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Catalytic production of hexane-1,2,5,6-tetrol from bio-renewable levoglucosanol in water: effect of metal and acid sites on (stereo)-selectivity

Journal Article · · Green Chemistry
DOI:https://doi.org/10.1039/C8GC02455C· OSTI ID:1477860
 [1];  [2];  [3];  [4];  [3];  [3]
  1. Univ. of Wisconsin, Madison, WI (United States). Department of Chemical and Biological Engineering; University of Wisconsin-Madison Department of Chemical and Biological Engineering
  2. Univ. of Wisconsin, Madison, WI (United States). Department of Chemical and Biological Engineering ; Utrecht University (The Netherlands). Faculty of Science, Debye Institute for Nanomaterials Science
  3. Univ. of Wisconsin, Madison, WI (United States). Department of Chemical and Biological Engineering
  4. Utrecht University (The Netherlands). Faculty of Science, Debye Institute for Nanomaterials Science
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In this article, we report on a new route to produce hexane-1,2,5,6-tetrol (tetrol) from cellulose-derived levoglucosanol (lgol). We investigate the reaction intermediates formed over metal and acid catalysts, and propose a reaction network for this process. Lgol is converted to tetrol in up to 90% yield over a bifunctional Pt/SiO2–Al2O3 catalyst at 150 °C. High tetrol yields are maintained at lgol concentrations of up to 21 wt% in water. threo- and erythro-lgol first undergo hydrolysis to 3,4-dideoxymannose (DDM) and 3,4-dideoxyglucose (DDG), respectively. This reaction can be carried out selectively over an Amberlyst 70 acid catalyst at a temperature of 100 °C. At a higher temperature of 150 °C with no added catalyst, DDM and DDG undergo aldose–ketose isomerization to 3,4-dideoxyfructose (DDF). DDM is hydrogenated to cis-tetrol over a Pt/SiO2 catalyst, while DDG is hydrogenated to trans-tetrol. Formation of DDF erases the stereocenter at the C2 position of lgol, and hydrogenation of DDF produces a nearly 1:1 mixture of cis- and trans-tetrol. Lastly, this catalytic approach to produce tetrol from biomass opens the door to sustainable chemicals derived from tetrol.

Research Organization:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B)
Contributing Organization:
University of Wisconsin-Madison Department of Chemistry; University of Wisconsin-Madison School of Pharmacy Analytical Instrumentation Center; Circa Group
Grant/Contract Number:
EE0006878
OSTI ID:
1477860
Alternate ID(s):
OSTI ID: 1471254
Journal Information:
Green Chemistry, Journal Name: Green Chemistry Journal Issue: 19 Vol. 20; ISSN GRCHFJ; ISSN 1463-9262
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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Cited By (1)

Catalytic hydrogenation of dihydrolevoglucosenone to levoglucosanol with a hydrotalcite/mixed oxide copper catalyst journal January 2019

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY