Efficient preparation of hybrid biofuels from biomass-derived 5-(acetoxymethyl)furfural and petroleum-derived aromatic hydrocarbons

Abstract

Fuel candidates containing both petroleum-derived and biomass-derived molecules in their structural motifs ensure both feedstocks are used optimally and coherently. This work reports a straightforward and efficient preparation of 5-(arylmethyl)furfurals (AMFFs), 2-(arylmethyl)furans (AMFs), and 2-(arylmethyl)-5-methylfurans (AMMFs) as hybrid biofuels (or fuel oxygenates) starting from carbohydrate-derived 5-(acetoxymethyl)furfural (AcMF) and petroleum-derived aromatic hydrocarbons. The AMFFs were prepared by Friedel–Crafts reaction between AcMF and aromatic hydrocarbons (e.g., BTX, mesitylene) by employing anhydrous ZnCl₂ as the catalyst. AMFs were prepared by decarbonylation of AMFFs over the Pd(OAc)₂ catalyst under solvent-free conditions. In contrast, AMMFs were produced by hydrogenating AMFFs in methanol using gaseous hydrogen and the 10% Pd/C catalyst. The catalytic transformations were optimized on various parameters, and all the biofuel candidates were obtained in good to excellent isolated yields (>80%) under moderate conditions.