Ionic liquid-mediated regeneration of cellulose dramatically improves decrystallization, TEMPO-mediated oxidation and alkyl/alkenyl succinylation.

This work demonstrated a successful strategy that simple ionic liquids (ILs) mediated pretreatment could effectively reduce crystallinity of cellulose from 71 % to 46 % (by CMIM.Cl) and 53 % (by CMIM.Cl). The IL-mediated regeneration of cellulose greatly promoted its reactivity for TEMPO-catalyzed oxidation, which the resulting COO density (mmol/g) increased from 2.00 for non-IL-treated cellulose to 3.23 (by CMIM.Cl) and 3.42 (CMIM.Cl); and degree of oxidation enhanced from 35 % to 59 % and 62 %, respectively. More significantly, the yield of oxidized cellulose increased from 4 % to 45-46 %, by 11-fold. IL-regenerated cellulose can also be directly subjected to alkyl/alkenyl succinylation without TEMPO-mediated oxidation, producing nanoparticles with properties similar to oxidized celluloses (55-74 nm in size, -70-79 mV zeta-potential and 0.23-0.26 PDI); but in a much higher overall yield (87-95 %) than IL-regeneration-coupling-TEMPO-oxidation (34-45 %). Alkyl/alkenyl succinylated TEMPO-oxidized cellulose showed 2-2.5 times higher ABTS* scavenging ability than non-oxidized cellulose; however, alkyl/alkenyl succinylation also resulted in a significant decline in Fe chelating property.