Application of nano-carbon supported monatomic palladium-based catalyst in catalytic hydrogenation of nitrile compound to prepare secondary amine

A technology for catalytic hydrogenation and compounding, which is applied in the preparation of amino compounds, organic compounds, physical/chemical process catalysts, etc. It can solve the problem of low selectivity, achieve good repeatability, easy access to materials, and increase the production of secondary amines. rate effect

Active Publication Date: 2020-02-14
INST OF METAL RESEARCH - CHINESE ACAD OF SCI
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  • 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 nano-carbon supported monatomic palladium-based catalyst in catalytic hydrogenation of nitrile compound to prepare secondary amine
  • Application of nano-carbon supported monatomic palladium-based catalyst in catalytic hydrogenation of nitrile compound to prepare secondary amine
  • Application of nano-carbon supported monatomic palladium-based catalyst in catalytic hydrogenation of nitrile compound to prepare secondary amine

Examples

Experimental program
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Effect test

Embodiment 1

[0026] A single-atom palladium-based catalyst (Pd 0.1 / ND@G) 20mg 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 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 application of a nano-carbon supported monatomic palladium-based catalyst in catalytic hydrogenation of a nitrile compound to prepare a secondary amine and belongs to the technical field of catalysts with application of catalytic hydrogenation of liquid-phase nitrile compounds. By adopting the monatomically dispersed palladium-based catalyst, a corresponding secondary aminecompound is generated with high selectivity under a mild condition, and the catalysis reaction conditions are that the reaction temperature is 45-90 DEG C and ammonia borane is adopted as a hydrogensource. In the catalyst disclosed by the invention, metals exist in a monatomic dispersion state, so that the utilization efficiency of the metals can be effectively improved, and the activity and theselectivity of the nitrile compound can be remarkably improved. In addition, the monatomically dispersed catalyst is convenient to prepare and low in cost, and has very good application prospects incatalytic hydrogenation of the nitrile compound to prepare the secondary amine.

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 Applications(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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