Biorefinery via Achmatowicz Rearrangement: Synthesis of Pentane-1,2,5-triol from Furfuryl Alcohol

Svilen P Simeonov; Martin A Ravutsov; Marko D Mihovilovic

doi:10.1002/cssc.201900601

Biorefinery via Achmatowicz Rearrangement: Synthesis of Pentane-1,2,5-triol from Furfuryl Alcohol

ChemSusChem. 2019 Jun 21;12(12):2748-2754. doi: 10.1002/cssc.201900601. Epub 2019 Jun 6.

Authors

Svilen P Simeonov¹, Martin A Ravutsov¹, Marko D Mihovilovic²

Affiliations

¹ Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bontchev str. Bl. 9, 1113, Sofia, Bulgaria.
² Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060, Wien, Austria.

PMID: 31050856
DOI: 10.1002/cssc.201900601

Abstract

A new scalable synthesis of pentane-1,2,5-triol from the furanics platform has been developed. Excellent yields of up to 92 % are obtained under flow conditions by using readily available catalysts from the existing pool. The strategy exploits the highly functionalized Achmatowicz product as a key intermediate, thus circumventing problems related to the low reactivity of the parent furfural and furfuryl alcohol. Besides expanding the portfolio of biomass-derived C₅ alcohols, this strategy may also be further applied for the establishment of a versatile bio-based chemical platform.

Keywords: Achmatowicz rearrangement; biorefinery; continuous production; furfuryl alcohol; pentane-1,2,5-triol.

Abstract

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