Vibrational properties of levulinic acid and furan derivatives: Raman spectroscopy and theoretical calculations

Authors

  • Taejin Kim,

    1. Chemical Sciences and Engineering, Division, Argonne National Laboratory, Argonne, IL 60439, USA
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  • 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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  • Larry A. Curtiss,

    1. Materials Science Division, Argonne National Laboratory, Argonne, IL 60439, USA
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  • Christopher L. Marshall,

    1. Chemical Sciences and Engineering, Division, Argonne National Laboratory, Argonne, IL 60439, USA
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  • Peter C. Stair

    Corresponding author
    1. Chemical Sciences and Engineering, Division, Argonne National Laboratory, Argonne, IL 60439, USA
    2. Department of Chemistry and Center for Catalysis and Surface Science, Northwestern University, Evanston, IL 60208, USA
    • Department of Chemistry and Center for Catalysis and Surface Science, Northwestern University, Evanston, IL 60208, USA.
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Abstract

In this work, the Raman spectra of furan, furfuryl alcohol (FA), furfural, hydroxymethylfurfural (HMF), and levulinic acid were obtained in the 500 to 4000 cm−1 spectral region at room temperature. Vibrational wavenumbers were calculated for these compounds with the B3LYP method using the 6-31 + G(2df,p) basis set. The experimentally determined C[DOUBLE BOND]C and C[BOND]C wavenumbers for furan and furan derivatives were in good agreement with the calculated wavenumbers without scaling factor, while the calculated C[DOUBLE BOND]O and C[BOND]H wavenumbers at ∼1660 and 3000 cm−1, respectively, showed larger deviations from the measured ones. The Raman spectra for furan and furan derivatives showed intense C[DOUBLE BOND]C bands, whereas the levulinic acid spectrum showed intense C[BOND]H vibrations with broad doublet C[DOUBLE BOND]O bands. We also found that an empirical method based on the chemical structure similarities is able to predict the HMF Raman spectrum from the combined furfural and FA spectra. Copyright © 2011 John Wiley & Sons, Ltd.

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