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 output: Contribution to journalArticle

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 languageEnglish
JournalCatalysis Letters
DOIs
Publication statusPublished - 1 Jan 2019

Fingerprint

Amination
Ketones
Gold
Oxides
Catalysts
Amines
Propiophenones
Imines
Toluene
Hydrogenation
Hydrogen
Catalyst activity
benzylamine
cyclohexanone

Keywords

  • Cyclohexanone
  • Gold catalysts
  • Propiophenone
  • Reductive amination

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Reductive Amination of Ketones with Benzylamine Over Gold Supported on Different Oxides. / Kolobova, E.; Mäki-Arvela, P.; Pestryakov, A.; Pakrieva, E.; Pascual, L.; Smeds, A.; Rahkila, J.; Sandberg, T.; Peltonen, J.; Murzin, D. Yu.

In: Catalysis Letters, 01.01.2019.

Research output: Contribution to journalArticle

Kolobova, E. ; Mäki-Arvela, P. ; Pestryakov, A. ; Pakrieva, E. ; Pascual, L. ; Smeds, A. ; Rahkila, J. ; Sandberg, T. ; Peltonen, J. ; Murzin, D. Yu. / Reductive Amination of Ketones with Benzylamine Over Gold Supported on Different Oxides. In: Catalysis Letters. 2019.
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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

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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

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KW - Reductive amination

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