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Issue 3, 2018
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A strategy of ketalization for the catalytic selective dehydration of biomass-based polyols over H-beta zeolite

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Abstract

Biomass contains plentiful hydroxyl groups that lead to an oxygen-rich structure compared to petroleum-based chemicals. Dehydration is the most energy-efficient technique to remove oxygen; however, multiple similar vicinal hydroxyl groups in sugar alcohols impose significant challenges for their selective dehydration. Here, we present a novel strategy to control the etherification site in sugar alcohols by the ketalization of the vicinal-diol group for the highly selective formation of tetrahydrofuran derivatives. A ketone firstly reacts with terminal vicinal hydroxyl groups to form the 1,3-dioxolane structure. This structure of the constrained 1,3-dioxolane ring would improve the accessibility of reactive groups to facilitate intramolecular etherification. As a better leaving group than water, the ketone can also promote intramolecular etherification. Consequently, a range of tetrahydrofuran derivatives are produced in excellent yields with the H-beta zeolite catalyst under mild reaction conditions. This strategy opens up new opportunities for the efficient upgrading of biomass via the modification or protection of hydroxyl groups.

Graphical abstract: A strategy of ketalization for the catalytic selective dehydration of biomass-based polyols over H-beta zeolite

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Supplementary files

Article information


Submitted
28 Oct 2017
Accepted
01 Dec 2017
First published
04 Dec 2017

Green Chem., 2018,20, 634-640
Article type
Paper

A strategy of ketalization for the catalytic selective dehydration of biomass-based polyols over H-beta zeolite

P. Che, F. Lu, X. Si, H. Ma, X. Nie and J. Xu, Green Chem., 2018, 20, 634
DOI: 10.1039/C7GC03248J

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