110th Anniversary: Properties of Imidazolium-based Ionic Liquids Bearing both Benzylic and n-Alkyl Substituents

Published

September 4, 2019

Author(s)

Joe W. Magee, Shuai Qian, Kathryn E. O'Harra, Grayson P. Dennis, Richard D. Noble, Jason E. Bara, Alexia Finotello

Abstract

Reports of imidazolium-based ionic liquids (ILs) with at least one benzylic substituent bound to the imidazolium cation is far less common than the ubiquitous 1-alkyl-3-methylimidazolium ILs ([Cnmim][X]). Yet, there is significant motivation to determining structure-property relationships for imidazolium-based ILs with at least one benzylic substituent. Not only are these ILs just as straightforward to synthesize as [C1mim][X] ILs, but ILs with benzylic substituents are representative segments of poly(ILs) and ionenes where imidazolium cations with benzylic groups are commonly found. This report focuses on the effects of benzyl and methylbenzyl substituents on the density and viscosity of a series of imidazolium cations paired with bis[(trifluoromethyl)sulfonyl]imide or more commonly, bistriflimide, ([Tf2N]-) anions. Furthermore, the solubility of CO2 in 1-benzyl-3-methylimidazolium bistriflimide [Bnmim][Tf2N] (CAS: 433337-24-7) was measured at 303.15, 318.15, 333.15 and 348.15 K at pressures in the range of (1 – 9) bar.

Citation

Industrial & Engineering Chemistry Research

Pub Type

Journals

Download Paper

https://doi.org/10.1021/acs.iecr.9b03159

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Keywords

imidazolium bistriflimide, benzylic substituent, density, viscosity, carbon dioxide solubility

Citation

Magee, J. , Qian, S. , O'Harra, K. , Dennis, G. , Noble, R. , Bara, J. and Finotello, A. (2019), 110th Anniversary: Properties of Imidazolium-based Ionic Liquids Bearing both Benzylic and n-Alkyl Substituents, Industrial & Engineering Chemistry Research, [online], https://doi.org/10.1021/acs.iecr.9b03159, https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=928059 (Accessed October 28, 2025)