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Microwave-Assisted Decarbonylation of Biomass-Derived Aldehydes Using Pd-Doped Hydrotalcites

preprint
submitted on 02.05.2019 and posted on 03.05.2019 by Nan An, Diana Ainembabazi, Kavya Samudrala, Christopher Reid, Karen Wilson, Adam Lee, Adelina Voutchkova-Kostal

Here we report the synthesis, characterization and activity of tunable Pd-doped hydrotalcites (Pd-HTs) for the decarbonylation of furfural, hydroxymethylfurfural (HMF), aromatic and aliphatic aldehydes under microwave conditions. The decarbonylation activity reported is a notable improvement over prior heterogeneous catalysts for this process. Furfural decarbonylation is optimized in a benign solvent compatible with biomass processing - ethanol, under relatively mild conditions and short reaction times. HMF selectively affords excellent yields of furfuryl alcohol with no humin formation, but longer reaction can also afford furan via tandem alcohol dehydrogenation and decarbonylation. Yields of substituted benzaldehydes are related to calculated Mulliken charge of the carbonyl carbon. The activity and selectivity differences can be traced to loading-dependent differences in Pd speciation on the catalysts. Poisoning studies show inverse correlation between Pd loading and metal leaching: Pd-HTs with lowest Pd loading, which consist of highly dispersed and oxidized Pd species, operate heterogeneously with negligible metal leaching. Recycling experiments are consistent with this trend, offering potential for further optimization to improve robustness.

Funding

NSF Catalysis

History

Email Address of Submitting Author

avoutchkova@gwu.edu

Institution

George Washington University and RMIT University

Country

USA and Australia

ORCID For Submitting Author

0000-0002-7016-5244

Declaration of Conflict of Interest

There is no inherent conflict of interest in the publication of this work.

Version Notes

version 1.0

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