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Title: 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/Al 2O 3 catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 °C) over a Pd/Al 2O 3 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/SiO 2–Al 2O 3 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:
 [1];  [1];  [1];  [1]; ORCiD logo [1]
  1. 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:
Journal Article: 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. doi: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. doi: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}
}

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Cited by: 12 works
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