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Effect of Metal Catalysts on Bond Cleavage Reactions of Lignin Model Compounds in Supercritical Water

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Abstract

Lignin depolymerization into its aromatic monomers is necessary for the valorization of lignocellulosic biomass, but cleavage of the C–O ether bonds and C–C bonds between the monomers is challenging. In this study, we investigated bond cleavage reactions of benzyl phenyl ether, diphenyl ether, and biphenyl, which served as models for lignin compounds with α–O–4, 4–O–5, and 5–5 linkages, respectively, by using various metal catalysts in supercritical water at 673 K and a water density of 0.5 g cm−3 without added hydrogen gas. Benzyl phenyl ether was decomposed without catalyst. We found that palladium, platinum, and rhodium catalysts supported on carbon showed activity for cleavage of the C–O ether bonds in benzyl phenyl ether and diphenyl ether but not for the bonds between the aromatic units of biphenyl. Using anisole as a model compound, we also found that methoxy groups, which are present in lignin containing coniferyl and sinapyl alcohol monomers, were converted into phenol groups or were decomposed. The reaction conditions described herein have great potential utility for the conversion of lignin, which can be decomposed and dissolved in supercritical water, into valuable aromatic compounds.

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Acknowledgements

This study was partially supported by a JSPS KAKENHI Grant (JP17H00803) and by the Japan Association of Chemical Innovation (JACI) through the New Chemical Technology Research Encouragement Award, Step-Up Award.

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Authors and Affiliations

  1. Research Institute for Chemical Process Technology, National Institute of Advanced Industrial Science and Technology (AIST), 4-2-1 Nigatake, Miyagino, Sendai, 983-8551, Japan

    Aritomo Yamaguchi, Naoki Mimura, Masayuki Shirai & Osamu Sato

  2. Department of Chemistry and Biological Sciences, Faculty of Science and Engineering, Iwate University, Ueda 4-3-5, Morioka, Iwate, 020-8551, Japan

    Masayuki Shirai

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  1. Aritomo Yamaguchi
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Correspondence to Aritomo Yamaguchi.

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Yamaguchi, A., Mimura, N., Shirai, M. et al. Effect of Metal Catalysts on Bond Cleavage Reactions of Lignin Model Compounds in Supercritical Water. Waste Biomass Valor 11, 669–674 (2020). https://doi.org/10.1007/s12649-019-00647-4

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