Hydrogenation of levoglucosenone to renewable chemicals
Abstract
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.
- Authors:
-
- Univ. of Wisconsin, Madison, WI (United States). Department of Chemical and Biological Engineering
- Publication Date:
- Research Org.:
- Univ. of Wisconsin, Madison, WI (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE)
- Contributing Org.:
- University of Wisconsin-Madison Department of Chemistry
- OSTI Identifier:
- 1477850
- Grant/Contract Number:
- EE0006878
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Green Chemistry
- Additional Journal Information:
- Journal Volume: 19; Journal Issue: 5; Journal ID: ISSN 1463-9262
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Krishna, Siddarth H., McClelland, Daniel J., Rashke, Quinn A., Dumesic, James A., and Huber, George W. Hydrogenation of levoglucosenone to renewable chemicals. United States: N. p., 2016.
Web. doi:10.1039/C6GC03028A.
Krishna, Siddarth H., McClelland, Daniel J., Rashke, Quinn A., Dumesic, James A., & Huber, George W. Hydrogenation of levoglucosenone to renewable chemicals. United States. https://doi.org/10.1039/C6GC03028A
Krishna, Siddarth H., McClelland, Daniel J., Rashke, Quinn A., Dumesic, James A., and Huber, George W. Mon .
"Hydrogenation of levoglucosenone to renewable chemicals". United States. https://doi.org/10.1039/C6GC03028A. https://www.osti.gov/servlets/purl/1477850.
@article{osti_1477850,
title = {Hydrogenation of levoglucosenone to renewable chemicals},
author = {Krishna, Siddarth H. and McClelland, Daniel J. and Rashke, Quinn A. and Dumesic, James A. and Huber, George W.},
abstractNote = {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.},
doi = {10.1039/C6GC03028A},
journal = {Green Chemistry},
number = 5,
volume = 19,
place = {United States},
year = {Mon Dec 12 00:00:00 EST 2016},
month = {Mon Dec 12 00:00:00 EST 2016}
}
Web of Science
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