Abstract
This work is concerned with the dissolution of cellulose in tetraallylammonium fluoride/DMSO; the thermal stability of electrolyte solution, and relevant mechanistic aspects of the biopolymer acylation. EMF measurements (fluoride ion-selective electrode) showed that the electrolyte is present as monohydrate. 1H NMR spectroscopy showed that it does not undergo elimination via ylide intermediate, even after heating for 21h at 70°C. A solution of TAAF in DMSO readily dissolves microcrystalline and fibrous celluloses (cotton and eucalyptus); the dissolved biopolymer can be derivatized into esters by reaction with carboxylic acid anhydrides. Cellulose ethanoate, butanoate, hexanoate, and mixed esters, ethanoate/butanoate, ethanoate/hexanoate were conveniently synthesized under homogeneous reaction conditions (3h at 60, 80, and 100°C). Using longer reaction times (12, 18h) lead to esters of low degree of substitution, due to fluoride-ion mediated ester-hydrolysis. The intermediate formation of acyl fluorides in this medium has been confirmed by FTIR spectroscopy.
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