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Selective Conversion of Cellulose to Hydroxymethylfurfural in Polar Aprotic Solvents

Authors

  • Ronen Weingarten,

    1. Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 3018 Engineering Hall, 1415 Engineering Drive, Madison, WI 53706-1691
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  • Alexandra Rodriguez-Beuerman,

    1. Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 3018 Engineering Hall, 1415 Engineering Drive, Madison, WI 53706-1691
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  • Dr. Fei Cao,

    1. Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 3018 Engineering Hall, 1415 Engineering Drive, Madison, WI 53706-1691
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  • Dr. Jeremy S. Luterbacher,

    1. Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 3018 Engineering Hall, 1415 Engineering Drive, Madison, WI 53706-1691
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  • Dr. David Martin Alonso,

    1. Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 3018 Engineering Hall, 1415 Engineering Drive, Madison, WI 53706-1691
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  • Prof. James A. Dumesic,

    1. Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 3018 Engineering Hall, 1415 Engineering Drive, Madison, WI 53706-1691
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  • Prof. George W. Huber

    Corresponding author
    1. Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 3018 Engineering Hall, 1415 Engineering Drive, Madison, WI 53706-1691
    • Department of Chemical and Biological Engineering, University of Wisconsin-Madison, 3018 Engineering Hall, 1415 Engineering Drive, Madison, WI 53706-1691

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Abstract

Herein, we report a new reaction pathway to produce hydroxymethylfurfural (HMF) from cellulose under mild reaction conditions (140–190 °C; 5 mM H2SO4) in polar aprotic solvents (i.e. THF) without the presence of water. In this system, levoglucosan is the major decomposition product of cellulose, followed by dehydration to produce HMF. Glucose, levulinic acid, and formic acid are also produced as a result of side reactions with water, which is a by-product of dehydration. The turnover frequency for cellulose conversion increases as the water content in the solvent decreases, with conversion rates in THF being more than twenty times higher than those in water. The highest HMF yield from cellulose was 44 % and the highest combined yield of HMF and levulinic from cellulose was 53 %, which are nearly comparable to yields obtained in ionic liquids or biphasic systems. Moreover, the use of a low boiling point solvent, such as THF, facilitates recovery of HMF in downstream processes.

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