Reductive Amination of Ketones with Benzylamine Over Gold Supported on Different Oxides

E. Kolobova, P. Mäki-Arvela, A. Pestryakov, E. Pakrieva, L. Pascual, A. Smeds, J. Rahkila, T. Sandberg, J. Peltonen, D. Yu Murzin

Research School of Chemistry & Applied Biomedical Sciences

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

3 Citations (Scopus)

Abstract

Abstract: Reductive amination of cyclohexanone with benzylamine was investigated at 100 °C under 30 bar hydrogen in toluene with five different gold catalysts prepared by deposition–precipitation method and supported on TiO₂, La₂O₃/TiO₂, CeO₂/TiO₂, La₂O₃ and CeO₂. Size of metallic gold varied in the range of 2.6–3.6 nm. The best catalysts in reductive amination of cyclohexanone with benzylamine were 4 wt% Au/TiO₂ and 4 wt% Au/CeO₂/TiO₂ giving 72% and 79% yield of the desired amine. The most acidic and basic catalysts were also unselective and exhibited low activity towards imine hydrogenation. The best catalyst 4 wt% Au/CeO₂/TiO₂ gave in reductive amination of propiophenone 56% selectivity to the corresponding amine at 20% conversion in 5 h. Graphical Abstract: [Figure not available: see fulltext.]

Original language	English
Journal	Catalysis Letters
DOIs	https://doi.org/10.1007/s10562-019-02917-1
Publication status	Published - 1 Jan 2019

Keywords

Cyclohexanone
Gold catalysts
Propiophenone
Reductive amination

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1007/s10562-019-02917-1

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Cite this

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title = "Reductive Amination of Ketones with Benzylamine Over Gold Supported on Different Oxides",

abstract = "Abstract: Reductive amination of cyclohexanone with benzylamine was investigated at 100 °C under 30 bar hydrogen in toluene with five different gold catalysts prepared by deposition–precipitation method and supported on TiO2, La2O3/TiO2, CeO2/TiO2, La2O3 and CeO2. Size of metallic gold varied in the range of 2.6–3.6 nm. The best catalysts in reductive amination of cyclohexanone with benzylamine were 4 wt% Au/TiO2 and 4 wt% Au/CeO2/TiO2 giving 72% and 79% yield of the desired amine. The most acidic and basic catalysts were also unselective and exhibited low activity towards imine hydrogenation. The best catalyst 4 wt% Au/CeO2/TiO2 gave in reductive amination of propiophenone 56% selectivity to the corresponding amine at 20% conversion in 5 h. Graphical Abstract: [Figure not available: see fulltext.]",

keywords = "Cyclohexanone, Gold catalysts, Propiophenone, Reductive amination",

author = "E. Kolobova and P. M{\"a}ki-Arvela and A. Pestryakov and E. Pakrieva and L. Pascual and A. Smeds and J. Rahkila and T. Sandberg and J. Peltonen and Murzin, {D. Yu}",

year = "2019",

month = jan,

day = "1",

doi = "10.1007/s10562-019-02917-1",

language = "English",

journal = "Catalysis Letters",

issn = "1011-372X",

publisher = "Springer Netherlands",

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TY - JOUR

T1 - Reductive Amination of Ketones with Benzylamine Over Gold Supported on Different Oxides

AU - Kolobova, E.

AU - Mäki-Arvela, P.

AU - Pestryakov, A.

AU - Pakrieva, E.

AU - Pascual, L.

AU - Smeds, A.

AU - Rahkila, J.

AU - Sandberg, T.

AU - Peltonen, J.

AU - Murzin, D. Yu

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Abstract: Reductive amination of cyclohexanone with benzylamine was investigated at 100 °C under 30 bar hydrogen in toluene with five different gold catalysts prepared by deposition–precipitation method and supported on TiO2, La2O3/TiO2, CeO2/TiO2, La2O3 and CeO2. Size of metallic gold varied in the range of 2.6–3.6 nm. The best catalysts in reductive amination of cyclohexanone with benzylamine were 4 wt% Au/TiO2 and 4 wt% Au/CeO2/TiO2 giving 72% and 79% yield of the desired amine. The most acidic and basic catalysts were also unselective and exhibited low activity towards imine hydrogenation. The best catalyst 4 wt% Au/CeO2/TiO2 gave in reductive amination of propiophenone 56% selectivity to the corresponding amine at 20% conversion in 5 h. Graphical Abstract: [Figure not available: see fulltext.]

AB - Abstract: Reductive amination of cyclohexanone with benzylamine was investigated at 100 °C under 30 bar hydrogen in toluene with five different gold catalysts prepared by deposition–precipitation method and supported on TiO2, La2O3/TiO2, CeO2/TiO2, La2O3 and CeO2. Size of metallic gold varied in the range of 2.6–3.6 nm. The best catalysts in reductive amination of cyclohexanone with benzylamine were 4 wt% Au/TiO2 and 4 wt% Au/CeO2/TiO2 giving 72% and 79% yield of the desired amine. The most acidic and basic catalysts were also unselective and exhibited low activity towards imine hydrogenation. The best catalyst 4 wt% Au/CeO2/TiO2 gave in reductive amination of propiophenone 56% selectivity to the corresponding amine at 20% conversion in 5 h. Graphical Abstract: [Figure not available: see fulltext.]

KW - Cyclohexanone

KW - Gold catalysts

KW - Propiophenone

KW - Reductive amination

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