Polymers of lignin-sourced components as a facile chemical integrant for the Passerini three-component reaction

Abstract

In this work, poly(methacrylated vanillin) (PMV) was investigated for its reactivity in multicomponent reactions as a reactive polymer that can be sourced from lignin-based components. To achieve sustainable polymer chemistry, the PMV reactivity in a Passerini three-component reaction (Passerini-3CR) was investigated because the reactants in the Passerini-3CR can be abundantly sourced from biobased compounds. First, the Passerini-3CR of the PMV in solution phases revealed that the PMV pendant aldehydes can be converted into the corresponding α-acyloxy amides with >90% conversions under the optimized conditions. Taking advantage of this high reactivity of PMV, its immobilized cellulose fabric (Cell-g-PMV), a wood biomass-sourced organic hybrid, was subjected to the Passerini-3CR. Although the aldehydes were not completely converted, the PMV segments surrounding the fabric surfaces successfully reacted via the Passerini-3CR to engraft carboxylic acid and isocyanide components on the cellulose-based fabrics. Poly(methacrylated vanillin) (PMV) was investigated for its reactivity in multicomponent reactions as a reactive polymer that can be sourced from lignin-based components. The Passerini three-component reaction (Passerini-3CR) of the PMV in solution phases revealed that the PMV pendant aldehydes can be converted into the corresponding α-acyloxy amides with >90% conversions under the optimized conditions. Taking advantage of this high reactivity of PMV in solution phase, its immobilized cellulose fabric (Cell-g-PMV), a wood biomass-sourced organic hybrid, was subjected to the Passerini-3CR, enabling an engraftment of carboxylic acid and isocyanide components on the cellulose-based fabrics.