Method for producing nitrobenzene compound

The technology of a compound, nitrobenzene, is applied in the field of manufacture of nitrobenzene compounds to achieve the effect of reducing the amount of waste, excellent yield, and improving safety

Active Publication Date: 2018-12-21
KUMIAI CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another problem is that dinitro compounds are produced as by-products
Compared with the conventional technology known before Patent Document 6, the method described in Patent Document 6 is superior, however, there is still room for improvement in the point of using hydrogen peroxide

Method used

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  • Method for producing nitrobenzene compound
  • Method for producing nitrobenzene compound
  • Method for producing nitrobenzene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0251] Manufacture of 2,6-Dichloronitrobenzene Using Nitric Acid

[0252] Add 2,6-dichloroaniline 16.2g (0.10mol), water 81.7mL and 69% nitric acid 21g (0.23mol) in the 200mL four-neck flask equipped with stirrer, reflux condenser, thermometer and dropping funnel, the mixture Heat at 60°C to dissolve. The mixture was cooled to 37°C while stirring, and after stirring at this temperature for 30 minutes, the mixture was further cooled to 0°C. After 19.0 g (0.11 mol) of a 40% sodium nitrite aqueous solution was added dropwise thereto at 0-5°C over 25 minutes, the reaction mixture was stirred at 0-5°C for 30 minutes. Thereafter, 36 mL of a 5% aqueous sodium bicarbonate solution was added dropwise to adjust the pH of the reaction mixture to 0.6-1.3, and then 17.5 mL of toluene and 30 g of water were added. After the mixture obtained above was partitioned into a toluene layer and an aqueous layer, the aqueous layer was separated.

[0253] Add copper oxide (I) 2.15g (0.015mol), tol...

Embodiment 2

[0255] Manufacture of 2,6-Dichloronitrobenzene Using Nitric Acid

[0256] Add 32.4g (0.20mol) of 2,6-dichloroaniline, 190mL of water and 42.0g (0.46mol) of 69% nitric acid in a 500mL four-necked separable flask equipped with a stirrer, reflux condenser, thermometer and dropping funnel , and the mixture was dissolved by heating at 60°C. The mixture was cooled to 37°C while stirring, and after stirring at this temperature for 30 minutes, the mixture was further cooled to 0°C. After 38.0 g (0.22 mol) of 40% sodium nitrite aqueous solution was added dropwise thereto at -3°C (minus 3°C) to 5°C over 35 minutes, the reaction mixture was stirred at -3°C to 5°C for 30 minutes. Thereafter, 72.2 mL of a 5% aqueous sodium bicarbonate solution was added dropwise to adjust the pH of the reaction mixture to 0.8-2.0, and then 30.4 mL of toluene was added. After the mixture obtained above was partitioned into a toluene layer and an aqueous layer, the aqueous layer was separated. The resulti...

Embodiment 3

[0294] Manufacture of methyl 3-chloro-2-nitrobenzoate using nitric acid

[0295] Add 35% isobutyl methyl ketone (MIBK) solution 106.1g (0.20mol) of 2-amino-3-chlorobenzoic acid methyl ester in the 300mL four-neck flask equipped with stirrer, reflux condenser, thermometer and dropping funnel and Water 96.8mL. While stirring the mixture, 42 g (0.46 mol) of 69% nitric acid was added dropwise over 30 minutes, and then cooled to -5°C to 0°C while stirring. After 39.9 g (0.22 mol) of a 38% sodium nitrite aqueous solution was added dropwise thereto at -5°C to 0°C over 1 hour, the reaction mixture was stirred at -5°C to 0°C for 1 hour. After the mixture obtained as described above was partitioned into MIBK layer and aqueous layer, the aqueous layer was separated. The resulting aqueous layer was submitted to differential scanning calorimetry and accelerated calorimetry.

[0296] Add 9.7g (0.068mol) of copper (I) oxide, 22.5mL of water, 168mL of 10% aqueous sodium bicarbonate solutio...

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Abstract

The purpose of the present invention to provide a method for producing a nitrobenzene compound represented by general formula (1), which is economically preferable, and suitable for industrialization.The present invention pertains to a method for producing a nitrobenzene compound represented by general formula (1) (in the formula, R1 represents a halogen atom; R2, R3, and R4 represent a hydrogenatom or the like; R5 represents a halogen atom or an alkoxycarbonyl group), comprising: (i) a step for reacting an aniline compound represented by general formula (2) (in the formula, R1, R2, R3, R4,and R5 are as defined above) with a metal salt of nitrous acid in the presence of nitric acid; and (ii) a step for reacting the product of step (i) with a metal salt of nitrous acid in the presence ofa copper compound.

Description

technical field [0001] The present invention relates to the manufacture method of the nitrobenzene compound of general formula (1): [0002] [chemical 1] [0003] [0004] In the formula, R 1 Represents a halogen atom; R 2 , R 3 and R 4 Can be the same or different, representing a hydrogen atom, a halogen atom or an alkyl group; R 5 represents a halogen atom or an alkoxycarbonyl group. Background technique [0005] The nitrobenzene compounds of the general formula (1) are useful as intermediates for the production of various beneficial organic compounds. In particular, 2,6-dichloronitrobenzene (see Patent Document 1 and Patent Document 2) and 2-chloro-6-alkoxycarbonylnitrobenzenes (see Patent Document 3 and Patent Document 4) are used as pharmaceuticals Intermediates with pesticides and the like are known. [0006] As a method for producing a nitrobenzene compound of the general formula (1), a production method consisting of diazotization of an aniline compound an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/10C07C205/12C07C205/58C07B61/00
CPCC07C201/06C07C205/12C07C205/58
Inventor 中村尊之加藤聡榎木真希田藤淳
Owner KUMIAI CHEM IND CO LTD
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