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Selective Oxidation of HMF via Catalytic and Photocatalytic Processes Using Metal-Supported Catalysts
Open AccessArticle

Gas Phase Hydrogenation of Furaldehydes via Coupling with Alcohol Dehydrogenation over Ceria Supported Au-Cu

Chemical Engineering, School of Engineering and Physical Sciences, Heriot Watt University, Edinburgh EH14 4AS, Scotland, UK
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Molecules 2018, 23(11), 2905; https://doi.org/10.3390/molecules23112905
Received: 7 October 2018 / Revised: 4 November 2018 / Accepted: 5 November 2018 / Published: 7 November 2018
(This article belongs to the Special Issue Platform Chemical: Hydroxymethylfurfural (HMF))
We have investigated the synthesis and application of Au-Cu/CeO2 (Cu: Au = 2) in the continuous gas phase (P = 1 atm; T = 498 K) coupled hydrogenation of 5-hydroxymethyl-2-furaldehyde (HMF) with 2-butanol dehydrogenation. STEM-EDX analysis revealed a close surface proximity of both metals in Au-Cu/CeO2 post-TPR. XPS measurements suggest (support → metal) charge transfer to form Auδ and strong metal-support interactions to generate Cu0 and Cu+. Au-Cu/CeO2 promoted the sole formation of 2,5-dihydroxymethylfuran (DHMF) and 2-butanone in the HMF/2-butanol coupling with full hydrogen utilisation. Under the same reaction conditions, Au/CeO2 was fully selective to DHMF in standard HMF hydrogenation (using an external hydrogen supply), but delivered a lower production rate and utilised less than 0.2% of the hydrogen supplied. Exclusive -C=O hydrogenation and -OH dehydrogenation is also demonstrated for the coupling of a series of m-substituted (-CH3, -CH2CH3, -CH2OH, -CF3, -N(CH3)2, -H) furaldehydes with alcohol (1-propanol, 1-butanol, 2-propanol, 2-butanol, cyclohexanol) dehydrogenation over Au-Cu/CeO2, consistent with a nucleophilic mechanism. In each case, we observed a greater hydrogenation rate and hydrogen utilisation efficiency with a 3–15 times lower E-factor in the coupling process relative to standard hydrogenation. Our results demonstrate the feasibility of using hydrogen generated in situ through alcohol dehydrogenation for the selective hydrogenation of m-furaldehydes with important industrial applications. View Full-Text
Keywords: HMF; coupling hydrogenation/dehydrogenation; m-furaldehydes; alcohols; Au/CeO2; Au-Cu/CeO2 HMF; coupling hydrogenation/dehydrogenation; m-furaldehydes; alcohols; Au/CeO2; Au-Cu/CeO2
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MDPI and ACS Style

Pischetola, C.; Collado, L.; Keane, M.A.; Cárdenas-Lizana, F. Gas Phase Hydrogenation of Furaldehydes via Coupling with Alcohol Dehydrogenation over Ceria Supported Au-Cu. Molecules 2018, 23, 2905.

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