Catalytic Cleavage of the C-O Bonds in Lignin and Lignin Model Compounds by Metal Triflate Catalysts

Abstract

The effective cleavage of C-O bonds in linkages of lignin was one of the significant strategies promoting lignin valorization. Herein, the strategy of C-O bonds cleavage of lignin using metal triflate as the catalyst was developed. The carboxylic acid or alcohol could be used as the nucleophile to stabilize the reactive intermediates formed during the depolymerization of lignin, and the corresponding ester/ether compounds could be obtained. This catalytic system was suitable for the C-O bond cleavage in α-O-4 and β-O-4 linkages with excellent efficiency. Additionally, reaction conditions were optimized. The reaction mixture was detected by ¹ H NMR, and no other byproducts were found. As for treated lignin samples, the cleavage of C-O bonds in linkages was determined by 2D HSQC NMR, the increased content of the phenol hydroxyl group was proved by FT-IR, and the reduced molecular weight was investigated by GPC. Furthermore, multiple phenolic compounds were detected by GC-MS in the reaction mixtures.

Keywords: C−O bond cleavage; biomass; lignin; metal triflate; nucleophile.