Preparation method of trifluoromethyl sulfinyl halide

A technology of trifluoromethyl sulfinyl halide and trichloromethyl sulfinyl chloride is applied in the preparation of sulfonic acid, the preparation of organic compounds, chemical instruments and methods, etc., and can solve the problems of compression filling, high toxicity, etc. To achieve the effect of saving manufacturing costs

Inactive Publication Date: 2020-04-14
ZHEJIANG AVILIVE CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Method 4) is better than the above three methods. The product obtained is trifluoromethylsulfinyl chloride, which does not require further oxidation in the subsequent preparation of fipronil, but its synthesis method is based on bis(trifluoromethyl)disulfide The raw material and intermediate are trifluoromethylsulfur chloride, which also has a low boiling point and exists in a gaseous state at room temperature. It needs to be compressed and filled for collection, especially the problem of high toxicity.

Method used

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  • Preparation method of trifluoromethyl sulfinyl halide
  • Preparation method of trifluoromethyl sulfinyl halide

Examples

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Embodiment 1

[0033] Example 1: In a four-neck flask made of glass, add 186g of sulfuric acid, heat up to 60°C, 245.4g (3.0mol) of sodium perborate, replace with nitrogen, stir for 30 minutes, drop into another containing 186g of trichloromethylsulfur chloride (1.0mol) glass reaction vial, controlled in the sampling center, 6% trichloromethylsulfinyl chloride, 88.8% trichloromethylsulfinyl chloride, 5.2% trichloromethanesulfinyl chloride, dichloromethane extraction and removal of dichloromethane Chloromethane, a total of 205 g of the mixture was obtained, and 175.9 g of trichloromethylsulfinyl chloride was obtained after rectification under reduced pressure at 5 mmHg, with a content of 99.5% and a yield of 87.1%.

Embodiment 2

[0034] Example 2: In a four-neck flask made of glass, add 186g of sulfuric acid, cool down to 0°C, 81.8g (1.0mol) of sodium perborate, replace with nitrogen, stir for 30 minutes, drop into another containing 186g of trichloromethylsulfur chloride (1.0mol) glass reaction vial, controlled in the sampling center, 6% trichloromethylsulfinyl chloride, 93.9% trichloromethylsulfinyl chloride, 0.1% trichloromethanesulfinyl chloride, dichloromethane extraction and removal of dichloromethane Chloromethane, a total of 205g of the mixture was obtained, and 185.9g of trichloromethylsulfinyl chloride was obtained after rectification under reduced pressure at 5mmHg, with a content of 99.5% and a yield of 92.1%.

Embodiment 3

[0035] Example 3: In a four-necked glass flask, add 186g of sulfuric acid, heat up to 100°C, 81.8g (2.0mol) of sodium perborate, replace with nitrogen, stir for 30 minutes, drop into another containing 186g of trichloromethylsulfur chloride (1.0mol) glass reaction vial, sampling control, 0% trichloromethylsulfinyl chloride, 49.0% trichloromethanesulfinyl chloride, 51.0% trichloromethanesulfonyl chloride, use dichloromethane to remove dichloromethane Chloromethane, a total of 220 g of the mixture was obtained, and 100 g of trichloromethanesulfinyl chloride was obtained after rectification under reduced pressure at 5 mmHg, with a content of 99.5% and a yield of 49.5%.

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Abstract

The present invention relates to a process for the preparation of a trifluoromethyl sulfinyl halide (Formula F<3>CSOX). The trifluoromethyl sulfinyl halide (Formula F<3>CSOX) is used for the preparation of insecticides, pharmaceuticals and fine chemicals, in particular for the preparation of insecticide fipronil. The preparation method comprises the following steps: 1) reacting trichloromethyl sulfur chloride, namely Cl<3>CSCl, with an oxidizing agent to obtain trichloromethyl sulfinyl chloride, namely Cl<3>CSOCl; and (2) enabling trichloromethyl sulfinyl chloride (Cl<3>CSOCl) to react with afluoride to obtain the trifluoromethyl sulfinyl halide, namely F<3>CSOX. The preparation method has the advantages that firstly, the preparation of trifluoromethyl sulfinyl halide avoids low-boiling-point and highly-toxic raw materials and intermediates, namely trifluoromethyl thionyl chloride and di (trifluoromethyl) disulfide, and has the advantages of simplicity, high efficiency, safety, convenience and the like; and 2, the cheap and easily available raw material trichloromethyl sulfur chloride or a mixture thereof is adopted, so that the manufacturing cost is reduced.

Description

technical field [0001] The present invention relates to a kind of trifluoromethylsulfinyl halide (chemical formula is F 3 CSOX), the compound is used for the preparation of insecticides, medicines and fine chemicals, especially for the preparation of the insecticide fipronil. Background technique [0002] Trifluoromethylsulfinyl halides are important chemicals used in the pharmaceutical, pesticide and fine chemical industries. The preparation of trifluoromethylsulfinyl halide mainly contains the following methods: [0003] 1) Published in Journal of fluorine chemistry, 1985, Iss85, 169-172, reported the synthesis of trifluoromethylthiolate by the reaction of potassium fluoride and thiophosgene. [0004] 2) Published in Journal of fluorine chemistry, 1995, Iss95, 171-176, reported the reaction of tetramethylammonium and thiophosgene to synthesize trifluoromethylthiolate. [0005] 3) US2884453 reported the preparation of a mixture of trifluoromethylsulfur chloride and bis(t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/22C07C303/02C07C309/80C07D231/44
CPCC07C303/02C07C303/16C07C303/22C07D231/44C07C309/80
Inventor 刘伟李兰杰张彦祥李惠跃楼新伟
Owner ZHEJIANG AVILIVE CHEM CO LTD
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