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Mechanistic investigation of the hydrodeoxygenation of furfural to 2- methylfuran over Ru/C using isotopic labeling techniques

Panagiotopoulou Paraskevi, Vlachos G. Dionisios, Gilkey Matthew, Bingjun Xu

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Summary

Fundamental understanding regarding the role of the surface mediated reactionmechanism in biomass upgrading to fuels and chemicals is key to the rational design of catalysts. Hydrodeoxygenation (HDO) of oxygenated furanics, e.g., furfural and 5-hydroxymethylfurfural, to reduced furanics, e.g., 2-methylfuran (2-MF) and 2,5-dimethylfuran, is an important step in the upgrade of cellulose/hemicellulose-based biomass to fuels and chemicals [1]. Previousstudies show that a mildly oxidized Ru/C catalyst performs furfural HDO toward 2-MF using catalytic transfer hydrogenation (CTH) using 2-propanol (IPA) as a hydrogen source [2, 3].However, the role of the catalyst in HDO remains unclear.Furfural HDO consists of 2 key steps: (1) the hydrogenation of furfural to furfurylalcohol (FA), and (2) hydrogenolysis of FA to 2-MF. We hypothesize that the hydrogenationstep can happen either via metal-mediated hydrogenation via surface adsorbed H-atoms from the dehydrogenation of IPA or via Lewis acid-mediated hydrogenation, where a hydrogen atom is transferred in one, concerted step from IPA in a Meerwein-Ponndorf-Verley type mechanism. Furthermore, we suspect that the hydrogenolysis step occurs either via direct hydrogenolysis, where a surface adsorbed hydrogen directly cleaves the C-O bond in FA, or via ring activation, where a hydrogen atom is first added to the ring before removal of oxygen.

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