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Title: 110th Anniversary: Properties of Imidazolium-Based Ionic Liquids Bearing Both Benzylic and n-Alkyl Substituents

Abstract

Reports of imidazoliumionic liquids (ILs) with at least one benzylic substituent bound to the imidazolium cation are far less common than the ubiquitous 1-alkyl-3-methylimidazolium ILs ([Cnmim][X]). Furthermore, there is significant motivation to determine structure–property relationships for imidazolium-based ILs with at least one benzylic substituent. Not only are these ILs just as straightforward to synthesize as [Cnmim][X] ILs, but ILs with benzylic substituents are also 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 (more commonly known as 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.

Authors:
ORCiD logo [1];  [2]; ORCiD logo [3];  [1];  [1];  [1];  [4]
+ Show Author Affiliations
  1. Univ. of Alabama, Tuscaloosa, AL (United States)
  2. The Dow Chemical Company, Lake Jackson, TX (United States)
  3. National Inst. of Standards and Technology (NIST), Boulder, CO (United States)
  4. Univ. of Colorado, Boulder, CO (United States)
Publication Date:
Research Org.:
Univ. of Alabama, Tuscaloosa, AL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1830551
Grant/Contract Number:  
SC0018181
Resource Type:
Accepted Manuscript
Journal Name:
Industrial and Engineering Chemistry Research
Additional Journal Information:
Journal Volume: 58; Journal Issue: 38; Journal ID: ISSN 0888-5885
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Imidazolium; Anions; Substituents; Viscosity; Cations

Citation Formats

Bara, Jason E., Finotello, Alexia, Magee, Joseph W., Qian, Shuai, O’Harra, Kathryn E., Dennis, Grayson P., and Noble, Richard D. 110th Anniversary: Properties of Imidazolium-Based Ionic Liquids Bearing Both Benzylic and n-Alkyl Substituents. United States: N. p., 2019. Web. doi:10.1021/acs.iecr.9b03159.
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Bara, Jason E., Finotello, Alexia, Magee, Joseph W., Qian, Shuai, O’Harra, Kathryn E., Dennis, Grayson P., & Noble, Richard D. 110th Anniversary: Properties of Imidazolium-Based Ionic Liquids Bearing Both Benzylic and n-Alkyl Substituents. United States. https://doi.org/10.1021/acs.iecr.9b03159
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Bara, Jason E., Finotello, Alexia, Magee, Joseph W., Qian, Shuai, O’Harra, Kathryn E., Dennis, Grayson P., and Noble, Richard D. Wed . "110th Anniversary: Properties of Imidazolium-Based Ionic Liquids Bearing Both Benzylic and n-Alkyl Substituents". United States. https://doi.org/10.1021/acs.iecr.9b03159. https://www.osti.gov/servlets/purl/1830551.
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@article{osti_1830551,
title = {110th Anniversary: Properties of Imidazolium-Based Ionic Liquids Bearing Both Benzylic and n-Alkyl Substituents},
author = {Bara, Jason E. and Finotello, Alexia and Magee, Joseph W. and Qian, Shuai and O’Harra, Kathryn E. and Dennis, Grayson P. and Noble, Richard D.},
abstractNote = {Reports of imidazoliumionic liquids (ILs) with at least one benzylic substituent bound to the imidazolium cation are far less common than the ubiquitous 1-alkyl-3-methylimidazolium ILs ([Cnmim][X]). Furthermore, there is significant motivation to determine structure–property relationships for imidazolium-based ILs with at least one benzylic substituent. Not only are these ILs just as straightforward to synthesize as [Cnmim][X] ILs, but ILs with benzylic substituents are also 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 (more commonly known as 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.},
doi = {10.1021/acs.iecr.9b03159},
journal = {Industrial and Engineering Chemistry Research},
number = 38,
volume = 58,
place = {United States},
year = {Wed Sep 04 00:00:00 EDT 2019},
month = {Wed Sep 04 00:00:00 EDT 2019}
}
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