Phenolation to Improve Lignin Reactivity toward Thermosets Application

Abstract

Phenolation can be used to improve the reactivity and decrease the molecular weight of lignin, thereby making it more useful for various applications. We report an effective phenolation process with only a catalytic amount of sulfuric acid and using phenol as solvent. The optimum phenolation conditions for pine kraft lignin and sweetgum biorefinery lignin were determined to be lignin/phenol (L/P, wt/wt) of 3/5, 5% acid charge at 90 °C for 2 h and L/P of 2/5, 5% acid charge at 110 °C for 2 h, respectively. Phenolation resulted in introducing 30 wt % of phenol onto pine kraft lignin and 60 wt % of phenol onto sweetgum biorefinery lignin and significantly decreasing in the molecular weight of lignin. Phenol was incorporated onto both the side chains and aromatic nuclei of lignin. All lignin substructures of β-O-4′, β-5′/α-O-4′, β–β′, α-carbonyl, etc. were reacted, resulting in a significant decrease in aliphatic hydroxyl groups and increase in the phenolic hydroxyl groups. The comprehensive characterization ...