On the prediction of critical temperatures of ionic liquids: Model development and evaluation

Abstract In this study, the Guggenheim equation was used to estimate the critical temperature ( T c ) of 106 ionic liquids using experimental surface tension data as inputs. A group contribution (GC) and a Quantitative Structure-Property Relationship (QSPR) model were also developed to correlate/predict the T c of ionic liquids. It was shown that a lack of sufficiently large database for T c leads to the development of models with low prediction capability. The models output as well as the T c values estimated from the surface tension data were compared with the critical temperatures calculated by the Valderrama et al. method. The results show that the Valderrama et al. method produces different data values compared with the values calculated by the Guggenheim equation. Neither the GC, QSPR, nor Valderrama's method is capable of reliable prediction of the T c of ionic liquids. Consequently, the calculated T c values are not reliable enough to be used in the development of corresponding state models for prediction of other thermophysical properties of ionic liquids. Any usage of critical properties of ionic liquids should be done with a serious caution.

[1]  A. Mohammadi,et al.  Prediction of refractive indices of ionic liquids – A quantitative structure-property relationship based model , 2015 .

[2]  Jin Young Kim,et al.  Effects of ionic liquid molecules in hybrid PbS quantum dot-organic solar cells. , 2013, ACS applied materials & interfaces.

[3]  Julián García,et al.  Liquid–liquid extraction of toluene from n-heptane by {[emim][TCM] + [emim][DCA]} binary ionic liquid mixtures , 2014 .

[4]  X. Liang.  Novel Efficient Procedure for Biodiesel Synthesis from Waste Oils Using Solid Acidic Ionic Liquid Polymer As the Catalyst , 2013 .

[5]  Maria Forsyth,et al.  A Review of Ionic Liquid Lubricants , 2013 .

[6]  Zhiyong Li,et al.  Effect of Substituent Groups in Anions on Some Physicochemical Properties of 1-Butyl-3-methylimidazolium Carboxylate Ionic Liquids , 2013 .

[7]  Chaohong He,et al.  Speed of sound of ionic liquids: Database, estimation, and its application for thermal conductivity prediction , 2014 .

[8]  George Wypych,et al.  Handbook of Solvents , 2000 .

[9]  A. Balducci,et al.  Protic ionic liquids as electrolytes for lithium-ion batteries , 2013 .

[10]  Andrzej Lewandowski,et al.  Ionic liquids as electrolytes for Li-ion batteries—An overview of electrochemical studies , 2009 .

[11]  Jairton Dupont,et al.  Room temperature dialkylimidazolium ionic liquid-based fuel cells , 2003 .

[12]  M. Ghatee,et al.  Critical-Point Temperature of Ionic Liquids from Surface Tension at Liquid—Vapor Equilibrium and the Correlation with the Interaction Energy , 2010 .

[13]  Jian‐mei Lu,et al.  Cross-Linked Alkaline Ionic Liquid-Based Polymer Electrolytes for Alkaline Fuel Cell Applications , 2010 .

[14]  M. Mohammadi,et al.  Molecular investigation of SO2 gas absorption by ionic liquids: Effects of anion type , 2014 .

[15]  R. Noble,et al.  Ideal CO2/Light Gas Separation Performance of Poly(vinylimidazolium) Membranes and Poly(vinylimidazolium)-Ionic Liquid Composite Films , 2013 .

[16]  A. Henni,et al.  Experimental and thermodynamic study of CO2 solubility in promising [TF2N and DCN] ionic liquids , 2014 .

[17]  Helene Olivier-Bourbigou,et al.  Ionic liquids and catalysis: Recent progress from knowledge to applications , 2010 .

[18]  S. Dai,et al.  Superbase-derived protic ionic liquid extractants for metal ion separation , 2014 .

[19]  A. Arce,et al.  Desulfurization of fuels by liquid–liquid extraction with 1-ethyl-3-methylimidazolium ionic liquids , 2013 .

[20]  D. Macfarlane,et al.  Crystalline vs. Ionic Liquid Salt Forms of Active Pharmaceutical Ingredients: A Position Paper , 2010, Pharmaceutical Research.

[21]  Neda Khanjari,et al.  Measurement and study of density, surface tension, and viscosity of quaternary ammonium-based ionic liquids ([N222(n)]Tf2N) , 2013 .

