Magnetic material loaded N-heterocyclic carbene copper catalyst as well as preparation method and application thereof

A nitrogen-heterocyclic carbene and magnetic material technology, which is applied in catalytic reactions, chemical instruments and methods, physical/chemical process catalysts, etc., can solve problems such as increasing the difficulty of product separation, increasing production costs, and destroying ecosystems. Industrial application prospects, cost saving, and high catalytic efficiency

Pending Publication Date: 2020-11-17
HUAIBEI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods are mature, but the use of metal catalysts and other additives in the production process will increase the difficulty of product separation and increase production costs, and the discharge of metal catalysts and other additives will pollute the environment, damage the ecosystem, and endanger human health.

Method used

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  • Magnetic material loaded N-heterocyclic carbene copper catalyst as well as preparation method and application thereof
  • Magnetic material loaded N-heterocyclic carbene copper catalyst as well as preparation method and application thereof
  • Magnetic material loaded N-heterocyclic carbene copper catalyst as well as preparation method and application thereof

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preparation example Construction

[0032] The invention provides a method for preparing a magnetic material-supported nitrogen heterocyclic carbene copper catalyst, comprising the following steps:

[0033] S1, with Fe 3 o 4 and tetraethyl orthosilicate as raw materials to prepare SiO under alkaline conditions 2 Coated Fe 3 o 4 magnetic nanoparticles;

[0034] S2, take 4-chloromethylphenethyltrimethoxysilane as raw material, in the SiO 2 Coated Fe 3 o 4 The surface of magnetic nanoparticles was functionalized with benzyl chloride to obtain intermediate product 1;

[0035] S3. Under a protective gas atmosphere, using N-substituted imidazole as a raw material, carry out imidazolium salt grafting on the surface of the intermediate product 1 to obtain an intermediate product 2;

[0036] S4. Under a protective gas atmosphere, disperse cuprous halide, sodium tert-butoxide or potassium tert-butoxide, and the intermediate product 2 in a solvent, stir and react at room temperature, and then use a magnet to adsorb...

Embodiment 1

[0042] A preparation method of a magnetic material loaded nitrogen heterocyclic carbene copper catalyst, comprising the following steps:

[0043] (1) Preparation of silica-coated magnetic nanoparticles

[0044] Commercial Fe 3 o 4 Particles (average diameter 20nm, 0.25g) were sonicated with 0.1M dilute hydrochloric acid for 5 minutes, separated and washed with a magnet, added to a 1000mL reaction bottle, and then NH 3 ·H 2 O (2.0 mL), deionized water (100.0 mL), ethanol (400.0 mL), and the mixed solution was sonicated for about 1 h. After the solid is fully dispersed, slowly add tetraethyl orthosilicate (TEOS, 0.4g) dropwise into the suspension, and continue to stir the suspension at room temperature for 12 hours. Wash with water until neutral, then wash with ethanol and ether three times respectively, and dry in vacuum to finally obtain 0.31 g of the product.

[0045] (2) Functionalization of the surface of silica-coated magnetic nanoparticles with benzyl chloride

[00...

Embodiment 2

[0052] A preparation method of a magnetic material loaded nitrogen heterocyclic carbene copper catalyst, comprising the following steps:

[0053] (1) Preparation of silica-coated magnetic nanoparticles

[0054] Commercial Fe 3 o 4 Particles (average diameter 20nm, 0.5g) were sonicated with 0.1M dilute hydrochloric acid for 15 minutes, separated and washed with a magnet, added to a 2000mL reaction bottle, and then NH 3 ·H 2 O (4.0 mL), deionized water (200.0 mL), ethanol (800.0 mL), and the mixed solution was sonicated for about 2 h. After the solids were fully dispersed, tetraethyl orthosilicate (TEOS, 0.6 g) was slowly added dropwise to the suspension, and the suspension was stirred at room temperature for 12 hours, and the finally obtained product was washed with deionized water until neutral, and then Wash with ethanol and ether three times respectively, and dry in vacuum to finally obtain 0.63 g of the product.

[0055] (2) Functionalization of the surface of silica-c...

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Abstract

The invention discloses a magnetic material loaded N-heterocyclic carbene copper catalyst as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The preparation method comprises: by taking 4-chloromethyl phenethyl trimethoxysilane as a raw material, carrying out benzyl chloride functionalization on the surfaces of SiO2 coated Fe3O4 magnetic nanoparticles to prepare an intermediate product 1; by taking N-substituted imidazole as a raw material, carrying out imidazolium salt grafting on the surface of the intermediate product 1 to prepare an intermediate product 2; dispersing cuprous halide, sodium tert-butoxide and the intermediate product 2 into a solvent, and carrying out stirring reaction at room temperature to obtain the magnetic material loaded N-heterocyclic carbene copper catalyst. The catalyst is applied for catalyzing alkyne and organic azide addition reaction to prepare 1,2,3-triazole compounds, and catalyzing a coupling reaction of terminal alkyne, aldehyde and amine to prepare a propargylamine compound. The catalyst can be repeatedly used for multiple times without reducing the catalytic activity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a nitrogen-heterocyclic carbene copper catalyst supported by a magnetic material and a preparation method and application thereof. Background technique [0002] 1,2,3-Triazole compounds and propargylamine compounds are important intermediates in organic synthesis, and are widely used in many fine chemical production fields such as medicine, pesticide, daily chemical industry, and materials. Among them, the preparation of 1,2,3-triazole compounds mainly uses monovalent copper to catalyze the addition reaction of alkynes and organic azides. The preparation of propargylamine compounds mainly adopts monovalent copper to catalyze the trimolecular coupling reaction of terminal alkynes, aldehydes and amines. These methods are mature, but the use of metal catalysts and other additives in the production process will increase the difficulty of product separation and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J35/00C07D249/06C07D295/03C07D295/023C07C209/60C07C211/28C07C211/27
CPCB01J31/2273B01J31/1633B01J35/0033C07D249/06C07D295/03C07D295/023C07C209/60B01J2531/16B01J2231/327B01J2231/4283C07C211/28C07C211/27
Inventor 李品华王磊王敏张义成
Owner HUAIBEI NORMAL UNIVERSITY
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