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Effect of formation behavior of hydrocarbons and solid component from cellulose on catalytic transfer hydrogenation in straight-chain aliphatic hydrocarbon solvent

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Abstract

Hydrogen transfer using a hydrogen donor solvent is promising for converting cellulose to liquid fuel. Alcohol and cyclic compounds are used as a hydrogen donor solvent, but the solvent affects the properties of liquid fuel. Therefore, the cellulose-derived liquid fuel and the solvent need to be separated. We focus on a straight-chain aliphatic hydrocarbon as a hydrogen source and solvent. Hydrogen transfer is expected by using palladium on activated catalyst (Pd/C) in combination with a solvent because palladium can dehydrogenate alkanes and is used as a hydrogenation metal. After the reaction, straight-chain aliphatic hydrocarbons remain in the cellulose-derived liquid fuel because they are similar to transportation fuel. Our previous study has reported that cellulose is converted into hydrocarbons by liquefaction using hexadecane containing Pd/C. However, the factors for deriving the optimum reaction conditions are unclear, such as the conversion route of cellulose to hydrocarbon and the formation mechanism of a solid component. In this study, we investigate the mechanism of the conversion of cellulose. The results indicate that the cellulose-derived oxygenates absorb on cellulose surface and form a solid component. In contrast, when Pd/C was added to tetradecane solvent, the oxygenates are hydrogenated to solvent-soluble compounds, resulting in suppressing the formation of solid components. The solvent-soluble compounds are deoxygenated to ketones, and then, the compounds changed to cyclopentanones and cyclohexanones which are the number of carbons > 6 at 330 °C because aldol condensation with the ketones occurs. Subsequently, the ketones are deoxygenated to hydrocarbons containing C10–C20 at 350 °C.

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  1. Kentaro Kimura

    Present address: Department of Materials and Applied Chemistry, Graduate School of Science and Technology, Nihon University, 1-8-14, Kanda-Surugadai, Chiyoda-ku, Tokyo, 101-8308, Japan

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  1. Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, 1-8-14, Kanda-Surugadai, Chiyoda-ku, Tokyo, 101-8308, Japan

    Yusuke Kakuta, Eri Watanabe & Kiyofumi Kurihara

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Kentaro Kimura, Yusuke Kakuta, and Kiyofumi Kurihara contributed to the conception or design of the work. Kentaro Kimura and Eri Watanabe helped in performing the catalytic reactions and analysis, and interpreted data for the study. All the authors debated the results and co-wrote the manuscript.

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Kimura, K., Kakuta, Y., Watanabe, E. et al. Effect of formation behavior of hydrocarbons and solid component from cellulose on catalytic transfer hydrogenation in straight-chain aliphatic hydrocarbon solvent. Biomass Conv. Bioref. 13, 9903–9917 (2023). https://doi.org/10.1007/s13399-021-01823-0

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