Elimination mechanism of vanillin from non-phenolic β-O-4-type terminals formed in guaiacyl lignin: a combined kinetic and theoretical study.

ABSTRACT: The alkaline aerobic oxidation of lignin to vanillin (4-hydroxy-3-methoxybenzaldehyde) has been employed as an industrial method for producing bio-based low-molecular-weight aromatic compounds. To deepen the molecular-level understanding of this reaction, we have been investigating the vanillin formation mechanism from native softwood lignin. One of the major reaction pathways involves oxidative degradation of β-O-4-type internal units, followed by alkaline-induced elimination of vanillin from the resulting vanillin end group. This study examined the reaction mechanism of a model compound, 4-[2-(3-ethoxy-4-methoxyphenyl)-2-hydroxy-1-(hydroxymethyl)ethoxy]-3-methoxybenzaldehyde, VE_β, which mimics the vanillin end group, in 4.0 mol L^-1 aqueous NaOH, with particular focu

SUBMITTER: Hirano Y 

PROVIDER: S-EPMC12573767 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature