Solubilities of 1-Methyl-3-(3-sulfopropyl)-imidazolium Hydrogen Sulfate in Selected Solvents

摘要/Abstract

摘要： Ionic liquid 1-methyl-3-(3-sulfopropyl)-imidazolium hydrogen sulfate([C₃SO₃HMIM][HSO₄]) was synthesized and characterized by infrared spectroscopy(IR),nuclear magnetic resonance(¹H and ¹³C NMR) and ultraviolet-visible(UV-Vis) spectra. Its thermal stability was also examined by thermogravimetric analysis(TGA) and a differential scanning calorimeter(DSC). The mole fraction solubilities of [C₃SO₃HMIM][HSO₄]) in 12 selected solvents(n-pentane,n-hexane,n-heptane,benzene,toluene,ethylbenzene,acetone,2-butanone,3-methyl-2-butanone,tetrahydrofuran,ethyl acetate and dichloromethane) in the temperature range from 289.15 to 363.15 K were measured using a static analytical method and correlated with an empirical equation.

关键词: Brφnsted acidic ionic liquid, solubility, organic solvent, static analytical method

Abstract: Ionic liquid 1-methyl-3-(3-sulfopropyl)-imidazolium hydrogen sulfate([C₃SO₃HMIM][HSO₄]) was synthesized and characterized by infrared spectroscopy(IR),nuclear magnetic resonance(¹H and ¹³C NMR) and ultraviolet-visible(UV-Vis) spectra. Its thermal stability was also examined by thermogravimetric analysis(TGA) and a differential scanning calorimeter(DSC). The mole fraction solubilities of [C₃SO₃HMIM][HSO₄]) in 12 selected solvents(n-pentane,n-hexane,n-heptane,benzene,toluene,ethylbenzene,acetone,2-butanone,3-methyl-2-butanone,tetrahydrofuran,ethyl acetate and dichloromethane) in the temperature range from 289.15 to 363.15 K were measured using a static analytical method and correlated with an empirical equation.

Key words: Brφnsted acidic ionic liquid, solubility, organic solvent, static analytical method

蔡双飞, 王利生, 闫国庆, 李毅. Solubilities of 1-Methyl-3-(3-sulfopropyl)-imidazolium Hydrogen Sulfate in Selected Solvents[J]. , 2010, 18(6): 1008-1012.

CAI Shuangfei, WANG Lisheng, YAN Guoqing, LI Yi. Solubilities of 1-Methyl-3-(3-sulfopropyl)-imidazolium Hydrogen Sulfate in Selected Solvents[J]. , 2010, 18(6): 1008-1012.

