Development of sustainable processes for production of monomers and a pharmaceutical ingredient from lignocellulosic biomass

The development of sustainable chemical processes is critical for society to supply commercial chemicals with limited natural resources. Here, we report catalytic reactions that are developed to upgrade lignocellulosic biomass into a pharmaceutical ingredient (rehmanone A) and monomers. Biomass-derived glucose is dissolved in an acetone/water co-solvent and used as a feed for sequential isomerization and dehydration to produce 5-hydroxymethyl furfural (HMF). This HMF is reacted with acetone to produce an aldol-condensed intermediate (HAH, adduct of two HMF and one acetone) in 94% isolation yield. The diol group in HAH is etherified with methanol to synthesize rehmanone A in 95% reaction yield. Alternatively, the C=C bonds in HAH are hydrogenated to produce monomers, such as partially hydrogenated HAH and fully hydrogenated HAH in 84% and 93% reaction yields, respectively. The experimental parameters are used to assess the economic potential of these synthesis-based processes by techno-economic analyses with a toll manufacturing scenario.