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Method for preparing aromatic amine compounds from aromatic nitro compounds by catalytic reduction of nano porous Cu@Cu2O catalyst

An aromatic nitro compound and nanoporous technology, which is applied in the preparation of amino compounds, imino compounds, and organic compounds, can solve the problems of high cost, difficult recovery of granular catalysts, and poor selectivity of target products, and achieve catalytic The effects of green and mild conditions, good recycling efficiency, and excellent structural stability

Active Publication Date: 2019-06-21
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Amine compounds are important organic synthesis intermediates in the chemical industry, and can be used in many industries, including antioxidants, dyes, active components, polymer modifiers, adhesives, photoresists, photosensitive materials, food additives As well as pharmaceutical industries, aromatic amine compounds are an important class of amine compounds. An effective preparation method is to obtain aromatic amine compounds by catalytic reduction of aromatic nitro compounds, but the traditional catalysts used are usually granular noble metals. Catalysts, on the one hand, have a high cost, and in addition, these granular catalysts are prone to structural agglomeration during the catalytic process, resulting in attenuation of catalytic activity, and the granular catalysts are not easy to recycle, resulting in low recycling performance
[0003] In the previous catalytic reduction method, hydrogen was used as the reducing agent. Although it has the advantages of complete reaction, less by-products, and less pollution, it often requires high temperature and high pressure, and has high requirements for production equipment and production process control, and equipment investment is large. , is not conducive to the promotion of industrialization
[0004] In addition, in aromatic nitro compounds, nitro often coexists with other unsaturated groups, such as carbonyl, ester, oxime, imino, cyano, etc., using traditional noble metal catalysts, nitro is catalytically reduced At the same time, other unsaturated groups are also easily reduced, resulting in poor selectivity of the target product and low yield. Therefore, the nitro group in this type of compound is selectively reduced to an amino group, which is useful for the preparation of aromatic amines. Significance

Method used

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  • Method for preparing aromatic amine compounds from aromatic nitro compounds by catalytic reduction of nano porous Cu@Cu2O catalyst
  • Method for preparing aromatic amine compounds from aromatic nitro compounds by catalytic reduction of nano porous Cu@Cu2O catalyst
  • Method for preparing aromatic amine compounds from aromatic nitro compounds by catalytic reduction of nano porous Cu@Cu2O catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The copper and aluminum are smelted in a vacuum arc furnace and stripped by a single-roll spin-quenching system to prepare Cu with atomic ratio 5 Al 95 The alloy strips are corroded in 0.5mol / L NaOH solution for 8h, washed and dried in ultrapure water several times to obtain nanoporous Cu@Cu 2 O catalyst.

Embodiment 2

[0041] Take the nanoporous Cu@Cu prepared in Example 1 2 10.0 mg of O catalyst, 1 mmol of aromatic nitro compound as substrate, 3 mmol of ammonia borane as hydrogen source in 8 ml of methanol, and reaction at room temperature for ten minutes to obtain the product.

Embodiment 3

[0043] Test nanoporous Cu@Cu 2 The substrate universality of O catalyst:

[0044] Aromatic nitro compounds are aromatic nitro compounds. Aromatic nitro compounds include a series of substrates in the following table. The yields of selected substrates are shown in the following table:

[0045]

[0046]

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Abstract

The invention discloses a method for preparing aromatic amine compounds from aromatic nitro compounds by catalytic reduction of a nano porous Cu@Cu2O catalyst. The nano porous Cu@Cu2O catalyst and thearomatic nitro compounds are taken as substrates and subjected to a reaction in methanol with ammonia borane as a hydrogen source at the room temperature, and a product is obtained. The high probability of agglomeration of granular catalysts is prevented, the nano porous Cu@Cu2O catalyst shows excellent structural stability and good recycling efficiency, has excellent universality, especially forthe aromatic nitro compounds, and has green and mild catalytic conditions, rapid reaction, high yield and good selectivity. The catalyst can be recycled by centrifugation, waste is avoided, and the catalyst shows high activity during the reaction and excellent stability under reaction conditions.

Description

Technical field [0001] The invention relates to the field of catalysts, in particular to a nanoporous Cu@Cu 2 O catalyst and a method for preparing aromatic amine compounds by catalytic reduction of aromatic nitro compounds. Background technique [0002] Amine compounds are important organic synthesis intermediates in the chemical industry and can be used in many industries, including antioxidants, dyes, active ingredients, polymer modifiers, adhesives, photoresist, photosensitive materials, food additives As well as in the pharmaceutical and other industries, aromatic amine compounds are an important class of amine compounds. An effective preparation method is to use aromatic nitro compounds to catalyze the reduction to obtain aromatic amine compounds, but the traditional catalysts used are usually particulate precious metals. On the one hand, the cost of the catalyst is relatively high. In addition, these particulate catalysts are prone to structural agglomeration during the ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J23/72B01J35/10C07C209/36C07C211/47C07C211/58C07C211/51C07C211/52C07C233/43C07C249/02C07C251/48C07C253/30C07C255/58C07C219/34C07C217/84C07D213/73
CPCY02P20/584
Inventor 徐彩霞杜加磊张园园
Owner UNIV OF JINAN