A group contribution method to predict the thermal decomposition temperature of ionic liquids

Abstract A new model based on group contribution method to predict the decomposition temperature of several ionic liquids is developed. Experimental data of 120 ionic liquids were used to obtain the contributions for the cation–anion groups in a correlation set. The optimum parameters of the method were obtained using a genetic algorithm-based on multivariate linear regression. Then, the melting temperatures of another 78 ionic liquids were predicted, and the results were compared with experimental data available in the literature. The results show that the group contribution method represents an excellent alternative for the estimation of the decomposition point of diverse ionic liquids from the knowledge of their molecular structure with a correlation coefficient of 0.9359 and average deviation of 4%.

[1]  U. Domańska.  Thermophysical properties and thermodynamic phase behavior of ionic liquids , 2006 .

[2]  Juan A. Lazzús,et al.  Estimation of Density as a Function of Temperature and Pressure for Imidazolium-Based Ionic Liquids Using a Multilayer Net with Particle Swarm Optimization , 2009 .

[3]  J. A. Lazzús.  Neural Network Based on Quantum Chemistry for Predicting Melting Point of Organic Compounds , 2009 .

[4]  P. Dyson,et al.  Metal Catalysed Reactions in Ionic Liquids , 2006 .

[5]  H. Gores,et al.  Characterisation and properties of new ionic liquids with the difluoromono[1,2-oxalato(2-)-O,O′]borate anion , 2007 .

[6]  K. Tsunashima,et al.  Physical and electrochemical properties of low-viscosity phosphonium ionic liquids as potential electrolytes , 2007 .

[7]  Michael D. Frenkel,et al.  ILThermo: A Free-Access Web Database for Thermodynamic Properties of Ionic Liquids† , 2007 .

[8]  J. Shreeve,et al.  Ionic Liquids with Fluorine-Containing Cations , 2005 .

[9]  Bruno Scrosati,et al.  Potentialities of ionic liquids as new electrolyte media in advanced electrochemical devices , 2006 .

[10]  Peter Wasserscheid,et al.  Ionic Liquids in Synthesis , 2002 .

[11]  M. Ribeiro,et al.  Molecular dynamics simulation of the ionic liquid N-ethyl-N,N-dimethyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide. , 2007, The journal of physical chemistry. B.

[12]  Xuezhong He,et al.  Physical Properties of Ionic Liquids: Database and Evaluation , 2006 .

[13]  M. Watanabe,et al.  Physicochemical properties and structures of room temperature ionic liquids. 2. Variation of alkyl chain length in imidazolium cation. , 2005, The journal of physical chemistry. B.

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

[15]  A. Headley,et al.  Design and synthesis of pyridinium chiral ionic liquids tethered to a urea functionality. , 2006, The Journal of organic chemistry.

[16]  Jong-Min Lee,et al.  Pysico-chemical properties of hydrophobic ionic liquids containing 1-octylpyridinium, 1-octyl-2-methylpyridinium or 1-octyl-4-methylpyridinium cations , 2006 .

[17]  H. Ohno,et al.  Effect of tetrabutylphosphonium cation on the physico-chemical properties of amino-acid ionic liquids. , 2006, Chemical communications.

[18]  V. Srinivasadesikan,et al.  On the Chemical Stabilities of Ionic Liquids , 2009, Molecules.

[19]  P. Hunt,et al.  Why does a reduction in hydrogen bonding lead to an increase in viscosity for the 1-butyl-2,3-dimethyl-imidazolium-based ionic liquids? , 2007, The journal of physical chemistry. B.

[20]  Li Yang,et al.  Ionic liquids based on aliphatic tetraalkylammonium dications and TFSI anion as potential electrolytes , 2007 .

[21]  John H. Holland,et al.  Adaptation in Natural and Artificial Systems: An Introductory Analysis with Applications to Biology, Control, and Artificial Intelligence , 1992 .

[22]  Suojiang Zhang,et al.  Hydroxyl Ammonium Ionic Liquids: Synthesis, Properties, and Solubility of SO2 , 2007 .

[23]  J. Pernak,et al.  Ionic Liquids and Paper , 2005 .

[24]  Kikuko Hayamizu,et al.  Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 1. Variation of Anionic Species , 2004 .

[25]  Paul Scovazzo,et al.  Gas Solubilities in Room-Temperature Ionic Liquids , 2004 .

[26]  Juan A. Lazzús,et al.  A GROUP CONTRIBUTION METHOD TO PREDICT ρ-T-P OF IONIC LIQUIDS , 2010 .

[27]  I. Marrucho,et al.  High-Pressure Densities and Derived Thermodynamic Properties of Imidazolium-Based Ionic Liquids , 2007 .

[28]  D. Macfarlane,et al.  Thermal degradation of cyano containing ionic liquids , 2006 .

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

[30]  Tamar L Greaves,et al.  Protic ionic liquids: properties and applications. , 2008, Chemical reviews.

[31]  J. Prausnitz,et al.  Synthesis and Properties of Seven Ionic Liquids Containing 1-Methyl-3-octylimidazolium or 1-Butyl-4-methylpyridinium Cations , 2006 .

[32]  John B. Kerr,et al.  Physicochemical properties and toxicities of hydrophobic piperidinium and pyrrolidinium ionic liquids , 2007 .

[33]  B. Yi,et al.  Correlation between the glass transition temperatures and multipole moments for polymers , 2007 .

[34]  R. Reid,et al.  The Properties of Gases and Liquids , 1977 .