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Preparation method of trimethyl sulfonium chloride

A technology of trimethylsulfonium chloride and methyl chloride, which is applied in the direction of organic chemistry, can solve the problems of low boiling point of dimethyl sulfide, large environmental impact, toxicity, etc., and achieve short reaction time, low production cost, and high product yield. high rate effect

Active Publication Date: 2018-04-20
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the synthesis method of trimethylsulfonium salt cationic part is mainly obtained by reacting dimethyl sulfide with methylating reagents (such as methyl iodide, methyl bromide, methyl chloride and dimethyl sulfate, etc.), and its representative literature is Anal. Chem. 1987, 59: 562-567; J. Polym. Res. 2012, 19: 9747; Synthetic Comm.1985, 15: 749; EP 0639198; CN106518812; It has a great impact on the environment during the transportation, storage and production of raw materials. This characteristic will bring environmental pressure to the large-scale production of trimethyl onium salt. The preparation process with the advantages of high cost, easy access to raw materials, simple process, and low environmental risk is meaningful

Method used

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  • Preparation method of trimethyl sulfonium chloride

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Effect test

Embodiment 1

[0016] Add 12.0 g of sodium sulfide nonahydrate and 30 mL of anhydrous methanol into a 50 mL tetrafluoroethylene-lined autoclave, feed 15.2 g of methyl chloride at low temperature, close the autoclave and heat up to an external bath at 65 °C for 10 h, cool, and the reaction solution Filtration, solvent removal by rotary evaporation, 5.4 g of crude product white solids were obtained, and the productive rate was 96.0%. 1 HNMR (D 2 0,600M): 2.87(s,9H). This product was used directly in subsequent reactions.

Embodiment 2

[0018] Add 12.0 g of sodium sulfide nonahydrate and 30 mL of anhydrous methanol into a 50 mL tetrafluoroethylene-lined autoclave, feed 14.7 g of methyl chloride at low temperature, close the autoclave and heat up to an external bath at 90 °C for 6 h, cool, and the reaction solution Filtration, rotary evaporation to remove solvent, almost theoretical yield was obtained as crude product white solid, and this product was recrystallized from ethanol to obtain colorless crystals, 1 HNMR (D 2 0,600M): 2.87(s,9H). The product content measured by nuclear magnetic resonance method is more than 99%.

Embodiment 3

[0020] Add 16.8 g of sodium sulfide nonahydrate and 50 mL of anhydrous n-propanol into a 100 mL tetrafluoroethylene-lined autoclave, feed 17.7 g of methyl chloride at low temperature, close the autoclave and raise the temperature to 100 °C for 4 h, cool, and the reaction solution Filtration, rotary evaporation to remove solvent, crude product white solid 6.6 g, productive rate 83.8%, 1 HNMR (D 2 0,600M): 2.87(s,9H). This product was directly used in the subsequent reaction, and if necessary, it could be recrystallized from ethanol to obtain a higher purity product.

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Abstract

The invention provides a preparation method of trimethyl sulfonium chloride which is directly synthesized by sodium sulfide nonahydrate and chloromethane through reaction. The preparation method comprises the following steps of using an alcohol as a solvent, putting the sodium sulfide nonahydrate and the chloromethane into a pressure reaction kettle, reacting for 4 to 10h at the temperature of 65to 100 DEG C, cooling to room temperature, filtering, and removing the solvent, so as to synthesize a target product, namely the trimethyl sulfonium chloride. The preparation method has the advantagesthat the method is simple, the price is low, the efficiency is high, the pollution is low, the resource can be recycled, and the preparation method is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a preparation method for synthesizing trimethylsulfonium chloride by reacting sodium sulfide nonahydrate and methyl chloride. Background technique [0002] Trimethylsulfonium chloride is a trimethylsulfonium salt, which can be used as a methylating agent for the methylation reaction of carboxylic acids and amine compounds, and can also be used in the reaction of aldehydes and ketones to prepare corresponding epoxy compounds, especially It can be used as a pesticide intermediate in the production of the herbicide glufosin. At present, the synthesis method of trimethylsulfonium salt cationic part is mainly obtained by reacting dimethyl sulfide with methylating reagents (such as methyl iodide, methyl bromide, methyl chloride and dimethyl sulfate, etc.), and its representative literature is Anal. Chem. 1987, 59: 562-567; J. Polym. Res. 2012, 19: 9747; Synthetic Comm.1985...

Claims

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Application Information

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IPC IPC(8): C07C381/12
CPCC07C381/12
Inventor 李焰武忠忠郭霆任君张万轩陈祖兴
Owner HUBEI UNIV
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