A new class of biodegradable anionic surfactants with structures based on 5-alkoxymethylfuroate was prepared starting from 5-hydroxymethylfurfural (HMF), through a one-pot-two-steps process which involves the selective etherification of HMF with fatty alcohols using heterogeneous solid acid, followed by a highly selective oxidation of the formyl group with a gold catalyst. The etherification step was optimized using aluminosilicates as acid catalysts with different pore topologies (H-Beta, HY, Mordenite, ZSM-5, ITQ-2, and MCM-41), different active sites (Bronsted or Lewis) and different adsorption properties. It was shown that highly hydrophobic defect-free H-Beta zeolites with Si/Al ratios higher than 25 are excellent acid catalysts to perform the selective etherification of HMF with fatty alcohols, avoiding the competitive self-etherification of HMF. Moreover, the 5-alkoxymethylfurfural derivatives obtained can be selectively oxidized to the corresponding furoic salts in excellent yield using Au/CeO2 as catalyst and air as oxidant, at moderated temperatures. Both H-Beta zeolite and Au/CeO2 could be reused several times without loss of activity.
Alkylation of aromatics with 5-hydroxymethylfurfural in the presence of large pore acid zeolites followed by hydrodeoxygenation yields high quality kerosene.
Biomass platform molecules such as glycerol and 5-hydroxymethylfurfural have been valorized into diol monomers by acetalization reaction in the presence of tridirectional large pore zeolites (HY and Beta), a laminar zeolite (ITQ-2) and a mesoporous aluminosilicate (MCM-41) and a conventional homogeneous acid catalyst (p-toluenesulfonic acid). The influence of the solvent polarity, pore structure, hydrophobic character and acidity of the catalyst on the activity and selectivity to HMF glyceryl acetals has been studied. Results showed that while the homogeneous catalyst mainly promotes polymerization reactions, tridirectional zeolites are more active catalysts but less selective and deactivate more rapidly than mesoporous MCM-41 and delaminated 2D zeolites. ITQ-2 and MCM-41 catalysts with smaller confinement effects, easy diffusion, and adequate surface polarity provide high yield (98 %) and selectivity (100%) to the target compound. These catalysts are stable and allow regeneration and reuse.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.