TY  - EJOU
AU  - Amarasekara, Ananda S. 
AU  - Morales, Gabriel Murillo 
AU  - Kommalapati, Raghava R. 

TI  - Vanillin Based Polymers: VI. <i>Poly</i>(hydrovanilloin-furfural) and <i>Poly</i>(hydrovanilloin-5-hydroxymethylfurfural)
T2  - Journal of Renewable Materials

PY  - 2024
VL  - 12
IS  - 9
SN  - 2164-6341

AB  - 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 <i>poly</i>(hydrovanilloin-furfural) [<i>poly</i>(HVL-Fur)] and <i>poly</i>(hydrovanilloin–5-hydromethylfurfural) [<i>poly</i>(HVL-5-HMF)]. Vanillin was dimerized to a mixtures of <i>meso/DL-</i>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 <i>poly</i>(HVL-Fur) with Mw = 8600 g mol<sup>−1</sup>, PDI = 1.28 in 78% yield. Similarly, condensation of hydrovanilloin with 5-hydroxymethylfurfural at 80°C for 48 h produced <i>poly</i>(HVL-5-HMF) with Mw = 12,100 g mol<sup>−1</sup>, PDI = 1.27 in 68% yield. <i>poly</i>(HVL-Fur) and <i>poly</i>(HVL-5-HMF) showed similar <i>T</i><sub><i>g</i></sub> values of 59°C and 60°C, respectively; whereas melting behaviors are dissimilar with <i>T</i><sub><i>m</i></sub> 171°C–173°C and 148°C–182°C, respectively.
KW  - Vanillin; hydrovanilloin; furfural; 5-hydroxymethylfurfural; renewable polymers

DO  - 10.32604/jrm.2024.052373