Synthesis method of 3,5-dichloroaniline

A synthesis method, technology of dichloroaniline, applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve the problems of high pressure, long reaction time, and difficult separation, and achieve short reaction steps and easy operation Simple, Wide-Source Effects

Active Publication Date: 2017-05-31
EAST CHINA NORMAL UNIV
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Problems solved by technology

This method has long steps, many wastes, and difficult separation; (2) the second method is to develop mixed dichlorobenzene as raw material, brominated to obtain mixed dichlorobromobenzene, and isomerized to obtain 3,5-dichlorobromobenzene Benzene is finally carried out through ammonification reaction, and the product is obtained by filtration. Although this process selects cheap and easy-to-obtain mixed dichlorobenzene raw materials, the strong acid hydrogen bromide produced in the bromination reaction is very polluting to the environment. In addition, the ammonification reaction needs to be At a higher temperature, potassium chlorate and ammonia water are used for reduction, which is unsafe to operate, and ammonia water also pollutes the environment, which cannot meet the requirements of clean production, and is not a green process
(3) The third method is the 3,5-dichloronitrobenzene reduction method, including hydrogenation reduction, sodium sulfide reduction, hydrochloric acid-iron powder reduction method, which also has the disadvantages of high raw material cost, low reduction efficiency, and many wastes.
Japan generally adopts the bromination and rearrangement of o-dichlorobenzene to obtain 3,5-dichlorobromobenzene, and then ammoniation to obtain 3,5-dichloroaniline. The device capacity is 2000 tons/year, but the same steps long, the three wastes produced are more
The methods for the synthesis of 3,5-dichloroaniline reported in literature and patents mainly include: (1) Chinese Patent Application No. 200410014747.9 discloses a 4-chloro-2-nitrotoluene produced by the production of 6-chloro-2-nitrotoluene 4,6-dichloro-o-nitrotoluene is obtained by chlorination and rectification separation, and then 4,6-dichloroaminobenzoic acid is obtained by oxidation reaction and hydrogenation reduction, and the product 3 is obtained after decarboxylation. 5-dichloroaniline, although the source of raw materials is sufficient and cheap, the total reaction yield is about 60%
(2) Chinese Patent Application No. 201210219294.8 discloses a kind of taking nitrochloro...

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  • Synthesis method of 3,5-dichloroaniline
  • Synthesis method of 3,5-dichloroaniline
  • Synthesis method of 3,5-dichloroaniline

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Embodiment 1

[0036] Add tris(dibenzylideneacetone)dipalladium (0.005mmol) and 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (0.02mmol) under nitrogen protection in a reaction tube , add 1mL of 1,4-dioxane solvent and stir for 20-60 minutes, the raw material 1,3,5-trichlorobenzene (0.5mmol), sodium tert-butoxide (2.25mmol), ammonium sulfate (0.75mmol) Place in a sealed tube, pump and ventilate under nitrogen protection, then add the coordinated catalyst, then add 5mL of solvent, seal the tube, heat to 100°C and stir for 24h, after the reaction is complete, the raw materials are detected by GCMS. After the reaction, add 5 mL of water to dilute, add 5 mL of tert-butyl methyl ether to extract three times, then add hydrochloric acid to adjust the pH11, extract three times with 5 mL of tert-butyl methyl ether, remove The product 3,5-dichloroaniline (72 mg, 89%) could be obtained by solvent removal.

Embodiment 2

[0038] Add tris(dibenzylideneacetone)dipalladium (0.005mmol) and 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (0.02mmol) under nitrogen protection in a reaction tube , add 1mL of 1,4-dioxane solvent and stir for 20-60 minutes, the raw material 1,3,5-trichlorobenzene (0.5mmol), sodium tert-butoxide (2.25mmol), ammonium sulfate (0.75mmol) Put it in a sealed tube, pump it for nitrogen protection, then add the coordinated catalyst, then add 2mL of 0.4mol / L ammonia gas 1,4-dioxane solution, and finally add 3mL of solvent, seal it up tube, heated to 100°C and stirred for 24h, after the reaction was completed, the reaction of the raw materials was detected by GCMS. After the reaction, add 5 mL of water to dilute, add 5 mL of tert-butyl methyl ether to extract three times, then add hydrochloric acid to adjust the pH11, extract three times with 5 mL of tert-butyl methyl ether, remove The product 3,5-dichloroaniline (69 mg, 85%) could be obtained by solvent removal.

Embodiment 3

[0040] Add bis-bis[(1,2,3)-1-phenyl-2-propene]dipalladium (0.005mmol) and 2-di-tert-butylphosphino-2',4' under nitrogen protection in a reaction tube, 6'-triisopropylbiphenyl (0.02mmol), add 1mL of 1,4-dioxane solvent and stir for 20-60 minutes, the raw material 1,3,5-trichlorobenzene (0.5mmol), tert-butyl Sodium alkoxide (2.25mmol) and ammonium sulfate (0.75mmol) were placed in a sealed tube, pumped and ventilated under nitrogen protection, then the coordinated catalyst was added, and 5mL of solvent was added, the sealed tube was sealed, heated to 100°C and Stir for 24 hours, after the reaction is completed, it is detected by GCMS that the reaction of the raw materials has been completed. After the reaction, add 5 mL of water to dilute, add 5 mL of tert-butyl methyl ether to extract three times, then add hydrochloric acid to adjust the pH11, extract three times with 5 mL of tert-butyl methyl ether, remove The product 3,5-dichloroaniline (73 mg, 90%) was obtained by solvent r...

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Abstract

The invention discloses a synthesis method of 3,5-dichloroaniline. 1,3,5-trichlorobenzene serves as a raw material, alkali or an ammonia solution or ammonium salt is added into an organic solvent to serve as an ammonia source, a coupling reaction is generated under the effect of a transition metal catalyst and ligand, and the product 3,5-dichloroaniline is obtained. According to the method, the raw materials are simple and easy to obtain, the cost is low, synthesis steps are simple, the product 3,5-dichloroaniline can be obtained through direct coupling of 1,3,5-trichlorobenzene and the ammonia source only through a one-step reaction, fewer byproducts are generated, fewer three wastes are generated, environmental friendliness is achieved, upgrading of the product process is achieved, and great significance is achieved for reducing the synthesis cost of 3,5-dichloroaniline and derivatives thereof.

Description

technical field [0001] The invention relates to 3,5-dichloroaniline and its synthesis method and application, belonging to the technical field of chemical substances and their synthesis. Background technique [0002] 3,5-Dichloroaniline is an intermediate of medicine, pesticide and dyestuff, its English name is 3,5-Dichloroaniline, CAS626-43-7, the pure product is needle crystal, m.p.51~53℃, b.p.259~260 ℃ / 98.7kPa, soluble in ethanol, ether, diethyl carbonate, insoluble in water, highly toxic, corrosive, mainly used in the manufacture of fungicides, procymidone, sclerotin, sclerotin, and sclerotia Li, ethylene clonozolin and iprodione, etc. The compound is also widely used in the synthesis of medicines, dyes, pigments, photochromic materials and plant growth promoters. At present, due to the increase in the output of cyclic imide agricultural fungicides, the intermediate 3,5-dichloroaniline has become a trend that the supply exceeds the demand. Therefore, it is of practica...

Claims

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Application Information

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IPC IPC(8): C07C209/10C07C209/86C07C211/52
CPCC07C209/10C07C209/86C07C211/52
Inventor 肖元晶周小凡胡岸靖程化毓李勇峰赵秋华张俊良
Owner EAST CHINA NORMAL UNIV
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