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Title: 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:
 [1];  [1];  [1];  [1];  [1];  [1]
  1. 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}
}

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