Method for preparing 4-methylsulfonyltoluene

A technology of thiamphenicol toluene and sodium toluene sulfinate, applied in the field of preparation of 4-thiamphenicol toluene, which can solve the problems of slow methylation rate, large loss of inorganic salt removal, long production cycle, etc.

Active Publication Date: 2013-11-13
浙江嘉福新材料科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above-mentioned preparation method has two root causes that affect the yield: the one is the separation of the reduction product 4-sodium methylbenzenesulfinate and the inorganic salt, and the loss of the inorganic salt in the organic salt is very large; the other is the methylation rate Slow, long production cycle

Method used

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  • Method for preparing 4-methylsulfonyltoluene
  • Method for preparing 4-methylsulfonyltoluene

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Dissolve a certain proportion of anhydrous sodium sulfite and sodium bicarbonate in water, stir evenly, and slowly add a certain amount of p-toluenesulfonyl chloride at 85°C. After the addition is completed, the reaction is kept for 1 hour, and the reaction is completed, cooling, suction filtration and drying to obtain crude sodium 4-methylbenzenesulfinate. Take 10g of 4-methylsulfonyl toluene and 100g of sodium 4-methylbenzenesulfinate (the content of sodium 4-methylbenzenesulfinate is measured by ultraviolet analysis, and the dosage is calculated based on the content. The same implementation is carried out in the following examples Example 1), 1 g of boron tetrafluoride 1-butyl-3-methylimidazole ionic liquid was added to the autoclave. The reaction kettle is connected to a methyl chloride cylinder. After the pressure stabilizes at 0.4Mpa, the temperature is raised to 80°C. After the reaction starts, the pressure drops to 0.2Mpa. Continue to keep the methyl chloride gas...

Embodiment 2

[0029] Take 20 g of 4-methylsulfonyl toluene, 100 g of sodium 4-methylbenzenesulfinate, and 2 g of boron tetrafluoride 1-butyl-3-methylimidazole ionic liquid, and put them into the autoclave. The reaction kettle is connected to a methyl chloride cylinder. After the pressure stabilizes at 0.5Mpa, the temperature is raised to 85°C. After the reaction starts, the pressure drops to 0.2Mpa. Keep the methyl chloride gas flowing. When the pressure is constant at 0.5Mpa, after reacting for 1 hour, Close the inflation valve. After the reaction, the reaction kettle is heated at 100°C and discharged. Add hot water and stir in the output mixture. When the water temperature is slightly cold, perform suction filtration, and then wash with a small amount of water. After cooling, white crystals are precipitated. The product is obtained after suction filtration and drying. 90.08g, the measured melting range: 87.3~87.9℃. The product was analyzed by gas chromatography with a purity of 98.1%.

Embodiment 3

[0031] Take 50 g of 4-methylsulfonyl toluene, 100 g of sodium 4-methylbenzenesulfinate, and 2 g of boron tetrafluoride 1-pentyl-3-methylimidazole ionic liquid, and add them to the autoclave. The reaction kettle is connected to a methyl chloride cylinder. After the pressure stabilizes at 0.4Mpa, the temperature is raised to 83°C. After the reaction starts, the pressure drops to 0.2Mpa. Keep the methyl chloride gas flowing. When the pressure is constant at 0.4Mpa, after reacting for 1 hour, Close the inflation valve. After the reaction, the reaction kettle is heated at 90°C and the material is discharged. Add hot water to the output mixture and stir. When the water temperature is slightly cold, suction filtration, and then wash it with a small amount of water. After cooling, white crystals are precipitated, and the product is obtained after suction filtration and drying. 85.98g, the measured melting range: 86~86.8℃. The product was analyzed by gas chromatography with a purity of...

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Abstract

The invention relates to a method for preparing 4-methylsulfonyltoluene, which comprises the following steps of: reacting anhydrous sodium sulphite and sodium bicarbonate with paratoluensulfonyl chloride to obtain a crude sodium 4-toluenesulfinate product; and mixing sodium 4-toluenesulfinate and a small amount of 4-methylsulfonyltoluene, heating for melting, adding imidazole quaternary ammonium salt ionic liquid serving as a catalyst, introducing chloromethane gas, and ensuring that chloromethane is dissolved in the 4-methylsulfonyltoluene and subjected to synthetic reaction with the sodium 4-toluenesulfinate to obtain the 4-methylsulfonyltoluene. In the method, methylation reaction is nucleophilic substitution, an organic phase is the chloromethane and the product 4-methylsulfonyltoluene, and the sodium 4-toluenesulfinate is taken as a nucleophilic reagent and carried by the ionic liquid serving as the catalyst into the organic phase to be subjected to nucleophilic substitution reaction with the chloromethane. Any other solvent except the product 4-methylsulfonyltoluene is not used, so that side reactions in the reaction are avoided, product yield is over 88 percent, purity is over 97 percent, and organic solvent recovery is reduced.

Description

Technical field [0001] The invention relates to a method for preparing 4-methylsulfone toluene, which belongs to the field of organic chemistry. Background technique [0002] 4-Methylsulfone toluene is widely used in the synthesis of medical antibiotics thiamphenicol, thiamphenicol glycinate hydrochloride, veterinary antibacterial drug fluprofen, agricultural herbicide sulcotrione and organic synthesis intermediates. Application value. The current production process of 4-methylsulfonyl toluene is based on 4-methylbenzenesulfonyl chloride as raw material. After reduction, sodium 4-methylbenzenesulfinate is obtained. The methylation reaction is carried out in the aqueous phase. The increase of the polarity of the system affects the reaction rate, it is necessary to separate the inorganic salt and then the methylation reaction. This process also uses the highly toxic reagent dimethyl sulfate. Patent documents "2008101626197", "200910018223.X" and "200910018412.7" etc. reported the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/14C07C315/00
Inventor 吴建一王宏亮缪程平宗乾收张洋屠晓华张丽赵丽丰
Owner 浙江嘉福新材料科技有限公司
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