A kind of synthetic method of trimethylsulfonium bicarbonate

A technology of trimethylsulfonium bicarbonate and a synthesis method, applied in directions such as organic chemistry, can solve the problems of high environmental protection treatment pressure, high cost of raw materials, and high toxicity of by-products, and achieves reduction of production energy consumption, convenient transportation and storage, and reaction conversion. high rate effect

Active Publication Date: 2020-07-31
HUBEI UNIV
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Problems solved by technology

[0008] The above-mentioned synthetic methods have their own characteristics, but their respective shortcomings are also very obvious. For example, some raw materials are expensive, some require high equipment, some by-products are highly toxic, and the pressure of environmental protection is high. In particular, most synthetic methods obtain three Methylsulfonium hydroxide aqueous solution is not suitable for the synthesis of solid trimethylsulfonium bicarbonate salt. Therefore, a new method for preparing trimethylsulfonium hydroxide solution that is simple, efficient, economical and environmentally friendly is developed, and then synthesized to facilitate transportation and storage. The solid trimethylsulfonium bicarbonate salt is of great interest

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  • A kind of synthetic method of trimethylsulfonium bicarbonate
  • A kind of synthetic method of trimethylsulfonium bicarbonate

Examples

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Embodiment 1

[0021] Embodiment one: 2.05 g of trimethylsulfonium chloride salts are dissolved in 15 mL of absolute ethanol, cooled and stirred in an ice-water bath, slowly dropwise add 10 mL of ethanol solution containing 0.80 g of sodium hydroxide, after the dropwise addition, continue to maintain for 10 Stir the reaction at ~15°C for 0.5h, let it stand for 1.0h, and filter to remove sodium chloride. Slowly inject 0.98 g of carbon dioxide gas into the filtrate until the pH value of the reaction solution is about 8.2, and recover ethanol by rotary evaporation under reduced pressure at 45°C. Obtain 2.37 g target product trimethylsulfonium bicarbonate salt, productive rate is 94.2%, 1 HNMR (D 2 O,600M): 2.98 (s.9H), the typical proton nuclear magnetic resonance spectrum of the product is attached figure 1 , this product can be used directly for subsequent applications.

Embodiment 2

[0022] Example 2: Dissolve 11.26g of trimethylsulfonium chloride salt in 50mL of anhydrous methanol, cool and stir in an ice-salt bath at -5°C, and slowly add dropwise 30mL of methanol solution containing 4.02g of sodium hydroxide. After the dropwise addition, Continue to maintain stirring reaction at 0~5°C for 2.0h, filter to remove sodium chloride, slowly pass 6.6 g of carbon dioxide gas into the filtrate until the pH value of the reaction solution is about 7.5, and recover methanol by rotary evaporation at 40°C to obtain 13.28 g The target product, trimethylsulfonium bicarbonate salt, has a yield of 96.1%. This product can be used directly for subsequent applications, and the crude product can also be reprocessed with anhydrous isopropanol to obtain higher purity trimethylsulfonium bicarbonate salt.

Embodiment 3

[0023] Example 3: Dissolve 11.25g of trimethylsulfonium chloride salt in 75mL of anhydrous isopropanol, stir in a water bath at room temperature, slowly add dropwise 30mL of methanol solution containing 4.02g of sodium hydroxide, after the dropwise addition, continue to stir After reacting for 1.0 h, remove sodium chloride by filtration, slowly pass through the filtrate with 6.0 g of carbon dioxide gas until the pH value of the reaction solution is about 8.0, and then recover the alcohol solvent by rotary evaporation under reduced pressure at 45 °C to obtain 12.82 g of the target product trimethyl base sulfonium bicarbonate salt, the productive rate is 92.8%, and this product can directly carry out follow-up application.

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Abstract

The invention provides a preparation method of a trimethyl-sulfonium-hydrocarbonate solid. The synthesis method comprises the steps that a trimethyl-sulfonium-chloride alcohol solution is mixed and reacts with an equimolar ratio of sodium hydroxide alcohol solution at -5-40 DEG C, filtration is carried out to prepare a trimethyl-sulfonium hydroxide alkaline alcohol solution, then a slight excess of carbon dioxide gas is introduced until the pH value of a reaction liquid is 7.5-8.5, then an alcohol solvent is removed under reduced pressure to obtain a trimethyl-sulfonium-hydrocarbonate solid product, and the yield can reach 96% or above. The synthesis method has the advantages that the operation is simple, the environmental pollution is small, the yield is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthetic method capable of industrially producing trimethylsulfonium bicarbonate solid salt. Background technique [0002] Trimethylsulfonium bicarbonate belongs to trimethylsulfonium salt, which can be used as a methylating agent in the methylation reaction of compounds such as carboxylic acids and amines, and can also be used in the preparation of corresponding epoxy compounds from aldehyde and ketone compounds, especially As a pesticide intermediate, it can be used in the production of the herbicide glufosin. At present, the synthesis method of trimethylsulfonium bicarbonate salt reported in document WO 9722612 A (1997) is to use an aqueous solution of trimethylsulfonium hydroxide to react with carbon dioxide to obtain an aqueous solution of trimethylsulfonium hydrogencarbonate salt, and its aqueous solution of sulfonium salt has good stability Howeve...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/12
CPCC07C381/12
Inventor 李焰李超罗文萍武忠忠任君陈祖兴
Owner HUBEI UNIV
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