参考文献

1 Hu, X.S., Li, Y.X., Cui, D.N., Chen, B.H., “Separation of ethyl acetate and ethanol by room temperature ionic liquids with the tetrafluoroborate anion”, J. Chem. Eng. Data, 53(2), 427-433(2008).
2 Huang, J.Y., Lei, M., Wang, Y.G., “A novel and efficient ionic liquid supported synthesis of oligosaccharides”, Tetrahedron Lett., 47(18), 3047-3050(2006).
3 Zhao, D.B., Wu, M., Kou, Y., Min, E., “Ionic liquids: Applications in catalysis”, Catal. Today, 74(1/2), 157-189(2002).
4 Earle, M.J., Seddon, K.R., “Ionic liquids green solvents for the future”, Pure Appl. Chem., 72(7), 1391-1398(2000).
5 Zhao, Y.W., Long, J.X., Deng, F.G., Liu, X.F., Li, Z., Xia, C.G., Peng, J.J., “Catalytic amounts of Br nsted acidic ionic liquids promoted esterification: study of acidity-activity relationship”, Catal. Commun., 10(5), 732-736(2009).
6 Cole, A.C., Jensen, J.L., Ntai, I., Tran, K.L.T., Weave, K.J., Forbes, D.C., Davis Jr., J.H., “Novel Br nsted acidic ionic liquids and their use as dual solvent-catalysts”, J. Am. Chem. Soc., 124(21), 5962-5963(2002).
7 Geng, Y.L., Hu, L.Y., Zhao, X.Q., An, H.L., Wang, Y.J., “Synthesis of 4,4′-MDC in the presence of sulfonic acid-functionalized ionic liquids”, Chin. J. Chem. Eng., 17(5), 756-760(2009).
8 Li, H.L., Yu, S.T., Liu, F.S., Xie, C.X., Li, L., “Synthesis of dioctyl phthalate using acid functionalized ionic liquid as catalyst”, Catal. Commun., 8(11), 1759-1762(2007).
9 Jiang, D., Wang, Y.Y., Tu, M., Dai, L.Y., “The alcoholysis of acetonitrile prompted by Br nsted acidic ionic liquid [HSO₃-pmim]HSO₄”, Chin. Chem. Lett., 19(8), 889-892(2008).
10 Yang, Q.W., Wei, Z.J., Xing, H.B., Ren, Q.L., “Br nsted acidic ionic liquids as novel catalysts for the hydrolyzation of soybean isoflavone glycosides”, Catal. Commun., 9(6), 1307-1311(2008).
11 Domańska, U., Marciniak, A., “Solubility of ionic liquid [emim][PF₆] in alcohols”, J. Phys. Chem. B, 108(7), 2376-2382(2004).
12 Yang, X.Z., Wang, J., Li, G.S., Zhang, Z.Z., “Solubilities of 1-ethylpyridinium hexafluorophosphate in ethanol + water from(278.15 to 345.15) K”, J. Chem. Eng. Data, 54(1), 75-77(2009).
13 Domańska, U., Casás, L.M., “Solubility of phosphonium ionic liquid in alcohols, benzene, and alkylbenzenes”, J. Phys. Chem. B, 111(16), 4109-4115(2007).
14 Domańska, U., ugowska, K., Pernak, J., “Phase equilibria of didecyldimethylammonium nitrate ionic liquid with water and organic solvents”, J. Chem. Thermodyn., 39(5), 729-736(2007).
15 Shang, H.T., Wu, J.S., Zhou, Q., Wang, L.S., “Solubilities of benzene, toluene, and xylene isomers in 1-butyl-3-methylimidazolium tetrafluoroborate”, J. Chem. Eng. Data, 51(4), 1286-1288(2006).
16 Wang, Z.W., Sun, Q.X., Wu, J.S., Wang, L.S., “Solubilities of 2-carboxyethyl-phenylphosphinic acid and 4-carboxyphenylphenylphinic acid in water”, J. Chem. Eng. Data, 48(4), 1073-1075(2003).
17 Zhu, M., “Solubility and density of disodium salt hemiheptahydrate of ceftriaxone in water + ethanol mixtures”, J. Chem. Eng. Data, 46(2), 175-176(2001).
18 Freire, M.G., Carvalho, P.J., Gardas, R.L., Santos, L.M.N.B.F., Marrucho, I.M., Coutinho, J.A.P., “Solubility of water in tetradecyltrihexylphosphonium-based ionic liquids”, J. Chem. Eng. Data, 53(10), 2378-2382(2008).
19 Cai, S.F., Wang, L.S., Hu, F.H., “Solubilities of MoO₂X₂L₂(X=Cl, Br; L=OPPh₃, OPMePh₂) in dichloromethane and H₂O₂(30%(by weight)) + H₂O solution”, J. Chem. Eng. Data, 54(8), 2235-2238(2009).
20 Freire, M.G., Carvalho, P.J., Gardas, R.L., Marrucho, I.M., Santos, L.M.N.B.F., Coutinho, J.A.P., “Mutual solubilities of water and the [C_nmim][Tf₂N] hydrophobic ionic liquids”, J. Phys. Chem. B, 112(6), 1604-1610(2008).

