The undesirable acetylation of cellulose by the acetate ion of 1-ethyl-3-methylimidazolium acetate

Abstract  

The ionic liquid (IL) 1-ethyl-3-methylimidazolium acetate (C2mim]OAc) is considered to be an inert solvent of cellulose and lignocellulosic biomass. Acetylation (1.7% mol, or DS 0.017) of cellulose after dissolution in technical grade C2mim]OAc (150 °C for 20 min), is demonstrated by compositional analysis, FTIR analysis and ¹³C NMR spectroscopy (in C2mim]OAc with ¹³C enriched acetate). This acetylation, in the absence of added acylating agents, has not been reported before and may limit C2mim]OAc utility in industrial scale biomass processing, even at this low extent. For example, cellulose acetylation may contribute to IL loss in processes where the IL is recovered and reused and inhibit enzyme saccharification of cellulose in lignocellulosic biofuel production processes based on saccharification and fermentation.