Chemical synthesis of β-O-4 type artificial lignin

Abstract

An artificial lignin polymer containing only the β-O-4 substructure was synthesized. The procedure consists of two key steps: 1) polycondensation of a brominated monomer by aromatic Williamson reaction; and 2) subsequent reduction of the carbonyl polymer. ¹³C-NMR and HMQC spectra of the polymer were consistent with β-O-4 substructures in milled wood lignin isolated from Japanese fir wood. The weight average degree of polymerization (DP_w) ranged from 19.5 to 30.6, which is comparable to enzymatically synthesized artificial lignin from p-hydroxycinnamyl alcohols (dehydrogenation polymer, DHP) and some isolated lignins. Using this new lignin model polymer, it will now be possible to reinvestigate the properties and reactivity of the main lignin structure in terms of its polymeric character.