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Novel Brønsted Acidic Ionic Liquids and Their Use as Dual Solvent−Catalysts
Abstract
The reaction of triphenylphosphine or N-butylimidazole with cyclic sultones gives zwitterions that are subsequently converted into ionic liquids by reaction with trifluoromethane sulfonic acid or p-toluenesulfonic acid. The resulting ionic liquids have cations to which are tethered alkane sulfonic acid groups. These Brønsted acidic ionic liquids are useful solvent/catalysts for several organic reactions, including Fischer esterification, alcohol dehydrodimerization and the pinacol rearrangement. The new ionic liquids combine the low volatility and ease of separation from product normally associated with solid acid catalysts, with the higher activity and yields normally found using conventional liquid acids.
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Citations
Cited by
Ionic liquids: solvent properties and organic reactivity
Chiappe, C., & Pieraccini, D. (2005) · Journal of Physical Organic Chemistry · doi:10.1002/poc.863 · Cited by 1,169
H. Davis, J. (2004) · Chemistry Letters · doi:10.1246/cl.2004.1072 · Cited by 1,053
Long, J., Lou, W., Wang, L., Yin, B., & Li, X. (2015) · Chemical Engineering Science · doi:10.1016/j.ces.2014.09.026 · Cited by 98
Esterification in Ionic Liquids: The Influence of Solvent Basicity
Wells, T. P., Hallett, J. P., Williams, C. K., & Welton, T. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo8005864 · Cited by 65
Catalytic depolymerization of organosolv sugarcane bagasse lignin in cooperative ionic liquid pairs
Li, Y., Cai, Z., Liao, M., Long, J., Zhao, W., Chen, Y., & Li, X. (2017) · Catalysis Today · doi:10.1016/j.cattod.2017.04.059 · Cited by 40
Metadata
- Authors
- Cole, A. C., Jensen, J. L., Ntai, I., Tran, K. L. T., Weaver, K. J., Forbes, D. C., & Davis, J. H.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-05-01
- Volume
- 124
- Issue
- 21
- Pages
- 5962-5963
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2060117943
- Cited by
- 1,197
- References
- 0
- FWCI
- 15.59
- Type
- journal article
- Language
- en
- Open access
- closed
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- Cole, A. C., Jensen, J. L., Ntai, I., Tran, K. L. T., Weaver, K. J., Forbes, D. C., & Davis, J. H. (2002). Novel Brønsted Acidic Ionic Liquids and Their Use as Dual Solvent−Catalysts. Journal of the American Chemical Society. https://doi.org/10.1021/ja026290w
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