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Journal ArticleDOI

Synthesis and properties of triethanolamine-based salts with mineral and organic acids as protic ionic liquids

01 Jan 2018-Journal of Molecular Liquids (Elsevier)-Vol. 249, pp 825-830
TL;DR: In this article, seven triethanolammonium-based protic ionic liquids (PILs) and three molten salts were synthesized by proton transfer reaction from carboxylic and inorganic acids to triethylammonium (TEOA) using FT-IR spectroscopic methods.
About: This article is published in Journal of Molecular Liquids.The article was published on 2018-01-01. It has received 23 citations till now. The article focuses on the topics: Ionic liquid & Triethanolamine.
Citations
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Journal ArticleDOI
TL;DR: Experimental data on viscosity of typical ionic liquids in the liquid state were compiled and critically evaluated in this paper, where the influence of contamination water and residual halide ions on the reported viscosities of these typical Ionic liquids was evaluated or quantitatively corrected.
Abstract: Experimental data on viscosity of typical ionic liquids in the liquid state were compiled and critically evaluated. The compilation contains data for 268 ionic liquids from 215 literature references and covers the period from 1998 through the end of December 2018. Equations for corrections of influences of contamination water and residual Cl− on viscosities of a series of typical ionic liquids are established. The influences of experimental methodology and the impurities (i.e., contamination water and residual halide ions) of the samples used on the reported viscosities of these typical ionic liquids are critically evaluated or quantitatively corrected, and the viscosities for these “pure” ionic liquids are recommended. The parameters of the Vogel–Fulcher–Tammann equation for temperature dependence of the recommended viscosities of these ionic liquids were reported. The effects of ionic structures on the viscosity of ionic liquids are presented.

42 citations

Journal ArticleDOI
TL;DR: In this article, nine salts, expected to be protic ionic liquids, have been synthesized by a direct reaction of proton transfer from a number of protic acids to methyl- or butyl-imidazole.

20 citations

Journal ArticleDOI
TL;DR: High-level quantum-chemical study of different cation-anion pairs representing the building units of protic ionic liquids based on triethanolammonium cation and anions of sulfuric, nitric, phosphoric, and phosphorus acids to provide essential insight into these phenomena at the molecular level.
Abstract: Structural features and interionic interactions play a crucial role in determining the overall stability of ionic liquids and their physicochemical properties. Therefore, we performed high-level quantum-chemical study of different cation–anion pairs representing the building units of protic ionic liquids based on triethanolammonium cation and anions of sulfuric, nitric, phosphoric, and phosphorus acids to provide essential insight into these phenomena at the molecular level. It was shown that every structure is stabilized through multiple H bonds between the protons in the N–H and O–H groups of the cation and different oxygen atoms of the anion acid. Using atoms in molecules topological parameters and natural bond orbital analysis, we determined the nature and strength of these interactions. Our calculations suggest that the N–H group of the cation has more proton donor-like character than the O–H group that makes the N–H···O hydrogen bonds stronger. A close relation between the binding energies of these ...

17 citations

Journal ArticleDOI
TL;DR: It has been shown that amine interaction with the acid leads to proton transfer from the acid to the amine and formation of ions held together in the ion pair by electrostatic interaction and a very strong hydrogen bond.
Abstract: We present the results of electronic structure calculations based on density functional theory (DFT) in order to investigate the reactions of the interaction of tertiary alkylamines with alkyl groups of different sizes (triethyl, tributyl, dimethylethyl, and diisopropylethyl) with trifluoroacetic acid. We have obtained data on the affinity of the studied amines with a proton. It has been shown that amine interaction with the acid leads to proton transfer from the acid to the amine and formation of ions held together in the ion pair by electrostatic interaction and a very strong hydrogen bond. We have also investigated the energy profiles of the proton transfer from the tertiary alkylammonium cation to the trifluoroacetate anion within the ion pair and found different correlations between the geometric characteristics of the H-bond and the parameters obtained by the natural bond orbitals and quantum theory of atoms in molecules analyses. It has been established that the interionic interactions in these sys...

16 citations

Journal ArticleDOI
TL;DR: The Transformer Convolutional Neural Network, which was based on the representation of molecules as text (SMILES), proposed a model with significantly higher prediction accuracy as compared to those developed using descriptors that were used in the previous studies.

12 citations

References
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TL;DR: It is expected that the fundamental properties of PILs will continue to be explored, along with continued interest in many existing and new applications, such as in electrochemistry, organic and inorganic synthesis, and biological applications.
Abstract: The thermal and physicochemical properties of protic ionic liquids (PILs) are reported. It is highly evident that there has been an extensive range of alkylammonium, imidazolium, and heterocyclic cations paired with many organic and inorganic anions that have been employed to prepare PILs. There has been strong interest in modifying the properties of PILs through the addition of water or other molecular solvents. For many applications, the presence of some water in the PILs is not detrimental, and instead leads to enhanced solvent properties such as lower viscosity, higher conductivities, and lower melting points. It remains an issue of definition though of how to refer to these resulting protic solutions. There is also an ongoing difficulty surrounding how to describe the proton activity in the PILs, analogous to pH in aqueous systems. For a broad range of applications, it has been reported that the acidity/basicity of the PIL or PIL-solvent system is crucial for their beneficial properties. It is expected that the fundamental properties of PILs will continue to be explored, along with continued interest in many existing and new applications, such as in electrochemistry, organic and inorganic synthesis, and biological applications. In particular, there has been a significant interest in a broad- range of PILs for use as electrolytes and incorporation in polymer electrolytes for fuel cells, and other energy storage devices.

676 citations

Journal ArticleDOI
TL;DR: The survey highlights the problems with voltammetric studies in highly viscous room temperature protic ionic liquids and also suggests the way forward with respect to their possible industrial use.
Abstract: Eighteen protic ionic liquids containing different combinations of cations and anions, hydrophobicity, viscosity, and conductivity have been synthesized and their physicochemical properties determined. In one series, the diethanolammonium cations were combined with acetate, formate, hydrogen sulfate, chloride, sulfamate, and mesylate anions. In the second series, acetate and formate anions were combined with amine bases, triethylamine, diethylamine, triethanolamine, di-n-propylamine, and di-n-butylamine. The electrochemical characteristics of the eight protic ionic liquids that are liquid at room temperature (RTPILs) have been determined using cyclic, microelectrode, and rotating disk electrode voltammetries. Potential windows of the RTPILs have been compared at glassy carbon, platinum, gold, and boron-doped diamond electrodes and generally found to be the largest in the case of glassy carbon. The voltammetry of IUPAC recommended potential scale reference systems, ferrocene/ferrocenium and cobaltocenium/cobaltocene, have been evaluated and found to be ideal in the case of the less viscous RTPILs but involve adsorption in the highly viscous ones. Other properties such as diffusion coefficients, ionic conductivity, and double layer capacitance also have been measured. The influence of water on the potential windows, viscosity, and diffusion has been studied systematically by deliberate addition of water to the dried ionic liquids. The survey highlights the problems with voltammetric studies in highly viscous room temperature protic ionic liquids and also suggests the way forward with respect to their possible industrial use.

256 citations