Room temperature catalytic upgrading of unpurified lignin depolymerization oil into bisphenols and butene-2

Abstract

Abstract Lignin is the largest source of renewable aromatics on earth. Despite numerous techniques for lignin depolymerization into mixtures of valuable monomers, methods for their upgrading into final products are scarce. The state of the art upgrading methods generally rely on catalytic funneling, requiring high temperatures, catalyst loadings and hydrogen pressure, and lead to the loss of functionality and bio-based carbon content. Here an alternative approach is presented, whereby the target monomers are selectively converted in unpurified mixtures into easily separable final products under mild conditions. We use reductive catalytic fractionation of wood to convert lignin into iso-eugenol and propenyl syringol enriched oil followed by an olefin metathesis to yield bisphenols and butene-2, thus, valorizing all bio-based carbons. To further demonstrate the synthetic utility of the obtained bisphenols we converted them into polyesters with a high glass transition temperature (T g = 140.3 °C) and thermal stability (Td 50% = 330 °C).