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A solution for 4-propylguaiacol hydrodeoxygenation without ring saturation

Author

Listed:
  • Zihao Zhang

    (Paul Scherrer Institute)

  • Qiang Li

    (University of Delaware)

  • Xiangkun Wu

    (Paul Scherrer Institute)

  • Claire Bourmaud

    (École Polytechnique Fédérale de Lausanne (EPFL), Station 6)

  • Dionisios G. Vlachos

    (University of Delaware
    University of Delaware)

  • Jeremy Luterbacher

    (École Polytechnique Fédérale de Lausanne (EPFL), Station 6)

  • Andras Bodi

    (Paul Scherrer Institute)

  • Patrick Hemberger

    (Paul Scherrer Institute)

Abstract

We investigate solvent effects in the hydrodeoxygenation of 4-propylguaiacol (4PG, 166 amu), a key lignin-derived monomer, over Ru/C catalyst by combined operando synchrotron photoelectron photoion coincidence (PEPICO) spectroscopy and molecular dynamics simulations. With and without isooctane co-feeding, ring-hydrogenated 2-methoxy-4-propylcyclohexanol (172 amu) is the first product, due to the favorable flat adsorption configuration of 4PG on the catalyst surface. In contrast, tetrahydrofuran (THF)—a polar aprotic solvent that is representative of those used for lignin solubilization and upgrading—strongly coordinates to the catalyst surface at the oxygen atom. This induces a local steric hindrance, blocking the flat adsorption of 4PG more effectively, as it needs more Ru sites than the tilted adsorption configuration revealed by molecular dynamics simulations. Therefore, THF suppresses benzene ring hydrogenation, favoring a demethoxylation route that yields 4-propylphenol (136 amu), followed by dehydroxylation to propylbenzene (120 amu). Solvent selection may provide new avenues for controlling catalytic selectivity.

Suggested Citation

  • Zihao Zhang & Qiang Li & Xiangkun Wu & Claire Bourmaud & Dionisios G. Vlachos & Jeremy Luterbacher & Andras Bodi & Patrick Hemberger, 2024. "A solution for 4-propylguaiacol hydrodeoxygenation without ring saturation," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50724-z
    DOI: 10.1038/s41467-024-50724-z
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    1. Yi Shao & Qineng Xia & Lin Dong & Xiaohui Liu & Xue Han & Stewart F. Parker & Yongqiang Cheng & Luke L. Daemen & Anibal J. Ramirez-Cuesta & Sihai Yang & Yanqin Wang, 2017. "Selective production of arenes via direct lignin upgrading over a niobium-based catalyst," Nature Communications, Nature, vol. 8(1), pages 1-9, December.
    2. Ambursa, Murtala M. & Juan, Joon Ching & Yahaya, Y. & Taufiq-Yap, Y.H. & Lin, Yu-Chuan & Lee, Hwei Voon, 2021. "A review on catalytic hydrodeoxygenation of lignin to transportation fuels by using nickel-based catalysts," Renewable and Sustainable Energy Reviews, Elsevier, vol. 138(C).
    3. Rong, Siteng & Tan, Hongzi & Pang, Zhaobin & Zong, Zhiyuan & Zhao, Rongrong & Li, Zhihe & Chen, Zhe-Ning & Zhang, Ning-Ning & Yi, Weiming & Cui, Hongyou, 2022. "Synergetic effect between Pd clusters and oxygen vacancies in hierarchical Nb2O5 for lignin-derived phenol hydrodeoxygenation into benzene," Renewable Energy, Elsevier, vol. 187(C), pages 271-281.
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