Preparation method of diaryl disulfide

A diaryl disulfide and sulfur powder technology, which is applied in the preparation of hydrogenated polysulfide/polysulfide, magnesium organic compounds, organic chemistry, etc., can solve the problems of high cost, large pollution, and low yield

Active Publication Date: 2020-02-11
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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Problems solved by technology

[0009] It is also reported that a synthetic route using halogenated aromatics as a synthetic raw material is shown in the following formula: under the action of a strong base, a heavy metal catalyst catalyzes the reaction of halogenated aromatics with sulfur to generate disulfide, but this reaction stays in the laboratory stage, and the catalyst is Heavy metals Rh, Pd, Cu, Fe, etc. need to add complex ligands at the same time, and there are problems such as low yield, many side reactions, high cost, and large pollution

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  • Preparation method of diaryl disulfide

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[0030] One embodiment of the present invention provides a method for preparing diaryl disulfides, comprising the steps of: reacting a halogenated aromatic hydrocarbon with magnesium powder to generate a Grignard reagent, then adding sulfur powder, and Under the action of the reaction, two aryl disulfides are obtained.

[0031] The preparation method uses cheap and easy-to-obtain halogenated aromatic hydrocarbons as synthetic raw materials to synthesize aromatic disulfide, firstly reacts it with magnesium powder to generate Grignard reagent, and then reacts with sulfur powder under the action of acid and oxidant to obtain disulfide disulfide. Aryl disulfides. The whole method process does not require heavy metal catalysis and complex ligands, and does not need to discharge materials in the middle. It is directly synthesized in one pot, and is environmentally friendly, with high conversion rate, high yield and purity, simple process and convenient operation, and is suitable for ...

Embodiment 1

[0056]

[0057]At room temperature, dissolve 80g of bromobenzene in 200mL of THF, stir evenly, under the protection of nitrogen, add 12g of magnesium chips into a three-necked flask with a thermometer, put a small amount of bromobenzene solution into a constant pressure dropping funnel, and add a small particle of iodine Elemental substance initiates the reaction, vigorously stirs and heats up to 60°C, the system begins to bubble and heat up, the reaction starts, slowly add the remaining bromobenzene solution dropwise, the process temperature is controlled at 45-60°C, after the dropwise addition, continue to stir for 1 hour, and the metal magnesium disappears completely , and then add sulfur powder 20g, reflux reaction 6-8h. Cool down to 5-10°C. Mix 200mL of 20wt% sulfuric acid solution and 100mL of 30wt% hydrogen peroxide evenly to prepare a mixed acid solution, slowly add it dropwise to the above reaction solution, the process control temperature is not higher than 20°C, ...

Embodiment 2

[0059]

[0060] At room temperature, dissolve 65g of o-chlorotoluene in 250mL of dimethyltetrahydrofuran, stir evenly, under the protection of nitrogen, add 12g of magnesium chips into a three-necked flask with a thermometer, put a small amount of bromobenzene solution into a constant pressure dropping funnel, and add 5mL Dibromoethane initiates the reaction, vigorously stirs and heats up to 65°C, the system starts to bubble and heat up, the reaction starts, slowly add the remaining o-chlorotoluene solution dropwise, the process temperature is controlled at 60-65°C, after the dropwise addition, continue to stir for 1 hour, Metal magnesium completely disappears, then add 20g of sulfur powder, and react at 60-65°C for 6-8h. Cool down to 5-10°C. Mix 200mL of 20wt% sulfuric acid solution and 100mL of 30wt% hydrogen peroxide to prepare a mixed acid solution, slowly add it dropwise to the above reaction solution, the process control temperature is not higher than 20°C, and contin...

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Abstract

The invention relates to a preparation method of diaryl disulfide. The method comprises the following steps: reacting halogenated aromatic hydrocarbon with magnesium powder to generate a Grignard reagent, adding sulfur powder, and carrying out a reaction under the action of an acid and an oxidant to obtain the diaryl disulfide. The aromatic disulfide is synthesized by using the cheap and easily available halogenated aromatic hydrocarbon as a synthesis raw material, and then reacts with the magnesium powder to generate the Grignard reagent, and the Grignard reagent reacts with the sulfur powderunder the action of the acid and the oxidant to obtain the diaryl disulfide. The whole method has the advantages of realization of direct synthesis without heavy metal catalysis or complex ligands inthe process and midway discharging, environmental friendliness, high conversion rate, high yield, high purity, simple process, convenience in operation, and suitableness for large-scale production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of diaryl disulfide. Background technique [0002] Aryl disulfide is an important class of organic reagents and synthetic intermediates, widely used in organic synthesis, polymer and other fields. It can be used as a vulcanizing agent for the production of synthetic rubber, natural rubber and other elastomers. At the same time, aryl disulfide is also an important drug synthesis intermediate, and can also be used in the synthesis of feed additives, flavors, pesticides, etc. [0003] There are many reports on the synthesis methods of symmetrical aryl disulfides. The most commonly used method is to start from thiophenol and obtain it by oxidation of hydrogen peroxide under the action of a catalyst, as shown in the following formula. However, the thiophenol used in this method has a foul smell and is very polluting to the environment, so it cannot be a...

Claims

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Application Information

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IPC IPC(8): C07C319/24C07C321/28
CPCC07C319/24C07F3/02C07C321/28
Inventor 唐杰曾春玲李凯宁状
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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