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Understanding the interplay between electrocatalytic C(sp3)‒C(sp3) fragmentation and oxygenation reactions

Nature Catalysis volume 7, pages 1021–1031 (2024)Cite this article

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Abstract

Achieving the selective electrocatalytic activation of C(sp3)–C(sp3) and C(sp3)−H bonds is key to enabling the electricity-driven synthesis of chemicals, the sustainable upgrading of plastics and the development of fuel cells operating on energy-dense liquid fuels. When exposed to electrodes under oxidative bias, hydrocarbons undergo both C–C bond fragmentation and oxygenation. Currently, we lack control over the bifurcation of these pathways. Here we provide insights into the complex network of alkyl transformation reactions, showing that under oxidizing potentials, adsorbed butane transforms to adsorbed CHx fragments, which can be desorbed as methane before oxidation to adsorbed CO. Identifying the branchpoint between C‒C fragmentation and oxygenation allowed us to steer selectivity by applying pulsed potentials tailored to the desorption potential of specific adsorbates and the kinetics of intermediate oxidation. Our findings provide design criteria for improved fuel cell catalysts and open the door to selective C‒C cleavage in electrosynthetic pathways.

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Fig. 1: EC-MS interrogation of the alkane fragmentation and oxidation branchpoint.
Fig. 2: Potential dependence of butane adsorption and fragmentation on Pt.
Fig. 3: Oxidative stripping of butane-derived adsorbates.
Fig. 4: Potential-induced transformation of adsorbed butane.
Fig. 5: Proposed bifurcation towards butane fragmentation and oxidation.
Fig. 6: Reaction network of butane oxidation and fragmentation.
Fig. 7: Pulsed potential programme for increased methane generation.

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Data availability

Experimental raw data underlying the results and conclusions of this work are publicly available via Zenodo at https://doi.org/10.5281/zenodo.12801616 (ref. 84). Other data are available from the authors upon reasonable request.

Code availability

The code used to transform ionic current data to species fluxes are publicly accessible via Zenodo at https://doi.org/10.5281/zenodo.12801616 (ref. 84).

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Acknowledgements

We thank M. Kelly for input. This work was supported by the Arnold and Mabel Beckman Foundation through a Beckman Young Investigator Award (https://doi.org/10.13039/100000997, M.S.). We also acknowledge summer salary support from an NSF CAREER award (CBET-2338627, M.S.) and the use of facilities and instrumentation at the UW–Madison Wisconsin Centers for Nanoscale Technology, partially supported by the NSF through the University of Wisconsin Materials Research Science and Engineering Center (DMR-1720415). This report is based upon work supported by the National Science Foundation Graduate Research Fellowship Program (grant no. DGE-1747503, C.L.). Any opinions, findings, and conclusions or recommendations expressed in this paper are those of the authors and do not necessarily reflect the views of the National Science Foundation. Support was also provided by the Graduate School and the Office of the Vice Chancellor for Research and Graduate Education at the University of Wisconsin–Madison with funding from the Wisconsin Alumni Research Foundation (C.L.).

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  1. Department of Chemical and Biological Engineering, University of Wisconsin–Madison, Madison, WI, USA

    Christine Lucky, Shengli Jiang, Chien-Rung Shih, Victor M. Zavala & Marcel Schreier

  2. Department of Chemistry, University of Wisconsin–Madison, Madison, WI, USA

    Marcel Schreier

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Contributions

C.L. and M.S. conceived the project. C.L. designed and performed the experiments. C-R.S. assisted with data collection. S.J. developed the mass spectrum deconvolution methodology and code with assistance from C.L. and V.M.Z. C.L., M.S. and S.J. analysed the data. C.L. and M.S. wrote the paper with S.J. and V.M.Z. contributing to revisions. M.S. and V.M.Z. provided funding acquisition and project supervision.

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Correspondence to Marcel Schreier.

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Competing interests

C.L. and M.S. are inventors for US patent application 17/959744 (2023), which has been filed on the partial basis of this work. All other authors have no competing interests.

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Lucky, C., Jiang, S., Shih, CR. et al. Understanding the interplay between electrocatalytic C(sp3)‒C(sp3) fragmentation and oxygenation reactions. Nat Catal 7, 1021–1031 (2024). https://doi.org/10.1038/s41929-024-01218-0

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