Institute of Chemistry, University of São Paulo, São Paulo, SP, Brazil.
Macromol Biosci. 2013 Feb;13(2):191-202. doi: 10.1002/mabi.201200296. Epub 2013 Jan 9.
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.
由于副反应的问题，使用具有氟阴离子（IL-F）的离子液体具有挑战性。纯 1-烯丙基-3-甲基咪唑氟化物（AlMeImF）被用作微波辅助纤维素酰化的溶剂。由于 IL 本身的副反应和产生的酯的 F（-）介导的水解，结果令人失望。当使用 AlMeImF/DMSO 混合物时，观察到显著的改善。结果可与使用纯 1-烯丙基-3-甲基咪唑氯时获得的结果相媲美。傅里叶变换红外光谱（FTIR）表明，在 IL-F 中溶解羧酸酐会导致酰氟的形成。因此，离子液体远非“旁观者”溶剂。这种新方法（使用 IL-F/DMSO）具有效率高、成本低且适用于任何聚合物的衍生化的优点，因此具有吸引力。
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