Abstract
The enthalpies of vaporization for the series of pyridinium-based ionic liquids with bis(trifluoromethylsulfonyl)imide anion [C n Py][NTf2] (n = 2, 3, 4, 5, and 6) have been determined with the quartz crystal microbalance technique combined with the Langmuir evaporation. The linear dependence of vaporization enthalpies on the chain length has been revealed. New approach based on volumetric, surface tension, and speed of sound measurements has been developed for estimation of heat capacity differences between gas and liquid phase, which were required for adjustment of measured vaporization enthalpies to the reference temperature 298 K.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Rantwijk FV, Sheldon RA. Biocatalysis in ionic liquids. Chem Rev, 2007, 107: 2757–2785
Greaves TL, Drummond CJ. Protic ionic liquids: Properties and applications. Chem Rev, 2008, 108: 206–237
Hapiot P, Lagrost C. Electrochemical reactivity in room-temperature ionic liquids. Chem Rev, 2008, 108: 2238–2264
Jessop PG, Subramaniam B. Gas-expanded liquids. Chem Rev, 2007, 107: 2666–2694
Visser AE, Rogers RD. Room-temperature ionic liquids: New solvents for f-element separations and associated solution chemistry. J Solid State Chem, 2003, 171: 109–113
Kim GT, Appetecchi GB, Alessandrini F, Passerini S. Solvent-free, PYR1ATFSI ionic liquid-based ternary polymer electrolyte systems I. Electrochemical characterization. J Power Sources, 2007, 171: 861–869
Orita A, Kamijima K, Yoshida M, Yang L. Application of sulfonium-, and thioxonium-based salts as electric double-layer capacitor electrolytes. J Power Sources, 2010, 195: 6970–6976
Lazzari M, Mastragostino M, Pandolfo AG, Ruiz V, Soavi F. Role of carbon porosity and ion size in the development of ionic liquid based supercapacitors. J Electrochem Soc, 2011, 158: A22–A25
Orita A, Kamijima K, Yoshida M. Allyl-functionalized ionic liquids as electrolytes for electric double-layer capacitors. J Power Sources, 2010, 195: 7471–7479
Fang SH, Yang L, Wei C, Peng CX, Tachibana K, Kamijima K. Low-viscosity and low-melting point asymmetric trialkylsulfonium based ionic liquids as potential electrolytes. Electrochem Commun, 2007, 9: 2696–2702
Kazock J, Taggougui M, Anouti M, Willman P, Carre B, Lemordant D. Ionic liquids based on 1-aza-bicyclo[2,2,2]cotane (quinuclidine)salts: synthesis and physicochemical properties. J Appl Electrochem, 2009, 39: 2461–2467
Sakaebe H, Matsumoto H. N-Methyl-N-propylpiperdinium bis(trifluoromethanesulfonyl) imide (PP13-TFSI)-novel electrolyte base for Li battery. Electrochem Commun, 2003, 5: 594–598
Yang L, Zhang ZX, Gao XH, Zhang HQ, Mashita K. Asymmetric sulfonium-based molten salts with TFSI- or PF6 anion as novel electrolytes. J Power Sources, 2006, 162: 614–619
Matsumoto H, Sakaebe H, Tatsumi K, Kikuta M, Ishiko E, Kono M. Fast cycling of Li/LiCoO2 cell with low-viscosity ionic liquids based on bis(fluorosulfony)imide[FSI]. J Power Sources, 2006, 160: 1308–1303
Liu QS, Yang M, Li PP, Sun SS, Welz-Biermann U, Tan ZC, Zhang QG. Physicochemical properties of ionic liquids [C3py][NTf2] and [C6py][NTf2]. J Chem Eng Data, 2011, 56: 4094–4101
Bittner B, Janus E, Milchert E. N-Hexylpyridinium bis(trifluorome-thylsulfonyl)imide and Lewis acids-catalytic systems for Diels-Alder reaction. Cent Eur J Chem, 2011, 9: 192–198
Papaiconomou N, Estager J, Traore Y, Bauduin P, Bas C, Legeai S, Viboud S, Draye M. Synthesis, physicochemical properties, and toxicity data of new hydrophobic ionic liquids containing dimethylpyridinium and trimethylpyridinium cations. J Chem Eng Data, 2010, 55: 1971–1979
Rodriguez-Cabo B, Francisco M, Soto A, Arce A. Hexyl dimethylpyridinium ionic liquids for desulfurization of fuels. Effect of the position of alkyl side chains. Fluid Phase Equil, 2012, 314: 107–111
Gaile AA, Zalishchevkii GD, Gafur NN, Semenov LV, Varshavski OM, Fedyanin NP, Koldobskaya LL. Removal of aromatic hydrocarbons from reforming naphtha. combined extraction-extractive-azeotropic distillation process. Chem Thechnol Fuels Oils, 2004, 40: 215–221
