Issue 13, 2022

Near quantitative conversion of xylose into bisfuran

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 °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.

Graphical abstract: Near quantitative conversion of xylose into bisfuran

Supplementary files

Article information

Article type
Communication
Submitted
16 Febr. 2022
Accepted
30 Maijs 2022
First published
31 Maijs 2022
This article is Open Access
Creative Commons BY license

Green Chem., 2022,24, 5052-5057

Near quantitative conversion of xylose into bisfuran

R. Zhang, A. Eronen, P. Vasko, X. Du, J. Install and T. Repo, Green Chem., 2022, 24, 5052 DOI: 10.1039/D2GC00640E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements