Physicochemical Properties of Hydrophobic Ionic Liquids Containing 1-Octylpyridinium, 1-Octyl-2-methylpyridinium, or 1-Octyl-4-methylpyridinium Cations

Abstract

This paper reports the synthesis of some ionic liquids containing cations 1-octylpyridinium [OPYR]+, 1-octyl-2-methylpyridinium [2MOPYR]+, or 1-octyl-4-methylpyridinium [4MOPYR]+ and anions dicyanamide [N(CN)2]-, bis(trifluoromethylsulfonyl)imide [Tf2N]-, bis(pentafluoroethylsulfonyl)imide [BETI]-, trifluoromethyl sulfonate [TfO]-, nonafluorobutyl sulfonate [NfO]-, tetrafluoroborate [BF4]-, trifluorophenylborate [BF3Ph]-, tetraphenylborate [BPh4]-, or hexafluoroarsenate [AsF6]-. Melting points, decomposition temperatures, densities, mutual solubilities with water, and viscosities have been measured. Unlike similar ionic liquids containing imidazolium cations, pyridinium ionic liquids studied here are nearly immiscible with water. Viscosities are similar, and water contents are slightly lower than those for ionic liquids containing imidazolium cations.

Densities and Derived Thermodynamic Properties of Imidazolium-, Pyridinium-, Pyrrolidinium-, and Piperidinium-Based Ionic Liquids

“…The IUPAC Ionic Liquid database (ILThermo) provides up-to-date information on thermophysical properties of ILs and their mixtures, with more than 40 000 total data points from 231 publications. 17 During the past few years, investigations on thermophysical and thermodynamic properties of pure ILs have increased; [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] however, they are by no means exhaustive, and it is necessary to accumulate a sufficiently large data bank not only for process and product design but also for the development of correlations for these properties.…”

Invoking Pairwise Interactions in Water‐Promoted Diels–Alder Reactions by using Ionic Liquids as Cosolvents

“…The ionic liquids that were used during the analysis were synthesized in our laboratory following standard reported procedures. [12,36] The ionic liquids were synthesized by the following two steps: 1) quarterization, which involved the synthesis of the organic cation, and 2) metathesis, where the existing anion is replaced by the desired anion by using the corresponding salt. The purity of the ionic liquids was characterized by using 1 H NMR spectroscopy.…”

“…[36,37] The fall in rate constants with an increase in the alkyl-chain length of the ionic-liquid cations is probably due to the stronger interactions of these alkyl groups with the initial reactants, which are apolar in nature, than with the transition state of the reaction.…”

Bondonic Chemistry: Predicting Ionic Liquids’ (IL) Bondons by Raman-IR Spectra

“…13.2) (Zhang et al 2009;Scammells et al 2005). Synthesis method obviously may suffer small variations depending on the type of ILs (Zhang et al 2009;Carrera et al 2010;Ohno and Fukumoto 2007;Pernak et al 2011;Zhao et al 2007;Scammells et al 2005;Harjani et al 2009;Papaiconomou et al 2007Papaiconomou et al , 2010. Commonly the cations are prepared essentially by protonation with a free acid, or by quaternization of an amine or an phosphine.…”

“…)-reaction of a Lewis-basic nucleophile heteroatom with an alkyl halide, the mixture being stirred and heated ( Fig. 13.2) (Zhang et al 2009;Pernak et al 2011;Zhao et al 2007;Scammells et al 2005;Harjani et al 2009;Papaiconomou et al 2007Papaiconomou et al , 2010. In the second step, the precursor obtained in the first step is used for anion metathesis with Lewis acids or metal salts of the desired anions finally obtaining a mixture which contain the desired IL ( Fig.…”