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Issue 2, 2015
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Renewable thermosetting resins and thermoplastics from vanillin

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Two cyanate ester resins and a polycarbonate thermoplastic have been synthesized from vanillin. The bisphenol precursors were prepared by both an electrochemical route as well as by a McMurry coupling reaction. 1,2-Bis(4-cyanato-3-methoxyphenyl)ethene (6) had a high melting point of 237 °C and did not cure completely under a standard cure protocol. In contrast, the reduced version, 1,2-bis(4-cyanato-3-methoxyphenyl)ethane (7) melted at 190 °C and underwent complete cure to form a thermoset material with Tg = 202 °C. 7 showed thermal stability up to 335 °C and decomposed via formation of phenolics and isocyanic acid. A polycarbonate was then synthesized from the reduced bisphenol by a transesterification reaction with diphenylcarbonate. The polymer had Mn = 3588, Mw/Mn = 1.9, and a Tg of 86 °C. TGA/FTIR data suggested that the polycarbonate decomposed via formation of benzodioxolones with concomitant elimination of methane. The results show that vanillin is a useful precursor to both thermosetting resins and thermoplastics without significant modification.

Graphical abstract: Renewable thermosetting resins and thermoplastics from vanillin

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The article was received on 19 Sep 2014, accepted on 27 Nov 2014 and first published on 27 Nov 2014

Article type: Paper
DOI: 10.1039/C4GC01825G
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Green Chem., 2015,17, 1249-1258

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    Renewable thermosetting resins and thermoplastics from vanillin

    B. G. Harvey, A. J. Guenthner, H. A. Meylemans, S. R. L. Haines, K. R. Lamison, T. J. Groshens, L. R. Cambrea, M. C. Davis and W. W. Lai, Green Chem., 2015, 17, 1249
    DOI: 10.1039/C4GC01825G

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