Molecular Oxygen Lignin Depolymerization: An Insight into the Stability of Phenolic Monomers.

During oxidative depolymerization of lignin in aqueous alkaline medium using molecular oxygen as oxidant, the highly functionalized primary phenolic monomers are not stable products, owing to various not fully identified secondary reaction mechanisms. However, better understanding of the mechanisms responsible for the instability of the main part of the products of interest derived from lignin is of much interest. Evaluation of their individual reactivities under oxidative conditions should significantly help to find a better way to valorize the lignin polymer and to maximize the yields of target value-added products. Consequently, the main objective of this study is to assess the individual stabilities of some selected lignin-based phenolic compounds, such as vanillin, vanillic acid, and acetovanillone, together with some other pure chemical compounds such as phenol and anisole to give an insight into the mechanisms responsible for the simultaneous formation and repolymerization of those products and the influence of the oxidation conditions. Various complementary strategies of stabilization are proposed, discussed, and applied for the oxidative depolymerization reactions of a technical lignin extracted from pinewood with a high content of β-O-4 interconnecting bonds to try to obtain enhanced yields of value-added products.