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

Penghua Che; Fang Lu; Xiaoqin Si; Hong Ma; Xin Nie; Jie Xu

doi:10.1039/C7GC03248J

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

Penghua Che,^a Fang Lu,*^a Xiaoqin Si,^a^b Hong Ma,^a Xin Nie^a and Jie Xu*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, PR China
E-mail: xujie@dicp.ac.cn, lufang@dicp.ac.cn

^b University of Chinese Academy of Sciences, Beijing, PR China

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.

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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., 2018,20, 634-640

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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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Green Chemistry

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

Abstract

Supplementary files

Publication details

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

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