Interactions of Ionic Liquids with Polysaccharides 1. Unexpected Acetylation of Cellulose with 1‐Ethyl‐3‐methylimidazolium Acetate
Abstract
The homogeneous conversion of cellulose in the ionic liquid 1‐ethyl‐3‐methylimidazolium acetate with 2‐furoyl chloride, p‐toluenesulfonyl chloride, and triphenylmethyl chloride yields surprisingly pure cellulose acetate samples in any case. From NMR spectroscopic studies, it may be concluded that during the homogeneous functionalization reactive intermediates including furane‐2‐carboxylic acid/acetic acid anhydride and acetic acid triphenylmethyl ester are formed leading to the cellulose acetates with DS values in the range from 0.55 to 1.86. magnified image
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Cellulose dissolution is an industrially attractive application of ionic liquids due to good solubilities (5-20 wt%, depending on ionic liquid and conditions), competitive properties of regenerated cellulose, increased stability of ionic liquid cellulose solutions, and low toxicity of certain relevant ionic liquids.
“Cellulose dissolution is an industrially attractive application of ionic liquids, due to good solubilities (5-20 wt%, depending on the ionic liquid and the conditions), the competitive properties of cellulose reprecipitated from the ionic liquid solutions, 73 the increased stability of ionic liquid cellulose solutions 74 and the low toxicity of certain relevant ionic liquids (for example, [C 2 C 1”
From Deconstruction of lignocellulosic biomass with ionic liquids (2013) · cites this paper as [74]
Very nucleophilic anions such as chloride and acetate can lower the onset temperature of decomposition of ionic liquids to around 200 °C.
“It has been shown that anions that are very nucleophilic, such as chloride and acetate, can lower T onset to around 200 °C, while dissolved cellulose appears to have no effect on the IL decomposition temperature, even up to 12% cellulose.74”
From Deconstruction of lignocellulosic biomass with ionic liquids (2013) · cites this paper as [74]
Dissolved cellulose has no effect on the ionic liquid decomposition temperature, even up to 12% cellulose.
“It has been shown that anions that are very nucleophilic, such as chloride and acetate, can lower T onset to around 200 °C, while dissolved cellulose appears to have no effect on the IL decomposition temperature, even up to 12% cellulose.74”
From Deconstruction of lignocellulosic biomass with ionic liquids (2013) · cites this paper as [74]
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Pandey, P., Somers, A. E., Hait, S. K., Forsyth, M., & Ramakumar, S. S. V. (2021) · Journal of Molecular Liquids · doi:10.1016/j.molliq.2021.116665 · Cited by 12 · see citing works
Dong, Y., Xu, F., Yin, X., & Yang, Q. (2024) · Separation and Purification Technology · doi:10.1016/j.seppur.2024.131018 · Cited by 11 · see citing works
Tarasova, E. V., Savale, N., Krasnou, I., Kudrjašova, M., Rjabovs, V., Reile, I., Vares, L., Kallakas, H., Kers, J., & Krumme, A. (2023) · Polymers · doi:10.3390/polym15193979 · Cited by 11 · see citing works
Non-Halide Ionic Liquids for Solvation, Extraction, and Processing of Cellulosic Materials
Hummel, M., Laus, G., Schwarzler, A., Bentivoglio, G., Rubatscher, E., Kopacka, H., Wurst, K., Kahlenberg, V., Gelbrich, T., Griesser, U. J., et al. (2010) · ACS symposium series · doi:10.1021/bk-2010-1033.ch013 · Cited by 11 · see citing works
Aryloxy Ionic Liquid-Catalyzed Homogenous Esterification of Cellulose with Low-Reactive Acyl Donors
Yoshizawa, A., Maruyama, C., Kusuma, S. B. W., Wada, N., Kuroda, K., Hirose, D., & Takahashi, K. (2023) · Polymers · doi:10.3390/polym15020419 · Cited by 10 · see citing works
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Cellulose: Chemistry of Cellulose Derivatization
Heinze, T. J., Koschella, A., Liebert, T. F., Harabagiu, V., & Coseri, S. (2012) · Springer eBooks · doi:10.1007/978-3-7091-0421-7_10 · Cited by 10 · see citing works
Self-citationBöhmdorfer, S., Hosoya, T., Röder, T., Potthast, A., & Rosenau, T. (2017) · Cellulose · doi:10.1007/s10570-017-1257-2 · Cited by 10 · see citing works
Kusuma, S. B. W., Hirose, D., & Takahashi, K. (2019) · Chemistry Letters · doi:10.1246/cl.190392 · Cited by 9 · see citing works
Partial cellulose acetylation in 1‐ethyl‐3‐methylimidazolium acetate induced by dichloromethane
Alfassi, G., Rein, D. M., & Cohen, Y. (2018) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.29220 · Cited by 9 · see citing works
Tarasova, E. V., Savale, N., Ausmaa, P.-M., Krasnou, I., & Krumme, A. (2024) · Rheologica Acta · doi:10.1007/s00397-024-01433-3 · Cited by 8 · see citing works
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Ionic Liquids as Solvents for Homogeneous Derivatization of Cellulose: Challenges and Opportunities
Heinze, T. J., & Gericke, M. (2013) · Biofuels and biorefineries · doi:10.1007/978-94-007-7711-8_5 · Cited by 7 · see citing works
Self-citationCellulose processing in ionic liquid based solvents
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- Authors
- Köhler, S., Liebert, T., Schöbitz, M., Schaller, J., Meister, F., Günther, W., & Heinze, T.
- Affiliations
- Friedrich Schiller University Jena (DE)
- Thuringian Institute of Textile and Plastics Research (DE)
- Corresponding author
- Heinze, Thomas
- ORCID
- Heinze, Thomas
- Venue
- Macromolecular Rapid Communications
- Publisher
- Wiley
- Published
- 2007-12-04
- Volume
- 28
- Issue
- 24
- Pages
- 2311-2317
- ISSN
- 1022-1336 (ISSN-L)
- 1521-3927
- OpenAlex
- W1968707830
- Cited by
- 136
- References
- 12
- Citations by year
- 2026: 2 · 2025: 2 · 2024: 7 · 2023: 5 · 2022: 2 · 2021: 5 · 2020: 8 · 2019: 9 · 2018: 9 · 2017: 8 · 2016: 9 · 2015: 6 · 2014: 4 · 2013: 8 · 2012: 13
- FWCI
- 3.88
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Macromolecular Rapid Communications (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › Advanced Cellulose Research Studies
- Physical Sciences › Chemical Engineering › Catalysis › Ionic liquids properties and applications
- Physical Sciences › Engineering › Biomedical Engineering › Catalysis for Biomass Conversion
- Keywords
- 1-ethyl-3-methylimidazolium acetate, ionic liquids, polysaccharide functionalization, p-toluenesulfonyl chloride, triphenylmethyl chloride, acetic anhydride, degree of acetylation, reactive intermediates
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