Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass

Green synthesis of adipic acid from renewable biomass is a very attractive goal of sustainable chemistry. Herein, we report efficient catalysts for a two-step transformation of cellulose-derived glucose into adipic acid via glucaric acid. Carbon nanotube-supported platinum nanoparticles are found to work efficiently for the oxidation of glucose to glucaric acid. An activated carbon-supported bifunctional catalyst composed of rhenium oxide and palladium is discovered to be powerful for the removal of four hydroxyl groups in glucaric acid, affording adipic acid with a 99 % yield. Rhenium oxide functions for the deoxygenation but is less efficient for four hydroxyl group removal. The co-presence of palladium not only catalyzes the hydrogenation of olefin intermediates but also synergistically facilitates the deoxygenation. This work presents a green route for adipic acid synthesis and offers a bifunctional-catalysis strategy for efficient deoxygenation.

Keywords: adipic acid; biomass; glucose; heterogeneous catalysis; sustainable chemistry.

© 2020 Wiley-VCH GmbH.

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References

    1. None
    1. K. Sato, M. Aoki, R. Noyori, Science 1998, 281, 1646-1647;
    1. K. C. Hwang, A. Sagadevan, Science 2014, 346, 1495-1498;
    1. J. Yang, J. Liu, H. Neumann, R. Franke, R. Jackstell, M. Beller, Science 2019, 366, 1514-1517.
    1. S. Van de Vyver, Y. Román-Leshkov, Catal. Sci. Technol. 2013, 3, 1465-1479.