Chemoselective hydrogenation of unsaturated nitriles to unsaturated primary amines: Conversion of cinnamonitrile on metal-supported catalysts

Segobia, Darío Jobino; Trasarti, Andrés Fernando; Apesteguı́a, C.R.

doi:10.1016/j.apcata.2015.01.028

Cited by 22 publications

(17 citation statements)

References 31 publications

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“…Continuing the investigations of hydrogenation of aromatic nitriles, Segobia and co-workers have looked at the chemoselective hydrogenation of cinnamonitrile over a range of supported metal catalysts [28]. That work, concentrating on the selective formation of the primary amine (cinnamylamine) establishes how the reaction profile may be influenced by the metal catalyst used and also its dispersion.…”

Section: Introductionmentioning

confidence: 99%

The application of a supported palladium catalyst for the hydrogenation of aromatic nitriles

McMillan

Gilpin

Baker

et al. 2016

Journal of Molecular Catalysis A: Chemical

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Section: Introductionmentioning

confidence: 99%

The application of a supported palladium catalyst for the hydrogenation of aromatic nitriles

McMillan

Gilpin

Baker

et al. 2016

Journal of Molecular Catalysis A: Chemical

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“…Nickel is a typically applied catalyst in the hydrogenation of nitriles in different forms, such as Raney-type one [10-14, 16-18, 24, 25], supported on silica [7,[26][27][28][29][30], alumina [31][32][33][34] or sepiolite [35], as well as NiAl alloy [36], Ni nanoparticles [37][38][39] or Ni 2 P [40].…”

Section: Base Metal Catalysts 21 Nickel-catalyzed Hydrogenationsmentioning

confidence: 99%

“…Cobalt is also a frequently used catalytic metal in the hydrogenation of nitriles in Raney-type [12,14,17,24] or supported [7,27,30,31,[41][42][43] forms. In 2004, Ansmann and Benisch [41] developed an industrially feasible process for preparing primary amines by cobalt-catalyzed hydrogenation of both aliphatic and aromatic nitriles.…”

Section: Hydrogenations Over Cobaltmentioning

confidence: 99%

Selective Heterogeneous Catalytic Hydrogenation of Nitriles to Primary Amines

Lévay

Hegedűs

2018

Period. Polytech. Chem. Eng.

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Primary amines are important intermediates, especially in the area of pharmaceutical, plastic and agrochemical industry. The heterogeneous catalytic hydrogenation of nitriles is one of the most frequently applied process for the synthesis of diverse amines. However, the control of the selectivity is a critical issue in this reaction. Over the past decade, many studies have been reported using heterogeneous transition metal catalysts for the selective reduction of nitriles to the corresponding primary amines. The type of the catalysts, especially, the chemical nature of metals in the catalysts is one of the most important factors to influence the selectivity, the reaction rate, and possibly also the reaction pathway and the deactivation of the catalyst. Thus, this review focuses on the heterogeneous transition metal catalysts and summarizes the recent developments achieved in the selective catalytic hydrogenation of nitriles to primary amines.

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“…The primary amine was obtained in a satisfying yield from aliphatic nitriles using nickel, cobalt and ruthenium catalysts . Copper and rhodium catalysts served mainly for the preparation of secondary amines, while a highly selective tertiary amine can be produced when platinum and palladium were employed . But a high selectivity still remains as a major technical challenge, which attracts many researchers’ interests .…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of N,N‐Bis(3‐dimethylaminopropyl)amine over Pd/γ‐Al₂O₃

Lin

Wang

Guo

et al. 2018

Bulletin Korean Chem Soc

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The synthesis of N,N‐bis(3‐dimethylaminopropyl)amine (BPA) from 3‐(dimethylamino)‐propionitrile (PN) and 3‐(N,N‐dimethylamino)propylamine (PA) over Pd/γ‐Al2O3 in autoclaves was investigated. A series of Pd catalysts were prepared by different methods and characterized by XRD, TEM, and N2 adsorption–desorption. It was found that their activities were obviously affected by calcination temperature and reducing agent. Among them, the catalyst calcined at 500 °C and reduced with NaBH4 exhibited the best performance in this reaction. It was possibly attributed to the better dispersion of palladium particles on γ‐Al2O3. Furthermore, reaction parameters were also optimized. Under optimal conditions (PN/PA molar radio 1:1, toluene as solvent), BPA was obtained in 87.9% yield with 95.6% conversion over the above catalyst. Meanwhile, split of PN was observed. A probable mechanism of retro‐Michael reaction was also proposed.

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Chemoselective hydrogenation of unsaturated nitriles to unsaturated primary amines: Conversion of cinnamonitrile on metal-supported catalysts

Cited by 22 publications

References 31 publications

The application of a supported palladium catalyst for the hydrogenation of aromatic nitriles

The application of a supported palladium catalyst for the hydrogenation of aromatic nitriles

Selective Heterogeneous Catalytic Hydrogenation of Nitriles to Primary Amines

Selective Synthesis of N,N‐Bis(3‐dimethylaminopropyl)amine over Pd/γ‐Al₂O₃

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Chemoselective hydrogenation of unsaturated nitriles to unsaturated primary amines: Conversion of cinnamonitrile on metal-supported catalysts

Cited by 22 publications

References 31 publications

The application of a supported palladium catalyst for the hydrogenation of aromatic nitriles

The application of a supported palladium catalyst for the hydrogenation of aromatic nitriles

Selective Heterogeneous Catalytic Hydrogenation of Nitriles to Primary Amines

Selective Synthesis of N,N‐Bis(3‐dimethylaminopropyl)amine over Pd/γ‐Al2O3

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Product

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Selective Synthesis of N,N‐Bis(3‐dimethylaminopropyl)amine over Pd/γ‐Al₂O₃