Cyclohexanone ammoximation via in situ H2O2 production using TS-1 supported catalysts

Richard J. Lewis; Kenji Ueura; Yukimasa Fukuta; Thomas E. Davies; David J. Morgan; Charlie B. Paris; James Singleton; Jennifer K. Edwards; Simon J. Freakley; Yasushi Yamamoto; Graham J. Hutchings

doi:10.1039/d2gc02689a

Cyclohexanone ammoximation via in situ H2O2 production using TS-1 supported catalysts

Richard J. Lewis, Kenji Ueura, Yukimasa Fukuta, Thomas E. Davies, David J. Morgan, Charlie B. Paris, James Singleton, Jennifer K. Edwards, Simon J. Freakley, Yasushi Yamamoto, Graham J. Hutchings

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

28 Citations (SciVal)

Abstract

The ammoximation of cyclohexanone to the corresponding oxime via in situ H₂O₂ formation offers an attractive alternative to the current industrial means of production, overcoming the significant economic and environmental concerns associated with the manufacture of a key reagent, H₂O₂. Herein we demonstrate the efficacy of a composite catalyst, consisting of precious metal nanoparticles supported on a commercial TS-1, towards the in situ synthesis of cyclohexanone oxime, bridging the wide condition gap that exists between the two distinct reaction pathways: H₂O₂ direct synthesis and cyclohexanone ammoximation. In particular, the alloying of Au with Pd and the introduction of low concentrations of Pt into AuPd nanoalloys are found to be key in promoting high catalytic performance.

Original language	English
Pages (from-to)	9496-9507
Number of pages	12
Journal	Green Chemistry
Volume	24
Issue number	24
Early online date	9 Sept 2022
DOIs	https://doi.org/10.1039/d2gc02689a
Publication status	Published - 9 Sept 2022

Bibliographical note

Funding Information:
The authors wish to thank UBE Corporation for financial support. R. J. L and G. J. H acknowledge the Max Planck Centre for Fundamental Heterogeneous Catalysis (FUNCAT) for financial support. In addition, S. J. F acknowledges the award of a Prize Research Fellowship from the University of Bath. XPS data collection was performed at the EPSRC National Facility for XPS (‘Harwell XPS’). Operated by Cardiff University and UCL, under contract no. PR16195. The authors would like to thank the CCI-Electron Microscopy Facility which has been part-funded by the European Regional Development Fund through the Welsh Government and The Wolfson Foundation.

Funding

The authors wish to thank UBE Corporation for financial support. R. J. L and G. J. H acknowledge the Max Planck Centre for Fundamental Heterogeneous Catalysis (FUNCAT) for financial support. In addition, S. J. F acknowledges the award of a Prize Research Fellowship from the University of Bath. XPS data collection was performed at the EPSRC National Facility for XPS (‘Harwell XPS’). Operated by Cardiff University and UCL, under contract no. PR16195. The authors would like to thank the CCI-Electron Microscopy Facility which has been part-funded by the European Regional Development Fund through the Welsh Government and The Wolfson Foundation.

Funders	Funder number
FUNCAT
Max Planck Centre for Fundamental Heterogeneous Catalysis
UBE Corporation
Llywodraeth Cymru
Engineering and Physical Sciences Research Council
University College London	PR16195
University of Bath
Cardiff University
Wolfson Foundation
European Regional Development Fund

ASJC Scopus subject areas

Environmental Chemistry
Pollution

Access to Document

10.1039/d2gc02689aLicence: CC BY

Cite this

@article{0b0a8e014a1d4f5ea14e776a046eb2af,

title = "Cyclohexanone ammoximation via in situ H2O2 production using TS-1 supported catalysts",

abstract = "The ammoximation of cyclohexanone to the corresponding oxime via in situ H2O2 formation offers an attractive alternative to the current industrial means of production, overcoming the significant economic and environmental concerns associated with the manufacture of a key reagent, H2O2. Herein we demonstrate the efficacy of a composite catalyst, consisting of precious metal nanoparticles supported on a commercial TS-1, towards the in situ synthesis of cyclohexanone oxime, bridging the wide condition gap that exists between the two distinct reaction pathways: H2O2 direct synthesis and cyclohexanone ammoximation. In particular, the alloying of Au with Pd and the introduction of low concentrations of Pt into AuPd nanoalloys are found to be key in promoting high catalytic performance.",

