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Mechanistic Investigation on Catalytic Deoxygenation of Phenol as a Model Compound of Biocrude Under Methane

  • Aiguo Wang
    Aiguo Wang
    Department of Chemical and Petroleum Engineering, University of Calgary, 2500 University Drive, NW, Calgary, Alberta T2N 1N4, Canada
    More by Aiguo Wang
  • Danielle Austin
    Danielle Austin
    Department of Chemical and Petroleum Engineering, University of Calgary, 2500 University Drive, NW, Calgary, Alberta T2N 1N4, Canada
  • Peng He
    Peng He
    Department of Chemical and Petroleum Engineering, University of Calgary, 2500 University Drive, NW, Calgary, Alberta T2N 1N4, Canada
    More by Peng He
  • Michelle Ha
    Michelle Ha
    Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta T6G 2G2, Canada
    More by Michelle Ha
  • Vladimir K. Michaelis
    Vladimir K. Michaelis
    Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta T6G 2G2, Canada
  • Lijia Liu
    Lijia Liu
    Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Institute of Functional Nano and Soft Materials (FUNSOM), Soochow University−Western University Centre for Synchrotron Radiation Research, Soochow University, Suzhou, Jiangsu 215123, China
    More by Lijia Liu
  • Hui Qian
    Hui Qian
    National Institute for Nanotechnology, National Research Council, Edmonton, Alberta T6G 2M9, Canada
    More by Hui Qian
  • Hongbo Zeng
    Hongbo Zeng
    Department of Chemical and Materials Engineering, University of Alberta, 9211-116 Street NW, Edmonton, Alberta T6G 1H9, Canada
    More by Hongbo Zeng
  • , and 
  • Hua Song*
    Hua Song
    Department of Chemical and Petroleum Engineering, University of Calgary, 2500 University Drive, NW, Calgary, Alberta T2N 1N4, Canada
    *Fax: +1 (403) 284-4852. Phone: +1 (403) 220-3792. E-mail: [email protected]
    More by Hua Song
Cite this: ACS Sustainable Chem. Eng. 2019, 7, 1, 1512–1523
Publication Date (Web):December 14, 2018
https://doi.org/10.1021/acssuschemeng.8b05272
Copyright © 2018 American Chemical Society

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    Abstract

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    A novel hydrogen-free approach is developed to effectively convert phenolic compounds into aromatics including benzene, toluene, ethylbenzene, and xylene (BTEX), a very important and widely used class of petrochemical intermediates, and naphthalene. High yield and selectivity of BTEX are achieved over Zn modified zeolite catalyst during phenol deoxygenation under a methane environment at 400 °C and 2 MPa. Methane can greatly enhance the liquid yield and selectivity of BTEX, but also improve the catalyst activity. Experimental analysis and mechanistic studies reveal that methane is incorporated into both the methyl group and aromatic ring. The embedding of methane into aromatic compounds is achieved via C-alkylation of phenyl ring, coaromatization with hydrocarbon radicals, and a ring-expansion/contraction mechanism. Liquid- and solid-state NMR investigations make evident the phenyl ring-opening in the reaction. Our mechanistic understanding of this process will provide valuable insights into the chemistry of phenolic deoxygenation, and open perspectives for valorization of biomass-derived oil with cheaper alternatives.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.8b05272.

    • XRD, TEM, DRIFT, NH3-TPD, H2-TPR, XPS, XAS, and solid-state NMR of 1%Zn/ZSM-5 at various life stages; solution-state NMR and GC-MS of gas and liquid products; and reaction rate measurement and calculation (PDF)

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    Cited By

    This article is cited by 13 publications.

    1. Abid Farooq, Gwang Hoon Rhee, Haneul Shim, Behzad Valizadeh, Jechan Lee, MoonisAli Khan, Byong-Hun Jeon, Seong-Ho Jang, Yong Jun Choi, Young-Kwon Park. Enhanced mono-aromatics production by the CH4-assisted pyrolysis of microalgae using Zn-based HZSM-5 catalysts. Chemosphere 2024, 351 , 141251. https://doi.org/10.1016/j.chemosphere.2024.141251
    2. Shijun Meng, Wenping Li, Zhaofei Li, Hua Song. Recent progress of the transition metal-based catalysts in the catalytic biomass gasification: A mini-review. Fuel 2023, 353 , 129169. https://doi.org/10.1016/j.fuel.2023.129169
    3. Hao Xu, Yimeng Li, Zhaofei Li, Yang Song, Yanyan Zhang, Hua Song. Methane-assisted waste cooking oil conversion for renewable fuel production. Fuel 2022, 311 , 122613. https://doi.org/10.1016/j.fuel.2021.122613
    4. Hua Song, Jack Jarvis, Shijun Meng, Hao Xu, Zhaofei Li, Wenping Li. Biomass Valorization Under Methane Environment. 2022, 163-193. https://doi.org/10.1007/978-3-030-88424-6_7
    5. Hua Song, Jack Jarvis, Shijun Meng, Hao Xu, Zhaofei Li, Wenping Li. Mechanism Studies on Biofuel Conversion Under Methane Environment. 2022, 195-248. https://doi.org/10.1007/978-3-030-88424-6_8
    6. Zhaofei Li, Yimeng Li, Hao Xu, Jack Jarvis, Shijun Meng, Hua Song. Effect of methane presence on catalytic heavy oil partial upgrading. Fuel 2021, 297 , 120733. https://doi.org/10.1016/j.fuel.2021.120733
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    8. Yimeng Li, Peng He, Zhaofei Li, Hao Xu, Jack Jarvis, Shijun Meng, Hua Song. Catalytic desulfurization of marine gas oil and marine diesel oil under methane environment. Fuel 2021, 289 , 119864. https://doi.org/10.1016/j.fuel.2020.119864
    9. Qinjie Cai, Taili Yu, Suping Zhang. Enhanced aromatic hydrocarbon production from bio-oil hydrotreating-cracking by Mo-Ga modified HZSM-5. Fuel 2020, 269 , 117386. https://doi.org/10.1016/j.fuel.2020.117386
    10. Yuan Xue, Ashokkumar Sharma, Jiajie Huo, Wangda Qu, Xianglan Bai. Low-pressure two-stage catalytic hydropyrolysis of lignin and lignin-derived phenolic monomers using zeolite-based bifunctional catalysts. Journal of Analytical and Applied Pyrolysis 2020, 146 , 104779. https://doi.org/10.1016/j.jaap.2020.104779
    11. Hehuan Peng, Aiguo Wang, Peng He, Jonathan Harrhy, Shijun Meng, Hua Song. Solvent-free catalytic conversion of xylose with methane to aromatics over Zn-Cr modified zeolite catalyst. Fuel 2019, 253 , 988-996. https://doi.org/10.1016/j.fuel.2019.05.088
    12. Aiguo Wang, Danielle Austin, Hua Song. Catalytic Upgrading of Biomass and its Model Compounds for Fuel Production. Current Organic Chemistry 2019, 23 (5) , 517-529. https://doi.org/10.2174/1385272823666190416160249
    13. Aiguo Wang, Danielle Austin, Hua Song. Investigations of thermochemical upgrading of biomass and its model compounds: Opportunities for methane utilization. Fuel 2019, 246 , 443-453. https://doi.org/10.1016/j.fuel.2019.03.015