Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural

Brentzel, Zachary J.; Barnett, Kevin J.; Huang, Kefeng; Maravelias, Christos T.; Dumesic, James A.; Huber, George W.

doi:10.1002/cssc.201700178

Title: Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural

Journal Article · Thu Mar 09 00:00:00 EST 2017 · ChemSusChem

DOI:https://doi.org/10.1002/cssc.201700178· OSTI ID:1533152

Brentzel, Zachary J. ^[1]; Barnett, Kevin J. ^[1]; Huang, Kefeng ^[1]; Maravelias, Christos T. ^[1]; Dumesic, James A. ^[1]; Huber, George W. ^[1]

Univ. of Wisconsin, Madison, WI (United States)

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.

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

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

Grant/Contract Number:: EE0006878

OSTI ID:: 1533152

Alternate ID(s):: OSTI ID: 1401522

Journal Information:: ChemSusChem, Vol. 10, Issue 7; ISSN 1864-5631

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 84 works

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Title: Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural

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