Comparison of Physicochemical Properties of New Ionic Liquids Based on Imidazolium, Quaternary Ammonium, and Guanidinium Cations

Abstract

More than 50 ionic liquids were prepared by using imidazolium, quaternary ammonium, and guanidinium cations and various anions. In these series, different cationic structures such as 1‐benzyl‐3‐methylimidazolium [Bzmim]+, 1,3‐dibenzylimidazolium [BzmiBz]+, 1‐octyl‐3‐methylimidazolium [C 8 mim]+, 1‐decyl‐3‐methylimidazolium [C 10 mim]+, tricapryl‐methylammonium [Aliquat]+, benzyltriethylammonium [BzTEA]+, phenyltrimethylammonium [PhTMA]+, and dimethyldihexylguanidinium [DMG]+ were combined with anions, p‐toluenesulfonate [TSA]−, dicyanoamide [DCA]−, saccharine (2‐sulfobenzoic acid imide sodium salt) [SAC]−, trifluoroacetate [TFA]−, bis(trifluoromethanesulfonyl)imide [Tf 2 N]−, trifluoromethanesulfonate [TfO]−, and thiocyanate [SCN]−. Important physical data for these ionic liquids are collated, namely solubility in common solvents, viscosity, density, melting point and water content. Apart from the viscosity, the Newtonian and non‐Newtonian behavior of these ionic liquids is also disclosed. Stability of these ionic liquids under thermal, basic, acidic, nucleophilic, and oxidative conditions was also studied. The features of the solid–liquid phase transition were analyzed, namely the glass transition temperature and the heat capacity jump associated with the transition from the non‐equilibrium glass to the metastable supercooled liquid. A degradation temperature of each ionic liquid was also determined. Comparisons of the properties of various ionic liquids were made.