Insights into the Solvation Characteristics of Zwitterionic Deep Eutectic Solvents Using Multiple Polarity Scales

Abbasi, Nabeel Mujtaba; Anderson, Jared L.

doi:10.1021/acs.iecr.2c04425

Insights into the Solvation Characteristics of Zwitterionic Deep Eutectic Solvents Using Multiple Polarity Scales

Journal Article · Mon Feb 27 00:00:00 EST 2023 · Industrial and Engineering Chemistry Research

DOI:https://doi.org/10.1021/acs.iecr.2c04425· OSTI ID:1959188

Abbasi, Nabeel Mujtaba ^[1]; ^[1]

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

Deep eutectic solvents (DESs) formed by mixing zwitterionic hydrogen bond acceptors (HBAs) with diol- and organic acid-based hydrogen bond donors (HBDs) are popular sustainable solvents. In addition to possessing an amphiphilic character, zwitterionic DESs offer unique solvation properties, unlike those composed of halide-containing HBAs. While all other popular classes of DESs have been investigated, no study has attempted to characterize the solvation characteristics of zwitterionic DESs. In this study, the solvation properties of betaine [Bet]-, sulfobetaine-, and l-carnitine [l-Car]-based DESs were thoroughly investigated for the first time using solvatochromic dye methods and inverse gas chromatography (IGC). Herein, the Nile red polarity scale revealed that DESs composed of organic acids were generally more polar than diol-based DESs. Kamlet–Taft solvent parameters revealed that glycerol-based DESs offered exceptionally high hydrogen bond donating ability compared to those composed of 1,4-butane diol and triethylene glycol. The Abraham solvation parameter model revealed hydrogen bond basicity to be the most dominant interaction, and it was generally higher for diol-based HBDs compared to organic acid-based HBDs. Additionally, sulfobetaine HBAs possessing longer alkyl chains generally offered higher dispersive-type interactions and hydrogen bond basicity compared to [Bet] and [l-Car] salts. This is the first study to combine and compare results from solvatochromic dye methods and IGC in an attempt to comprehensively explain and predict the solvation characteristics of zwitterionic DESs.

View Accepted Manuscript (DOE)

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:: 1959188

Report Number(s):: IS-J--11,007

Journal Information:: Industrial and Engineering Chemistry Research, Journal Name: Industrial and Engineering Chemistry Research Journal Issue: 9 Vol. 62; ISSN 0888-5885

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Insights into the Solvation Characteristics of Zwitterionic Deep Eutectic Solvents Using Multiple Polarity Scales

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