Abstract
Density, speed of sound and refractive index of the imidazolium-based ionic liquids (ILs), 1-methyl-3-octylimidazolium chloride [C8mim][Cl], 1-butyl-3-methylimidazolium methyl sulfate [C4mim][C1OSO3], and 1-butyl-3-methylimidazolium octyl sulfate [C4mim][C8OSO3], have been measured in the temperature range from 283.15 to 343.15 K. Experimental density and speed of sound have been used to calculate the internal pressure p i of the ILs. The p i values were found to be higher than those of water and molecular organic liquids, but lower than those of classical molten salts. We also calculated molar refraction R M from the measured refractive index n D in the temperature range from 288.15 to 343.15 K. Refractive indices of ILs were also higher than those of normal organic liquids, but comparable to long-chain hydrocarbon organic solvents. The structure-property correlation of the ILs has been discussed and the results have been compared to our earlier studies (Kumar in J. Solution Chem. 37:203–214, 2008).
Similar content being viewed by others
References
Earle, M.J., McCormac, P.B., Seddon, K.R.: Regioselective alkylation in ionic liquids. Chem. Commun. 2245–2246 (1998)
Welton, T.: Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 99, 2071–2084 (1999)
Earle, M.J., Seddon, K.R., Adams, C.J., Roberts, G.: Friedel–Crafts reactions in room temperature ionic liquids. Chem. Commun. 2097–2098 (1998)
Wasserscheid, P., Keim, W.: Ionic liquids—new “solutions” for transition metal catalysis. Angew. Chem., Int. Ed. 39, 3772–3789 (2000)
Anderson, J.L., Ding, J., Welton, T., Armstrong, D.W.: Characterizing ionic liquids on the basis of multiple solvation interactions. J. Am. Chem. Soc. 124, 14247–14254 (2002)
Leadbeater, N.E., Torenius, H.M.: A study of the ionic liquid mediated microwave heating of organic solvents. J. Org. Chem. 67, 3145–3148 (2002)
Seddon, K.R.: Ionic liquids: A taste of the future. Nature Mat. 2, 363–365 (2003)
Wasserscheid, P., Welton, T.: Ionic Liquids in Synthesis. Wiley, New York (2003)
Gordon, C.M., Holbrey, J.D., Kennedy, A.R., Seddon, K.R.: Ionic liquid crystals: hexafluorophosphate salts. J. Mater. Chem. 8, 2627–2636 (1998)
Seddon, K.R.: Room-temperature ionic liquids: neoteric solvents for clean catalysis. Kinet. Katal. 37, 693–697 (1996)
Singh, T., Kumar, A.: Aggregation behavior of ionic liquids in aqueous solutions: Effect of alkyl chain length, cations, and anions. J. Phys. Chem. B 111, 7843–7851 (2007)
Singh, T., Kumar, A.: Fluorescence behavior and specific interactions of an ionic liquid in ethylene glycol derivatives. J. Phys. Chem. B 112, 4079–4086 (2008)
Jaeger, D.A., Tucker, C.E.: Diels-Alder reactions in ethylammonium nitrate, a low-melting fused salt. Tetrahedron Lett. 30, 1785–1788 (1989)
Lee, C.W.: Diels-Alder reactions in chloroaluminate ionic liquids: acceleration and selectivity enhancement. Tetrahedron Lett. 40, 2461–2464 (1999)
Holbrey, J.D., Seddon, K.R.: Ionic liquids. Clean Prod. Process. 1, 223–236 (1999)
Pinto, A.C., Moreira Lapis, A.A., Vasconcellos da Silva, B., Bastos, R.S., Dupont, J., Neto, B.A.D.: Pronounced ionic liquid effect in the synthesis of biologically active isatin-3-oxime derivatives under acid catalysis. Tetrahedron Lett. 49, 5639–5641 (2008)
Dack, M.R.J.: The importance of solvent internal pressure and cohesion to solution phenomena. Chem. Soc. Rev. 4, 211–229 (1975)
Kumar, A.: Can internal pressure describe the effect of salt in aqueous Diels-Alder reaction? A possible explanation. J. Org. Chem. 59, 230–231 (1994)
Kumar, A.: Rate enhancement in Diels-Alder reactions by perchlorate salts in nonaqueous solvents: An alternate explanation. J. Org. Chem. 59, 4612–4617 (1994)
Kumar, A.: Stereoselectivities and reaction rates in Diels-Alder reactions promoted by non-aqueous solvents and their aqueous mixtures: Correlations with non-adjustable parameters. J. Phys. Org. Chem. 9, 287–292 (1996)
