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Method utilizing catalytic hydrogenation synthesis of nitrobenzene compounds to prepare aniline compounds

A technology of aniline compounds and nitrobenzenes, which is applied in the field of catalytic hydrogenation to synthesize aniline compounds, can solve problems such as low efficiency and long catalytic reaction time, and achieve the effects of improving reaction efficiency, shortening reaction time, and easy operation control

Inactive Publication Date: 2015-03-11
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned patented technologies can prepare high-yield aniline compound products, but they have the disadvantages of long catalytic reaction time and low efficiency, so the use of Raney Ni urgently needs a method to improve reaction efficiency

Method used

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  • Method utilizing catalytic hydrogenation synthesis of nitrobenzene compounds to prepare aniline compounds
  • Method utilizing catalytic hydrogenation synthesis of nitrobenzene compounds to prepare aniline compounds
  • Method utilizing catalytic hydrogenation synthesis of nitrobenzene compounds to prepare aniline compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 Effect of Different Chloride Salts on the Raney Ni Catalyzed Hydrogenation of p-Chloronitrobenzene (4-CNB) to Synthesize p-Chloroaniline (4-CAN)

[0023] Measure 80mL of 4-chloronitrobenzyl alcohol solution with a concentration of 10g / L and add it to a 100mL three-necked flask, then weigh 0.2g Raney Ni catalyst; add different chloride salts according to 1mol% of the amount of the substrate substance into the reaction system; with N 2 The air in the system was replaced three times, followed by H 2 Replace three times; then pass H 2 , H 2 The flow rate was controlled at 10mL / min, the reaction temperature was controlled at 40°C, and the reaction pressure was normal pressure. The reaction was carried out for 3 hours under continuous stirring with a magnetic stirrer at a speed of 1500r / min. The specific experimental results are shown in Table 1.

[0024] Table 1 Effect of different chlorides on the catalytic hydrogenation of 4-CNB

[0025]

Embodiment 2

[0026] Example 2 Effects of different sodium salts on Raney Ni catalyzed 4-CNB hydrogenation to synthesize 4-CAN

[0027] Measure the 4-chloronitrobenzyl alcohol solution that 80mL concentration is 10g / L and join in the there-necked flask of 100mL, then take by weighing 0.2g Raney Ni catalyst; In the reaction system; use N 2 The air in the system was replaced three times, followed by H 2 Replace three times; then pass H 2 , H 2 The flow rate was controlled at 10mL / min, the reaction temperature was controlled at 20-60°C, and the reaction pressure was normal pressure. The reaction was carried out for 3 hours under continuous stirring with a magnetic stirrer at a speed of 1500r / min. The specific experimental results are shown in Table 2.

[0028] Table 2 Effects of different sodium salts on the catalytic hydrogenation of 4-CNB

[0029]

[0030]

Embodiment 3

[0031] Example 3 Effect of different NaF additions on Raney Ni catalyzed 4-CNB hydrogenation to synthesize 4-CAN

[0032] Measure 80mL of 4-chloronitrobenzyl alcohol solution with a concentration of 10g / L and add it to a 100mL three-neck flask, then weigh 0.2g Raney Ni catalyst; add different amounts of NaF to the reaction system according to the percentage of the amount of substrate In, add 0mol%, 1mol%, 5mol%, 10mol% NaF respectively; Use N 2 The air in the system was replaced three times, followed by H 2 Replace three times; then pass H 2 , H 2 The flow rate was controlled at 10mL / min, the reaction temperature was controlled at 40°C, and the reaction pressure was normal pressure. The reaction was performed for 3 hours under continuous stirring with a magnetic stirrer at a speed of 1500r / min. The specific experimental results are shown in Table 3.

[0033] Table 3 Effect of different NaF additions on the catalytic hydrogenation of 4-CNB

[0034]

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Abstract

The invention relates to a catalytic hydrogenation synthesis method to prepare aniline compounds, and specifically relates to a method utilizing catalytic hydrogenation synthesis of nitrobenzene compounds to prepare aniline compounds. Raney Ni is taken as the catalyst, hydrogen gas is taken as the hydrogen source, and then metal salts are added into a liquid phase system to make nitrobenzene compounds carry out catalytic hydrogenation reactions to generate the aniline compounds. The addition amount of the metal salts is 1 to 10 mol% of the amount of substance of the reaction substrate. The provided method has the advantages of mild conditions, high reaction efficiency, simple operation, easy control, and low investment cost.

Description

technical field [0001] The invention relates to a method for synthesizing aniline compounds by catalytic hydrogenation, in particular to a method for synthesizing aniline compounds by catalytic hydrogenation of nitrobenzene compounds. Background technique [0002] As an important class of organic synthesis intermediates, aniline compounds have been widely used in the synthesis process of pharmaceuticals, pesticides, dyes, spices and daily chemicals, and occupy a very important position in the field of fine chemicals. The production methods of aniline compounds are mainly prepared by reduction of corresponding nitrobenzene compounds, such as: chemical reduction method, electrolytic reduction method and catalytic hydrogenation reduction method, etc. Among them, the liquid-phase catalytic hydrogenation reduction method is favored by people because of its simple operation process, high product yield, good product quality and low energy consumption; in addition, this method theor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/36C07C211/52C07C211/46C07C255/58C07C253/30C07C229/60C07C227/04
Inventor 夏传海刘霞马宣宣王建华
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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