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A kind of oxygen-bridged tetranuclear amidinoaluminum catalyst and its preparation method and application

A tetranuclear amidine aluminum and catalyst technology is applied in chemical instruments and methods, oxygen-containing functional group reduction preparation, physical/chemical process catalysts, etc. Achieve the effect of large steric hindrance, mild catalytic conditions and simple preparation process

Active Publication Date: 2020-06-02
TAIYUAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to solve the technical problems of the MPV reaction using the metal alkoxide catalyst, such as complex preparation process of the catalyst, the catalyst is greatly affected by the environment, easy to absorb moisture, the amount of the catalyst used in the catalysis process is too large, and the catalytic effect is poor. Oxygen-bridged tetranuclear amidinoaluminum catalyst, preparation method and application

Method used

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  • A kind of oxygen-bridged tetranuclear amidinoaluminum catalyst and its preparation method and application
  • A kind of oxygen-bridged tetranuclear amidinoaluminum catalyst and its preparation method and application
  • A kind of oxygen-bridged tetranuclear amidinoaluminum catalyst and its preparation method and application

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Effect test

Embodiment 1

[0018] A kind of tetranuclear amidinate aluminum catalyst of oxygen bridging in the present embodiment, its structural formula is:

[0019]

[0020] Wherein, Ar is 2,6-dimethylphenyl.

[0021] The method for the tetranuclear amidino-aluminum catalyst of described oxygen bridge, comprises the following steps:

[0022] Under the protection of an inert gas, a toluene solution of trimethylaluminum (2M, 2.0mL, 4.00mmol) was first added to N-phenyl-N'-(2,6-dimethyl)phenylcarbodiimide ( 0.444g, 2.0mmol) in toluene solution, stirred at room temperature for 4 hours to obtain a yellow clear solution, then the yellow clear solution was slowly dripped into the reaction solution with water (0.036g, 2.0mmol ), the reaction continued to stir for 1 hour after returning to room temperature, filtered, concentrated the filtrate in vacuo, placed 2 days at a temperature of 0°C, and separated out a colorless transparent crystal that was the tetranuclear amidinate aluminum catalyst of oxygen bri...

Embodiment 2

[0026] The structure of the oxygen-bridged tetranuclear amidinoaluminum catalyst in this example is the same as that in Example 1.

[0027] The method for the tetranuclear amidino-aluminum catalyst of described oxygen bridge, comprises the following steps:

[0028] Under the protection of an inert gas, a toluene solution of trimethylaluminum (2M, 2.0mL, 4.00mmol) was first added to N-phenyl-N'-(2,6-dimethyl)phenylcarbodiimide ( 0.444g, 2.0mmol) in the toluene solution, stirred at room temperature for 8 hours to obtain a yellow clear solution, then the yellow clear solution was slowly dripped into the reaction solution with water (0.036g, 2.0mmol ), the reaction continued to stir for 2 hours after returning to room temperature, filtered, and the filtrate was concentrated in vacuo, placed at a temperature of -20°C for 5 days, and a colorless transparent crystal was precipitated, which was the tetranuclear amidinate aluminum catalyst of oxygen bridge, and the yield was 70 %.

Embodiment 3

[0030] The structure of the oxygen-bridged tetranuclear amidinoaluminum catalyst in this example is the same as that in Example 1.

[0031] The method for the tetranuclear amidino-aluminum catalyst of described oxygen bridge, comprises the following steps:

[0032] Under the protection of an inert gas, a toluene solution of trimethylaluminum (2M, 2.0mL, 4.00mmol) was first added to N-phenyl-N'-(2,6-dimethyl)phenylcarbodiimide ( 0.444g, 2.0mmol) in toluene solution, stirred at room temperature for 6 hours to obtain a yellow clear solution, then the yellow clear solution was slowly dripped into the reaction solution with water (0.036g, 2.0mmol ), the reaction continued to stir for 1.5 hours after returning to room temperature, filtered, and the filtrate was concentrated in vacuo, and placed for 3 days at a temperature of 5° C., and a colorless transparent crystal was separated out, which was the tetranuclear amidinate aluminum catalyst of oxygen bridge, and the productive rate w...

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Abstract

The invention provides an oxygen-bridged tetranuclear amidino aluminum catalyst as well as a preparation method and an application thereof, and relates to the MPV (Meerwein-Ponndorf-Verley) reaction,in particular to a metallic aluminum catalyst for efficiently and selectively reducing carbonyl groups in carbonyl compound molecules containing other unsaturated functional groups into correspondingalcohol compounds. The preparation method of the catalyst comprises steps as follows: under the protection of inert gas, firstly, a toluene solution of trimethylaluminum is added to a toluene solutionof N-phenyl-N'-(2,6-dimethyl)phenyl carbodiimide, a mixed solution is stirred for 4-8 h at the room temperature, then water is slowly dropwise added at the temperature of subzero 78 DEG C, filteringis performed after the reaction, a filtrate is subjected to vacuum concentration and left to stand for 2-5 d at the temperature of subzero 20 DEG C-5 DEG C, and a colorless and transparent crystal isprecipitated and is the oxygen-bridged tetranuclear amidino aluminum catalyst. The preparation method of the catalyst is simple and convenient, raw materials are easily available, the catalyst is quite stable and has higher catalysis activity for a reduction reaction of carbonyl compounds, time for the catalytic reaction is short, the yield is high, and the catalyst has good application prospect.

Description

technical field [0001] The invention belongs to a Meerwein-Ponndorf-Verley (MPV) reaction catalyst, and specifically relates to an oxygen-bridged tetranuclear amidinate aluminum catalyst, a preparation method and an application. Background technique [0002] As an important organic intermediate, unsaturated alcohol has been widely used in fine chemicals, spices and medicine. The usual synthesis methods are: oxidation of alkenes and alkylation of carbonyl groups, but a more commonly used method is: reduction of carbonyl groups. The Meerwein-Ponndorf-Verley (MPV) reaction is a method that can efficiently realize the conversion process, especially the efficient and selective reduction of the carbonyl group in the carbonyl compound molecule containing other unsaturated functional groups to the corresponding alcohol. In the method, isopropanol is used as a hydrogen source, and unsaturated aldehydes and ketones can be reduced to unsaturated alcohols in the presence of a catalyst....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/14C07F5/06C07C29/14C07C33/20C07C33/46C07C33/32C07C35/08
Inventor 韩红斐
Owner TAIYUAN NORMAL UNIV
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