Near quantitative conversion of xylose into bisfuran

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Zhang , R , Eronen , A , Vasko , P , Du , X , Install , J & Repo , T 2022 , ' Near quantitative conversion of xylose into bisfuran ' , Green Chemistry , vol. 24 , no. 13 , pp. 5052-5057 . https://doi.org/10.1039/d2gc00640e

Title: Near quantitative conversion of xylose into bisfuran
Author: Zhang, Rui; Eronen, Aleksi; Vasko, Petra; Du, Xiangze; Install, Joseph; Repo, Timo
Contributor organization: Doctoral Programme in Chemistry and Molecular Sciences
Department of Chemistry
Date: 2022-07-04
Language: eng
Number of pages: 6
Belongs to series: Green Chemistry
ISSN: 1463-9262
DOI: https://doi.org/10.1039/d2gc00640e
URI: http://hdl.handle.net/10138/346545
Abstract: Renewable and abundant carbohydrates are promising feedstocks for producing valuable chemicals. Here we report a highly efficient Zr-catalysed conversion of xylose and acetylacetone (acac) to a new type of bisfuranic monomer, 1-(4-((4-acetyl-5-methylfuran-2-yl)methyl)-2-methylfuran-3-yl)ethenone (MFE). The formation of MFE stems from the intermediate obtained through the nucleophilic addition of acac to xylose. Under optimized conditions (microwave irradiation, 140 degrees C, 24 min, NaI as an additive), MFE is obtained in near-quantitative yield (98%). Importantly, the reaction selectivity can be tuned by the inclusion of an additive. When NaCl is used, the reaction gives 3-(furan-2-ylmethylene)pentane-2,4-dione (FMPD, 55%), a jet-fuel precursor, and MFE (30%) with a total carbon yield of 85%. To the best of our knowledge, this is the first report on straightforward xylose transformation to a bisfuranic compound with excellent carbon efficiency. This Garcia Gonzalez (GG) reaction inclusive strategy is remarkable and could lead to many innovations in bio-based polymer synthesis.
Subject: LIGNOCELLULOSIC BIOMASS
FURAN-DERIVATIVES
PLATFORM
SUGARS
XYLAN
TRANSFORMATION
CONDENSATION
CHEMICALS
CATALYST
116 Chemical sciences
Peer reviewed: Yes
Rights: cc_by
Usage restriction: openAccess
Self-archived version: publishedVersion


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