Poster

P3.5 – Bio-based polymers based on dehydrovanillin.

Eric Nijkamp

Linköping University / WWSC

Co-author(s):
Peter Olsén, Wallenberg Wood Science Center, Laboratory of Organic Electronics (LOE, Linköping University)

Bio-based vanillin is a relevant building block for a plethora of green polymer concepts. It can be obtained from the oxidative depolymerization of Kraft lignin [1]. This bio-based vanillin provides a lower CO_2 footprint compared to synthetic vanillin and is potentially scalable. Here we explore bio-based polyether concepts based on dehydrovanillin. The synthesis of dehydrovanillin from vanillin can be performed through a known enzymatic pathway using laccase [2]. The two C_α carbonyls in dehydrovanillin, were reduced to hydroxyl functional groups using NaBH_4 in ethanol with acidic workup. The formed hydroxyl groups potentially undergo a hypothesized polycondensation with primary and secondary alcohols forming a polyether. These polymers have the potential to be chemically recyclable and dynamic. From current results the reduction was successful and the polycondensation of the reduced was found to yield small oligomers. Despite optimal polymerization conditions yet to be found, here we show intriguing new polymer concepts using   dehydrovanillin.

References:1. Audrey Llevot, E. G., Stéphane Carlotti, Stéphane Grelier, Henri Cramail. (2016). Selective laccase-catalyzed dimerization of phenolic compounds derived from lignin: Towards original symmetrical bio-based (bis) aromatic monomers. Journal of Molecular Catalysis B: Enzymatic, 125, 34-41. https://doi.org/https://doi.org/10.1016/j.molcatb.2015.12.006 2. García-Rollán, M., Rivas-Márquez, M. N., Bertran-Llorens, S., Deuss, P. J., Ruiz-Rosas, R., Rosas, J. M., Rodríguez-Mirasol, J., & Cordero, T. (2024). Biobased Vanillin Production by Oxidative Depolymerization of Kraft Lignin on a Nitrogen- and Phosphorus-Functionalized Activated Carbon Catalyst. Energy & Fuels, 38(8), 7018-7032. https://doi.org/10.1021/acs.energyfuels.4c00108

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