[1]	Jingzhou Guo, Yuanzuo Zou, Bo Shi, Yuan Pu, Jiexin Wang, Dan Wang, Jianfeng Chen. Experimental verification of nanonization enhanced solubility for poorly soluble optoelectronic molecules[J]. 中国化学工程学报, 2023, 60(8): 8-15.
[2]	Xingjuan Liang, Dehua Xu, Zhengjuan Yan, Jingxu Yang, Xinlong Wang, Zhiye Zhang, Jingli Wu, Honggang Zhen. Solid-liquid phase equilibrium for the system ammonium polyphosphate-urea ammonium nitrate-potassium chloride-water at 273.2 K[J]. 中国化学工程学报, 2023, 60(8): 131-142.
[3]	Huiqi Wang, Jianpo Ren, Shihao Zhang, Jiayu Dai, Yue Niu, Ketao Shi, Qiuxiang Yin, Ling Zhou. Measurement and correlation of solubility of 9-fluorenone in 11 pure organic solvents from T = 283.15 to 323.15 K[J]. 中国化学工程学报, 2023, 60(8): 235-241.
[4]	Wen Yu, Yiyang Bo, Yiling Luo, Xiyan Huang, Rixiang Zhang, Jiaheng Zhang. Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation[J]. 中国化学工程学报, 2023, 59(7): 160-168.
[5]	Zhonghao Li, Yuanyuan Yang, Huanong Cheng, Yun Teng, Chao Li, Kangkang Li, Zhou Feng, Hongwei Jin, Xinshun Tan, Shiqing Zheng. Measurement and model of density, viscosity, and hydrogen sulfide solubility in ferric chloride/trioctylmethylammonium chloride ionic liquid[J]. 中国化学工程学报, 2023, 59(7): 210-221.
[6]	Yun-Zhang Liu, Lu-Yao Zhang, Dan He, Li-Zhen Chen, Zi-Shuai Xu, Jian-Long Wang. Solubility measurement, correlation and thermodynamic properties of 2, 3, 4-trichloro-1, 5-dinitrobenzene in fifteen mono-solvents at temperatures from 278.15 to 323.15 K[J]. 中国化学工程学报, 2023, 58(6): 224-233.
[7]	Pengbao Lian, Lizhen Chen, Dan He, Guangyuan Zhang, Zishuai Xu, Jianlong Wang. Crystallization thermodynamics of 2,4(5)-dinitroimidazole in binary solvents[J]. 中国化学工程学报, 2023, 57(5): 173-182.
[8]	Peng Yang, Shengzhe Jia, Yan Wang, Zongqiu Li, Songgu Wu, Jingkang Wang, Junbo Gong. Dissolution behavior, thermodynamic and kinetic analysis of malonamide by experimental measurement and molecular simulation[J]. 中国化学工程学报, 2023, 53(1): 260-269.
[9]	Pengbao Lian, Lizhen Chen, Daozhen Huang, Jianxin Xu, Zishuai Xu, Cai Cao, Jiaxiang Zhao, Jianlong Wang. Crystallization thermodynamics of 2,4(5)-dinitroimidazole in eleven pure solvents[J]. 中国化学工程学报, 2022, 48(8): 236-243.
[10]	Haoyu Yao, Dongxia Yan, Xingmei Lu, Qing Zhou, Yinan Bao, Junli Xu. Solubility determination and thermodynamic modeling of bis-2-hydroxyethyl terephthalate (BHET) in different solvents[J]. 中国化学工程学报, 2022, 45(5): 294-300.
[11]	Fanfan Shen, Lizhen Chen, Pengbao Lian, Jianlong Wang, Duanlin Cao. Solubility and metastable zone width measurement of 2,4-diaminobenzenesulfonic acid in (H₂SO₄ + H₂O) system[J]. 中国化学工程学报, 2022, 44(4): 384-391.
[12]	Xi Wu, Shuaishuai Yang, Shiming Xu, Xinjie Zhang, Yujie Ren. Measurement and correlation of the solubility of sodium acetate in eight pure and binary solvents[J]. 中国化学工程学报, 2022, 44(4): 474-484.
[13]	Alireza Afsharpour. A new approach for correlating of H₂S solubility in [emim][Lac], [bmim][ac] and [emim][pro] ionic liquids using two-parts combined models[J]. 中国化学工程学报, 2022, 44(4): 521-527.
[14]	Yu Dong, Tiantian Ping, Shufeng Shen. Solubility of CO₂ in nonaqueous system of 2-(butylamino)ethanol with 2-butoxyethanol: Experimental data and model representation[J]. 中国化学工程学报, 2022, 41(1): 441-448.
[15]	Jipeng Li, Huan Xu, Jingqi Wang, Yujun Wang, Diannan Lu, Jichang Liu, Jianzhong Wu. Theoretical insights on the hydration of quinones as catholytes in aqueous redox flow batteries[J]. 中国化学工程学报, 2021, 37(9): 72-78.