Controlled hydrogenation of a biomass-derived platform chemical formed by aldol-condensation of 5-hydroxymethyl furfural (HMF) and acetone over Ru, Pd, and Cu catalysts

Gilcher, Elise B.; Chang, Hochan; Huber, George W.; Dumesic, James A.

doi:10.1039/d1gc04650k

Title: Controlled hydrogenation of a biomass-derived platform chemical formed by aldol-condensation of 5-hydroxymethyl furfural (HMF) and acetone over Ru, Pd, and Cu catalysts

Journal Article · Wed Feb 09 00:00:00 EST 2022 · Green Chemistry

DOI:https://doi.org/10.1039/d1gc04650k· OSTI ID:1978798

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University of Wisconsin, Madison, WI (United States)

Her we report that we studied the hydrogenation at temperatures from 313–393 K of a biomass-derived platform molecule, 5-hydroxymethyl furfural (HMF)-acetone-HMF (HAH) over Pd, Ru, and Cu based catalysts. HAH was selectively hydrogenated to produce partially-hydrogenated monomers (PHAH) over Cu and Ru catalysts and to fully-hydrogenated HAH monomers (FHAH) over the Ru catalyst. Pd based catalysts yielded a mixture of partially and fully hydrogenated monomers. Lumped reaction kinetics models were employed to quantify the kinetic behavior for hydrogenation over Ru, Cu, and Pd catalysts. The 5-step pathway exhibited over Pd and Ru catalysts consists of both series and parallel reaction steps, where HAH is both converted to fully hydrogenated products sequentially via series reactions of partially hydrogenated intermediates, as well as converted directly in parallel reactions to form the fully hydrogenated products. In contrast, the 3-step pathway over the Cu catalyst consists only of the consecutive reaction steps, where the final product was formed via series reactions of intermediate products. Additionally, reaction over the Cu catalyst did not hydrogenate the furan rings of the HAH molecule and yielded a different final product than those hydrogenation over Pd and Ru catalysts. Batch conditions are determined for each hydrogenated product that give the highest yields in both batch and plug flow reactors.

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Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER); USDOE Office of Science (SC), Basic Energy Sciences (BES); National Institutes of Health (NIH); Paul J. and Margaret M. Bender Foundation

Grant/Contract Number:: SC0014058; SC0018409; 1S10 OD020022-1

OSTI ID:: 1978798

Alternate ID(s):: OSTI ID: 1845363

Journal Information:: Green Chemistry, Vol. 24, Issue 5; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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