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Selective production of methylindan and tetralin with xylose or hemicellulose

Author

Listed:
  • Zhufan Zou

    (Chinese Academy of Sciences
    Dalian University of Technology
    University of Chinese Academy of Sciences)

  • Zhenjie Yu

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Weixiang Guan

    (Chinese Academy of Sciences)

  • Yanfang Liu

    (Chinese Academy of Sciences)

  • Yumin Yao

    (Chinese Academy of Sciences)

  • Yang Han

    (Chinese Academy of Sciences)

  • Guangyi Li

    (Chinese Academy of Sciences)

  • Aiqin Wang

    (Chinese Academy of Sciences
    Chinese Academy of Sciences)

  • Yu Cong

    (Chinese Academy of Sciences)

  • Xinmiao Liang

    (Chinese Academy of Sciences)

  • Tao Zhang

    (Chinese Academy of Sciences
    Dalian University of Technology
    Chinese Academy of Sciences)

  • Ning Li

    (Chinese Academy of Sciences)

Abstract

Indan and tetralin are widely used as fuel additives and the intermediates in the manufacture of thermal-stable jet fuel, many chemicals, medicines, and shockproof agents for rubber industry. Herein, we disclose a two-step route to selectively produce 5-methyl-2,3-dihydro-1H-indene (abbreviated as methylindan) and tetralin with xylose or the hemicelluloses from agricultural or forestry waste. Firstly, cyclopentanone (CPO) was selectively formed with ~60% carbon yield by the direct hydrogenolysis of xylose or hemicelluloses on a non-noble bimetallic Cu-La/SBA-15 catalyst. Subsequently, methylindan and tetralin were selectively produced with CPO via a cascade self-aldol condensation/rearrangement/aromatization reaction catalyzed by a commercial H-ZSM-5 zeolite. When we used cyclohexanone (another lignocellulosic cycloketone) in the second step, the main product switched to dimethyltetralin. This work gives insights into the selective production of bicyclic aromatics with lignocellulose.

Suggested Citation

  • Zhufan Zou & Zhenjie Yu & Weixiang Guan & Yanfang Liu & Yumin Yao & Yang Han & Guangyi Li & Aiqin Wang & Yu Cong & Xinmiao Liang & Tao Zhang & Ning Li, 2024. "Selective production of methylindan and tetralin with xylose or hemicellulose," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-48101-x
    DOI: 10.1038/s41467-024-48101-x
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    References listed on IDEAS

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    1. Pazhamalai Anbarasan & Zachary C. Baer & Sanil Sreekumar & Elad Gross & Joseph B. Binder & Harvey W. Blanch & Douglas S. Clark & F. Dean Toste, 2012. "Integration of chemical catalysis with extractive fermentation to produce fuels," Nature, Nature, vol. 491(7423), pages 235-239, November.
    2. Wang, Tiejun & Li, Kai & Liu, Qiying & Zhang, Qing & Qiu, Songbai & Long, Jinxing & Chen, Lungang & Ma, Longlong & Zhang, Qi, 2014. "Aviation fuel synthesis by catalytic conversion of biomass hydrolysate in aqueous phase," Applied Energy, Elsevier, vol. 136(C), pages 775-780.
    3. Yuriy Román-Leshkov & Christopher J. Barrett & Zhen Y. Liu & James A. Dumesic, 2007. "Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates," Nature, Nature, vol. 447(7147), pages 982-985, June.
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