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Transition-metal-free decarboxylation of D-glucaric acid to furan catalyzed by SnCl4 in a biphasic system by Teng Li; Guangyu Sun; Lu Xiong; Boying Zheng; Yaqi Duan; Rui Yu; Jun Jiang; Yantao Wang; Weiran Yang is a Chemistry article available to read on EtoBox.

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As a useful chemical, furan can be produced from bio-based chemicals, such as furfural and furoic acid (FA). There were few reports on the preparation of furan from bio-based C6 aldaric acids. Herein, a new method was developed to produce furan from D-glucaric acid (GA) without transition metals, and nearly 80% yield of furan was produced in the water/toluene biphasic system with SnCl 4 at 200 • C in 2 h. 3-Hydroxy-2-pyrone (3-HP) and FA were proved to be the key intermediates in the formation of furan from GA, and the reaction pathway was proposed to be GA→ 3-HP→ FA→ furan based on the kinetic study, model substrate reaction, and isotope labeling experiments. SnCl 4 gave the highest furan yield among the common acid catalysts, and the contrast experiments suggested that H + , Cl -and Sn 4+ all have promoting effect on GA conversion to furan. This method was also applicable with other C6 aldaric acids.

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Author

Teng Li; Guangyu Sun; Lu Xiong; Boying Zheng; Yaqi Duan; Rui Yu; Jun Jiang; Yantao Wang; Weiran Yang

Publisher

Elsevier BV

Published

2021

Language

EN

Field

Chemistry (Physical Sciences)