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Selective hydrogenation reduction method for aromatic nitro compound

A technology for aromatic nitro compounds, which is applied in the field of selective hydrogenation reduction of aromatic nitro compounds, can solve the problems of restricting the wide application of catalysts and complex preparation, and achieve the effects of strong practicability, mild reduction conditions, and easy operation

Active Publication Date: 2012-06-13
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although such catalysts have good selectivity, their preparation is usually complicated, and the additives must be strictly quantitative
Corma's research group loaded nano-gold on TiO 2 or Fe 2 o 3 Chemoselective hydrogenation reduction of nitro groups can be achieved, but the reaction needs to be carried out under high temperature (such as 140 ° C) and high pressure (25 bar) conditions (Science, 2006, 313, 332), which limits to a certain extent Wide application of this type of catalyst

Method used

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  • Selective hydrogenation reduction method for aromatic nitro compound
  • Selective hydrogenation reduction method for aromatic nitro compound

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Take 3g of cyanamide, dissolve it in 3g of water, add 407.5g of Ludox HS, raise the temperature to 80°C to remove water, and obtain a white solid, heat up to 550°C at 2.5°C / min to polymerize for 4h, cool to room temperature and use 4M / L Ammonium bifluoride solution removes the template agent, and after drying, a yellow mesoporous carbon nitride material is obtained. There are two peaks in XRD analysis, and 2θ=27.4° is the (002) peak of the material, representing that the distance between the material layers is 0.34nm , 2θ=13.0° is the (100) peak of the material, which represents the regularity of the layered structure of the material, and the specific surface area of ​​the material is 200m 2 / g.

[0024] Add 0.2g of mesoporous carbon nitride material into a 250mL beaker, add 100mL of deionized water, ultrasonically shake for 30 minutes, and then add 4ml of PdCl with a concentration of 0.056mmol / ml 2 Aqueous solution, ultrasonic vibration for 30 minutes, add 5mg NaBH 4...

Embodiment 2

[0027] The Pdmpg-C prepared by embodiment 1 3 N 4 Put 15mg of catalyst into a 50ml three-neck round-bottom flask, add 2ml of water, take 1mmol of the substrate p-amidonitrobenzene and put it into the round-bottom flask, replace the air in the round-bottom flask with hydrogen for three times, and connect the round-bottom flask to a hydrogen bag at atmospheric pressure , reacted at room temperature for 7 hours. After the reaction is completed, filter and rinse with ethanol three times. Gas chromatography analysis shows that p-nitrobenzonitrile is completely converted into p-amidoaniline, and the conversion rate and selectivity are both greater than 99%.

Embodiment 3

[0029] The Pdmpg-C prepared by embodiment 1 3 N 4 Catalyst 15mg is packed into 50ml three-neck round-bottomed flask, add 2ml water, get substrate p-nitrobenzaldehyde 1mmol and add into round-bottomed flask, replace the air in the round-bottomed flask with hydrogen for three times, connect the round-bottomed flask with the atmospheric pressure hydrogen bag, The reaction was carried out at room temperature for 7 hours. After the reaction is completed, filter and rinse with ethanol three times. Gas chromatography analysis shows that p-nitrobenzonitrile is completely converted into p-aminobenzaldehyde, and the conversion rate and selectivity are both greater than 99%.

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Abstract

The invention discloses a selective hydrogenation reduction method for an aromatic nitro compound. The selective hydrogenation reduction method for the aromatic nitro compound comprises the following steps of: adding nanopalladium catalyst loaded by mesoporous carbon nitride, water and aromatic nitro compound into a reaction container; reacting completely in a hydrogen atmosphere; and processing to obtain a corresponding aromatic amino compound. In the method, the nanopalladium catalyst loaded by the mesoporous carbon nitride is used for selectively reducing the aromatic nitro compound, and the selectivity and the conversion rate are above 99 percent; reducing conditions are mild; and the selective hydrogenation reduction method for the aromatic nitro compound is high in operability, so that the selective hydrogenation reduction method for the aromatic nitro compound has a bright marketing prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for selectively hydrogenating and reducing aromatic nitro compounds under the condition of coexistence of multiple reducing groups by using nano-palladium particles supported by mesoporous carbon nitride as a heterogeneous catalyst. Background technique [0002] Amine compounds are important intermediates for the synthesis of drugs, polymers, organic pigments, coatings, dyes, pesticides and other fine chemicals. [0003] They are generally prepared by reduction of their corresponding nitro compounds by catalytic hydrogenation. At present, the catalytic hydrogenation technology directly targeting simple nitro compounds has been quite mature (such as the catalytic hydrogenation of nitrobenzene to aniline), but when other reducible functional groups such as cyano, carbonyl, and double bonds coexist, the nitro Selective reduction is extremely challengin...

Claims

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Application Information

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IPC IPC(8): C07B43/04C07C253/30C07C255/58C07C231/12C07C233/43C07C221/00C07C223/06B01J27/24
Inventor 王勇徐旋李翼李浩然
Owner ZHEJIANG UNIV
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