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Ambient-pressure alkoxycarbonylation for sustainable synthesis of ester

Author

Listed:
  • Bin Zhang

    (CAS Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    Cardiff Catalysis Institute, School of Chemistry, Cardiff University)

  • Haiyang Yuan

    (Shanghai Engineering Research Center of Hierarchical Nanomaterials, School of Materials Science and Engineering, East China University of Science and Technology, 130 Meilong Road)

  • Ye Liu

    (CAS Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    Wuhan University of Technology)

  • Zijie Deng

    (CAS Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Mark Douthwaite

    (Cardiff Catalysis Institute, School of Chemistry, Cardiff University)

  • Nicholas F. Dummer

    (Cardiff Catalysis Institute, School of Chemistry, Cardiff University)

  • Richard J. Lewis

    (Cardiff Catalysis Institute, School of Chemistry, Cardiff University)

  • Xingwu Liu

    (Synfuels China Co., Ltd, Huairou District)

  • Sen Luan

    (CAS Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Minghua Dong

    (CAS Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Tianjiao Wang

    (CAS Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Qingling Xu

    (University of Chinese Academy of Sciences)

  • Zhijuan Zhao

    (Chinese Academy of Sciences)

  • Huizhen Liu

    (CAS Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Buxing Han

    (CAS Laboratory of Colloid and Interface and Thermodynamics, Center for Carbon Neutral Chemistry, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Graham J. Hutchings

    (Cardiff Catalysis Institute, School of Chemistry, Cardiff University)

Abstract

Alkoxycarbonylation reactions are common in the chemical industry, yet process sustainability is limited by the inefficient utilization of CO. In this study, we address this issue and demonstrate that significant improvements can be achieved by adopting a heterogeneously catalyzed process, using a Ru/NbOx catalyst. The Ru/NbOx catalyst enables the direct synthesis of methyl propionate, a key industrial commodity, with over 98% selectivity from CO, ethylene and methanol, without any ligands or acid/base promoters. Under ambient CO pressure, a high CO utilization efficiency (336 mmolestermolCO−1h−1) is achieved. Mechanistic investigations reveal that CO undergoes a methoxycarbonyl (COOCH3) intermediate pathway, attacking the terminal carbon atom of alkene and yielding linear esters. The origins of prevailing linear regioselectivity in esters are revealed. The infrared spectroscopic feature of the key COOCH3 species is observed at 1750 cm−1 (C=O vibration) both experimentally and computationally. The broad substrate applicability of Ru/NbOx catalyst for ester production is demonstrated. This process offers a sustainable and efficient approach with high CO utilization and atom economy for the synthesis of esters.

Suggested Citation

  • Bin Zhang & Haiyang Yuan & Ye Liu & Zijie Deng & Mark Douthwaite & Nicholas F. Dummer & Richard J. Lewis & Xingwu Liu & Sen Luan & Minghua Dong & Tianjiao Wang & Qingling Xu & Zhijuan Zhao & Huizhen L, 2024. "Ambient-pressure alkoxycarbonylation for sustainable synthesis of ester," Nature Communications, Nature, vol. 15(1), pages 1-13, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52163-2
    DOI: 10.1038/s41467-024-52163-2
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    References listed on IDEAS

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    1. Shaopeng Li & Minghua Dong & Junjuan Yang & Xiaomeng Cheng & Xiaojun Shen & Shulin Liu & Zhi-Qiang Wang & Xue-Qing Gong & Huizhen Liu & Buxing Han, 2021. "Selective hydrogenation of 5-(hydroxymethyl)furfural to 5-methylfurfural over single atomic metals anchored on Nb2O5," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    2. Insoo Ro & Ji Qi & Seungyeon Lee & Mingjie Xu & Xingxu Yan & Zhenhua Xie & Gregory Zakem & Austin Morales & Jingguang G. Chen & Xiaoqing Pan & Dionisios G. Vlachos & Stavros Caratzoulas & Phillip Chri, 2022. "Bifunctional hydroformylation on heterogeneous Rh-WOx pair site catalysts," Nature, Nature, vol. 609(7926), pages 287-292, September.
    3. Haifeng Qi & Yurou Li & Zhitong Zhou & Yueqiang Cao & Fei Liu & Weixiang Guan & Leilei Zhang & Xiaoyan Liu & Lin Li & Yang Su & Kathrin Junge & Xuezhi Duan & Matthias Beller & Aiqin Wang & Tao Zhang, 2023. "Synthesis of piperidines and pyridine from furfural over a surface single-atom alloy Ru1CoNP catalyst," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
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