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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
Author(s) -
Casarano Romeu,
El Seoud Omar A.
Publication year - 2013
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.201200296
Subject(s) - ionic liquid , fluoride , acylation , chemistry , cellulose , dissolution , chloride , solvent , hydrolysis , organic chemistry , green chemistry , polymer chemistry , acyl chloride , derivatization , inorganic chemistry , catalysis , high performance liquid chromatography
The use of ionic liquids with fluoride anion (IL‐F) is challenging because of side reactions. Neat 1‐allyl‐3‐methylimidazolium fluoride (AlMeImF) is used as a solvent in microwave‐assisted acylation of cellulose. The results are disappointing due to side reactions in the IL proper, and F – ‐mediated hydrolysis of the produced ester. A dramatic improvement is observed, when AlMeImF/DMSO mixture is employed. The results are comparable to those obtained when pure 1‐allyl‐3‐methylimidazolium chloride is employed. FTIR spectroscopy shows that dissolving a carboxylic acid anhydride in IL‐F leads to the formation of acyl fluoride. Thus ILs are far from being “spectator” solvents. The new approach (use of IL‐F/DMSO) is attractive because of its efficiency, low cost, and applicability to the derivatization of any polymer.