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Method for preparing ethylsulfonyl acetonitrile

A technology of ethylsulfonylacetonitrile and ethylthioacetonitrile, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry and other directions, can solve problems such as multiple organic solvents, difficult waste liquid treatment, etc., and achieves easy operation and product yield. The effect of high rate and lower production cost

Inactive Publication Date: 2011-06-08
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It uses acetic acid as the reaction solvent, hydrogen peroxide as the oxidant, and oxidizes ethylthioacetonitrile to ethylsulfonylacetonitrile under the catalysis of sodium tungstate. During the reaction process, it needs to consume more organic solvents, and the waste liquid treatment is more complicated. difficulty

Method used

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  • Method for preparing ethylsulfonyl acetonitrile
  • Method for preparing ethylsulfonyl acetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 Add 10.1g (0.10mol) ethylthioacetonitrile to a 1000mL three-necked flask, stir at room temperature, and dropwise add an aqueous solution of potassium monopersulfate complex tetrabutylammonium bromide (92.1g potassium monopersulfate complex Compound and 9.7g tetrabutylammonium bromide were dissolved in 500mL of water, containing active ingredients potassium monopersulfate 0.30mol, tetrabutylammonium bromide 0.03mol), 1h dripped. Stir at below 40°C for 2h, add 100mL chloroform and extract twice. The organic layer was taken and the solvent was evaporated to obtain 12.1 g of the product with a yield of 91.0% and a content of 98.9% (quantitative analysis by gas chromatography). The NMR data of the product obtained: 1 HNMR (CDCl 3 )δ: (ppm) 1.50-1.55 (t, 3H, -CH 2 CH 3 ), 3.30-3.37 (q, 2H, -CH 2 CH 3 ), 3.97-3.98 (m, 2H, -CH 2 CN).

Embodiment 2

[0019] Example 2 Add 10.1g (0.10mol) ethylthioacetonitrile to a 1000mL three-necked flask, stir at room temperature, and dropwise add an aqueous solution of potassium monopersulfate complex-benzyltriethylammonium chloride (61.5g monopersulfate Potassium hydrogen complex and 2.3g of benzyltriethylammonium chloride were dissolved in 400mL of water, containing active ingredients potassium monopersulfate 0.20mol, benzyltriethylammonium chloride 0.01mol), dripping over 1.5h. Stir at below 20°C for 1.5h, add 100mL chloroform and extract twice. The organic layer was taken and the solvent was evaporated to obtain 12.0 g of the product with a yield of 90.2% and a content of 97.7% (quantitative analysis by gas chromatography).

Embodiment 3

[0020] Example 3 Add 10.1g (0.10mol) ethylthioacetonitrile to a 2000mL three-necked flask, stir at room temperature, and dropwise add an aqueous solution of potassium monopersulfate complex-tetrabutylammonium bromide (123.0g potassium monopersulfate The complex and 16.1g of tetrabutylammonium bromide were dissolved in 800mL of water, containing active ingredients potassium monopersulfate 0.40mol, tetrabutylammonium bromide 0.05mol), and dripped for 1 hour. Stir at below 50°C for 4h, add 100mL ethyl acetate to extract twice. The organic layer was taken and the solvent was evaporated to obtain 12.1 g of the product with a yield of 91.0% and a content of 97.8% (quantitative analysis by gas chromatography).

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Abstract

The invention discloses a method for preparing ethylsulfonyl acetonitrile. In the method, a potassium monopersulfate complex is taken as an oxidant, quaternary ammonium salt is taken as a catalyst, and ethylthio acetonitrile is oxidized into the ethylsulfonyl acetonitrile in an aqueous phase. The reaction conditions are mild, the method is easy and convenient to operate and easy to control, an organic solvent is not needed to be used in the reaction process, the product yield and content are high, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of ethylsulfonyl acetonitrile. Background technique [0002] Ethylacetonitrile is an intermediate in the synthesis of the sulfonylurea herbicide rimsulfuron. Usually, ethylsulfonyl acetonitrile is prepared by oxidizing thioether compound ethylthioacetonitrile to sulfone. The main methods are as follows: ①Using dichloromethane as solvent and m-chloroperoxybenzoic acid as oxidant. ② Using acetic acid as solvent and hydrated sodium perborate as oxidant (Nie Hui, Tong Xiaoxu, Wu Ciwen, etc. Hebei Chemical Industry. 1996, 19(4): 38-45; Zhou Weiqing, Zhang Likang, Xu Xiaoqing, etc. Journal of Inorganic Chemistry. 1990 , 6(1):83-86; Yue Guoren, Wang Jianhua, Zhang Zheng, etc. Applied Chemistry, 1995, 12(4):93-95. etc.). ③ Use acetic acid as solvent and hydrogen peroxide as oxidant (WO Patent 2004101505; Zhao Liqin, Zhang Tao. World of Chemistry, 2000, 55(...

Claims

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Application Information

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IPC IPC(8): C07C317/44C07C315/02
Inventor 谭晓军杨秀利刘善奎王芳王海龙
Owner UNIV OF JINAN
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