Colloidal and Nanosized Catalysts in Organic Synthesis: XXIII. Reductive Amination of Carbonyl Compounds Catalyzed by Nickel Nanoparticles in a Plug-Flow Reactor

Мохов, В. М.; Popov, Yu. V.; Paputina, A. N.; Nebykov, D. N.; Shishkin, E. V.

doi:10.1134/s1070363219120016

Cited by 6 publications

(7 citation statements)

References 24 publications

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“…Reductive amination of aldehydes and ketones with amines has been demonstrated over Pd and Ni supported on a static mixer [20] and over Ni supported on different supports. [74] A comparative study of continuous amination of several amines with aldehydes and ketones was performed over Ni supported . Concentration profiles in HMF amination with aniline over Pd supported on poly-paraphenylenediamine modified metal organic framework catalyst UiO-67 in ethanol at 50°C under 5 bar hydrogen adapted from.…”

Section: Continuous Amination Of Carbonyl Compounds With Amines Over Heterogeneous Catalysts With Molecular Hydrogenmentioning

confidence: 99%

“…on NaX zeolite, carbon and magnesium oxide in the temperature range of 60-240°C under atmospheric pressure. [74] Synthesis of several secondary amines was successfully demonstrated over these catalysts, however, time-on-stream behavior was not reported. [74] Interestingly even dehydroaromatization of cyclohexylamine occurred over Ni/MgO in its amination with butylamine forming N-butylaniline instead of N-butylcyclohexylamine.…”

Section: Continuous Amination Of Carbonyl Compounds With Amines Over Heterogeneous Catalysts With Molecular Hydrogenmentioning

confidence: 99%

“…[74] Synthesis of several secondary amines was successfully demonstrated over these catalysts, however, time-on-stream behavior was not reported. [74] Interestingly even dehydroaromatization of cyclohexylamine occurred over Ni/MgO in its amination with butylamine forming N-butylaniline instead of N-butylcyclohexylamine. [74] Continuous reductive amination in a tubular reactor containing a static mixer printed with Ni or Pd was demonstrated.…”

Section: Continuous Amination Of Carbonyl Compounds With Amines Over Heterogeneous Catalysts With Molecular Hydrogenmentioning

confidence: 99%

“…[74] Interestingly even dehydroaromatization of cyclohexylamine occurred over Ni/MgO in its amination with butylamine forming N-butylaniline instead of N-butylcyclohexylamine. [74] Continuous reductive amination in a tubular reactor containing a static mixer printed with Ni or Pd was demonstrated. [20] The metals were loaded either via cold spraying (Ni) or electroplating (Pd).…”

Section: Continuous Amination Of Carbonyl Compounds With Amines Over Heterogeneous Catalysts With Molecular Hydrogenmentioning

confidence: 99%

“…[61] In addition, results on amination of carbonyl compounds in a continuous mode will be discussed in detail. [20,24,63,[71][72][73][74] Another aim is also to understand the catalyst property-performance relationship and elucidate the reaction mechanisms, [2,48,49,54,56,59,63] related to production of secondary amines from carbonyl compounds. Reductive amination of aldehyde/ketone with a primary amine forming in the first step an imine, which is then hydrogenated to an amine, is discussed in Section 2 (Figure 3a), while onepot reductive amination of nitrocompounds with primary amines, which includes as an additional step hydrogenation of the nitro compound to amine, is summarized in Section 3 (Figure 3b).…”

Section: Introductionmentioning

confidence: 99%

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One-pot amination of aldehydes and ketones over heterogeneous catalysts for production of secondary amines

2021

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This review summarizes the recent studies on the synthesis of secondary amines by one-pot amination of aldehydes and ketones over heterogeneous catalysts. Amines are widely applied as the key intermediates in chemical industry for the synthesis of various commodities such as agrochemicals, drugs, detergents, lubricants, food-additives and polymers. Direct catalytic reductive amination of carbonyl compounds was considered which generally includes two steps: (i) formation of imines by interactions of aldehydes or ketones with amines, and (ii) subsequent hydrogenation of imines. Synthesis of secondary amines from carbonyl compounds and amines generated in situ under reaction conditions from their progenitors, e.g., respectively, alcohols or nitro-compounds, is also discussed in detail. Recent progress in application of hydrogen sources alternative to gaseous H 2 , such as formic acid, NaBH 4 , CO and water, favored development of metal-free catalysts including solid acid catalysts. The review addresses the scope of the amination reaction with aldehydes/ketones and nitro/amine compounds of different structure, the effect of the solvent, reaction conditions and catalyst properties. In addition, catalyst regeneration and reuse, kinetic regularities and kinetic modeling with an emphasis on the continuous mode of one-pot amination have been systematically summarized and discussed. It is suggested that the future work should focus on revealing the role of the catalytically active sites addressing their acid-base properties and the correlation between catalyst properties and the reaction performance, elucidating kinetic parameters and designing feasible reactor system for further industrial implementation.

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Section: Continuous Amination Of Carbonyl Compounds With Amines Over Heterogeneous Catalysts With Molecular Hydrogenmentioning

confidence: 99%

Section: Continuous Amination Of Carbonyl Compounds With Amines Over Heterogeneous Catalysts With Molecular Hydrogenmentioning

confidence: 99%

Section: Continuous Amination Of Carbonyl Compounds With Amines Over Heterogeneous Catalysts With Molecular Hydrogenmentioning

confidence: 99%

Section: Continuous Amination Of Carbonyl Compounds With Amines Over Heterogeneous Catalysts With Molecular Hydrogenmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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One-pot amination of aldehydes and ketones over heterogeneous catalysts for production of secondary amines

2021

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A robust, versatile, and reusable heterogeneous hydrogenation catalyst based on a simple Ni(II) diimine complex and its application to the syntheses of amines

Michalke,

Böhm,

Schmiedbauer

et al. 2024

Tetrahedron Green Chem

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Reductive N-Alkylation of Amines with Ketones Using Heterogeneous Polysilane–Palladium Catalysts under Continuous-Flow Conditions

Senzaki,

Saito,

Kobayashi

2024

Org. Lett.

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This work reports a continuous-flow reductive N-alkylation of amines with ketones using molecular hydrogen. The reaction, performed with highly active polysilane-modified heterogeneous palladium catalysts, enables the efficient synthesis of diversely substituted amines under mild flow conditions. The developed catalyst exhibits sustained activity for 5 days (turnover number of >2400). Moreover, the utility of the method is demonstrated by the synthesis of a key intermediate of the active pharmaceutical ingredient teneligliptin.

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Colloidal and Nanosized Catalysts in Organic Synthesis: XXIII. Reductive Amination of Carbonyl Compounds Catalyzed by Nickel Nanoparticles in a Plug-Flow Reactor

Cited by 6 publications

References 24 publications

One-pot amination of aldehydes and ketones over heterogeneous catalysts for production of secondary amines

One-pot amination of aldehydes and ketones over heterogeneous catalysts for production of secondary amines

A robust, versatile, and reusable heterogeneous hydrogenation catalyst based on a simple Ni(II) diimine complex and its application to the syntheses of amines

Reductive N-Alkylation of Amines with Ketones Using Heterogeneous Polysilane–Palladium Catalysts under Continuous-Flow Conditions

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