Substituted benzoyl urea insect growth regulator synthesizing method

A technology for growth regulators and benzoyl ureas, which is applied in the field of synthesis of substituted benzoyl urea insect growth regulators, can solve the problems of dangerous operation, product separation, low yield and the like, and achieves easy industrialization Production, simplifying industrial operations, increasing productivity

Inactive Publication Date: 2005-02-16
INST OF ZOOLOGY CHINESE ACAD OF SCI
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0023] The purpose of the present invention is to overcome the long fluorination reaction time and low yield when synthesizing substituted benzoylurea insect growth regulators in the prior art, and the hydrolysis reaction has special requirements for equipment and dangerous operation due to the use of acid catalysis , and the disadvantages of high cost of esterification reaction, separation of products, and insufficient addition reaction rate, thus providing a catalyst using highly active potassium fluoride and quaternary ammonium salt, which greatly shortens the fluorination reaction time and uses A base-catalyzed hydrolysis reaction reduces the special requirements for equipment, and uses phosgene to replace oxalyl chloride, reduces the cost of esterification reaction, and uses a catalyst to increase the yield of addition reaction. A synthetic method for substituted benzoylurea insect growth regulators

Method used

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  • Substituted benzoyl urea insect growth regulator synthesizing method
  • Substituted benzoyl urea insect growth regulator synthesizing method
  • Substituted benzoyl urea insect growth regulator synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] 1) Fluorination: add 500Kg of sulfolane into a 1000L reactor, add spray-dried fine-grained potassium fluoride (450 mesh) 88.4Kg (1.5KM), dichlorobenzonitrile 172Kg (1KM) while stirring, and The catalyst mixture composed of 40wt% tetrabutylammonium chloride and 60wt% methyl trioctyl ammonium chloride was 1.72Kg, heated at 200°C for 8 hours, filtered to remove the precipitated potassium chloride, and the filtrate was fractionated to obtain difluoro Benzoonitrile 133.6Kg (0.96KM), the yield was 96.1%, the content was 98.4%, and the solvent sulfolane was recovered;

[0048] 2) Hydrolysis: add 109.9Kg (0.79KM) of difluorobenzonitrile and 1.10Kg of sodium hydroxide as the catalyst into the reactor, turn on the hot steam to increase the temperature, add 72.63Kg (2.14KM) of hydrogen peroxide dropwise within 2 hours, and add dropwise After completion, keep it at 40°C for 1 hour, negative pressure excess hydrogen peroxide, and spin dry the reactants with a centrifuge to obtain a difl...

Embodiment 2

[0052]1) Fluorination: add 500Kg of sulfolane into a 1000L reactor, add spray-dried granular potassium fluoride (550 mesh) 117.8Kg (2KM), dichlorobenzonitrile 172Kg (1KM) while stirring, and A catalyst mixture composed of 60wt% tetrabutylammonium chloride and 40wt% methyl trioctyl ammonium chloride was 5.16Kg, heated at 200°C for 10 hours, filtered to remove the precipitated potassium chloride, and the filtrate was fractionated to obtain difluorobenzene Nitrile 134.1Kg (0.965KM), the yield was 96.5%, the content was 99.3%, and the solvent sulfolane was recovered;

[0053] 2) Hydrolysis: add 109.9Kg (0.79KM) of difluorobenzonitrile, catalyst sodium hydroxide 1.10Kg and sodium carbonate 1.10Kg into the reaction kettle, turn on the hot steam to increase temperature, add 51Kg (1.5KM) peroxide dropwise within 2 hours After the addition of hydrogen, keep it at 40°C for 1 hour, negative pressure excess hydrogen peroxide, and spin dry the reactants with a centrifuge to obtain a difluorobe...

Embodiment 3

[0057] 1) Fluorination: add 500Kg of sulfolane into a 1000L reactor, add spray-dried fine-grained potassium fluoride (500 mesh) 106.0Kg (1.8KM), dichlorobenzonitrile 172Kg (1KM) while stirring, and The catalyst mixture consisting of 50wt% tetrabutylammonium chloride and 50wt% methyl trioctyl ammonium chloride was 3.44Kg, heated at 200°C for 9 hours, filtered to remove the precipitated potassium chloride, and the filtrate was fractionated to obtain difluoro Benzoonitrile 133.7Kg (0.96KM), the yield was 96.2%, the content was 98.8%, and the solvent sulfolane was recovered;

[0058] 2) Hydrolysis: add 109.9Kg (0.79KM) of difluorobenzonitrile, catalyst sodium bicarbonate 1.65Kg and sodium carbonate 1.65Kg into the reaction kettle, turn on the hot steam to increase temperature, add 102Kg (3.0KM) peroxide dropwise within 2 hours After the addition of hydrogen, keep it at 40°C for 1 hour, negative pressure excess hydrogen peroxide, and spin dry the reactants with a centrifuge to obtain a...

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Abstract

The invention refers to a synthetic method of insect growth regulator of substituted benzoyl urea and to be specific involves the synthetic method of fluorin bell urea, fluorin insect urea and diflubenzuron. It chooses the 2, 6-difluoro benzonitrile as the starting material and gets the compound of the substituted benzoyl urea after fluorination, hydrolysis, esterification and addition. The method adopts the potasium fluoride with high activity and quaternary ammonium salt as the catalyzer during the fluorination, which shortens the time of the fluorination reaction greatly, chooses the base catalysis during the hydrolysis, which reduces the special requirement to the equipment, uses the phosgene instead of the oxalyl chloride during the esterification to decrease the reaction cost and employs the catalyzer during the addition to increase the yield of the reaction. The invention is featured by the high yield, simple steps and cheap raw material and is more adaptable to the scale of the industrial production. Through the method, the yield of the diflubenzuron is 97%, which of the fluorin bell urea 93% and that of the fluorin insect urea 86%.

Description

Technical field [0001] The invention relates to a method for synthesizing a substituted benzoyl urea insect growth regulator, in particular to a method for synthesizing hexaflumuron, flufenuron and diflubenzuron. technical background [0002] Benzoyl urea compounds are effective insecticides and acaricides that act by inhibiting the synthesis of insect chitin, or are called insect growth regulators. Among them, the most common ones are hexaflumuron, flufenoxuron and diflubenzuron developed by DOW ELAN in 1987. [0003] The synthesis of these compounds is mostly based on 2,6-difluorobenzonitrile as the starting material, through fluorination, hydrolysis, esterification, and addition to obtain substituted benzoylurea compounds. For example, the reaction formula is as follows: [0004] 1) Fluorination: [0005] [0006] 2) Hydrolysis: [0007] [0008] 3) Esterification: [0009] [0010] 4) Bonus: [0011] [0012] among them, [0013] [0014] The synthesis of diflubenzu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N47/28C07C275/30
Inventor 曾益良宋建军张平南秦小薇栗心贞陈志祥
Owner INST OF ZOOLOGY CHINESE ACAD OF SCI
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