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Cleaving the β[BOND]O[BOND]4 Bonds of Lignin Model Compounds in an Acidic Ionic Liquid, 1-H-3-Methylimidazolium Chloride: An Optional Strategy for the Degradation of Lignin

Authors

  • Songyan Jia,

    1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, 158 Zhongshan Road, Dalian, Liaoning 116012 (PR China)
    2. Department of Chemical Engineering, The University of Texas at Austin, 1 University Station C0400, Austin, TX 78712 (USA), Fax: (+1) 512-471-7060
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  • Blair J. Cox,

    1. Department of Chemical Engineering, The University of Texas at Austin, 1 University Station C0400, Austin, TX 78712 (USA), Fax: (+1) 512-471-7060
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  • Prof. Xinwen Guo,

    1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, 158 Zhongshan Road, Dalian, Liaoning 116012 (PR China)
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  • Dr.  Z. Conrad Zhang,

    1. KiOR Inc. 13001 Bay Park Road, Pasadena, TX 77507 (USA)
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  • Dr. John G. Ekerdt

    1. Department of Chemical Engineering, The University of Texas at Austin, 1 University Station C0400, Austin, TX 78712 (USA), Fax: (+1) 512-471-7060
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Abstract

The hydrolysis of β[BOND]O[BOND]4 bonds in two lignin model compounds was studied in an acidic ionic liquid, 1-H-3-methylimidazolium chloride. The β[BOND]O[BOND]4 bonds of both guaiacylglycerol-β-guaiacyl ether and veratrylglycerol-β-guaiacyl ether underwent catalytic hydrolysis to produce guaiacol as the primary product with more than 70 % yield at 150 °C. Up to 32 wt % substrate concentration could be treated in the system without a decrease in guaiacol production. The ionic liquid could be reused without loss of activity in guaiacol production from both guaiacylglycerol-β-guaiacyl ether and veratrylglycerol-β-guaiacyl ether. A possible mechanism accounting for the guaiacol production is presented.

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