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The preparation method of 4,4'-dichlorodiphenyl sulfone

A technology of dichlorodiphenyl sulfone and dichlorodiphenyl sulfoxide, which is applied in the field of preparation of 4,4´-dichlorodiphenyl sulfone, can solve the problems of cumbersome post-processing steps, complicated processes, equipment corrosion, etc. The effect of simple treatment method, simple treatment method and mild reaction conditions

Active Publication Date: 2021-10-29
FUHAI (DONGYING) ADVANCED MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Hydrogen peroxide is used as an oxidant in the traditional sulfoxide oxidation method, but the purity of the obtained 4,4´-dichlorodiphenyl sulfone is low; after further improvement, many industrial productions use a large amount of sulfuric acid to enhance the acidity of the system, mixed with acetic acid or Peroxyacid has an oxidation effect, but a large amount of mixed acid is used, which has a high degree of corrosion to equipment, and it is difficult to treat the mixed waste liquid of mixed acid and solvent, and the separation of acid and solvent is relatively difficult. The separation cost is high, and the prepared 4 ,4´-dichlorodiphenyl sulfone post-treatment steps are more cumbersome, the process is more complicated, which virtually increases the production cost of the enterprise
[0004] As a further improvement, the quaternary ammonium phosphotungstic acid catalyst was used in the research, but the matching special quaternary ammonium salt phase transfer agent is expensive. As a cost consideration, enterprises are limited in its promotion and application
[0005] CN107540581A adopts formic acid or glacial acetic acid, and corresponding peroxyacid as medium reaction, but obtains lower purity
[0006] CN106349126A adopts concentrated sulfuric acid catalyst, chlorobenzene and glacial acetic acid as solvent, hydrogen peroxide oxidation, the prepared 4,4'-dichlorodiphenyl sulfone, although the mixed solvent can be used next time, but the purity and yield are all low
[0007] CN108047101A mentions that the mixture of hydrogen peroxide and acetic acid or concentrated sulfuric acid is used in the oxidation stage, the yield is low, and the mixed acid is difficult to handle
[0008] The use of concentrated sulfuric acid, organic peroxyacids, and a large amount of mixed acids used in the above patents will lead to corrosion of equipment, difficulty in waste liquid separation, and acid crystallization of 4,4´-dichlorodiphenyl sulfone, which is difficult to use with alkali The liquid is completely cleaned and the purity is low
[0009] In CN105732447B, phosphotungstic heteropolyacid quaternary ammonium salt is used as catalyst, benzene is solvent, hydrogen peroxide is oxidant, and the molar ratio of hydrogen peroxide to 4,4'-dichlorodiphenyl sulfoxide is 4~6:1. 4,4´-dichlorodiphenylsulfoxide is oxidized to 4,4´-dichlorodiphenylsulfone, and the catalyst can be reused, but the preparation process of the catalyst is complex and expensive, and the amount of hydrogen peroxide used is large and strong The carcinogen benzene is used as the problem of the solvent, and the yield of the product is low

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  • The preparation method of 4,4'-dichlorodiphenyl sulfone
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  • The preparation method of 4,4'-dichlorodiphenyl sulfone

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Experimental program
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Effect test

Embodiment 1

[0043] The preparation method of 4,4'-dichlorobenyl sulfone is used, including the steps of:

[0044] (1) 0.40 g of ammonium molybdate, 0.37 g of oxalic acid, 24.75 g of hydrogen peroxide, 24.75 g of hydrogen peroxide, and 24.75 g of hydrogen peroxide, resulting in a mixture;

[0045] (2) The above mixed liquid was added dropwise to the four-mouth flask equipped with 54.50 g of 4,4'-dichlorophenyl sulfoxide and 110.00 g of dichloropropane, warmed to 80 ° C, reaction for 5 hours;

[0046] (3) After the reaction is completed, 0.17 g of activated carbon is added to the reaction liquid for 0.5 hours, induce, decolorized, heat filtering the activated carbon, the resulting solution is cooled to 5 ° C, cooling crystals for 1.5 hours, filtered again, to obtain filter cakes and remaining The filtrate was dried at 85 ° C for 7 hours to give high purity 4,4'-dichlorobenyl sulfone; the yield of 4,4'-dichlorobenyl sulfone was 97.2%, and purity was tested by HPLC. It is 99.86%;

[0047] (4) The...

