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Method for synthesizing akarol fenisobromolate

A synthesis method and technology of bromodifen, applied in the field of the synthesis of acaricides, bromodifen, can solve the problems of high cost, low yield, long synthesis process route, etc., and achieve low cost, high yield, favorable The effect of industrial production

Active Publication Date: 2009-08-12
浙江禾本科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis process route is long, the yield is low, and the cost is high

Method used

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  • Method for synthesizing akarol fenisobromolate
  • Method for synthesizing akarol fenisobromolate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the preparation of 4,4'-dibromodiphenylacetic acid

[0028] Put 72g of glyoxylic acid into a 500mL four-neck flask, distill under reduced pressure to remove 40g of water (glyoxylic acid contains 60% water, the same below), cool to 0-5°C, and add 45g of chlorosulfur dropwise within 30 minutes Acid (tail gas water absorption), continue to stir for 15 minutes, add 140g of bromobenzene dropwise within 15 minutes, then add 45g of chlorosulfonic acid dropwise again within 2.0 hours. Raise the temperature to 25°C and keep it warm for 20 hours. After the reaction was finished, 150 g of water was added dropwise into the reaction mixture, and the excess bromobenzene was distilled off by heating up. After cooling, the water was sucked off, and the residue was recrystallized with toluene to obtain 90 g of 4,4'-dibromodiphenylacetic acid with a content of more than 95% and a yield of 59.4%.

Embodiment 2

[0029] Embodiment 2: Preparation of 4,4'-dibromodiphenylacetic acid

[0030] Put 72g of glyoxylic acid into a 500ml four-neck flask, remove 40g of water by distillation under reduced pressure, cool to 0-5°C, add 40ml of acetic acid dropwise within 30 minutes, continue stirring for 15 minutes, and add 140g of bromobenzene within 15 minutes. Then 95 g of chlorosulfonic acid were added dropwise over 2.0 hours. Raise the temperature to 25°C and keep it warm for 20 hours. After the reaction was finished, 150 g of water was added dropwise to the reaction mixture, and the excess bromobenzene was evaporated by heating up. After cooling, the water was sucked off, and the residue was recrystallized with toluene to obtain 92g of 4,4'-dibromodiphenylacetic acid with a content of more than 95% and a yield of 60.7%.

Embodiment 3

[0031] Embodiment 3: Preparation of 4,4'-dibromodiphenylacetic acid

[0032] Put 72g of glyoxylic acid into a 500ml four-neck flask, remove 40g of water by distillation under reduced pressure, cool to 0-5°C, add 50g of 98% concentrated sulfuric acid dropwise within 30 minutes, continue stirring for 15 minutes, and add 140g bromobenzene. Then, 85 g of chlorosulfonic acid were added dropwise over 2.0 hours. Raise the temperature to 25°C and keep it warm for 20 hours. After the reaction was finished, 160 g of water was added dropwise to the reaction mixture, and the excess bromobenzene was evaporated by heating up. After cooling, the water was sucked off, and the residue was recrystallized with toluene to obtain 98g of 4,4'-dibromodiphenylacetic acid with a content of more than 95% and a yield of 64.7%.

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Abstract

The invention provides a method for synthesizing bromofen, which uses glyoxylic acid as the starting material, and first conducts condensation reaction with bromobenzene to obtain 4,4'-dibromodiphenylacetic acid, which is mixed with isopropanol The esterification reaction is carried out to obtain 4,4'-dibromodiphenylacetic acid isopropyl ester, and the generated ester is catalyzed and oxidized with oxygen in the presence of a catalyst to obtain the bromofen. The beneficial effects of the present invention are mainly reflected in: short synthetic route, high yield, low cost, high product purity, and favorable industrial production.

Description

(1) Technical field [0001] The invention relates to a synthetic method of bromofen, an acaricide, in particular to a synthetic method of bromofen with glyoxylic acid as the main raw material. (2) Background technology [0002] The chemical name of bromofen is 4,4'-dibromodiphenylglycolic acid isopropyl ester, the structural formula is shown in formula (I), and the molecular formula is: C 17 h 16 Br 2 o 3 , is a low-toxic, high-efficiency, broad-spectrum acaricide with strong contact activity and long-lasting effect. It has good contact effect on adults, nymphs and eggs, and the temperature change has little effect on the efficacy. It is widely used in fruit trees, vegetables, tea, cotton and farmland crops to prevent and control various harmful mites such as spider mites, gall mites, barb mites, and nematodes. Due to the unique mechanism of action of bromofen, its usage is gradually expanding. [0003] [0004] The industrialized synthesis process mainly includes the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/732C07C67/31
Inventor 曾仲武曾挺唐勇建
Owner 浙江禾本科技股份有限公司
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