Abstract
The molar enthalpies of solution of an alanine-based ionic liquid (IL) [C4mim][Ala], 1-butyl-3-methylimidazolium alanine, containing various amount of water and various molalities Δsol H m(wc), were measured with a solution-reaction isoperibol calorimeter at (298.15±0.01) K, where wc denotes water content. According to Archer’s method, the standard molar enthalpies of solution of [C4mim][Ala] containing known amounts of water, \(\Delta_{\mathrm{sol}}H_{\mathrm{m}}^{\mathrm{o}}(\mathrm{wc})\) , were obtained. In order to eliminate the effect of the small amount of residual water in the source [C4mim][Ala], a linear fitting of \(\Delta_{\mathrm{sol}}H_{\mathrm{m}}^{\mathrm{o}}(\mathrm{wc})\) against water content was carried out, yielding a good straight line where the intercept is the standard molar enthalpy of solution of anhydrous [C4mim][Ala], \(\Delta_{\mathrm{sol}}H_{\mathrm{m}}^{\mathrm{o}}(\mathrm{pure}\ \mathrm{IL})=-(61.42\pm 0.08)\) kJ⋅mol−1. The hydration enthalpy of the alanine anion [Ala]− was estimated using Glasser’s lattice energy theory.
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Tao, G.H., He, L., Sun, N., Kou, Y.: New generation ionic liquids: cations derived from amino acids. Chem. Commun. (Camb.) 3562–3564 (2005). doi:10.1039/b504256a
Tao, G.H., He, L., Liu, W.-S., Xu, L., Xiong, W., Wang, T., Kou, Y.: Preparation, characterization and application of amino acid-based green ionic liquids. Green Chem. 8, 639–646 (2006). doi:10.1039/b600813e
Fukumoto, K., Ohno, H.: New generation ionic liquids: cations derived from amino acids. Chem. Commun. (Camb.) 3081–3083 (2006). doi:10.1039/b606613e
Fukumoto, K., Yoshizawa, M., Ohno, H.: New generation ionic liquids: cations derived from amino acids. J. Am. Chem. Soc. 127, 2398–2399 (2005). doi:10.1021/ja043451i
Ohno, H., Fukumoto, K.: Amino acid ionic liquids. Acc. Chem. Res. 40, 1122–1129 (2007). doi:10.1021/ar700053z
Zhang, Z.-F., Li, J.-G., Zhang, Q.-G., Guan, W., Yang, J.-Z.: Enthalpy of solution of amino acid ionic liquid 1-ethyl-3-methylimidazolium ammonioacetate. J. Chem. Eng. Data 53, 1196–1198 (2008). doi:10.1021/je700599z
Guan, W., Xue, W.-F., Li, N., Tong, J.: The enthalpy of solution of amino acid ionic liquid 1-butyl-3-methylimidazolium glycine. J. Chem. Eng. Data 53, 1401–1403 (2008). doi:10.1021/je800067m
Fang, D.-W., Guan, W., Tong, J., Wang, Z.-W., Yang, J.-Z.: Study on physico-chemical properties of ionic liquids based on alanine [C n mim][Ala] (n=2,3,4,5,6). J. Phys. Chem. B 112, 7499–7505 (2008). doi:10.1021/jp801269u
Yang, J.-Z., Zhang, Q.-G., Wang, B., Tong, J.: Study on the properties of amino acid ionic liquid EMIGly. J. Phys. Chem. B 110, 22521–22524 (2006). doi:10.1021/jp0648691
Najdanovic-Visak, V., Ksperanca, J.M.S.S., Rebelo, L.P.N., Da Ponte, M.N., Guedes, H.J.R., Seddon, K.R., Sydlowski, J.: Phase behaviour of room temperature ionic liquid solution: an unusually large co-solvent effect in (water + ethanol). Phys. Chem. Chem. Phys. 4, 1701–1703 (2002). doi:10.1039/b201723g
Tong, J., Hong, M., Guan, W., Yang, J.-Z.: Studies on the thermodynamic properties of new ionic liquids: 1-methyl-3-pentylimidazolium salts containing metal of group III. J. Chem. Thermodyn. 38, 1416–1421 (2006). doi:10.1016/j.jct.2006.01.017
Rogers, R.D., Seddon, K.R.: Ionic Liquids as Green Solvents. ACS Symposium Series, vol. 856. American Chemical Society, Washington (2003)
Yang, J.-Z., Tong, J., Li, J.-B.: Study of the volumetric properties of the aqueous ionic liquid 1-methyl-3-pentylimidazolium tetrafluoroborate. J. Solution Chem. 36, 573–582 (2007). doi:10.1007/s10953-007-9134-5
Yang, J.-Z., Guan, W., Tong, J., Wang, H., Li, L.: Studies on thermo-chemical properties of a new ionic liquid prepared by mixing 1-methyl-3-pentylimidazolium chloride with InCl3. J. Solution Chem. 35, 845–852 (2006). doi:10.1007/s10953-006-9028-y
Archer, D.G., Widegren, J.A., Kirklin, D.R., Magee, J.W.: Enthalpy of solution of 1-octyl-3-methylimidazolium tetrafluoroborate in water and in aqueous sodium fluoride. J. Chem. Eng. Data 50, 1484–1491 (2005). doi:10.1021/je050136i
Glasser, L.: Lattice and phase transition thermodynamics of ionic liquids. Thermochim. Acta 421, 87–93 (2004). doi:10.1016/j.tca.2004.03.015
Wilkes, J.S., Levisky, J.A., Wilson, R.A.: Dialkylimidazolium chloroaluminate metal: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy, and synthesis. Inorg. Chem. 21, 1263–1264 (1982). doi:10.1021/ic00133a078
Di, Y.Y., Qu, S.S., Liu, Y., Wen, D., Tang, C.H., Li, L.W.: A thermochemical study of the solid-state coordination reactions of two α-amino acids with copper(II) acetate. Thermochim. Acta 387, 115–119 (2002). doi:10.1016/S0040-6031(01)00831-0
Yu, H.G., Liu, Y., Tan, Z.C., Dong, J.X., Zou, T.J., Huang, X.M., Qu, S.S.: A solution-reaction isoperibol calorimeter and standard molar enthalpies of formation of Ln(hq)2Ac (Ln = La, Pr). Thermochim. Acta 401, 217–224 (2003). doi:10.1016/S0040-6031(02)00566-X
Rychly, R., Pekarek, V.: The use of potassium chloride and tris(hydroxymethyl) aminomethane as standard substances for solution calorimetry. J. Chem. Thermodyn. 9, 391–396 (1977). doi:10.1016/0021-9614(77)90060-X
Montgomery, R.L., Melaugh, R.A., Lau, C.-C., Meier, G.H., Chan, H.H., Rossini, F.D.: Determination of the energy equivalent of a water solution calorimeter with a standard substance. J. Chem. Thermodyn. 9, 915–936 (1977). doi:10.1016/0021-9614(77)90214-2
Pitzer, K.S.: In: Pitzer, K.S. (ed.) Activity Coefficients in Electrolyte Solutions, Chap. 3. CRC, Boca Raton (1991), revised edn.
Marcus, Y.: Ion Solvation, p. 108. Wiley, Chichester (1985)
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Guan, W., Xue, WF., Tong, J. et al. The Enthalpy of Solution of the Alanine-Based Ionic Liquid [C4mim][Ala]. J Solution Chem 38, 1463–1469 (2009). https://doi.org/10.1007/s10953-009-9458-4
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DOI: https://doi.org/10.1007/s10953-009-9458-4