title: Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural.
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.affiliation: Department of Chemical and Biological Engineering, University of Wisconsin-Madison, Madison, WI, 53706, USA.
authors.forename: Zachary J
authors.initials: ZJ
authors.lastname: Brentzel
authors.affiliation: Department of Chemical and Biological Engineering, University of Wisconsin-Madison, Madison, WI, 53706, USA.
authors.forename: Kevin J
authors.initials: KJ
authors.lastname: Barnett
authors.affiliation: Department of Chemical and Biological Engineering, University of Wisconsin-Madison, Madison, WI, 53706, USA.
authors.forename: Kefeng
authors.initials: K
authors.lastname: Huang
authors.affiliation: Department of Chemical and Biological Engineering, University of Wisconsin-Madison, Madison, WI, 53706, USA.
authors.forename: Christos T
authors.initials: CT
authors.lastname: Maravelias
authors.affiliation: Department of Chemical and Biological Engineering, University of Wisconsin-Madison, Madison, WI, 53706, USA.
authors.forename: James A
authors.initials: JA
authors.lastname: Dumesic
authors.affiliation: Department of Chemical and Biological Engineering, University of Wisconsin-Madison, Madison, WI, 53706, USA.
authors.forename: George W
authors.initials: GW
authors.lastname: Huber
mesh_terms: D018533:Biomass; D005662:Furaldehyde / Q000737:chemistry*; D006018:Glycols / Q000737:chemistry*; D006865:Hydrogenation; D007536:Isomerism; D010420:Pentanes / Q000737:chemistry*
chemical_list: D006018:Glycols; D010420:Pentanes; C578469:1,5-pentanediol; D005662:Furaldehyde
keywords: biomass; catalysis; hydrogenation; sustainable chemistry; α,ω-diols