Synthesis, Physicochemical Properties, and Toxicity Data of New Hydrophobic Ionic Liquids Containing Dimethylpyridinium and Trimethylpyridinium Cations

Abstract

O2M3M5MPYR] as the cation and bis(trifluoromethanesulfonyl)imide [NTf 2 ], trifluoromethanesulfonate [TfO], dicyanamide [N(CN) 2 ], thiocyanate [SCN] or iodide as the anion have been synthesized, and their physicochemial properties have been studied. Thermal properties, solubilities in water and water contents, UV-vis spectra, densities, refractive indices, electrochemical windows, and toxicities on Vibrio fischeri have been measured. These ionic liquids, most of which are liquid at room temperature, exhibit high refractive indices and increased hydrophobicity. Despite high toxicity values toward V. fischeri, ionic liquids containing a dialkylpyridinium or trialkylpyridinium cation with an octyl chain represent good alternatives to extracting solvents. † Part of the "Josef M. G. Barthel Festschrift".

Physico-Chemical Properties of Task-Specific Ionic Liquids

“…Heating and cooling cycles were repeated during four cycles to ensure reproducibility (uncertainty was determined to be 0.01 K). Physical-chemical properties of pyrrolidinium ILs have been reviewed by Domańska [61] while new hydrophobic pyridinium-based ILs have been reported by Papaiconomou et al [62] (for some ILs both T g and T m could be determined by DSC, 10 ºC/min rate). A pool of 53 amidinium based potential ILs were synthesised by Dechambenoit et al For some of them the melting point was reported, and it was found that only a few of them qualified as ILs.…”

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.…”

“…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. 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. The resulting mixtures can form either a biphasic system or a homogeneous phase with water, which depends on the IL solubility in water (Zhang et al 2009;Scammells et al 2005).…”

“…Papaiconomou et al (2007Papaiconomou et al ( , 2010 find that in many cases the melting point is higher for the imidazolium or pyridinium cations substituted with methyl substituents than those ionic liquids containing no alkyl substituents. Also they find that some pyridinium-based ILs containing iodine anions are solid at room temperature (e.g.…”