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Application of polyhydroxy fullerene for catalyzing addition reaction of nitroparaffin and aromatic aldehyde

A technology of polyhydroxyfullerene and hydroxyfullerene is applied in the formation/introduction of hydroxyl groups, chemical instruments and methods, preparation of organic compounds, etc., to achieve the effects of high catalytic efficiency, high catalytic selectivity, and long catalytic life.

Active Publication Date: 2010-12-08
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on applications, especially in the field of catalysis.

Method used

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  • Application of polyhydroxy fullerene for catalyzing addition reaction of nitroparaffin and aromatic aldehyde
  • Application of polyhydroxy fullerene for catalyzing addition reaction of nitroparaffin and aromatic aldehyde
  • Application of polyhydroxy fullerene for catalyzing addition reaction of nitroparaffin and aromatic aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 10mL tetrahydrofuran, 2mmol (107μL) nitromethane and 0.5mmol (75mg) 4-nitrobenzaldehyde in a 25mL single-necked bottle, then add 10mg polyhydroxy fullerene catalyst, and react with magnetic stirring at 25°C for 10 hours, The nitroalcohol product represented by formula III is obtained.

[0041] Get the mixture in the bottle and centrifuge to remove the catalyst, and the supernatant is analyzed by high-performance liquid chromatography. The analysis conditions are as follows: methanol: water=7: 3 (V: V), flow rate: 1ml / min, ultraviolet detection wavelength: 200nm, chromatographic Column: reverse phase C18 column, column temperature: 25°C. The result is as figure 1 shown. Depend on figure 1 It can be seen that the conversion rate of nitromethane is 98%, the yield of nitroalcohol product is 97%, and the selectivity is 100%.

[0042] In order to verify the correctness of the structure of the obtained nitroalcohol product, the supernatant obtained by centrifugation co...

Embodiment 2

[0047] Add 10mL tetrahydrofuran, 2mmol (107μL) nitromethane and 0.5mmol (65.6mg) 4-cyanobenzaldehyde into a 25mL single-necked bottle, then add 10mg polyhydroxy fullerene catalyst, and react with magnetic stirring at 25°C for 10 hours , to obtain the nitroalcohol product shown in formula III.

[0048] Get the mixture in the bottle and centrifuge to remove the catalyst, and the supernatant is analyzed by high-performance liquid chromatography. The analysis conditions are as follows: methanol: water=6: 4 (V: V), flow rate: 1ml / min, ultraviolet detection wavelength: 200nm, chromatographic Column: reverse phase C18 column, column temperature: 25°C. The result is as figure 2 shown. Depend on figure 2 It can be seen that the conversion rate of nitromethane is 99%, the yield of nitroalcohol product is 98%, and the selectivity is 100%.

[0049] In order to verify the correctness of the structure of the obtained nitroalcohol product, the supernatant obtained by centrifugation con...

Embodiment 3

[0054] Add 10mL of dichloromethane, 2mmol (107μL) of nitromethane and 0.5mmol (68.3μL) of 4-trifluoromethylbenzaldehyde into a 25mL single-necked bottle, then add 10mg of polyhydroxy fullerene catalyst, and magnetically The reaction was stirred for 10 hours to obtain the nitroalcohol product represented by formula III.

[0055] Get the centrifugation of the mixture in the bottle to remove the catalyzer, and the supernatant is analyzed by high-performance liquid chromatography. The analysis conditions are the same as in Example 1, and the obtained results are as follows: image 3 shown. Depend on image 3 It can be seen that the conversion rate of nitromethane is 98%, the yield of nitroalcohol product is 97%, and the selectivity is 100%.

[0056] In order to verify the correctness of the structure of the obtained nitroalcohol product, the supernatant obtained by centrifugation continued to be analyzed by mass spectrometry (EI ion source, ion source temperature: 200 ° C), and ...

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Abstract

The invention discloses an application of polyhydroxy fullerene for catalyzing the addition reaction of nitroparaffin and aromatic aldehyde. The application is that polyhydroxy fullerene is used as catalyst to catalyze the addition reaction of nitroparaffin and aromatic aldehyde, wherein the addition reaction comprises the following step: under the catalysis of polyhydroxy fullerene, using nitroparaffin and aromatic aldehyde to perform the addition reaction and obtain a product. When used in the addition reaction of nitroparaffin and aromatic aldehyde, polyhydroxy fullerene has high catalysis efficiency, the yield of the additional product is up to above 95%, and the conversion rate of aromatic aldehyde is up to 99%. The catalyst also has high catalytic selectivity, the nitroalcohol product selectivity is 100%, and no byproduct is generated.

Description

technical field [0001] The invention relates to the application of polyhydroxy fullerene in catalyzing the addition reaction of nitroalkane and aromatic aldehyde. Background technique [0002] The addition reaction between nitroalkanes and carbonyl-containing aldehydes or ketones is an effective way to generate carbon-carbon bonds in organic synthesis, and the resulting nitro-containing products can be easily transformed into Oxygen- or nitrogen-containing derivatives, such as nitroalkenes, aminoalcohols, and amino acids. This type of reaction has been widely concerned by organic synthesis workers. At present, a variety of catalysts have been used in the catalytic research of this type of reaction, such as metal Lewis acid catalysts (JOC, 2009, 74, 2242-2245) or organic bases. Small molecule catalysts (Angew. Chem. Int. Ed., 2006, 45, 929-931), etc. During the Lewis acid-catalyzed reaction, the metal Lewis acid mainly accepts the lone pair of electrons on the oxygen atom o...

Claims

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Application Information

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IPC IPC(8): B01J21/18C07B41/02C07C201/12C07C205/19C07C253/30C07C255/53C07C205/26C07C205/16C07C205/32
Inventor 宋卫国牛芳王春儒
Owner INST OF CHEM CHINESE ACAD OF SCI
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