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

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

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1351-1355
Number of pages5
JournalChemSusChem
Volume10
Issue number7
DOIs
StatePublished - Apr 10 2017
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Chemical Engineering(all)
  • Materials Science(all)
  • Energy(all)

Keywords

  • biomass
  • catalysis
  • hydrogenation
  • sustainable chemistry
  • α,ω-diols

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