author = "Lewis, \{Richard J.\} and Kenji Ueura and Yukimasa Fukuta and Davies, \{Thomas E.\} and Morgan, \{David J.\} and Paris, \{Charlie B.\} and James Singleton and Edwards, \{Jennifer K.\} and Freakley, \{Simon J.\} and Yasushi Yamamoto and Hutchings, \{Graham J.\}",

note = "Funding Information: The authors wish to thank UBE Corporation for financial support. R. J. L and G. J. H acknowledge the Max Planck Centre for Fundamental Heterogeneous Catalysis (FUNCAT) for financial support. In addition, S. J. F acknowledges the award of a Prize Research Fellowship from the University of Bath. XPS data collection was performed at the EPSRC National Facility for XPS ({\textquoteleft}Harwell XPS{\textquoteright}). Operated by Cardiff University and UCL, under contract no. PR16195. The authors would like to thank the CCI-Electron Microscopy Facility which has been part-funded by the European Regional Development Fund through the Welsh Government and The Wolfson Foundation. ",

year = "2022",

month = sep,

day = "9",

doi = "10.1039/d2gc02689a",

language = "English",

volume = "24",

pages = "9496--9507",

journal = "Green Chemistry",

issn = "1463-9262",

publisher = "Royal Society of Chemistry",

number = "24",

}

TY - JOUR

T1 - Cyclohexanone ammoximation via in situ H2O2 production using TS-1 supported catalysts

AU - Lewis, Richard J.

AU - Ueura, Kenji

AU - Fukuta, Yukimasa

AU - Davies, Thomas E.

AU - Morgan, David J.

AU - Paris, Charlie B.

AU - Singleton, James

AU - Edwards, Jennifer K.

AU - Freakley, Simon J.

AU - Yamamoto, Yasushi

AU - Hutchings, Graham J.

N1 - Funding Information: The authors wish to thank UBE Corporation for financial support. R. J. L and G. J. H acknowledge the Max Planck Centre for Fundamental Heterogeneous Catalysis (FUNCAT) for financial support. In addition, S. J. F acknowledges the award of a Prize Research Fellowship from the University of Bath. XPS data collection was performed at the EPSRC National Facility for XPS (‘Harwell XPS’). Operated by Cardiff University and UCL, under contract no. PR16195. The authors would like to thank the CCI-Electron Microscopy Facility which has been part-funded by the European Regional Development Fund through the Welsh Government and The Wolfson Foundation.

PY - 2022/9/9

Y1 - 2022/9/9

N2 - The ammoximation of cyclohexanone to the corresponding oxime via in situ H2O2 formation offers an attractive alternative to the current industrial means of production, overcoming the significant economic and environmental concerns associated with the manufacture of a key reagent, H2O2. Herein we demonstrate the efficacy of a composite catalyst, consisting of precious metal nanoparticles supported on a commercial TS-1, towards the in situ synthesis of cyclohexanone oxime, bridging the wide condition gap that exists between the two distinct reaction pathways: H2O2 direct synthesis and cyclohexanone ammoximation. In particular, the alloying of Au with Pd and the introduction of low concentrations of Pt into AuPd nanoalloys are found to be key in promoting high catalytic performance.

AB - The ammoximation of cyclohexanone to the corresponding oxime via in situ H2O2 formation offers an attractive alternative to the current industrial means of production, overcoming the significant economic and environmental concerns associated with the manufacture of a key reagent, H2O2. Herein we demonstrate the efficacy of a composite catalyst, consisting of precious metal nanoparticles supported on a commercial TS-1, towards the in situ synthesis of cyclohexanone oxime, bridging the wide condition gap that exists between the two distinct reaction pathways: H2O2 direct synthesis and cyclohexanone ammoximation. In particular, the alloying of Au with Pd and the introduction of low concentrations of Pt into AuPd nanoalloys are found to be key in promoting high catalytic performance.

UR - http://www.scopus.com/inward/record.url?scp=85139413533&partnerID=8YFLogxK

U2 - 10.1039/d2gc02689a

DO - 10.1039/d2gc02689a

M3 - Article

AN - SCOPUS:85139413533

SN - 1463-9262

VL - 24

SP - 9496

EP - 9507

JO - Green Chemistry

JF - Green Chemistry

IS - 24

ER -

Cyclohexanone ammoximation via in situ H2O2 production using TS-1 supported catalysts

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this