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Heterogeneous catalytic dehydrogenative coupling of ethylene glycol and primary alcohols into α-hydroxycarboxylic acids

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Abstract

Lactic acid and other α-hydroxycarboxylic acids (α-HCAs) play crucial roles in various applications. Synthesizing α-HCAs from biomass platform feedstocks such as ethylene glycol (EG) and primary alcohols is novel and attractive. It was reported that the dehydrogenative cross-coupling of EG and primary alcohols can be achieved via homogeneous catalysis. Herein, we report a heterogeneous catalytic strategy to produce a series of α-HCAs through the same reaction pathway. Impressive catalytic activity and selectivity were achieved using various metals (Ru, Ir, Pt and Pd) supported on the nanodiamond-graphene (ND@G), with Ru exhibiting the best performance. This universally applicable process enables the easy synthesis of gram-scale α-HCAs, providing a straightforward and compelling C-C bond cross-coupling strategy for the utilization of alcohols derived from biomass feedstocks.

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Acknowledgements

This work received financial support from the National Key R&D Program of China (2022YFA1504800), the Natural Science Foundation of China (22005007, 21725301, 22232001), China National Petroleum Corporation-Peking University Strategic Cooperation Project of Fundamental Research, and the New Cornerstone Science Foundation. W.Z. acknowledges support from the Beijing Outstanding Young Scientist Program (BJJWZYJH01201914430039). D. M. acknowledges support from the Tencent Foundation through the XPLORER PRIZE. The XAFS was conducted at Beijing Synchrotron Radiation Facility.

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Author notes

  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Beijing National Laboratory for Molecular Sciences, New Cornerstone Science Laboratory, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China

    Shuheng Tian, Jiarui Li, Yao Xu, Maoling Wang, Haoyi Tang, Meng Wang & Ding Ma

  2. School of Physical Sciences and CAS Key Laboratory of Vacuum Sciences, University of Chinese Academy of Sciences, Beijing, 100049, China

    Xingjie Peng & Wu Zhou

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  1. Shuheng Tian
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  2. Jiarui Li
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  3. Xingjie Peng
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  4. Yao Xu
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  5. Maoling Wang
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  6. Haoyi Tang
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  7. Wu Zhou
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  8. Meng Wang
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  9. Ding Ma
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Corresponding authors

Correspondence to Meng Wang or Ding Ma.

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Conflict of interest The authors declare no conflict of interest.

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Supporting information The supporting information is available online at https://chem.scichina.com and https://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Tian, S., Li, J., Peng, X. et al. Heterogeneous catalytic dehydrogenative coupling of ethylene glycol and primary alcohols into α-hydroxycarboxylic acids. Sci. China Chem. 66, 2583–2589 (2023). https://doi.org/10.1007/s11426-023-1734-x

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  • DOI: https://doi.org/10.1007/s11426-023-1734-x

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