Diformylxylose as a new polar aprotic solvent produced from renewable biomass

Abstract

Demand for sustainable polar aprotic solvents is increasing due to their unique solubilizing properties and the toxicity of conventional analogs, which are facing pressure from extensive safety legislation. Polar aprotic solvents are particularly difficult to produce renewably because polar molecules that lack hydroxyl groups are rarely found in abundance in the natural world. Here, we explore the use of diformylxylose (DFX), a xylose-derived molecule that can be produced in a single step from lignocellulosic biomass, as a novel polar aprotic bio-based solvent. We notably demonstrate that diformylxylose shows a similar performance to conventional polar aprotic solvents (DMF, NMP, DMSO) in alkylation, cross-coupling (Heck), and hydrogenation reactions. We also demonstrate its straightforward production from commercial xylose and show that it is non-mutagenic, according to the Ames test. Renewable DFX appears to be a greener alternative to common polar aprotic solvents that are considered problematic for industry.