Highly efficient catalytic production of oximes from ketones using in situ-generated H2O2

Richard J. Lewis, Kenji Ueura, Xi Liu, Yukimasa Fukuta, Thomas E. Davies, David J. Morgan, Liwei Chen, Jizhen Qi, James Singleton, Jennifer K. Edwards, Simon J. Freakley, Christopher J. Kiely, Yasushi Yamamoto, Graham J. Hutchings

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Abstract

The ammoximation of cyclohexanone using preformed hydrogen peroxide (H2O2) is currently applied commercially to produce cyclohexanone oxime, an important feedstock in nylon-6 production. We demonstrate that by using supported gold-palladium (AuPd) alloyed nanoparticles in conjunction with a titanium silicate-1 (TS-1) catalyst, H2O2 can be generated in situ as needed, producing cyclohexanone oxime with >95% selectivity, comparable to the current industrial route. The ammoximation of several additional simple ketones is also demonstrated. Our approach eliminates the need to transport and store highly concentrated, stabilized H2O2, potentially achieving substantial environmental and economic savings. This approach could form the basis of an alternative route to numerous chemical transformations that are currently dependent on a combination of preformed H2O2 and TS-1, while allowing for considerable process intensification.

Original languageEnglish
Pages (from-to)615-620
Number of pages6
JournalScience (New York, N.Y.)
Volume376
Issue number6593
DOIs
Publication statusPublished - 5 May 2022

Bibliographical note

Funding Information:
The authors thank UBE Corporation for financial support. XPS data collection was performed at the EPSRC National Facility for XPS (“HarwellXPS”), operated by Cardiff University and UCL, under contract PR16195. R.J.L. and G.J.H. gratefully acknowledge Cardiff University and the Max Planck Centre for Fundamental Heterogeneous Catalysis (FUNCAT) for financial support. X.L. acknowledges financial support from the National Natural Science Foundation of China (22872163 and 22072090). L.C. acknowledges financial support from the National Natural Science Foundation of China (21991153). In addition, S.J.F. acknowledges the award of a Prize Research Fellowship from the University of Bath.

Data and materials availability:
The data supporting the findings of this study are available within the article and its supplementary materials or from the authors upon reasonable request, with the underlying data found at the Cardiff University Data Repository (38).

ASJC Scopus subject areas

  • General

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