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Application of nanocarbon-supported single-atom palladium-based catalysts in the catalytic hydrogenation of nitrile compounds to prepare secondary amines

A technology for catalytic hydrogenation and compounding, which is applied in the preparation of amino compounds, the preparation of organic compounds, catalysts for physical/chemical processes, etc., can solve problems such as low selectivity, and achieve the effects of good repeatability, mature production technology and low cost.

Active Publication Date: 2021-10-15
INST OF METAL RESEARCH - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the catalytic hydrogenation of nitrile compounds, a mixture of several products such as primary amines, secondary amines, and tertiary amines is often produced, and the selectivity for one product is relatively low. Therefore, using a suitable catalyst, one of them can be generated with high selectivity The product is very necessary; due to the problem of the reaction selectivity, it is mainly a catalyst for the hydrogenation of nitrile compounds to obtain primary amines at present, and there is little research on the catalyst for the hydrogenation of nitrile compounds to obtain secondary amines. Catalytic hydrogenation to synthesize secondary amines, the research on its catalyst is very necessary and critical

Method used

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  • Application of nanocarbon-supported single-atom palladium-based catalysts in the catalytic hydrogenation of nitrile compounds to prepare secondary amines
  • Application of nanocarbon-supported single-atom palladium-based catalysts in the catalytic hydrogenation of nitrile compounds to prepare secondary amines
  • Application of nanocarbon-supported single-atom palladium-based catalysts in the catalytic hydrogenation of nitrile compounds to prepare secondary amines

Examples

Experimental program
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Effect test

Embodiment 1

[0026] A single-atom palladium-based catalyst (Pd 0.1 / ND@G) 20mg into a 50ml pressure-resistant reaction bottle, add 4mmol of ammonia borane, then add 10ml of methanol solution containing 0.5mmol of the reaction substrate, and react at a reaction temperature of 60°C for 8h. After the reaction, the conversion rate of benzonitrile is 55%, the selectivity of the product dibenzylamine is 98%, and the total selectivity of other by-products is 2%.

Embodiment 2

[0028] A single-atom palladium-based catalyst (Pd 0.1 / ND@G) 30mg was added to a 50ml pressure-resistant reaction bottle, 4mmol of ammonia borane was added, and 10ml of methanol solution containing 0.5mmol of the reaction substrate was added, and the reaction was carried out at a reaction temperature of 60°C for 8h. After the reaction, the conversion rate of benzonitrile is >99.9%, the selectivity of the product dibenzylamine is 98%, and the total selectivity of other by-products is 2%.

[0029] Under the condition that other conditions remain unchanged, only changing the reaction time, the activity and selectivity of the catalyst at different reaction times will change as follows: figure 2 shown.

Embodiment 3

[0033] A single-atom palladium-based catalyst (Pd 0.1 / ND@G) 30mg was added to a 50ml pressure-resistant reaction bottle, 3mmol of ammonia borane was added, and 10ml of methanol containing 0.5mmol of the reaction substrate was added, and the reaction was carried out at a reaction temperature of 60°C for 8h. After the reaction, the conversion rate of benzonitrile was 54%, the selectivity of the product dibenzylamine was 98%, and the total selectivity of other by-products was 2%.

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Abstract

The invention discloses the application of a nano-carbon-supported single-atom palladium-based catalyst in the catalytic hydrogenation of nitrile compounds to prepare secondary amines, and belongs to the technical field of catalysts for catalytic hydrogenation of liquid-phase nitrile compounds. The monoatomically dispersed palladium-based catalyst can generate corresponding secondary amine compounds with high selectivity under mild conditions; the catalytic reaction conditions are: reaction temperature 45-90°C, hydrogen source is ammonia borane. In the catalyst of the present invention, the metal exists in a dispersed state of single atoms, which more effectively improves the utilization efficiency of the metal, so that the activity and selectivity of hydrogenation of nitrile compounds are obviously improved. Moreover, the atomically dispersed catalyst is easy to prepare and low in cost, and has good application prospects in the hydrogenation of nitrile compounds to prepare secondary amines.

Description

technical field [0001] The invention relates to the technical field of application catalysts for catalytic hydrogenation of liquid-phase nitrile compounds, in particular to the application of a nano-carbon-supported single-atom palladium-based catalyst in the preparation of secondary amines by catalytic hydrogenation of nitrile compounds. Background technique [0002] Secondary amines are an important compound in organic chemistry. There are examples of such compounds in natural products, bioactive molecules and industrial materials, and they have a very wide range of applications. There are many ways to synthesize secondary amines, but none of them are easy. Common methods include direct alkylation of primary amines, reductive amination, and hydrogenation of nitrile compounds; among them, catalytic hydrogenation of nitrile compounds has high atom utilization efficiency, and the reaction is more ecologically and economically advantageous, so Its development has attracted mu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/48C07C211/27C07C211/29
CPCB01J23/44C07C209/48C07C211/27C07C211/29
Inventor 刘洪阳刘治博
Owner INST OF METAL RESEARCH - CHINESE ACAD OF SCI
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