One-step Pd/C and Eu(OTf)(3) catalyzed hydrodeoxygenation of branched C-11 and C-12 biomass-based furans to the corresponding alkanes

Abstract

Solvent-free NaOH catalyzed aldol condensation of biomass-derived 5-hydroxymethyl furfural (HMF) and furfural with methyl isobutyl ketone (MIBK) was studied, producing branched C-11 and C-12 furan compounds in high yields of up to 96%. Through use of a Pd/C and Eu(OTf)(3) catalytic system, the condensation products of the bio-based starting materials were further hydrodeoxygenated (HDO) in one-step to biofuel compatible branched alkanes 2-methylundecane (3) and 2-methyldecane (4) in excellent yields of 90% and 98%, respectively. In the one-step HDO developed herein, the variation of solvent had a significant effect on the reaction route and degree of conversion of furans to alkanes in the HDO process. Very high overall yields of alkanes 3 (86%) and 4 (94%) were obtained starting from the biomass-based HMF and furfural. (C) 2017 Elsevier B.V. All rights reserved.