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Non-noble metal copper-based catalyst and application thereof in benzylamine oxidative coupling reaction

A technology of copper-based catalysts and non-noble metals, applied in catalytic reactions, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve high reaction temperature, large amount of metal, and large amount of reaction solvent and other problems, to achieve the effect of simple preparation and stable performance

Pending Publication Date: 2022-02-08
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, the catalyst system for the preparation of imines by the oxidative coupling reaction of benzylamine still faces many challenges, such as the excessive amount of reaction solvent, the use of noble metals in the catalyst and the large amount of metal used, and the high reaction temperature.

Method used

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  • Non-noble metal copper-based catalyst and application thereof in benzylamine oxidative coupling reaction
  • Non-noble metal copper-based catalyst and application thereof in benzylamine oxidative coupling reaction
  • Non-noble metal copper-based catalyst and application thereof in benzylamine oxidative coupling reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Cu 2 Preparation of complexes

[0025] Put copper chloride (40 mg, 0.2 mmol) into a round bottom flask, then add 15 mL of methanol and 5 mL of N,N-dimethylformamide, stir for 5 minutes, then add diphenyl-2-pyridylphosphine ( 80mg, 0.3mmol), the solution turns dark green; continue to stir for 15min, add NaBH containing NaBH to the above solution 4 (20mg, 0.52mmol) in 0.5mL deionized water, the solution turned yellow. Stirring was continued for 9 hours and the stirring was stopped. After the reaction stopped, the aqueous phase was removed, followed by deionized water and CH 2 Cl 2 Wash the organic phase several times. The dichloromethane phase was recovered, and the obtained dichloromethane solution was spin-dried. Solid with a small amount of CH 2 Cl 2 The solution is dissolved, and it is stored in a single crystal bottle, and the upper layer of the single crystal bottle is covered with n-hexane solution (dichloromethane: normal hexane volume ratio is ...

Embodiment 2

[0026] Example 2: Cu 2 / γ-Al 2 o 3 preparation of

[0027] γ-Al 2 o 3 (100mg) was dissolved in a mixed solution of 15mL methanol and 5mL dichloromethane, then Cu 2 The complex (1.2 mg) was dissolved in N,N-dimethylformamide (0.5 mL), which was added dropwise to a mixed solution of methanol and dichloromethane. After stirring for 6 hours, the stirring was stopped. The product was collected by centrifugation (10000 rpm) and washed twice with methanol. Finally, the solid was dried in a vacuum oven at 50 °C overnight, and the solid was collected to obtain Cu 2 / γ-Al2 o 3 catalyst. attached image 3 for Cu 2 / γ-Al 2 o 3 TEM image, it can be seen from the image that Cu 2 / γ-Al 2 o 3 It is in the form of nano flakes, and there are no metal particles on the surface.

Embodiment 3

[0028] Example 3: γ-Al 2 o 3 Catalyzes the oxidative coupling reaction of benzylamine.

[0029] Add 0.46mmol benzylamine and 30mgγ-Al to a 10mL Schlenk reaction flask in sequence 2 o 3 Catalyst, 100 microliters of tert-butanol hydroperoxide (TBHP) and 1 mL of acetonitrile, stirred and reacted at 50°C for 13h, after the reaction was completed, the temperature of the reaction solution was cooled to room temperature, and the solid and liquid were separated by centrifugation (10000rpm), and the reaction solution was passed through According to GC analysis, the yield was 27.5%.

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Abstract

The invention discloses a non-noble metal copper-based catalyst and application thereof in benzylamine oxidative coupling reaction, the non-noble metal copper-based catalyst is obtained by loading a copper complex on a gamma-Al2O3 carrier, the molecular formula of the copper complex is [Cu2 (C17H14NP) 2Cl4], and the molecular formula of the non-noble metal copper-based catalyst is Cu2 (C17H14NP) 2Cl4 / gamma-Al2O3, which is simply recorded as Cu2 / gamma-Al2O3. The Cu2 / gamma-Al2O3 catalyst can catalyze the oxidative coupling reaction of benzylamine under mild conditions, and meanwhile, the catalyst can be recycled for at least five times, the activity is kept unchanged, the substrate universality is relatively good, and the catalyst has very good practicability.

Description

technical field [0001] The invention relates to a non-noble metal copper-based catalyst and its application in benzylamine oxidative coupling reaction. Background technique [0002] In the organic industry, imines and their derivatives are important intermediates, which play an important role in the synthesis of pharmaceuticals, fine chemicals and materials and other chemical products. In order to increase the yield in the process of traditional oxidation of benzylamine to imine, a higher reaction temperature is generally selected. For example, in 2016, the Akiya Ogawa group used a metal-free organic catalyst, oxygen as the oxidant, and toluene as the solvent to perform the oxidative coupling reaction of benzylamine at a temperature of 80 °C (ACS Omega 2016, 1, 799-807). Subsequently, it was found that the use of noble metals also has the property of improving catalytic activity. In 2019, Li benxia's research group published a report on the synthesis of imines by the oxida...

Claims

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Application Information

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IPC IPC(8): B01J31/24B01J31/26C07C249/02C07C251/24
CPCB01J31/2404B01J31/26C07C249/02B01J2231/4283C07C251/24Y02P20/584
Inventor 盛鸿婷朱亚楠张静朱满洲
Owner ANHUI UNIVERSITY
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