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Sustainable synthesis of novel 3-(2-furyl)acrylic acids and their derivatives from carbohydrate-derived furfurals by chemical catalysis

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Abstract

This work reports the renewable synthesis of 3-(2-furyl)acrylic acid and its novel-substituted derivatives, with potential applications as sustainable chemical building units, starting from carbohydrate-derived 5-substituted-2-furaldehydes and malonic acid employing various organocatalysts. Piperidinium acetate as the catalyst afforded good to excellent isolated yields of the acrylic acids under solvent-free conditions. The substituted 3-(2-furyl)acrylic acids were esterified using MeSO3H/SiO2 as a heterogeneous acid catalyst. The 3-(2-furyl)acrylic acids containing acid-sensitive functional groups on the furan ring were esterified by dimethyl carbonate as the sustainable reagent by base-catalyzed transesterification reaction. Moreover, the olefinic group was selectively reduced by catalytic hydrogenation using 5%Pd/C as the catalyst. The catalytic processes were optimized on various reaction parameters, and the synthesized compounds were characterized by FTIR, NMR (1H, 13C), and elemental analysis.

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Data availability

The supplementary information available with this manuscript contains the spectroscopic (FTIR, 1H-NMR, and 13C-NMR) characterization and elemental analysis data of all synthesized compounds reported in this manuscript.

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Acknowledgements

The authors thank Central Research Facility (CRF), NITK, Surathkal, and Raman Research Institute (RRI), Bangalore, for their assistance in collecting the NMR and Elemental Analysis data. Saikat Dutta thanks the Center for Sustainable Energy Engineering (CSEE) at NITK, Surathkal, for helpful discussions. PSP thanks NITK, Surathkal, for scholarship support.

Funding

This study is funded by DST-SERB under the Core Research Grant (CRG) scheme (file no. CRG/2022/009346).

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Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, Mangalore, Karnataka, 575025, India

    Poornachandra Shamanna Prabhakar & Saikat Dutta

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  1. Poornachandra Shamanna Prabhakar
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  2. Saikat Dutta
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Contributions

Poornachandra Shamanna Prabhakar performed the experiments and analyzed the synthetic and spectroscopic data. Saikat Dutta conceptualized the idea, supervised the work, and wrote the original manuscript.

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Correspondence to Saikat Dutta.

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Prabhakar, P.S., Dutta, S. Sustainable synthesis of novel 3-(2-furyl)acrylic acids and their derivatives from carbohydrate-derived furfurals by chemical catalysis. Biomass Conv. Bioref. (2023). https://doi.org/10.1007/s13399-023-05029-4

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