4.7 Article

Acidity Scale in a Choline Chloride- and Ethylene Glycol-Based Deep Eutectic Solvent and Its Implication on Carbon Dioxide Absorption

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 9, Pages 5368-5376

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02942

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An equilibrium acidity scale for 16 Bro''nsted organic acids was established in a deep eutectic solvent. The scale showed a similar range to that in water. The solvent properties of the deep eutectic solvent were found to be different from other molecular solvents. The absorption capacity of carbon dioxide in anion-functionalized deep eutectic solvents was measured and found to be dependent on the basicity of the choline salt anion.
An equilibrium acidity (pKa) scale that comprises 16 Bro''nsted organic acids, including phenols, carboxylic acids, azoles, and phenylmalononitriles, was established in a choline chloride/EG-based deep eutectic solvent (DES) ([Ch][Cl]:2EG) by ultraviolet-visible (UV-Vis) spectroscopic methods. The established acidity scale spans about 6 pK units in the DES, which is similar to that for these acids in water. The acidity comparisons and linear correlations between the DES and other solvents show that the solvent property of [Ch][Cl]:2EG is quite different from those of amphiphilic protic and dipolar aprotic molecular solvents. The carbon dioxide absorption capabilities as well as apparent absorption kinetics for a series of anion-functionalized DESs ([Ch][X]:2EG) were measured, and the results show that the basicity of comprising anion [X] of choline salt is essential for the maximum carbon dioxide absorption capacity, i.e., a stronger basicity leads to a greater absorption capacity. The possible absorption mechanisms for carbon dioxide absorption in these DESs were also discussed based on the spectroscopic evidence.

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