Embodiment 2

[0049] The preparation method of 4,4'-dichlorobenyl sulfone is used, including the steps of:

[0050] (1) 0.40 g of ammonium molybdate, 0.37 g of oxalic acid, 24.75 g of hydrogen peroxide, 24.75 g of hydrogen peroxide, and 24.75 g of hydrogen peroxide, resulting in a mixture;

[0051] (2) The above mixture was added dropwise to the four-mouth flask equipped with 54.50 g of 4,4'-dichlorophenyl sulfoxide and 110.00 g of chlorobenzene, warmed to 80 ° C, and the reaction was 5 hours;

[0052] (3) After the reaction, 1.00 g of the activated carbon reaction was added to the reaction liquid for 0.5 hours, buproped, decolorized, heat filtered through the activated carbon, the resulting solution was cooled to 5 ° C, cooled crystallization for 1.5 hours, filtered again, to obtain filter cakes and remaining The filtrate was dried at 85 ° C for 7 hours to give high purity 4,4'-dichlorophenyl sulfone; the resulting rate of 4,4'-dichlorobenyl sulfone was 97.8%, and the purity was tested by HPLC...

Embodiment 3

[0055]The preparation method of 4,4'-dichlorobenyl sulfone is used, including the steps of:

[0056] (1) 0.40 g of molybdate, 0.42 g of propenic acid, 24.75 g of hydrogen peroxide, 24.75 g of hydrogen peroxide, and 24.75 g of hydrogen peroxide, resulting in a mixture;

[0057] (2) The above mixture was added dropwise to the four-mouth flask equipped with 54.50 g of 4,4'-dichlorophenyl sulfoxide and 110.00 g of chlorobenzene, warmed to 80 ° C, and the reaction was 5 hours;

[0058] (3) After the reaction, 1.00 g of the activated carbon reaction was added to the reaction liquid for 0.5 hours, buproped, decolorized, heat filtered through the activated carbon, the resulting solution was cooled to 5 ° C, cooled crystallization for 1.5 hours, filtered again, to obtain filter cakes and remaining The filtrate was dried at 85 ° C for 7 hours to give high purity 4,4'-dichlorobenyl sulfone; the yield of 4,4'-dichlorobenyl sulfone was 97.3%, and the purity was tested by HPLC. 99.87%;

[0059]...

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Abstract

The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of high-purity 4,4´-dichlorodiphenyl sulfone. The preparation method of the high-purity 4,4´-dichlorodiphenyl sulfone comprises: first mixing molybdate, organic dicarboxylic acid and hydrogen peroxide, and adding them dropwise to 4,4´-dichlorodiphenyl sulfone The reaction is carried out in the mixture of phenyl sulfoxide and solvent. After completion, post-treatment is carried out to obtain high-purity 4,4´-dichlorodiphenyl sulfone and the remaining filtrate; the remaining filtrate is directly used for the next round of reaction after layering ; 4,4´-dichlorodiphenyl sulfoxide:molybdate:organic dicarboxylic acid:hydrogen peroxide molar ratio is 1:0.01~0.05:0.02~0.1:1~3. The invention provides a method for preparing high-purity 4,4´-dichlorodiphenyl sulfone, which has low catalyst cost, simple preparation steps and simple post-treatment steps, and the remaining filtrate from the reaction can be recycled and efficiently utilized, with high purity and high yield .

Description

Technical field [0001] The present invention belongs to the art of organic synthesis, and more particularly to the preparation of 4,4'-dichlorophenyl sulfones. Background technique [0002] 4,4'-dichlorophenyl sulfone as an important chemical raw material, there are many methods for producing 4,4'-dichlorobenyl sulfone in industrial, 4,4'-two for sulfoxide oxidation method There are also many reports of chlorine diphenyl sulfone. [0003] The conventional sulfoxide oxidation method utilizes hydrogen peroxide as an oxidant, but the purity of 4,4'-dichlorobenyl sulfone is low; after further improvement, many industrial production use a large amount of sulfuric acid reinforcing system acidity, mixing with acetic acid or Peroxide is oxidative, but a large amount of mixed acid is used, and the degree of corrosion of the apparatus is high, and the mixture of the mixed acid and the solvent is difficult to treat, the separation of the acid and the solvent is relatively difficult to separ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/00C07C317/14
CPCC07C315/00C07C317/14
Inventor 周玉有黄森彪王敏廖广明
Owner FUHAI (DONGYING) ADVANCED MATERIAL TECH CO LTD