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Improved method for synthesizing indoxacarb intermediate chlorocarbonyl[4-(trifluoromethoxy)phenyl]carbamic acid methyl ester

A technology of methyl carbamate and trifluoromethoxyaniline, which is applied in the field of pesticide preparation, can solve the problems of shortening reaction period, reducing production cost, long reaction period and the like, and achieves shortening reaction period, reducing production cost and reducing mass fraction. Effect

Inactive Publication Date: 2019-05-03
山东华阳农药化工集团有限公司
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] Aiming at problems such as long reaction cycle and high risk in the prior art, the present invention proposes an improved method for synthesizing methyl chloroformyl [4-(trifluoromethoxy)phenyl] carbamate, using phosgene instead of For solid phosgene and diphosgene, by controlling the speed of phosgene, the reaction is carried out directly at room temperature by adopting the method of back-dropping slurry under the catalysis of the catalyst, avoiding the use of highly corrosive sodium cyanide or poor stability Mixed alkali is used as the initiator. At the same time, there is no need to strictly control the low temperature reaction environment, which simplifies the operation steps, shortens the reaction cycle, and reduces the production cost.

Method used

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  • Improved method for synthesizing indoxacarb intermediate chlorocarbonyl[4-(trifluoromethoxy)phenyl]carbamic acid methyl ester
  • Improved method for synthesizing indoxacarb intermediate chlorocarbonyl[4-(trifluoromethoxy)phenyl]carbamic acid methyl ester
  • Improved method for synthesizing indoxacarb intermediate chlorocarbonyl[4-(trifluoromethoxy)phenyl]carbamic acid methyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Step 1: Put 0.25mol p-trifluoromethoxyaniline, 0.14mol sodium carbonate, 3.4mol water, and toluene into a 500ml reaction flask, stir, adjust the temperature to 5-15°C, and add 0.27mol chloroformic acid dropwise Methyl ester, after 1 hour of dropwise addition, the temperature was raised to 30°C and kept for 2 hours.

[0041] Step 2: After the heat preservation is completed, the reaction solution is filtered and separated, and the filtered white solid is washed and dried, and the oil phase can be reused.

[0042] Step 3: Mix the obtained solid with toluene, cut the water for 0.5h, add 0.016mol potassium tert-butoxide, fractionally distill and cut the water to 105°C, the mixed solution is in the form of slurry,

[0043] Step 4: Pass phosgene into the toluene solution at a temperature of 10°C, the phosgene is generated according to a conventional method, and the mass content is: COCl 2 91.9%, Cl 2 0.13%, CO 2 3.01%, CO 3.96%, N 2 0.6%, O 2 0.1%, impurity 0.3%,

...

Embodiment 2

[0051]Step 1: Put 0.25mol p-trifluoromethoxyaniline, 0.15mol sodium carbonate, 3.6mol water, and toluene into a 1000ml reaction flask, stir, adjust the temperature to 15-25°C, and add 0.5mol chloroformic acid dropwise Methyl ester, after 3 hours of dropwise addition, the temperature was raised to 40°C, and the temperature was kept for 1 hour.

[0052] Step 2: After the heat preservation is completed, the reaction solution is filtered and separated, and the filtered white solid is washed and dried, and the oil phase can be reused.

[0053] Step 3: Mix the obtained solid with toluene, cut the water for 0.5h, add 0.02mol potassium tert-butoxide, fractionally distill and cut the water to 110°C, the mixed solution is in the form of slurry,

[0054] Step 4: Pass phosgene into the toluene solution at a temperature of 15°C, the phosgene is generated according to a conventional method, and the mass content is: COCl 2 92.9%, Cl 2 0.13%, CO 2 2.01%, CO 3.56%, N 2 0.8%, O 2 0.3%...

Embodiment 3

[0062] Step 1: Put 0.25mol p-trifluoromethoxyaniline, 0.16mol sodium carbonate, 4.2mol water, and toluene into a 1000ml reaction flask, stir, adjust the temperature to 25-35°C, and add 0.38mol chloroform dropwise Methyl ester, after 2 hours of dropwise addition, the temperature was raised to 35°C and kept for 1.5 hours.

[0063] Step 2: After the heat preservation is completed, the reaction solution is filtered and separated, and the filtered white solid is washed and dried, and the oil phase can be reused.

[0064] Step 3: Mix the obtained solid with toluene, cut the water for 0.4h, add 0.025mol potassium tert-butoxide, fractionally distill and cut the water to 115°C, the mixed solution is in the form of slurry,

[0065] Step 4: Pass phosgene into the toluene solution at a temperature of 20°C, the phosgene is generated according to a conventional method, and the mass content is: COCl 2 91.7%, Cl 2 0.14%, CO 2 2.91%, CO 3.06%, N 2 1%, O 2 0.6%, impurity 0.3%,

[006...

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Abstract

The invention discloses an improved method for synthesizing indoxacarb intermediate chlorocarbonyl[4-(trifluoromethoxy)phenyl]carbamic acid methyl ester, and relates to the field of pesticide preparation. The method provided by the invention uses phosgene instead of solid phosgene and diphosgene without considering risk that the solid phosgene and the diphosgene are easily decomposed at high temperature and a phosgene toluene solution overflows easily and instantaneously at high temperature; at the same time, a manner that slurry is added dropwise reversely is adopted under the catalyst catalysis, a reaction is directly performed at room temperature, and strong-corrosivity sodium cyanide or a poorer-stability mixed alkali is avoided from being used as an initiator; the low-temperature reaction environment does not need to be strictly controlled, the operation steps are simplified, the reaction cycle is shortened, the production costs are reduced, and the reaction process can be controlled through control of an introduction speed of the phosgene; and the method reduces a mass fraction of sodium carbonate in the reaction system and improves a product yield.

Description

technical field [0001] The invention discloses an improved method, which relates to the field of pesticide preparation; in particular, it relates to an improved method for synthesizing methyl chloroformyl [4-(trifluoromethoxy)phenyl]carbamate, an indoxacarb intermediate. Background technique [0002] Indoxacarb (C22H17ClF3N3O7, common name indoxacarb) is a high-efficiency and low-toxicity new type of oxadiazine sodium channel blocking insecticide developed by DuPont Company of the United States at the end of last century. It has a wide insecticidal spectrum and quick effect. It has excellent control effect on resistant pests such as beet armyworm, diamondback moth and cotton bollworm, and has no cross-resistance with other insecticides, and has no carcinogenic, teratogenic and mutagenic effects. [0003] Methyl chloroformyl[4-(trifluoromethoxy)phenyl]carbamate is one of the important intermediates in the synthesis of indoxacarb, in the form of white crystals. Existing synth...

Claims

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Application Information

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IPC IPC(8): C07C269/06C07C271/66
Inventor 孙绪兵李和娟闫新华高文陈永平王同涛李振兴
Owner 山东华阳农药化工集团有限公司
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