Kumar, A.: Estimates of internal pressure and molar refraction of imidazolium based ionic liquids as a function of temperature. J. Solution Chem. 37, 203–214 (2008)
Huddleston, J.G., Visser, A.E., Reichert, W.M., Willauer, H.D., Broker, G.A., Rogers, R.D.: Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem. 3, 156–164 (2001)
Letcher, T.M., Deenadayalu, N., Soko, B., Ramjugernath, D., Naicker, P.K.: Ternary liquid–liquid equilibria for mixtures of 1-methyl-3-octylimidazolium chloride + an alkanol + an alkane at 298.2 K and 1 bar. J. Chem. Eng. Data 48, 904–907 (2003)
Gonzalez, E.J., Alonso, L., Dominguez, A.: Physical properties of binary mixtures of the ionic liquid 1-methyl-3-octylimidazolium chloride with methanol, ethanol, and 1-propanol at T=(298.15, 313.15, and 328.15) K and at P=0.1 MPa. J. Chem. Eng. Data 51, 1446–1452 (2006)
Gomez, E., Gonzalez, B., Dominguez, A., Tojo, E., Tojo, J.: Dynamic viscosities of a series of 1-alkyl-3-methylimidazolium chloride ionic liquids and their binary mixtures with water at several temperatures. J. Chem. Eng. Data 51, 696–701 (2006)
Arce, A., Rodriguez, O., Soto, A.: Experimental determination of liquid–liquid equilibrium using ionic liquids: tert-amyl ethyl ether + ethanol + 1-octyl-3-methylimidazolium chloride system at 298.15 K. J. Chem. Eng. Data 49, 514–517 (2004)
Pereiro, A.B., Verdia, P., Tojo, E., Rodriguez, A.: Physical properties of 1-butyl-3-methylimidazolium methyl sulfate as a function of temperature. J. Chem. Eng. Data 52, 377–380 (2006)
Domanska, U., Pobudkowska, A., Wisniewska, A.: Solubility and excess molar properties of 1,3-dimethylimidazolium methylsulfate, or 1-butyl-3-methylimidazolium methylsulfate, or 1-butyl-3-methylimidazolium octylsulfate ionic liquids with n-alkanes and alcohols: Analysis in terms of the PFP and FBT models. J. Solution Chem. 35, 311–334 (2006)
Wandschneider, A., Lehmann, J.K., Heintz, A.: Surface tension and density of pure ionic liquids and some binary mixtures with 1-propanol and 1-butanol. J. Chem. Eng. Data 53, 596–599 (2008)
Dávila, M.J., Aparicio, S., Alcalde, R., García, B., Leal, J.M.: On the properties of 1-butyl-3-methylimidazolium octylsulfate ionic liquid. Green Chem. 9, 221–232 (2007)
Fredlake, C.P., Crosthwaite, J.M., Hert, D.G., Aki, S.N.V.K., Brennecke, J.F.: Thermophysical properties of imidazolium-based ionic liquids. J. Chem. Eng. Data 49, 954–964 (2004)
Fernandez, A., Torrecilla, J.S., Garcia, J., Rodriguez, F.: Thermophysical properties of 1-ethyl-3-methylimidazolium ethylsulfate and 1-butyl-3-methylimidazolium methylsulfate ionic liquids. J. Chem. Eng. Data 52, 1979–1983 (2007)
Tekin, A., Safarov, J., Shahverdiyev, A., Hassel, E.: (p,ρ,T) properties of 1-butyl-3-methylimidazolium tetrafluoroborate and 1-butyl-3-methylimidazolium hexafluorophosphate at T=(298.15 to 398.15) K and pressures up to p=40 MPa. J. Mol. Liquids 136, 170–182 (2007)
Brennecke, J.F., Gu, Z.: Volume expansivities and isothermal compressibilities of imidazolium and pyridinium-based ionic liquids. J. Chem. Eng. Data 47, 339–345 (2002)
Woodcock, L.V., Singer, K.: Thermodynamic and structural properties of liquid ionic salts obtained by Monte Carlo computation. Trans. Faraday Soc. 67, 12–30 (1971)
Lewis, J.W.E., Singer, K.: Thermodynamic properties and self-diffusion of molten sodium chloride. J. Chem. Soc. Faraday Trans. 2 71, 41–53 (1975)
Lopes, J.N.A.C., Pádua, A.A.H.: Nanostructural organization in ionic liquids. J. Phys. Chem. B 110, 3330–3335 (2006)
Marcus, Y.: The Properties of Solvents. Wiley, New York (1998)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Singh, T., Kumar, A. Temperature Dependence of Physical Properties of Imidazolium Based Ionic Liquids: Internal Pressure and Molar Refraction. J Solution Chem 38, 1043–1053 (2009). https://doi.org/10.1007/s10953-009-9429-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10953-009-9429-9