[22]  A. Abbott,et al.  Electroplating Using Ionic Liquids , 2013 .

[23]  Sung-Hoon Ahn,et al.  Graphene-ionic liquid based hybrid nanomaterials as novel lubricant for low friction and wear. , 2013, ACS applied materials & interfaces.

[24]  F. Rodríguez,et al.  CO2/N2 Selectivity Prediction in Supported Ionic Liquid Membranes (SILMs) by COSMO-RS , 2011 .

[25]  A. Henni,et al.  Solubility of carbon dioxide in three [Tf2N] ionic liquids , 2014 .

[26]  A. Shariati,et al.  Critical properties and acentric factors of ionic liquids , 2013, Korean Journal of Chemical Engineering.

[27]  Qingguo Zhang,et al.  Synthesis and Physicochemical Properties of Amino Acid Ionic Liquid 1‑Butyl-3-methylimidazolium Aspartate and Binary Mixture with Methanol , 2013 .

[28]  F. Gharagheizi,et al.  Determination of the speed of sound in ionic liquids using a least squares support vector machine group contribution method , 2014 .

[29]  R. Noble,et al.  Physically Gelled Room-Temperature Ionic Liquid-Based Composite Membranes for CO2/N2 Separation: Effect of Composition and Thickness on Membrane Properties and Performance , 2013 .

[30]  U. Domańska,et al.  Synthesis, physical, and thermodynamic properties of 1-alkyl-cyanopyridinium bis{(trifluoromethyl)sulfonyl}imide ionic liquids , 2013 .

[31]  H. Grande,et al.  A sulfide/polysulfide-based ionic liquid electrolyte for quantum dot-sensitized solar cells. , 2011, Journal of the American Chemical Society.

[32]  E. A. Guggenheim.  The Principle of Corresponding States , 1945 .

[33]  L. Lepori,et al.  Excess enthalpies of mixtures of mono-carboxylic acid with dibutylether , 2012, Journal of Thermal Analysis and Calorimetry.

[34]  P. Wasserscheid,et al.  Catalyst Recycling Using Ionic Liquids , 2006 .

[35]  Pramod K. Singh,et al.  Synthesis, characterization and application of biopolymer-ionic liquid composite membranes , 2010 .

[36]  Xinwen Guo,et al.  Effective Hydrolysis of Cellulose into Glucose over Sulfonated Sugar-Derived Carbon in an Ionic Liquid , 2013 .

[37]  J. Valderrama,et al.  Critical Properties, Normal Boiling Temperatures, and Acentric Factors of Fifty Ionic Liquids , 2007 .

[38]  Z. Es’haghi,et al.  Pre-concentration and determination of amitriptyline residues in waste water by ionic liquid based immersed droplet microextraction and HPLC , 2012, Journal of pharmaceutical analysis.

[39]  Xianlai Zeng,et al.  A novel dismantling process of waste printed circuit boards using water-soluble ionic liquid. , 2013, Chemosphere.

[40]  F. Endres,et al.  Electroplating of mild steel by aluminium in a first generation ionic liquid: A green alternative to commercial Al-plating in organic solvents , 2006 .

[41]  Estimation of the Heat Capacity of Ionic Liquids: A Quantitative Structure–Property Relationship Approach , 2013 .

[42]  U. Domańska,et al.  Effect of Temperature and Composition on the Surface Tension and Thermodynamic Properties of Binary Mixtures of Boltorn U3000 with Alcohols and Ether , 2010 .

[43]  S. Verevkin,et al.  Experimental vapor pressures of 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides and a correlation scheme for estimation of vaporization enthalpies of ionic liquids. , 2006, The journal of physical chemistry. A.

[44]  Juan A. Lazzús,et al.  Critical Properties, Normal Boiling Temperature, and Acentric Factor of Another 200 Ionic Liquids , 2008 .

[45]  P. Trulove,et al.  Natural Fiber Welding: Ionic Liquid Facilitated Biopolymer Mobilization and Reorganization , 2012 .

[46]  Jason E. Bara,et al.  Room-Temperature Ionic Liquid−Amine Solutions: Tunable Solvents for Efficient and Reversible Capture of CO2 , 2008 .

[47]  Bassem A. Kheireddin,et al.  Inorganic nanoparticle-based ionic liquid lubricants , 2013 .

