Application of fullerenes as catalysts in the catalytic hydrogenation of nitro groups in nitroaromatic compounds under light irradiation

A nitroaromatic and catalytic hydrogenation technology, which is applied in the preparation of amino compounds, organic compounds, physical/chemical process catalysts, etc., can solve the problems of high cost, waste of resources, pollution of the environment, etc., and achieve high selectivity and low Ecological hazard and environmental hazard, highly active effect

Inactive Publication Date: 2012-02-01
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 1. The metal powder-acid chemical reduction method produces a large amount of inorganic salt waste and by-products, which not only pollutes the environment, but also wastes resources and does not meet the requirements of green chemistry and resource conservation
Electrochemical reduction method has high requirements on electrodes, electrolyte and electrolytic cell, and is not suitable for mass production
[0004] 2. The catalysts used in the catalytic hydrogenation method are metal catalysts such as Raney nickel and platinum. Metal catalysts have the disadvantages of environmental pollution, ecological hazards and high cost
[0005] 3. When there are hydrogenation functional groups such as aldehydes, ketones, and nitriles in nitroaromatic compounds, the selective control of nitrohydrogenation is a common problem with the catalysts currently in use.
But so far there is no report on its application in nitroaromatic compounds

Method used

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  • Application of fullerenes as catalysts in the catalytic hydrogenation of nitro groups in nitroaromatic compounds under light irradiation
  • Application of fullerenes as catalysts in the catalytic hydrogenation of nitro groups in nitroaromatic compounds under light irradiation
  • Application of fullerenes as catalysts in the catalytic hydrogenation of nitro groups in nitroaromatic compounds under light irradiation

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0021] The preparation method of each substance is as follows:

[0022] Monovalent C 60 Preparation of negative ions: in 25mL tetrahydrofuran, add 0.036g C 60 , 0.130g Ni-Al alloy powder, 0.400g sodium hydroxide, under stirring, pass into nitrogen bubble to remove dissolved air, add freshly distilled distilled water 5.0mL after 30 minutes to initiate the reaction, after 60 minutes, stop stirring, stand still 30 minutes, the system is divided into two layers, monovalent C 60 Negative ions are dissolved in tetrahydrofuran, and the upper layer of tetrahydrofuran C is taken out 60 Negative ion solution, spare.

[0023] Monovalent C 70 Preparation of negative ions: in 25mL tetrahydrofuran, add 0.036g C 70 , 0.130g Ni-Al alloy powder, 0.400g sodium hydroxide, under stirring, pass into nitrogen bubble to remove dissolved air, add freshly distilled distilled water 5.0mL after 30 minutes to initiate the reaction, after 60 minutes, stop stirring, stand still 30 minutes, the system...

specific Embodiment 1

[0024] Photo-excited catalytic reaction test: The photo-excited catalytic reaction was carried out under the irradiation of a 300W high-pressure Hg lamp, and 0.036g of catalyst C was added to the columnar quartz reactor 60 , 1.0g of nitrobenzene reaction substrate and 250ml of tetrahydrofuran solvent, bubbling hydrogen for 30 minutes, removing dissolved air, turning on the light source, and bubbling hydrogen under magnetic stirring, the temperature of the whole system is maintained at 25°C by circulating water cooling, and the reaction After 1.0 hour, the stirring and hydrogen bubbling were stopped, and a sample of the reaction solution was taken out for GC-MS analysis. The catalyst was recovered and characterized by centrifugation. The conversion rate of nitrobenzene was 82.6%, and the selectivity of aniline was 78.9%.

specific Embodiment 2

[0025] Photo-excited catalytic reaction test: The photo-excited catalytic reaction was carried out under the irradiation of a 300W high-pressure Hg lamp, and 0.036g of catalyst C was added to the columnar quartz reactor 60 , 1.0g nitrobenzene and 250ml tetrahydrofuran solvent, bubbling hydrogen for 30 minutes, removing dissolved air, turning on the light source, and bubbling hydrogen under magnetic stirring. , stop stirring and hydrogen bubbling, take out a sample of the reaction solution for GC-MS analysis, and the catalyst is recovered and characterized by centrifugation. The conversion rate of nitrobenzene is 100%, and the selectivity of aniline is 92.4%.

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PUM

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Abstract

The invention discloses the application of a fullerene as a catalyst in the catalytic hydrogenation reaction of nitro groups in nitroaromatic compounds under light irradiation conditions. Nitroaromatic compounds include nitrobenzene, chloronitrobenzene and nitroaromatic ketones and nitriles. The fullerene catalyst is any one of monovalent C60 anion, neutral C60 or neutral C70. The invention utilizes a non-metallic catalytic system to activate hydrogen molecules and selectively catalyze the hydrogenation reaction of nitro groups under light irradiation, normal temperature and normal pressure conditions. The fullerene catalyst has the outstanding advantages of high activity and high selectivity. Ecological hazards and environmental hazards generated by catalytic reactions are reduced.

Description

technical field [0001] The present invention relates to a kind of application of catalyzer, specifically fullerene is used as catalyzer at normal temperature, normal pressure (1 H 2 Air pressure) and the application of selective hydrogenation of nitroaromatic compounds to prepare aminoaromatic compounds under light conditions. Background technique [0002] Efficient and selective catalytic hydrogenation of aromatic nitro compounds is of great significance in the industrial field. Aminoaromatic compounds are very important chemical intermediates, which can be used to synthesize various fine chemicals such as pesticides, drugs, and photoelectric functional molecules. At present, the preparation methods of aminoaromatic compounds include: chemical reduction method of metal powder under acidic conditions, electrochemical reduction method and catalytic hydrogenation method. [0003] 1. The metal powder-acid chemical reduction method produces a large amount of inorganic salt was...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B43/04B01J21/18C07C211/46C07C211/52C07C209/36C07C225/22C07C221/00C07C255/58C07C255/42C07C253/30C07C237/30C07C231/12
Inventor 徐正李保军
Owner NANJING UNIV
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