Abstract
A new amino acid-functionalized ionic liquid (IL), monoethanolamine glycinate ([MEA][GLY]), was synthesized and characterized. Its physical properties were measured, including density, viscosity, surface tension, conductivity, and refractive index. The solubility of CO2 in [MEA][GLY] was determined. The ability of [MEA][GLY] to absorb CO2 was evaluated. [MEA][GLY] with an active amino group exhibits representative physical properties of a functionalized IL. The solubility of CO2 in the IL is more than 0.5 mol CO2/mol IL at room temperature and atmospheric pressure. The [MEA][GLY] and aqueous [MEA][GLY] ILs are thus good absorbents of CO2. The CO2 partial pressure and [MEA][GLY] concentration have a significant impact on their absorption.
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Rogers, R.D., Seddon, K.R.: Ionic liquids—solvents of the future. Science 302, 792–793 (2003)
Martins, M., Frizzo, C.P., Moreira, D.N., Zanatta, N., Bonacorso, H.G.: Ionic liquids in heterocyclic synthesis. Chem. Rev. 108, 2015–2050 (2008)
Hallett, J.P., Welton, T.: Room-temperature ionic liquids: solvents for synthesis and catalysis. 2. Chem. Rev. 111, 3508–3576 (2011)
Yue, C., Fang, D., Liu, L., Yi, T.-F.: Synthesis and application of task-specific ionic liquids used as catalysts and/or solvents in organic unit reactions. J. Mol. Liq. 163, 99–121 (2011)
Silva, S.S., Duarte, A.R., Carvalho, A.P., Mano, J.F., Reis, R.L.: Green processing of porous chitin structures for biomedical applications combining ionic liquids and supercritical fluid technology. Acta Biomater. 7, 1166–1172 (2011)
Lu, J., Yan, F., John, T.: Advanced applications of ionic liquids in polymer science. Prog. Polym. Sci. 34, 431–448 (2009)
Ma, J., Hong, X.: Application of ionic liquids in organic pollutants control. J. Environ. Manag. 99, 104–109 (2012)
Kavitha, T., Attri, P., Venkatesub, P., Rama-Devi, R.S., Hofman, T.: Influence of temperature on thermo physical properties of ammonium ionic liquids with N-methyl-2-pyrrolidone. Thermochim. Acta 45, 131–140 (2012)
Attri, P., Venkatesu, P.: Thermodynamic characterization of the biocompatible ionic liquid effects on protein model compounds and their functional groups. Phys. Chem. 13, 6566–6575 (2011)
Blath, J., Christ, M., Deubler, N., Hirth, T., Schiestel, T.: Gas solubilities in room temperature ionic liquids—correlation between RTIL-molar mass and Henry’s law constant. Chem. Eng. J. 172, 167–176 (2011)
Brennecke, J.F., Maginn, E.J.: Ionic liquids: innovative fluids for chemical processing. AIChE J. 47, 2384–2389 (2001)
Cussler, E.L., Wei, J.: Chemical product engineering. AIChE J. 49, 1072–1075 (2003)
Zhang, S.-J., Liu, X.-M., Yao, X.Q., Dong, H.F., Zhang, X.P.: Frontiers, progress and applications of ionic liquids. Sci. China B 39, 1134–1144 (2009)
Abbott, A.P., Capper, G., Davies, D.L., Munro, H.L., Rasheed, R.K., Tambyrajah, V.: Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem. Commun. 19, 2010–2011 (2001)
Yu, G., Zhang, S., Zhou, G., Liu, X., Chen, X.: Structure, interaction and properties of amino-functionalized imidazolium ionic liquids by abinitio calculation and molecular dynamics simulation. AIChE J. 53, 3210–3221 (2007)
Davis, J.H.: Task-specific ionic liquids. Chem. Lett. 33, 1072–1077 (2004)
Bates, E.D., Mayton, R.D., Ntai, I., Davis, J.H.: CO2 capture by a task-specific ionic liquid. J. Am. Chem. Soc. 124, 926–927 (2002)
Zhang, Y.Q., Zhang, S.J., Lu, X.M., Zhou, Q., Fan, W., Zhang, X.P.: Dual amino-functionalised phosphonium ionic liquids for CO2 capture. Chem. Eur. J. 15, 3003–3011 (2009)
Gurkan, B.E., de la Fuente, J.C., Mindrup, E.M., Ficke, L.E., Goodrich, B.F., Price, E.A., Schneider, W.F., Brennecke, J.F.: Equimolar CO2 absorption by anion-functionalized ionic liquids. J. Am. Chem. Soc. 132, 2116–2117 (2010)
Goodrich, B.F., de la Fuente, J.C., Gurkan, B.E., Lopez, Z.K., Price, E.A., Huang, Y., Brennecke, J.F.: Effect of water and temperature on absorption of CO2 by amine-functionalized anion-tethered ionic liquids. J. Phys. Chem. B. 115, 9140–9150 (2011)