[48]  B. Mokhtarani,et al.  Extraction of toluene from alkane using [Bmim][NO3] or [Omim][NO3] ionic liquid at 298.15 K and atmospheric pressure , 2014 .

[49]  Robin D. Rogers,et al.  Applying ionic liquids for controlled processing of polymer materials , 2005 .

[50]  Omar M. Basha,et al.  Development of a Conceptual Process for Selective Capture of CO2 from Fuel Gas Streams Using Two TEGO Ionic Liquids as Physical Solvents , 2014 .

[51]  K. Khimeche,et al.  Phase diagram of ibuprofen with fatty acids , 2013, Journal of Thermal Analysis and Calorimetry.

[52]  Elizabeth J. Biddinger,et al.  Reversible Ionic Liquid Stabilized Carbamic Acids: A Pathway Toward Enhanced CO2 Capture , 2013 .

[53]  Mohammad Ali Ahmadi,et al.  Estimation of H2S solubility in ionic liquids using a rigorous method , 2014 .

[54]  A. B. de Haan,et al.  COSMO-RS-Based Ionic-Liquid Selection for Extractive Distillation Processes , 2012 .

[55]  Alireza Baghban,et al.  Estimating hydrogen sulfide solubility in ionic liquids using a machine learning approach , 2014 .

[56]  J. Shereshefsky,et al.  Surface Tension of Saturated Vapors and the Equation of Eötvös , 1930 .

[57]  F. Gharagheizi,et al.  A chemical structure based model for the determination of speed of sound in ionic liquids , 2014 .

[58]  Marc Uerdingen,et al.  Ionic Liquids as Lubricants , 2010 .

[59]  A. Mohammadi,et al.  A group contribution method for estimating the refractive indices of ionic liquids , 2014 .

[60]  José O. Valderrama,et al.  Critical Properties and Normal Boiling Temperature of Ionic Liquids. Update and a New Consistency Test , 2012 .

[61]  F. Gharagheizi,et al.  Development of a group contribution method for the estimation of heat capacities of ionic liquids , 2014, Journal of Thermal Analysis and Calorimetry.

[62]  H. Piekarski,et al.  Enthalpic interaction coefficients of NaI–alkanediol pairs in methanol and in water , 2012, Journal of Thermal Analysis and Calorimetry.

[63]  Haichao Jiang,et al.  Density and surface tension of pure ionic liquid 1-butyl-3-methyl-imidazolium l-lactate and its binary mixture with alcohol and water , 2013 .

[64]  Eduardo Filipe,et al.  On the critical temperature, normal boiling point, and vapor pressure of ionic liquids. , 2005, The journal of physical chemistry. B.

[65]  U. Domańska,et al.  Effect of temperature and composition on the density, viscosity, surface tension, and thermodynamic properties of binary mixtures of N-octylisoquinolinium bis{(trifluoromethyl)sulfonyl}imide with alcohols , 2012 .

[66]  J. Valderrama,et al.  Generalized rackett-type correlations to predict the density of saturated liquids and petroleum fractions , 1989 .

[67]  A. Madram,et al.  A simple accurate model for prediction of deflagration temperature of energetic compounds , 2013, Journal of Thermal Analysis and Calorimetry.

[68]  F. Gharagheizi,et al.  Prediction of molecular diffusivity of pure components into air: a QSPR approach. , 2008, Chemosphere.

[69]  Hugo F. D. Almeida,et al.  Surface tension and refractive index of pure and water-saturated tetradecyltrihexylphosphonium-based ionic liquids , 2013 .

[70]  YoonKook Park,et al.  Experimental determination and prediction of phase behavior for 1-butyl-3-methylimidazolium nonafluorobutyl sulfonate and carbon dioxide , 2014, Korean Journal of Chemical Engineering.

[71]  K. Sirkar,et al.  Solubilities of CO2 and Helium in an Ionic Liquid Containing Poly(amidoamine) Dendrimer Gen 0 , 2013 .

[72]  W. Wieczorek,et al.  Estimation of extraction properties of new imidazolide anion based ionic liquids on the basis of activity coefficient at infinite dilution measurements , 2013 .

[73]  E. Min,et al.  Ionic liquids: applications in catalysis , 2002 .

[74]  Xiangping Zhang,et al.  A Novel Dual Amino-Functionalized Cation-Tethered Ionic Liquid for CO2 Capture , 2013 .