Synthesis method of O, O-dialkyl thiphosphoryl chloride

The technology of an alkyl thiophosphoryl and a synthesis method is applied in the field of preparation of pesticide intermediates, can solve the problems of three wastes and the like, and achieves the effects of improving safety and environmental protection level, low comprehensive cost and reducing production cost.

Active Publication Date: 2018-07-27
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Since the production of traditional alkyl monochlorides faces a large number of three wastes that are difficult to deal with, it is necessary to develop a new green synthesis process for alkyl monochlorides based on atomic economics

Method used

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  • Synthesis method of O, O-dialkyl thiphosphoryl chloride
  • Synthesis method of O, O-dialkyl thiphosphoryl chloride
  • Synthesis method of O, O-dialkyl thiphosphoryl chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0041]Add 329.3g (2mol) methyl sulfide (96%) and 0.6g Iron powder catalyst, feed chlorine gas at a controlled temperature of 40°C, and absorb the hydrogen chloride produced with water. The system gradually became cloudy, producing a yellow solid. When about 150 g of chlorine gas is introduced, the system is turned to a pressure of -0.04 MPa and the reaction temperature is maintained at 40°C. With the introduction of chlorine gas, the yellow solid gradually disappears, and brown-red sulfur dichloride is collected by rectification and condensation. Chlorine gas was fed for 5 hours (total feed time), and no obvious liquid was collected when 319 g (4.4 mol, total feed amount) was fed, and the reaction was stopped. A total of 210 g of sulfur dichloride was collected. The chlorine gas flow was stopped, and high vacuum rectification at -0.099 MPa obtained 303.8 g of O, O-dimethylphosphorylthiochloride (purity 99%), yield 94.0%.

Embodiment 2

[0043] Add 391.6g (2mol) ethyl sulfide (96%) and 1.0g Iron powder catalyst, feed chlorine gas at a controlled temperature of 45°C, and absorb the hydrogen chloride produced with water. The system gradually became cloudy, producing a yellow solid. When about 160g of chlorine gas is fed in, the system is turned to a pressure of -0.04MPa while maintaining a reaction temperature of 45°C. The yellow solid gradually disappears as the chlorine gas is fed in, and brown-red sulfur dichloride is collected by rectification and condensation. Chlorine gas was passed in for 4.5 hours, and no obvious liquid was collected when 306 g (4.3 mol) was passed in, so the reaction was stopped. A total of 205 g of sulfur dichloride was collected. Chlorine flow was stopped, and high vacuum rectification at -0.099MPa gave 355.7g of O,O-diethylphosphorylthiochloride (purity 99%), yield 93.4%.

Embodiment 3

[0045] Add 329.3g (2mol) methyl sulfide (96%) and 0.4g Iron powder catalyst, feed chlorine gas at 30°C, and absorb the generated hydrogen chloride with water. The system gradually became cloudy, producing a yellow solid. When about 170g of chlorine gas is introduced, the system is turned to a pressure of -0.05MPa while maintaining a reaction temperature of 30°C. With the introduction of chlorine gas, the yellow solid gradually disappears, and brown-red sulfur dichloride is collected by rectification and condensation. Chlorine gas was passed through for 5 hours, and when 355 g (5.0 mol) was passed through, no obvious liquid was collected, and the reaction was stopped. A total of 207 g of sulfur dichloride was collected. Chlorine flow was stopped, and high vacuum rectification at -0.099MPa gave 302.6g of O,O-dimethylphosphorylthiochloride (purity: 99%), with a yield of 93.6%.

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Abstract

The invention discloses a synthesis method of O, O-diakyl thiphosphoryl chloride. In a reaction system where O, O-dialkyl S-hydro-phophorodithioate and chlorine are subjected to a chlorination reaction to prepare O, O-dialkyl thiphosphoryl chloride, an excess chlorine is introduced to make sulphur generated in the reaction be converted into disulfur dichloride, and disulfur dichloride is convertedinto sulfur dichloride afterwards; and by controlling the reaction temperature and arranging the reaction system to be in the negative pressure state, sulfur dichloride is moved out of the reaction system in the reaction process through distillation and condensing. The synthesis method substantially achieves the atomic economy based on a green chemistry concept; the overall cost of raw materialsis far lower than that in a traditional method, the amount of the three wastes is less, and the three wastes are easy to dispose; a traditional solid-liquid separation step is cancelled, automated production is facilitated, and meanwhile, improvement of the safety and environment production level of the device is facilitated; and O, O-dialkyl thiphosphoryl chloride is not in contact with water, disintegration of the product is avoided, the yield rate is as high as 93%, and the product content can reach 99%.

Description

technical field [0001] The invention belongs to the technical field of preparation of pesticide intermediates, and in particular relates to a synthesis method of O, O-dialkylphosphoryl thiochloride. Background technique [0002] O, O-dialkylphosphoryl thiochloride (referred to as alkyl monochloride, the same below) is a special intermediate for the synthesis of phosphorothioate pesticides, and is the most representative of O, O-dialkylphosphoryl thiochloride The most common ones are O, O-dimethylphosphoryl thiochloride (referred to as methyl monochloride, the same below) and O, O-diethylphosphoryl thiochloride (abbreviated as ethyl monochloride, the same below). Methyl monochloride and ethyl monochloride can be used to prepare nearly twenty kinds of high-efficiency, medium-low toxicity organophosphorus pesticides, such as acephate, pirimiphos-methyl, chlorpyrifos-methyl, fenitrothion, methyl-trimethoprim Cylphos, fenthion, pimofos, chlorpyrifos, chlorpyrifos, chlorpyrifos, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/20
Inventor 王宇马保德陈明刘卫东蒋彪
Owner HUNAN CHEM RES INST
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