Ionic liquids: Solubility parameters and selectivities for organic solutes

Ionic liquids (ILs) are innovative solvents for chemical processing. In this work, a database on activity coefficients of organic solutes at infinite dilution in ILs was collected from literature sources. The activity coefficients have been correlated by activity coefficient model for the regular solution and have been used to estimate the solubility parameter of ILs. The solubility parameters of ILs have been further correlated based on a concept of the group contribution method. Through the analysis of the database and the prediction results of selectivities, it was shown here that as compared with conventional organic solvents, higher selectivity can be achieved by using ILs as working solvents for separation of alkane/aromatic, aromatic/aromatic hydrocarbon mixtures via extraction or supported liquid membrane. © 2013 American Institute of Chemical Engineers AIChE J, 59: 3034–3041, 2013

[1]  J. D. L. Fuente,et al.  Activity Coefficients at Infinite Dilution in 1-Alkyl-3-methylimidazolium Tetrafluoroborate Ionic Liquids , 2006 .

[2]  T. Yan Separation of p-xylene and ethylbenzene from C8 aromatics using medium-pore zeolites , 1989 .

[3]  C. L. Young,et al.  The use of gas-liquid chromatography to determine activity coefficients and second virial coefficients of mixtures I. Theory and verification of method of data analysis , 1966, Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences.

[4]  D. H. Everett Effect of gas imperfection on G.L.C. measurements : a refined method for determining activity coefficients and second virial coefficients , 1965 .

[5]  Wolfgang Arlt,et al.  Separation of Azeotropic Mixtures Using Hyperbranched Polymers or Ionic Liquids , 2004 .

[6]  A. Gedanken,et al.  Are Ionic Liquids Really a Boon for the Synthesis of Inorganic Materials? A General Method for the Fabrication of Nanosized Metal Fluorides , 2006 .

[7]  C. Ye,et al.  Rapid and accurate estimation of densities of room-temperature ionic liquids and salts. , 2007, The journal of physical chemistry. A.

[8]  I. Kikic,et al.  On the combinatorial part of the UNIFAC and UNIQUAC models , 1980 .

[9]  Li-sheng Wang,et al.  Solubilities of Benzene, Toluene, and Xylene Isomers in 1-Butyl-3-methylimidazolium Tetrafluoroborate , 2006 .

[10]  J. Brennecke,et al.  Ionic liquids: Innovative fluids for chemical processing , 2001 .

[11]  Andrzej Marciniak,et al.  Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate. , 2008, The journal of physical chemistry. B.

[12]  R. Sheldon,et al.  Recovery of pure products from ionic liquids using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations , 2006 .

[13]  J. Gmehling,et al.  Measurement of Activity Coefficients at Infinite Dilution Using Gas−Liquid Chromatography. 5. Results for N-Methylacetamide, N,N-Dimethylacetamide, N,N-Dibutylformamide, and Sulfolane as Stationary Phases , 1997 .

[14]  G. El‐Hiti,et al.  Regioselective mononitration of simple aromatic compounds under mild conditions in ionic liquids , 2005 .

[15]  P. Scovazzo,et al.  Long-term, continuous mixed-gas dry fed CO2/CH4 and CO2/N2 separation performance and selectivities for room temperature ionic liquid membranes , 2009 .

[16]  Yun Feng,et al.  Activity Coefficients of Organic Solutes at Infinite Dilution in Ionic Liquids. 1. 1-Hexyl-3-Methylimidazolium Hexafluorophosphate and 1-Octyl-3-Methylimidazolium Hexafluorophosphate and Their Application to Alkane/Aromatic and Aromatic/Aromatic Hydrocarbon Separation , 2011 .

[17]  D. Cole-Hamilton,et al.  Homogeneous Catalysis--New Approaches to Catalyst Separation, Recovery, and Recycling , 2003, Science.

[18]  J. Prausnitz,et al.  Selective extraction of copper, mercury, silver and palladium ions from water using hydrophobic ionic liquids. , 2008 .

[19]  Jianliang Xiao,et al.  Ionic liquid-promoted, highly regioselective Heck arylation of electron-rich olefins by aryl halides. , 2005, Journal of the American Chemical Society.

[20]  Ryo Kato,et al.  Activity coefficients at infinite dilution of various solutes in the ionic liquids [MMIM]+[CH3SO4]−, [MMIM]+[CH3OC2H4SO4]−, [MMIM]+[(CH3)2PO4]−, [C5H5NC2H5]+[(CF3SO2)2N]− and [C5H5NH]+[C2H5OC2H4OSO3]− , 2004 .

[21]  Peisheng Ma,et al.  A group contribution method to estimate the densities of ionic liquids , 2010 .

[22]  George Xomeritakis,et al.  Separation of xylene isomer vapors with oriented MFI membranes made by seeded growth , 2001 .

[23]  Jürgen Gmehling,et al.  Measurement of Activity Coefficients at Infinite Dilution in Ionic Liquids Using the Dilutor Technique , 2002 .

[24]  Jason E. Bara,et al.  Interpretation of CO2 Solubility and Selectivity in Nitrile-Functionalized Room-Temperature Ionic Liquids Using a Group Contribution Approach , 2008 .

[25]  Andrzej Marciniak,et al.  The Solubility Parameters of Ionic Liquids , 2010, International journal of molecular sciences.

[26]  Yi Li,et al.  Activity Coefficients at Infinite Dilution of Polar Solutes in 1-(2-Hydroxyethyl)-3-methylimidazolium Tetrafluoroborate Using Gas—Liquid Chromatography , 2008 .