Acid-catalyzed furfuryl alcohol polymerization: Characterizations of molecular structure and thermodynamic properties

Taejin Kim, Rajeev S. Assary, Christopher L. Marshall, David J. Gosztola, Larry A. Curtiss, Peter C. Stair

Research output: Contribution to journalArticle

64 Citations (Scopus)

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,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. I'm with the band: The strong aliphatic C,C band (1654cm-1) observed in the measured Raman spectra is crucial evidence to understand the polymerization reaction mechanism (see figure). The formation of a conjugated diene structure instead of a diketone structure is involved in the furfuryl alcohol polymerization reaction. The B3LYP level of theory also indicates that the formation of diene is preferred over the formation of diketone.

Original languageEnglish
Pages (from-to)1451-1458
Number of pages8
JournalChemCatChem
Volume3
Issue number9
DOIs
Publication statusPublished - Sep 19 2011

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Keywords

  • Density functional theory
  • Diene
  • Furfuryl alcohol
  • Polymerization
  • Raman spectroscopy

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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