Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural
Abstract
Abstract A process for the synthesis of 1,5‐pentanediol (1,5‐PD) with 84 % yield from furfural is developed, utilizing dehydration/hydration, ring‐opening tautomerization, and hydrogenation reactions. Although this process has more reaction steps than the traditional direct hydrogenolysis of tetrahydrofurfuryl alcohol (THFA), techno‐economic analyses demonstrate that this process is the economically preferred route for the synthesis of biorenewable 1,5‐PD. 2‐Hydroxytetrahydropyran (2‐HY‐THP) is the key reaction pathway intermediate that allows for a decrease in the minimum selling price of 1,5‐PD. The reactivity of 2‐HY‐THP is 80 times greater than that of THFA over a bimetallic hydrogenolysis catalyst. This enhanced reactivity is a result of the ring‐opening tautomerization to 5‐hydoxyvaleraldehyde and subsequent hydrogenation to 1,5‐PD.
- Authors:
-
- Univ. of Wisconsin, Madison, WI (United States)
- Publication Date:
- Research Org.:
- Univ. of Wisconsin, Madison, WI (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE)
- OSTI Identifier:
- 1533152
- Alternate Identifier(s):
- OSTI ID: 1401522
- Grant/Contract Number:
- EE0006878
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ChemSusChem
- Additional Journal Information:
- Journal Volume: 10; Journal Issue: 7; Journal ID: ISSN 1864-5631
- Publisher:
- ChemPubSoc Europe
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS; chemistry; science & technology; α,ω-diols; biomass; catalysis; hydrogenation; sustainable chemistry
Citation Formats
Brentzel, Zachary J., Barnett, Kevin J., Huang, Kefeng, Maravelias, Christos T., Dumesic, James A., and Huber, George W. Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural. United States: N. p., 2017.
Web. doi:10.1002/cssc.201700178.
Brentzel, Zachary J., Barnett, Kevin J., Huang, Kefeng, Maravelias, Christos T., Dumesic, James A., & Huber, George W. Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural. United States. https://doi.org/10.1002/cssc.201700178
Brentzel, Zachary J., Barnett, Kevin J., Huang, Kefeng, Maravelias, Christos T., Dumesic, James A., and Huber, George W. Thu .
"Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural". United States. https://doi.org/10.1002/cssc.201700178. https://www.osti.gov/servlets/purl/1533152.
@article{osti_1533152,
title = {Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural},
author = {Brentzel, Zachary J. and Barnett, Kevin J. and Huang, Kefeng and Maravelias, Christos T. and Dumesic, James A. and Huber, George W.},
abstractNote = {Abstract A process for the synthesis of 1,5‐pentanediol (1,5‐PD) with 84 % yield from furfural is developed, utilizing dehydration/hydration, ring‐opening tautomerization, and hydrogenation reactions. Although this process has more reaction steps than the traditional direct hydrogenolysis of tetrahydrofurfuryl alcohol (THFA), techno‐economic analyses demonstrate that this process is the economically preferred route for the synthesis of biorenewable 1,5‐PD. 2‐Hydroxytetrahydropyran (2‐HY‐THP) is the key reaction pathway intermediate that allows for a decrease in the minimum selling price of 1,5‐PD. The reactivity of 2‐HY‐THP is 80 times greater than that of THFA over a bimetallic hydrogenolysis catalyst. This enhanced reactivity is a result of the ring‐opening tautomerization to 5‐hydoxyvaleraldehyde and subsequent hydrogenation to 1,5‐PD.},
doi = {10.1002/cssc.201700178},
journal = {ChemSusChem},
number = 7,
volume = 10,
place = {United States},
year = {Thu Mar 09 00:00:00 EST 2017},
month = {Thu Mar 09 00:00:00 EST 2017}
}
Web of Science
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