Dataset Information

Preparation and Hydrophilicity/Lipophilicity of Solubility-Switchable Ionic Liquids.

ABSTRACT: Various solubility-switchable ionic liquids were prepared. Their syntheses were readily achieved in a few steps from glyceraldehyde dimethylacetal or its derivatives. Pyridinium, imidazolium, and phosphonium derivatives also exhibited solubility-switchable properties; acetal-type ionic liquids were soluble in organic solvents, while diol-type ones exhibited a preference for being dissolved in the aqueous phase. The solubility of the ionic liquids prepared in this study also depended on the number of carbon atoms in the cationic parts of the ionic liquids. Interconversion between the diol-type and the acetal-type ionic liquids was readily achieved under the standard conditions for diol acetalization and acetal hydrolysis. One of the prepared ionic liquids was also examined as a solvent for an organic reaction.

SUBMITTER: Kamimura A

PROVIDER: S-EPMC9798742 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Preparation and Hydrophilicity/Lipophilicity of Solubility-Switchable Ionic Liquids.

Kamimura Akio A Yanagisawa Keiya K Kaneko Nao N Kawamoto Takuji T Fujii Kenta K

ACS omega 20221215 51

Various solubility-switchable ionic liquids were prepared. Their syntheses were readily achieved in a few steps from glyceraldehyde dimethylacetal or its derivatives. Pyridinium, imidazolium, and phosphonium derivatives also exhibited solubility-switchable properties; acetal-type ionic liquids were soluble in organic solvents, while diol-type ones exhibited a preference for being dissolved in the aqueous phase. The solubility of the ionic liquids prepared in this study also depended on the numbe ...[more]

PMID: 36591188

Similar Datasets

Project description:Precursor solubility is a crucial factor in industrial applications, dominating the outcome of reactions and purification steps. The outcome and success of thermodynamic modelling of this industrially important property with equations of states, such as Perturbed-Chain Statistical Associating Fluid Theory (PC-SAFT), vastly depends on the quality of the pure-component parameters. The pure-component parameters for low-volatile compounds such as ionic liquids (ILs) have been commonly estimated using mixture properties, e. g. the osmotic pressure of aqueous solutions. This leads to parameters that depend on the solvent, and transferability to other mixtures often causes poor modeling results. Mixture-independent experimental properties would be a more suitable basis for the parameter estimation offering a way to universal parameter sets. Model parameters for ILs are available in the literature [10.1016/j.fluid.2012.05.029], but they were estimated using pure-IL density data. The present work focuses on a step towards a more universal estimation strategy that includes new experimental vapor-pressure data of the pure IL. ILs exhibit an almost negligible vapor pressure in magnitude of usually 10-5 Pa even at elevated temperatures. In this work, such vapor-pressure data of a series of 1-ethyl-3-methyl-imidazolium-based [C2 mim]-ILs with various IL-anions (e. g. tetrafluoroborate [BF4 ]- , hexafluorophosphate [PF6 ]- , bis(trifluoromethylsulfonyl)imide [NTf2 ]- ) were experimentally determined and subsequently used for PC-SAFT parameter estimation. The so-determined parameters were used to predict experimental molecular precursor solubility in ILs and infinitely diluted activity coefficients of various solvents in ILs. The parameters were further compared to modeling results using classical parametrization methods (use of liquid-density data only for the molecular PC-SAFT and the ion-based electrolyte PC-SAFT). As a result, the modeled precursor solubilities using the new approach are much more precise than using the classical parametrization methods, and required binary parameters were found to be much smaller (if needed). In sum, including the pure-component vapor-pressure data of ILs opens the door towards parameter estimation that is not biased by mixture data. This procedure might be suitable also for polymers and for all kind of ionic species but needs extension to ion-specific parametrization in the long term.

Dataset Information

Preparation and Hydrophilicity/Lipophilicity of Solubility-Switchable Ionic Liquids.

Publications

Preparation and Hydrophilicity/Lipophilicity of Solubility-Switchable Ionic Liquids.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets