The production of tyramine<i>via</i>the selective hydrogenation of 4-hydroxybenzyl cyanide over a carbon-supported palladium catalyst

McAllister, Mairi I.; Boulho, Cédric; McMillan, Liam; Gilpin, Lauren F.; Wiedbrauk, Sandra; Brennan, Colin; Lennon, David

doi:10.1039/c8ra05654d

Cited by 10 publications

(19 citation statements)

References 31 publications

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“…Among the precious metals, palladium is the most frequently used heterogeneous catalyst in the hydrogenation of nitriles, exclusively in supported form: on activated carbon [46][47][48][49][50][51][52][53], on alumina [51,52,[54][55][56][57][58][59][60][61][62], on MCM-41 [63] or on silica [64].…”

Section: Precious Metal Catalysts 31 Hydrogenations Over Palladiummentioning

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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Section: Precious Metal Catalysts 31 Hydrogenations Over Palladiummentioning

confidence: 99%

Selective Heterogeneous Catalytic Hydrogenation of Nitriles to Primary Amines

Lévay

Hegedűs

2018

Period. Polytech. Chem. Eng.

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“…Whilst there are several instances where hydrogenolytic removal of a functional group is undesirable, such as the hydrogenolysis of benzylamine to yield toluene, 19,20 there are occasions where no hydrogenolysis of the amine functionality is observed. 21 Adding a further degree of complication, there are instances where the selective hydrogenolysis of one functional group in the presence of another is required. 21 The occurrence or absence of a hydrogenolysis step has previously been rationalised, primarily by Scheme 1 Two-step nitrile hydrogenation to the primary amine proposed by Sabatier et al 6 work undertaken by Maschmeyer et al, 17 which suggested that it is the positioning of the heteroatom with respect to the aromatic group which dictates the viability of the process.…”

Section: Introductionmentioning

confidence: 99%

“…21 Adding a further degree of complication, there are instances where the selective hydrogenolysis of one functional group in the presence of another is required. 21 The occurrence or absence of a hydrogenolysis step has previously been rationalised, primarily by Scheme 1 Two-step nitrile hydrogenation to the primary amine proposed by Sabatier et al 6 work undertaken by Maschmeyer et al, 17 which suggested that it is the positioning of the heteroatom with respect to the aromatic group which dictates the viability of the process. Recent work by McAllister and co-workers regarding the hydrogenation of 4-hydroxybenzyl cyanide supports this assertion.…”

Section: Introductionmentioning

confidence: 99%

“…Recent work by McAllister and co-workers regarding the hydrogenation of 4-hydroxybenzyl cyanide supports this assertion. 21 Whilst aliphatic nitriles and, more recently, simple aromatic nitriles such as benzonitrile, have been extensively studied, chemical systems of greater complexity have not been examined in as much detail. 2,3,22,23 Cyanohydrins are organic compounds dened by the presence of both a nitrile group and a hydroxyl group on the same carbon atom.…”

Section: Introductionmentioning

confidence: 99%

“…Recent work by McAllister and co-workers regarding the hydrogenation of 4-hydroxybenzyl cyanide supports this assertion. 21 …”

Section: Introductionmentioning

confidence: 99%

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The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding

et al. 2019

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Continuous Hydrogenation of Nitriles to Primary Amines with High Selectivity in Flow by Using Raney Cobalt

Yu,

Ming,

Zhang

et al. 2024

ChemistrySelect

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Primary amines produced by selective catalytic hydrogenation of cyano compounds are widely used as basic chemicals, but due to the complexity of the hydrogenation mechanism and the inefficient mass transfer of the intermittent reaction, the process tends to produce secondary and tertiary amines as undesirable by‐products. In this research, a continuous hydrogenation system employing a micropacked‐bed reactor (μPBR) was established for the catalytic hydrogenation of 3‐ethylaminopropionitrile (3‐EAPN) to synthesize N‐ethyl‐1,3‐propanediamine (3‐EAPA). Under optimal experimental conditions using Raney cobalt as a catalyst, complete conversion of 3‐EAPN was achieved, and a high selectivity of 99.6 % for the primary amine (3‐EAPA) was obtained. On this basis, the system was extended with other cyano compounds of different structures as hydrogenation substrates, demonstrating the general applicability of this continuous hydrogenation system by using Raney cobalt as a catalyst in a μPBR for the hydrogenation of various nitriles.

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The production of tyramineviathe selective hydrogenation of 4-hydroxybenzyl cyanide over a carbon-supported palladium catalyst

Abstract: Tyramine hydrogen sulphate is produced via the heterogeneously catalysed selective hydrogenation of 4-hydroxybenzyl cyanide within a three-phase reactor.

Cited by 10 publications

References 31 publications

Selective Heterogeneous Catalytic Hydrogenation of Nitriles to Primary Amines

Selective Heterogeneous Catalytic Hydrogenation of Nitriles to Primary Amines

The hydrogenation of mandelonitrile over a Pd/C catalyst: towards a mechanistic understanding

Continuous Hydrogenation of Nitriles to Primary Amines with High Selectivity in Flow by Using Raney Cobalt

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