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

Abstract

Biomass contains plentiful hydroxyl groups that cause oxygen-rich structure compared with 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 ketalization of vicinal-diol group for highly selective formation of tetrahydrofuran derivatives. Ketone firstly reacts with terminal vicinal hydroxyl groups to form 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, ketone can also promote the intramolecular etherification. Consequently, a range of tetrahydrofuran derivatives are produced in excellent yields with H-beta zeolite catalyst under mild reaction conditions. This strategy opens up new opportunities for efficient upgrading of biomass via modification or protection of hydroxyl groups.

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Publication details

The article was received on 28 Oct 2017, accepted on 01 Dec 2017 and first published on 04 Dec 2017


Article type: Paper
DOI: 10.1039/C7GC03248J
Citation: Green Chem., 2017, Accepted Manuscript
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    A strategy of ketalization for 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., 2017, Accepted Manuscript , DOI: 10.1039/C7GC03248J

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