Preparation method for symmetric diaryl disulfide

A diaryl disulfide, symmetrical technology, applied in the field of preparation of symmetrical diaryl disulfide, can solve the problems of high cost, limited sources of halogenated hydrocarbons and thiophenols, and achieve short reaction time and cheap reagents The effect of easy availability, high application value and industrial production value

Inactive Publication Date: 2019-04-05
沾化大荣化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The cost of using halogenated hydrocarbons and thiophenols as starting materials is higher than that of aromatic hydrocarbons, and the sources of halogenated hydrocarbons and thiophenols are limited

Method used

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  • Preparation method for symmetric diaryl disulfide
  • Preparation method for symmetric diaryl disulfide
  • Preparation method for symmetric diaryl disulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The following reaction schemes are provided as illustrations:

[0030]

[0031] Add 33.55g of tert-butylbenzene and 80g of 1,2-dichloroethane into a 500ml four-neck flask equipped with a stirring rod, condenser, thermometer and constant pressure dropping funnel. After cooling down to 5°C, start adding dropwise Add 34.95g of chlorosulfonic acid for 1 hour. After the dropwise addition, continue to keep warm for 5 hours, then raise the temperature to 60°C, add 35.68g of thionyl chloride dropwise for 1 hour, keep warm for 5 hours, and then distill under reduced pressure Remove 1,2-dichloroethane to obtain p-tert-butylbenzenesulfonyl chloride, which can be directly used to prepare disulfide;

[0032] Add the 39g p-tert-butylbenzenesulfonyl chloride prepared above, 3.34g potassium iodide, 150g glacial acetic acid in a 500ml four-necked flask with a stirring rod, a condenser tube, a thermometer and a constant pressure dropping funnel, and heat up to 85°C with The solid fee...

Embodiment 2

[0034] The following reaction schemes are provided as illustrations:

[0035]

[0036] Add 22.00 g of 2,6-dimethyl-4-tert-butylbenzene, 80 g of cyclohexane in a 500 ml four-necked flask with a stirring rod, condenser, thermometer and constant pressure dropping funnel, and cool to 5 After ℃, start to add 15.64g of chlorosulfonic acid dropwise for 1h. After the dropwise addition, continue the heat preservation reaction for 5h, then raise the temperature to 80°C and add 15.91g of thionyl chloride dropwise for 1h. 5h, followed by distillation under reduced pressure to remove cyclohexane to obtain 3-chloro-2,6-dimethyl-4-tert-butylbenzenesulfonyl chloride, which can be directly used to prepare disulfide;

[0037] In the 500ml four-necked flask that has stirring bar, condenser tube, thermometer and constant pressure dropping funnel, add above-mentioned prepared 2,6-dimethyl-4-tert-butylbenzenesulfonyl chloride 33g, potassium iodide 2.23g, 150g of glacial acetic acid, heat up to ...

Embodiment 3

[0039] The following reaction schemes are provided as illustrations:

[0040]

[0041] Add 19.53g of benzene and 80g of ethyl acetate into a 500ml four-necked flask equipped with a stirring rod, condenser, thermometer and constant pressure dropping funnel. The duration is 1h. After the dropwise addition, continue to keep warm for 5h, heat up to 65°C, add 35.68g of thionyl chloride dropwise, add dropwise for 1h, keep warm for 5h, and then distill off ethyl acetate under reduced pressure to obtain benzenesulfonate Acyl chlorides can be directly used to prepare disulfides;

[0042] Add 12.9g of benzenesulfonyl chloride and 150g of glacial acetic acid prepared above into a 500ml four-necked flask equipped with a stirring rod, condenser, thermometer and constant pressure dropping funnel, raise the temperature to 80°C, and slowly add 6.05g of phosphorous acid dropwise , added dropwise for 1 hour, after 1 hour of heat preservation reaction, slowly pour the reaction solution into ...

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Abstract

The invention discloses a preparation method for symmetric diaryl disulfide. The preparation method comprises the following steps: using aromatic hydrocarbon as shown in a general formula (I) as a rawmaterial and reacting with chlorosulfonic acid to generate aryl chlorosulfonic acid, and reacting with sulfoxide chloride to synthesize aryl sulfonyl chloride as shown in a general formula (II); andpreparing the symmetric diaryl disulfide as shown in a general formula (III) under the action of a reducing agent through a reduction reaction by the aryl sulfonyl chloride as shown in the general formula (II). The disclosed preparation method for the symmetric diaryl disulfide has many advantages of low toxicity of the reaction raw material, short reaction time, cheap reagents and easy acquisition, convenient separation and purification and the like, and has very high application value and industrial production value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of a symmetrical diaryl disulfide. Background technique [0002] Disulfide (R-S-S-R') is an important organic reagent and synthetic intermediate, widely used in organic synthesis, polymer and other fields. In the field of polymers, disulfide can be used as a vulcanizing agent for the production of synthetic rubber, natural rubber and other elastomers, which can make them have good tensile strength. In the field of medicine, disulfide is an important drug synthesis intermediate. In addition, allyl disulfide, diallyl disulfide, etc. have a very obvious effect on lowering blood pressure, can be used to prevent fatty liver, etc., and at the same time have a very obvious effect on reducing blood viscosity and aggregation. In addition, disulfide extreme pressure anti-wear additive is also an important lubricating oil additive, which can be widely used i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/02C07C309/86C07C319/24C07C321/30
CPCC07C303/02C07C319/24C07C309/86C07C321/30
Inventor 马立亮冯柏成于法暖许雯郭超
Owner 沾化大荣化工科技有限公司
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