Open Access

ARTICLE

Vanillin Based Polymers: VI. Poly(hydrovanilloin-furfural) and Poly(hydrovanilloin-5-hydroxymethylfurfural)

Ananda S. Amarasekara^1,2,*, Gabriel Murillo Morales^1,2, Raghava R. Kommalapati^2,3

1 Department of Chemistry, Prairie View A&M University, 700 University Drive, Prairie View, TX 77446, USA
2 Center for Energy & Environmental Sustainability, Prairie View A&M University, 700 University Drive, Prairie View, TX 77446, USA
3 Department of Civil and Environmental Engineering, Prairie View A&M University, 700 University Drive, Prairie View, TX 77446, USA

* Corresponding Author: Ananda S. Amarasekara. Email:

(This article belongs to the Special Issue: Recent Advances on Renewable Materials)

Journal of Renewable Materials 2024, 12(9), 1495-1506. https://doi.org/10.32604/jrm.2024.052373

Received 31 March 2024; Accepted 30 July 2024; Issue published 25 September 2024

Abstract

Renewable resources based polymers provides a sustainable alternative to petroleum derived polymeric materials. As a part of our series on synthesis of vanillin based renewable polymers, we report the synthesis of poly(hydrovanilloin-furfural) [poly(HVL-Fur)] and poly(hydrovanilloin–5-hydromethylfurfural) [poly(HVL-5-HMF)]. Vanillin was dimerized to a mixtures of meso/DL-hydrovanilloins with 94% meso product by electrochemical reductive coupling in aqueous sodium hydroxide using lead electrodes in quantitative yield. Then sodium hydroxide catalyzed condensation of hydrovanilloin with furfural in water at 80°C for 72 h was used to synthesize poly(HVL-Fur) with Mw = 8600 g mol⁻¹, PDI = 1.28 in 78% yield. Similarly, condensation of hydrovanilloin with 5-hydroxymethylfurfural at 80°C for 48 h produced poly(HVL-5-HMF) with Mw = 12,100 g mol⁻¹, PDI = 1.27 in 68% yield. poly(HVL-Fur) and poly(HVL-5-HMF) showed similar T_g values of 59°C and 60°C, respectively; whereas melting behaviors are dissimilar with T_m 171°C–173°C and 148°C–182°C, respectively.

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