl phosphoric acid-2-ethylhexyl ester[J]. Chinese Journal of Chemical Engineering, 2018, 26(2): 317-321.|
|||Sajjad Aghazadeh, Mahdi Gharabaghi, Ziaedin Shafaei. Thermodynamical and catalytic aspects of zinc separation from aqueous solution[J]. Chinese Journal of Chemical Engineering, 2018, 26(12): 2455-2460.|
|||Carlos Eduardo de Araújo Padilha, Juliana Chris Silva de Azevedo, Francisco Canindé de Sousa Júnior, Sérgio Dantas de Oliveira Júnior, Domingos Fabiano de Santana Souza, Jackson Araújo de Oliveira, Gorete Ribeiro de Macedo, Everaldo Silvino dos Santos. Recovery of polyphenols from camu-camu (Myrciaria dubia H.B.K. McVaugh) depulping residue by cloud point extraction[J]. Chinese Journal of Chemical Engineering, 2018, 26(12): 2471-2476.|