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

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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.
Funding Information
  • Office of Energy Efficiency and Renewable Energy (DE-EE0006878)

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