Hydrogenation of levoglucosenone to renewable chemicals

Krishna, Siddarth H.; McClelland, Daniel J.; Rashke, Quinn A.; Dumesic, James A.; Huber, George W.

doi:10.1039/C6GC03028A

Hydrogenation of levoglucosenone to renewable chemicals

Journal Article · Mon Dec 12 00:00:00 EST 2016 · Green Chemistry

DOI:https://doi.org/10.1039/C6GC03028A· OSTI ID:1477850

Krishna, Siddarth H. ^[1]; McClelland, Daniel J. ^[2]; Rashke, Quinn A. ^[2]; Dumesic, James A. ^[2]; ^[2]

Univ. of Wisconsin, Madison, WI (United States). Department of Chemical and Biological Engineering; University of Wisconsin-Madison Department of Chemical and Biological Engineering
Univ. of Wisconsin, Madison, WI (United States). Department of Chemical and Biological Engineering

Here, we have studied the hydrogenation of levoglucosenone (LGO) to dihydrolevoglucosenone (Cyrene), levoglucosanol (Lgol), and tetrahydrofurandimethanol (THFDM) and elucidated the reaction network over supported palladium catalysts. At low temperature (40 °C) over a Pd/Al₂O₃ catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 °C) over a Pd/Al₂O₃ catalyst, Cyrene is selectively hydrogenated to Lgol, with an excess of the exo-Lgol isomer produced over the endo-Lgol isomer. At higher temperatures (150 °C) over a bifunctional Pd/SiO₂–Al₂O₃ catalyst, Lgol is converted to THFDM in 58% selectivity, with 78% overall selectivity to 1,6-hexanediol precursors. The ratio of cis-THFDM relative to trans-THFDM is approximately 2.5, and this ratio is independent of the Lgol feed stereoisomer ratio. Finally, tetrahydropyran-2-methanol-5-ketone (THP2M5one) and tetrahydropyran-2-methanol-5-hydroxyl (THP2M5H) are side-products of Lgol hydrogenolysis, but neither of these species are precursors to THFDM.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Contributing Organization:: University of Wisconsin-Madison Department of Chemistry

Grant/Contract Number:: EE0006878

OSTI ID:: 1477850

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 5 Vol. 19; ISSN GRCHFJ; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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