Investigating the Variation in Solvation Interactions of Choline Chloride-Based Deep Eutectic Solvents Formed Using Different Hydrogen Bond Donors

Abbasi, Nabeel Mujtaba; Farooq, Muhammad Qamar; Anderson, Jared L.

doi:10.1021/acssuschemeng.1c04375

Title: Investigating the Variation in Solvation Interactions of Choline Chloride-Based Deep Eutectic Solvents Formed Using Different Hydrogen Bond Donors

Journal Article · 22 August 2021 · ACS Sustainable Chemistry & Engineering

DOI: https://doi.org/10.1021/acssuschemeng.1c04375 · OSTI ID:1817648

Abbasi, Nabeel Mujtaba ^[1]; Farooq, Muhammad Qamar ^[1];

^[1]

Ames Lab., and Iowa State Univ., Ames, IA (United States)

Choline chloride-based deep eutectic solvents (DESs) have gained widespread recognition as green solvents in catalysis and separation science as their designer properties permit solvation properties to be modulated by the choice of the hydrogen bond donor (HBD) as well as its molar ratio. Despite being one of the most popular classes of DESs, very little is currently understood regarding how their solvation characteristics differ among themselves as well as from other classes of DESs. Previous studies have shown that the catalytic activity, extraction efficiency, and solubilities of natural compounds can be influenced by the type of choline salt and HBD, but no study has systematically related these parameters with its solvation properties. In this study, inverse gas chromatography was employed for the first time to study the individual solvation characteristics of a diverse range of choline chloride and acetate-based DESs composed of amides, diols, organic acids, and carbohydrates. Furthermore, hydrogen bond acidity was found to be a dominant interaction for all DESs, especially those composed of organic acid HBDs. DESs composed of isomers of butane diol and hexane diol as HBDs exhibited higher hydrogen bond basicity and dispersive-type interactions compared to those composed of urea, acetamide, and organic acids with the position of the hydroxyl functional group influencing their solvation interactions. Choline acetate-based DESs exhibited lower dipolarity and stronger hydrogen bond basicity and dispersive-type interactions compared to choline chloride DESs. The solvation models developed in this study were used to interpret and explain DES behavior in previously reported studies involving catalysis, organic synthesis, and extractions demonstrating that the measured solute–solvent interactions can serve to predict the performance of choline chloride-based DESs when used in various applications.

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Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC02-07CH11358

OSTI ID:: 1817648

Report Number(s):: IS-J 10,577

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 35 Vol. 9; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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organic compounds
separations
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Title: Investigating the Variation in Solvation Interactions of Choline Chloride-Based Deep Eutectic Solvents Formed Using Different Hydrogen Bond Donors

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