Successful application of an ionic liquid carrying the fluoride counter-ion in biomacromolecular chemistry: microwave-assisted acylation of cellulose in the presence of 1-allyl-3-methylimidazolium fluoride/DMSO mixtures.

作者: Romeu Casarano , Omar A. El Seoud

DOI: 10.1002/MABI.201200296

关键词:

摘要: The use of ionic liquids with fluoride anion (IL-F) is challenging because side reactions. Neat 1-allyl-3-methylimidazolium (AlMeImF) used as a solvent in microwave-assisted acylation cellulose. results are disappointing due to reactions the IL proper, and F(-) -mediated hydrolysis produced ester. A dramatic improvement observed, when AlMeImF/DMSO mixture employed. comparable those obtained pure chloride FTIR spectroscopy shows that dissolving carboxylic acid anhydride IL-F leads formation acyl fluoride. Thus ILs far from being "spectator" solvents. new approach (use IL-F/DMSO) attractive its efficiency, low cost, applicability derivatization any polymer.

参考文章(64)
ANTOINETTE C. O'SULLIVAN, Cellulose: the structure slowly unravels Cellulose. ,vol. 4, pp. 173- 207 ,(1997) , 10.1023/A:1018431705579
Thomas Rosenau, Antje Potthast, Immanuel Adorjan, Andreas Hofinger, Herbert Sixta, Heinrich Firgo, Paul Kosma, Cellulose solutions in N-methylmorpholine-N-oxide (NMMO) – degradation processes and stabilizers Cellulose. ,vol. 9, pp. 283- 291 ,(2002) , 10.1023/A:1021127423041
Antti Kivinen, Mechanisms of substitution at the COX group Acyl Halides (1972). pp. 177- 230 ,(2010) , 10.1002/9780470771273.CH6
Björn Lindman, Gunnar Karlström, Lars Stigsson, On the mechanism of dissolution of cellulose Journal of Molecular Liquids. ,vol. 156, pp. 76- 81 ,(2010) , 10.1016/J.MOLLIQ.2010.04.016
Richard C. Remsing, Zhiwei Liu, Ivan Sergeyev, Guillermo Moyna, Solvation and Aggregation ofN,N′-Dialkylimidazolium Ionic Liquids: A Multinuclear NMR Spectroscopy and Molecular Dynamics Simulation Study The Journal of Physical Chemistry B. ,vol. 112, pp. 7363- 7369 ,(2008) , 10.1021/JP800769U
Scott T. Handy, Maurice Okello, The 2-position of imidazolium ionic liquids: substitution and exchange. Journal of Organic Chemistry. ,vol. 70, pp. 1915- 1918 ,(2005) , 10.1021/JO0480850
Małgorzata Ewa Zakrzewska, Ewa Bogel-Łukasik, Rafał Bogel-Łukasik, None, Solubility of Carbohydrates in Ionic Liquids Energy & Fuels. ,vol. 24, pp. 737- 745 ,(2010) , 10.1021/EF901215M
D. R. Dodds, R. A. Gross, Chemicals from Biomass Science. ,vol. 318, pp. 1250- 1251 ,(2007) , 10.1126/SCIENCE.1146356