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Method for synthesizing m-trifluoromethyl benzyl cyanide

A technology of trifluoromethyl benzene acetonitrile and trifluoromethyl benzene is applied in the field of synthesis of organic fluorine compounds, and can solve the problems of environmental pollution, large chemical solvent, unsuitable for industrial production and the like

Active Publication Date: 2006-05-31
SHANGHAI NO 4 REAGENT & H V CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthesis process is too long, and a large amount of toxic and harmful chemical solvents are used, causing great environmental pollution, which is obviously not suitable for industrial production

Method used

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  • Method for synthesizing m-trifluoromethyl benzyl cyanide

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Embodiment 1

[0021] The synthesis of embodiment 1 m-trifluoromethyl benzyl cyanide

[0022] In the reaction pot, add 100 kilograms of 85% sulfuric acid, 298 kilograms of 98% trifluoromethylbenzene (2.00kmol) and 90 kilograms of 98% paraformaldehyde (2.94kmol, melting point 64-67 ℃), at 15 ℃ ~ 25 ℃ Next, 265 kg of 98% chlorosulfonic acid (2.23 kmol) were added dropwise. After the dropwise addition, react at 40°C for 2 hours, remove the acidic aqueous phase after resting, wash twice with water, then neutralize to PH6 with 10% sodium hydroxide solution, carry out vacuum distillation at a vacuum degree of 0.092MPa, and collect 110 kilograms of trifluoromethylbenzene in front of 50~55 DEG C, content 96% (applicable), then collect 75~80 DEG C of fractions under vacuum degree of 0.099MPa, obtain 170 kilograms of m-trifluoromethyl chloromethylbenzenes, The content is 97.5%, and the yield is 66.73% (based on trifluoromethylbenzene). Residual liquid can make 3,3'-two (trifluoromethyl) phenyl metha...

Embodiment 2

[0034] The synthesis of embodiment 2 m-trifluoromethyl benzyl cyanide

[0035] In the reaction pot, add 100 kilograms of 75% sulfuric acid, 298 kilograms of 98% trifluoromethylbenzene (2.00kmol) and 90 kilograms of 98% paraformaldehyde (2.94kmol, melting point 121-123 ° C), at 15 ° C ~ 25 ° C Next, 265 kg of 98% chlorosulfonic acid (2.23 kmol) were added dropwise. After the dropwise addition, react at 55°C for 1 hour, remove the acidic aqueous phase after resting, wash twice with water, then neutralize to PH6 with 10% sodium hydroxide solution, carry out vacuum distillation at a vacuum of 0.092MPa, and collect 114 kg of trifluoromethylbenzene at 50-55°C, with a content of 96.5% (applicable), and 164 kg of m-trifluoromethylchloromethylbenzene at 75-80°C, with a content of 97.1 %, the yield is 65.7% (calculated in trifluoromethylbenzene). Residual liquid can make 3,3'-two (trifluoromethyl) phenyl methane 29 kilograms.

[0036] In the reaction pot, add 164 kilograms of 97.1% m...

Embodiment 3

[0038] Embodiment 3 The comparative example corresponding to the second step cyanation reaction of embodiment 1

[0039] In the reaction pot, add 170 kilograms of 97.5% m-trifluoromethyl chloromethylbenzene (0.85kmols), 165 kilograms of 33% sodium cyanide aqueous solution (1.11kmols) and 2 kilograms of tetrabutylammonium bromide to carry out cyanation reaction , reacted at 45°C for 12 hours, without mass tracking, and the impurity content of the organic phase was 5.5%. The water phase was separated, washed twice with water, and distilled under reduced pressure at a vacuum of 0.099MPa to collect fractions at 94-97°C. Obtain 146 kilograms of trifluoromethyl benzyl nitrile product, total content reaches 98.7%, and its middle-trifluoromethyl benzyl nitrile content reaches 94.0%, ortho-trifluoromethyl benzyl nitrile content is 1.4%, p-trifluoromethyl benzyl nitrile The content of phenylacetonitrile is 3.3%, and the reaction yield is 87.05% (calculated as m-trifluoromethylchlorometh...

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Abstract

A kind of synthetic method of m-trifluoromethyl benzyl nitrile comprises two reaction steps: the first step is a chloromethylation reaction, the second step is a cyanation reaction, and the first step reaction is trifluoromethylbenzene, Paraformaldehyde and chlorosulfonic acid are raw materials, react in the presence of mineral acids to generate m-trifluoromethyl chloromethylbenzene; in the second step reaction, gas chromatography analysis is used to control the organic phase impurity content to be lower than 3%, which is beneficial to the reaction Yield improvement. The method has the advantages of easy-to-obtain production raw materials, simple operation, convenient control, high reaction yield, low production cost, reduced environmental pollution, etc., and is a synthetic method suitable for industrial production.

Description

technical field [0001] The present invention relates to the synthetic method of organic fluorine compound, is specifically about the synthetic method of m-trifluoromethyl benzyl nitrile. Background technique [0002] m-Trifluoromethylphenylacetonitrile belongs to a kind of fluorinated aromatic chemical products. In the field of pesticide synthesis, it can be used to prepare herbicides; in the field of pharmaceutical production, it can be used to synthesize antibacterial drugs, weight loss drugs and coronary vasodilators. [0003] Existing technical reports mainly contain the synthetic methods of the following several m-trifluoromethyl benzyl nitriles. [0004] In 1979, the synthetic method of the m-trifluoromethyl phenylacetonitrile reported in U.S. The Dow Chemical Company patent US 4,144,265 was to use trifluoromethylbenzene, chloromethyl methyl ether and chlorosulfonic acid as raw materials to prepare m-trifluoromethyl phenylacetonitrile Methyl chloromethyl benzene, und...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/35C07C253/00
Inventor 陆稼麟陆炜陈张民杜骏
Owner SHANGHAI NO 4 REAGENT & H V CHEM
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