Lv, B., Shi, Y., Sun, C., Liu, N., Li, W., Li, S.: CO2 capture by a highly-efficient aqueous blend of monoethanolamine and a hydrophilic amino acid ionic liquid [C2OHmim][Gly]. Chem. Eng. J. 270, 372–377 (2015)
Wickramanayake, S., Hopkinson, D., Myers, C., Sui, L., Luebke, D.: Investigation of transport and mechanical properties of hollow fiber membranes containing ionic liquids for pre-combustion carbon dioxide capture. J. Membr. Sci. 439, 58–67 (2013)
Ramdin, M., de Loos, T.W., Vlugt, T.J.H.: State-of-the-art of CO2 capture with ionic liquids. Ind. Eng. Chem. Res. 51, 8149–8177 (2012)
Yuan, X.L., Zhang, S.J., Lu, X.M.: Hydroxyl ammonium ionic liquids: synthesis, properties, and solubility of SO2. J. Chem. Eng. Data 56, 596–599 (2007)
Yuan, X., Zhang, S., Liu, J., Lu, X.: Solubilities of CO2 in hydroxyl ammonium ionic liquids at elevated pressures. Fluid Phase Equilib. 257, 195–200 (2007)
Zhang, H., Lu, C.-T., Lu, J.-G., Gao, L., Hai, G.-P., Tang, Y.-Q., Chen, L.-X., Hua, A.-C., Wang, L.-J.: Density, viscosity and excess molar volume of the aqueous ionic liquid tris(monoethanolamine) citrate at 293.15–323.15 K. J. Solution Chem. 43, 2117–2132 (2014)
Lu, J.-G., Fan, F., Liu, C., Zhang, H., Ji, Y., Chen, M.-D.: Density, viscosity, and surface tension of aqueous solutions of potassium glycinate + piperazine in the range of (288.15 to 323.15) K. J. Chem. Eng. Data 56, 2706–2709 (2011)
Lu, J.-G., Hua, A.-C., Xu, Z.-W., Fan, F., Cheng, L., Lin, F.-Y.: Measurement and prediction of densities, viscosities, and surface tensions for aqueous solutions of potassium citrate. Fluid Phase Equilib. 327, 9–13 (2012)
Tong, J., Hong, M., Chen, Y., Wang, H., Guan, W., Yang, J.-Z.: The surface tension, density and refractive index of amino acid ionic liquids: C3mim.Gly. and C4mim.Gly. J. Chem. Thermodyn. 54, 352–357 (2012)
Lu, J.-G., Liu, C., Fan, F., Ji, Y., Zhang, H.: Solubility of carbon dioxide in mixed solution of MDEA–AMP. J. Fuel Chem. Technol. 38, 730–732 (2010)
Zare, A., Abi, F., Moosavi-Zare, A.R., Beyzavi, M.H., Zolfigol, M.A.: Synthesis, characterization and application of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient catalyst for the preparation of hexahydroquinolines. J. Mol. Liq. 178, 113–121 (2013)
Caplow, M.: Kinetics of carbamate formation and breakdown. J. Am. Chem. Soc. 90, 6795–6803 (1968)
Zhang, J.M., Zhang, S.J., Dong, K., Zhang, Y.Q., Shen, Y.Q., Lu, X.M.: Supported absorption of CO2 by tetrabutylphosphonium amino acid ionic liquids. Chem. Eur. J. 12, 4021–4026 (2006)
Tomida, D., Kumagai, A., Qiao, K., Yokoyama, C.: Viscosity of bmimPF6 and bmimBF4 at high pressure. Int. J. Thermophys. 27, 39–47 (2006)
Kumar, P.S., Hogendoorn, J.A., Versteeg, G.F., Feron, P.H.M.: Kinetics of the reaction of CO2 with aqueous potassium salt of taurine and glycine. AIChE J. 49, 203–213 (2003)
Luo, X., Guo, Y., Ding, F., Zhao, H., Cui, G., Li, H., Wang, C.: Significant improvements in CO2 capture by pyridine-containing anion-functionalized ionic liquids through multiple-site cooperative interactions. Angw. Chem. Int. Ed. 53, 7053–7057 (2014)
Acknowledgments
This work was funded by the University Graduate Scientific Research and Innovation Project of Jiangsu Province (Grant No. KYLX-0857), Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), the Students Practice and Innovation Project of Jiangsu Province (Grant No. 201510300078), and the Students Practice and Innovation of NUIST (Grant No. 201410300128). The reviewers are greatly appreciated for their very valuable and helpful comments.
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Lu, JG., Lu, ZY., Cao, S. et al. Synthesis, Characterization, Physical Properties, and CO2 Absorption Performance of Monoethanolamine Glycinate Ionic Liquid. J Solution Chem 44, 1997–2007 (2015). https://doi.org/10.1007/s10953-015-0392-3
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DOI: https://doi.org/10.1007/s10953-015-0392-3