Highly efficient catalytic production of oximes from ketones using in situ–generated H 2 O 2

Author:

Lewis Richard J.1ORCID,Ueura Kenji2,Liu Xi34ORCID,Fukuta Yukimasa2ORCID,Davies Thomas E.1ORCID,Morgan David J.15ORCID,Chen Liwei36ORCID,Qi Jizhen7ORCID,Singleton James1,Edwards Jennifer. K.1,Freakley Simon J.8ORCID,Kiely Christopher J.9ORCID,Yamamoto Yasushi2,Hutchings Graham J.1ORCID

Affiliation:

1. Max Planck–Cardiff Centre on the Fundamentals of Heterogeneous Catalysis FUNCAT, Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK.

2. UBE Corporation, 1978-5, Kogushi, Ube, Yamaguchi 755-8633, Japan.

3. School of Chemistry and Chemical, In-situ Centre for Physical Sciences, Shanghai Jiao Tong University, Shanghai 200240, P.R. China.

4. SynCat@Beijing, Synfuels China Technology Co. Ltd., Beijing 101407, P.R. China.

5. Harwell XPS, Research Complex at Harwell (RCaH), Didcot OX11 0FA, UK.

6. School of Chemistry and Chemical Engineering, Frontiers Science Centre for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P.R. China.

7. i-Lab, CAS Centre for Excellence in Nanoscience, Suzhou Institute of Nano-Tech and Nano-Bionics, Chinese Academy of Sciences, Suzhou 215123, P.R. China.

8. Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK.

9. Department of Materials Science and Engineering, Lehigh University, Bethlehem, PA 18015, USA.

Abstract

The ammoximation of cyclohexanone using preformed hydrogen peroxide (H 2 O 2 ) 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, H 2 O 2 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 H 2 O 2 , 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 H 2 O 2 and TS-1, while allowing for considerable process intensification.

Publisher

American Association for the Advancement of Science (AAAS)

Subject

Multidisciplinary

Reference80 articles.

1. HDIN Research Global Nylon 6 production capacity to reach 8.86 million tons in 2024 (2019); www.hdinresearch.com/news/56

2. A cleaner way to nylon?

3. Cyclohexanone Ammoximation: A Break Through In The 6-Caprolactam Production Process

4. P. Roffia M. Padovan G. Leofanti M. A. Mantegazza G. De Alberti G. R. Tauszik (Montedipe SpA) US Patent US4794198A (1987).

5. Catalytic properties of crystalline titanium silicalites III. Ammoximation of cyclohexanone

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