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

TY - JOUR

T1 - Ionic liquid-mediated regeneration of cellulose dramatically improves decrystallization, TEMPO-mediated oxidation and alkyl/alkenyl succinylation

AU - Li, Ziqian

AU - Zhang, Guoqiang

AU - Charalampopoulos, Dimitris

AU - Guo, Zheng

PY - 2023/5

Y1 - 2023/5

N2 - This work demonstrated a successful strategy that simple ionic liquids (ILs) mediated pretreatment could effectively reduce crystallinity of cellulose from 71 % to 46 % (by C 2MIM.Cl) and 53 % (by C 4MIM.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 C 2MIM.Cl) and 3.42 (C 4MIM.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 2+ chelating property.

AB - This work demonstrated a successful strategy that simple ionic liquids (ILs) mediated pretreatment could effectively reduce crystallinity of cellulose from 71 % to 46 % (by C 2MIM.Cl) and 53 % (by C 4MIM.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 C 2MIM.Cl) and 3.42 (C 4MIM.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 2+ chelating property.

KW - Antioxidation

KW - Cellulose

KW - Emulsifier

KW - Ionic liquids

KW - Succinylation

KW - TEMPO-mediated oxidation

KW - Cellulose/chemistry

KW - Oxidation-Reduction

KW - Nanoparticles/chemistry

KW - Ionic Liquids/chemistry

KW - Cellulose, Oxidized/chemistry

U2 - 10.1016/j.ijbiomac.2023.123983

DO - 10.1016/j.ijbiomac.2023.123983

M3 - Journal article

C2 - 36907307

SN - 0141-8130

VL - 236

JO - International Journal of Biological Macromolecules

JF - International Journal of Biological Macromolecules

M1 - 123983

ER -