A method for preparation of perfluoroalkyl sulfenyl chloride

A technology of perfluoroalkylsulfinyl chloride and trifluoromethylthiomethylbenzene, applied in chemical methods for liquid-liquid reactions, preparation of sulfides, chemical instruments and methods, etc., capable of solving inherent dangers and insecurity , not commercially attractive, etc.

Active Publication Date: 2012-11-21
克基·霍尔穆斯吉·阿加尔达
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process disclosed in the patent application involves the use of hydrogen fluoride at high temperatures, noting that the process is inherently dangerous and unsafe because hydrogen fluoride is difficult to control at such high temperatures, making the process commercially unattractive

Method used

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  • A method for preparation of perfluoroalkyl sulfenyl chloride
  • A method for preparation of perfluoroalkyl sulfenyl chloride
  • A method for preparation of perfluoroalkyl sulfenyl chloride

Examples

Experimental program
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example 1

[0117]A glass reactor equipped with a central stirrer and a vertical condenser was charged with anhydrous acetonitrile (2.0 L), activated potassium fluoride (6.0 moles), potassium bifluoride (0.3 moles), and o-chlorobenzyl chloride ( 1.0 mol), and the obtained reaction mass was cooled to -15°C. After approximately 2 hours, low temperature thiophosgene (1.2 mol) was injected into the reaction mixture along with 300 mL of acetonitrile. The reaction mixture was then stirred for 2 hours, allowing the temperature of the mixture to rise to 0°C. The reaction mixture was stirred for a further 2 hours and the temperature was raised to 30°C, after which the mixture was kept at this temperature for 2 hours. 0.2 mol of thiophosgene was injected into the reaction mixture, the temperature of the mixture was raised to 80°C, kept at 80°C for 2 hours, and then cooled to 30°C. Additional thiophosgene (0.2 moles) was injected and the reaction temperature was raised to 80°C. Only 1% conversion...

example 2

[0119] A glass reactor equipped with a central stirrer and a vertical condenser was charged with anhydrous acetonitrile (2.0 L), tetramethylammonium fluoride (3.04 mol) and o-chlorobenzyl chloride (1.0 mol) to obtain The reaction mass was cooled to -40°C. After approximately 2 hours, low temperature thiophosgene (1.0 mol) was injected into the reaction mixture along with 300 mL of acetonitrile. The reaction mixture was stirred for 2 hours, the temperature of the mixture was raised to 0° C., and then the reaction mixture was stirred for an additional 2 hours. The temperature of the mixture was then raised to 30°C, and the mixture was kept at that temperature for 2 hours. Thiophosgene (0.2 mol) was injected into the reaction mixture and the temperature was raised to 80°C. The mixture was maintained at 80°C for 2 hours and then cooled to 30°C. Another 0.2 mole of thiophosgene was injected, and the temperature of the mixture was raised to 80°C. Only 2% conversion was observed ...

example 3

[0121] Charge anhydrous acetonitrile (2.0 L), activated potassium fluoride (6.0 mol), potassium bifluoride (0.3 mol), o-chlorobenzyl chloride (1.0 mol) into a glass reactor equipped with a central vertical stirrer and benzyltrimethylammonium fluoride (0.2 mol). The process steps in Example 1 were repeated. Only 1% conversion was observed after 10 hours. No increase in conversion was observed even after holding for several more hours.

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Abstract

A process for the preparation of perfluoroalkyl sulfenyl chloride; said process comprising i) reacting a compound of formula (I) wherein R represents an aromatic group with or without a substituent; and R' represents a halogen, with at least one fluoride compound and thiophosgene in a solvent to obtain a reaction mass; ii) pulverizing the reaction mass with the help of beads to obtain a mixture containing trifluoromethyl thiomethyl benzene derivative; iii) isolating the trifluoromethyl thiomethyl benzene derivative from the mixture; iv) distilling the trifluoromethyl thiomethyl benzene derivative to obtain a purified trifluoromethyl thiomethyl benzene derivative; v) dissolving the purified trifluoromethyl thiomethyl benzene derivative in a solvent selected from the group consisting of dichloromethane, toluene, benzene, ethylene dichloride, mono chloro benzene, carbon tctra chloride, ortho dichloro benzene and tri chloro benzene; and vi) cleaving the trifluoromethyl thiomethyl benzene derivative by selective chlorinolysis by passing chlorine gas at a temperature in the range of about -10 to about 30 DEG C to obtain perfluoroalkyl sulfenyl chloride.

Description

technical field [0001] The invention relates to a method for preparing perfluoroalkylsulfinyl chloride, which is used as an intermediate substance for preparing pesticides and medicines. Background technique [0002] Perfluoroalkylsulfinyl chlorides are important chemicals used in the pharmaceutical and pesticide industries. The preparation of perfluoroalkylsulfinyl chlorides involves two-phase reactions, such as the reaction of potassium fluoride solids in polar solvents and thiophosgene. The solid-liquid phase reaction needs to meet the critical reaction conditions before the reaction can occur, the required transformation and the increase in yield can occur. Therefore, the mixing of solid and liquid reactants is a key link in the preparation process. [0003] Fluorides are difficult to synthesize. The reactivity of fluorine is extremely poor, and it is difficult or impossible to directly prepare fluorine derivatives. The process of preparing fluorine derivatives inclu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C313/08C07C313/02C07C313/00C07C319/14
CPCB01J14/00B01F15/066B01J19/1881B01J2219/00081B01F3/1271B01F2015/061B01J19/0066C07C313/08B01F7/18B01F5/10B01J2219/00065B01J8/20C07C319/14B01J2219/00063B01F7/00633B01F23/59B01F25/50B01F27/191B01F27/90B01F35/93B01F2035/98C07C323/07
Inventor 克基·霍尔穆斯吉·阿加尔达
Owner 克基·霍尔穆斯吉·阿加尔达
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