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Method for preparing 4-benzoyl-4'-methyl-diphenyl sulfide

A technology of benzoyl and diphenyl sulfide, which is applied in the field of preparation of photoinitiator 4-benzoyl-4'-methyl-diphenyl sulfide, can solve the problems of unavailable raw materials, market shortage, and impact on industrial sustainability. Production and other issues

Inactive Publication Date: 2019-05-10
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] From the existing method of preparing 4-benzoyl-4'-methyl-diphenyl sulfide, there are still many disadvantages. In the preparation method of taking p-cresyl thiophenol as raw material, the p-cresyl thiophenol raw material is more expensive, and the market It is relatively scarce, raw materials are not easy to obtain, and the reaction also needs relatively expensive strontium carbonate or ionic liquid, etc. The overall preparation cost of this type of method is high, and the raw materials are not easy to obtain, which affects the continuous production of the industry; the reducing agent Tebbe reagent used in the method of sulfoxide reduction (titanocene methylidenecomplex), and the reaction conditions need to be carried out under low temperature conditions, so the existing process still cannot meet the industrial production conditions, and it is necessary to develop a new process for the production of 4-benzoyl-4'-methyl-diphenyl sulfide

Method used

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  • Method for preparing 4-benzoyl-4'-methyl-diphenyl sulfide

Examples

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Embodiment 1

[0028] Embodiment 1: the preparation of 4-benzoyl-4'-methyl-diphenylsulfide

[0029] 1) Preparation of diphenyl disulfide

[0030] After mixing 200mL of benzene and aluminum trichloride (43g, 0.4mol) evenly, connect the tail gas absorption device, slowly add sulfur monochloride (54g, 0.4mol) dropwise while stirring, and keep the reaction temperature at 30-35°C. After dripping and keeping warm, monitor the reaction by TLC or GC. After the reaction is complete, pour it into ice water for hydrolysis reaction. After the reaction, let it stand and separate layers. The organic phase is washed with water and precipitated. Recrystallization was carried out to obtain 77.7 g of a white solid with a GC content of 99.0% and a melting point of 58-59°C.

[0031] 2) Preparation of phenylthionyl chloride

[0032] Take the above-prepared diphenyl disulfide (65.5g, 0.3mol) and dissolve it in 180mL of dichloroethane, connect the tail gas absorption device, then slowly introduce chlorine gas, c...

Embodiment 2

[0037] Embodiment 2: the preparation of 4-benzoyl-4'-methyl-diphenylsulfide

[0038] 1) Preparation of phenylsulfenyl chloride

[0039] Dissolve the diphenyl disulfide (65.5 g, 0.3 mol) prepared by the method in Example 1 in 200 mL of chlorobenzene, connect the tail gas absorption device, and then slowly introduce chlorine gas, control the reaction temperature 0-5 ° C, after the reaction is complete , first remove the solvent, then distill and purify phenylthionyl chloride under reduced pressure, and collect 41.6g of red liquid at b.p.82-83℃@10mmHg.

[0040] 2) The preparation method of 4-benzoyl-4'-methyl-diphenyl sulfide

[0041]Mix 250mL dichloroethane, aluminum trichloride (40.0g, 0.3mol) and toluene (32.2g, 0.35mol) evenly, connect the tail gas absorption device, and slowly add the benzene prepared by step 1) dropwise under vigorous stirring. Sulfenyl chloride (43.4g, 0.3mol), the reaction temperature is maintained at 25-35 ° C, 1h drop, TLC or GC monitoring reaction, a...

Embodiment 3

[0042] Embodiment 3: the preparation of 4-benzoyl-4'-methyl-diphenylsulfide

[0043] 1) Preparation of phenylsulfenyl chloride

[0044] Dissolve the diphenyl disulfide (65.5 g, 0.3 mol) prepared by the method in Example 1 in 180 mL of dichloroethane, connect the tail gas absorption device, then slowly feed chlorine gas, control the reaction temperature at 0-5 ° C, and react After completion, remove the solvent first, then distill and purify phenylthionyl chloride under reduced pressure, and collect 40.8g of red liquid at b.p.82-83°C@10mmHg.

[0045] 2) The preparation method of 4-benzoyl-4'-methyl-diphenyl sulfide

[0046] Mix 250mL dichloroethane, aluminum trichloride (72.0g, 0.54mol) and toluene (32.2g, 0.35mol) evenly, connect the tail gas absorption device, and slowly add the benzene prepared by step 1) dropwise under vigorous stirring. Sulfenyl chloride (43.4g, 0.3mol), the reaction temperature was maintained at 25-35°C, and the drop was completed after 1h, and the reac...

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Abstract

The invention relates to a preparation method of a photoinitiator 4-benzoyl-4'-methyl-diphenyl sulfide, in particular to a method for preparing phenyl sulfenyl chloride by taking benzene, sulfur monochloride and chlorine as raw materials, then carrying out thioetherification reaction with toluene, and finally carrying out acylation reaction with benzoyl chloride. According to the preparation method of the 4-benzoyl-4'-methyl-diphenyl sulfide provided by the invention, the shortcomings of an existing method are avoided, the used raw materials are cheap and easy to obtain, the reaction conditions are mild, the method is easy to operate, the yield is high, the cost is low, and the method is suitable for industrial stable production.

Description

technical field [0001] The invention relates to a preparation method of photoinitiator 4-benzoyl-4'-methyl-diphenyl sulfide. Background technique [0002] 4-Benzoyl-4'-methyl-diphenyl sulfide is referred to as photoinitiator BMS, with a melting point of 83.0-86.0°C. It is used in paint systems in combination with photoinitiators ITX and EDB. It has good solubility and is compatible with liquid photosensitizers. Good miscibility, low odor, also suitable for white paint or varnish and colored system. [0003] [0004] The method for preparing 4-benzoyl-4'-methyl-diphenyl sulfide at present is as follows: [0005] One is prepared from p-methylthiophenol: Literature Liu, Bin; Lim, Chern-Hooi; Miyake, Garret M.; Journal of the American Chemical Society; vol.139; nb.39; (2017); p.13616-13619 discloses the preparation of p-methylthiophenol and 4-bromobenzophenone in DMSO under the promotion of visible light with strontium carbonate (Cs2CO3); Zhang, Xiao; Lu, Guo-Ping; Cai , C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/20C07C323/22
Inventor 毛桂红张齐王晓蒙许昊武瑞李欢欢
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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