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Acid-Catalyzed Furfuryl Alcohol Polymerization: Characterizations of Molecular Structure and Thermodynamic Properties

Authors

  • Dr. Taejin Kim,

    1. Chemical Sciences and Engineering Division, Argonne National Laboratory, Argonne, IL 60439 (USA)
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  • Dr. Rajeev S. Assary,

    1. Materials Science Division, Argonne National Laboratory, Argonne, IL 60439 (USA)
    2. Department of Chemical and Biological Engineering, Northwestern University, Evanston, IL 60208 (USA)
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  • Dr. Christopher L. Marshall,

    1. Chemical Sciences and Engineering Division, Argonne National Laboratory, Argonne, IL 60439 (USA)
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  • Dr. David J. Gosztola,

    1. Center for Nanoscale Materials, Argonne National Laboratory, Argonne, IL 60439 (USA), Fax: (+1) 630-252-9555
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  • Dr. Larry A. Curtiss,

    Corresponding author
    1. Materials Science Division, Argonne National Laboratory, Argonne, IL 60439 (USA)
    2. Center for Nanoscale Materials, Argonne National Laboratory, Argonne, IL 60439 (USA), Fax: (+1) 630-252-9555
    • Materials Science Division, Argonne National Laboratory, Argonne, IL 60439 (USA)
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  • Prof. Peter C. Stair

    Corresponding author
    1. Chemical Sciences and Engineering Division, Argonne National Laboratory, Argonne, IL 60439 (USA)
    2. Department of Chemistry, Northwestern University, Evanston, IL 60208 (USA), Fax: (+1) 847-467-1018
    • Chemical Sciences and Engineering Division, Argonne National Laboratory, Argonne, IL 60439 (USA)
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Abstract

The liquid-phase polymerization of furfuryl alcohol catalyzed by sulfuric acid catalysts and the identities of molecular intermediates were investigated by using Raman spectroscopy and density functional theory calculation. At room temperature, with an acid catalyst, a vigorous furfuryl alcohol polymerization reaction was observed, whereas even at a high water concentration, furfuryl alcohol was very stable in the absence of an acid catalyst. Theoretical studies were carried out to investigate the thermodynamics of protonation of furfuryl alcohol, initiation of polymerization, and formation of conjugated dienes and diketonic species by using the B3LYP level of theory. A strong aliphatic C[DOUBLE BOND]C band observed in the calculated and measured Raman spectra provided crucial evidence to understand the polymerization reaction mechanism. It is confirmed that the formation of a conjugated diene structure rather than a diketone structure is involved in the furfuryl alcohol polymerization reaction.

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