Verevkin SP, Zaitsau DH, Emel’yanenko VN, Heintz A. A new method for the determination of vaporization enthalpies of ionic liquids at low temperatures. J Phys Chem B, 2011, 115: 12889–12895
Zaitsau DH, Verevkin SP, Emel’yanenko VN, Heintz A. Vaporization enthalpies of imidazolium based ionic liquids: Dependence on alkyl chain length. ChemPhysChem, 2011, 12: 3609–3613
Zaitsau DH, Fumino K, Emel’yanenko VN, Yermalaeu AV, Ludwig R, Verevkin SP. Structure-property relationships in ILs: A study of the anion dependence in vaporisation enthalpies of imidazolium based ionic liquids. ChemPhysChem, 2012, in press
Verevkin SP, Zaitsau DH, Emel’yanenko VN, Ralys RV, Schick C. Express thermo-gravimetric method for the vaporization enthalpies appraisal for very low volatile molecular and ionic compounds. Thermochim Acta, 2012, accepted
Sauerbrey G. Verwendung von Schwingquarzen zur Wägung dünner Schichten und zur Mikrowägung. Z Phys A, 1959, 155: 206–222
Paulechka YU, Kabo GJ, Blokhin AV, Vydrov OA, Magee JW, Frenkel M. Thermodynamic properties of 1-butyi-3-methylimidazolium hexafluorophosphate in the ideal gas state. J Chem Eng Data, 2003, 48: 457–462
Moelwyn-Hughes EA. Physical Chemistry. New York, London, Paris: Pergamon Press, 1954
Paulechka YU, Zaitsau DH, Kabo GJ. On the difference between isobaric and isochoric heat capacities of liquid cyclohexyl esters. J Mol Liq, 2004, 115: 105–111
Diedrichs A, Gmehling J. Measurement of heat capacities of ionic liquids by differential scanning calorimetry. Fluid Phase Equilib, 2006, 244: 68–77
Paulechka Y. Heat capacity of room-temperature ionic liquids: A critical review. J Phys Chem Ref Data, 2010, 39(3): 033108 1–23
Wang C, Luo H, Li H, Dai S. Direct UV-spectroscopic measurement of selected ionic-liquid vapors. PhysChem Chem Phys, 2010, 12: 7246–7250
Deyko A, Lovelock KRJ, Corfield JA, Taylor AW, Gooden PN, Villar-Garcia IJ, Licence P, Jones RG, Krasovskiy VG, Chernikova EA, Kustov LM. Measuring and predicting ΔvapH298 values of ionic liquids. Phys Chem Chem Phys, 2009, 11: 8544–8555
Kulikov D, Verevkin SP, Heintz A. Enthalpies of vaporization of a series of aliphatic alcohols: Experimental results and values predicted by the ERAS-model. Fluid Phase Equil, 2001, 192: 187–207
Emel’yanenko VN, Verevkin SP, Koutek B, Doubsky J. Vapour pressures and enthalpies of vapourization of a series of the linear aliphatic nitriles. J Chem Thermodyn., 2005, 37: 73–81
Verevkin SP, Krasnykh EL, Vasiltsova TV, Koutek B, Doubsky J, Heintz A. Vapor pressures and enthalpies of vaporization of a series of the linear aliphatic aldehydes. Fluid Phase Equil, 2003, 206: 331–339
Verevkin SP, Zaitsau DH, Emel’yanenko VN, Schick C, Liu H, Maginn E, Bulut S, Krossing I, Kalb R. Obscured vaporization enthalpies of ionic liquids: Milky way, bent up, or straight ahead? new experimental data on 1-alkyl-3-methylimidazolium bis-(trifluoro-methylsulfonyl)-imides with the even and odd number of C-atoms in the alkyl chain. J Am Chem Soc, 2012, submitted
Mansson M, Sellers P, Stridh G, Sunner S. Enthalpies of vaporization of some l-substituted n-alkanes. J Chem Thermodyn, 1977, 9: 91–97
Zaitsau DH, Kabo GJ, Strechan AA, Paulechka YU, Tschersich A, Verevkin SP, Heintz A. Experimental vapor pressures of 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides and a correlation scheme for estimation of vaporization enthalpies of ionic liquids. J Phys Chem A, 2006, 110: 7303–7306
Deyko A, Hessey SG, Licence P, Chernikova EA, Krasovskiy VG, Kustov LM, Jones RG. The enthalpies of vaporisation of ionic liquids: new measurements and predictions. Phys Chem Chem Phys, 2012, 14: 3181–3193
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Zaitsau, D.H., Yermalayeu, A.V., Emel’yanenko, V.N. et al. Structure-property relationships in ILs: A study of the alkyl chain length dependence in vaporisation enthalpies of pyridinium based ionic liquids. Sci. China Chem. 55, 1525–1531 (2012). https://doi.org/10.1007/s11426-012-4662-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-012-4662-2