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Vanillin based polymers: III. Electrochemical dimerization of vanillin revisited and synthesis of hydrovanilloin–formaldehyde polymer

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Abstract

Electrochemical dimerization of vanillin in basic medium produced mixtures of meso/DL-hydrovanilloins, in contrary to earlier claims of the formation of meso-hydrovanilloin as the sole product. In the reinvestigation we have found that meso-percentage depends on the current density and the highest meso-percentage of 94% is achieved under 64 mA/cm2 current density, using Pb electrodes and 1.25 M aqueous NaOH as the electrolyte. Condensation of the renewable resources based monomer hydrovanilloin with formaldehyde in aqueous NaOH gives hydrovanilloin–formaldehyde polymer in 91% yield. The linear polymer is shown to contain hydrovanilloin units with methylene bridges connecting C-6 positions of the aromatic rings.

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Authors and Affiliations

  1. Department of Chemistry, Prairie View A&M University, Prairie View, Texas, 77446, USA

    Ananda S. Amarasekara & Muhammad A. Hasan

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  1. Ananda S. Amarasekara
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  2. Muhammad A. Hasan
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Correspondence to Ananda S. Amarasekara.

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Amarasekara, A.S., Hasan, M.A. Vanillin based polymers: III. Electrochemical dimerization of vanillin revisited and synthesis of hydrovanilloin–formaldehyde polymer. Polym. Sci. Ser. B 58, 307–312 (2016). https://doi.org/10.1134/S1560090416030015

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  • DOI: https://doi.org/10.1134/S1560090416030015

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