Production process of lambda-cyhalothric acid

A technology of trifluorochloro chrysanthemic acid and solvent, which is applied in the field of organic synthesis, can solve the problems of long cycle, low cis-trans ratio of cyclization reaction products, low production capacity, etc. Effect

Inactive Publication Date: 2018-05-29
LIANYUNGANG CCA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing public production process, the cis-trans ratio of the cyclization reaction product is low, and the whole reaction process has a long cycle and low production capacity

Method used

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  • Production process of lambda-cyhalothric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Addition: put 1250kg of methyl bentinate into the reaction kettle, 2500kg of trifluorotrichloroethane, 1250kg of solvent tert-butanol, 25kg of catalyst cuprous chloride, 60kg of 1-ethanolamine, heat up to about 100°C, 0.2 ~0.3MPa pressure-holding reaction for 12 hours, sampling analysis, control the content of pyridyl ester within 2%, steam trifluorotrichloroethane and tert-butanol under normal pressure after passing the test, and then steam the unreacted pyridyl ester under reduced pressure, The remaining adduct in the kettle is 2800kg, the content is more than 96%, and the yield is 95.6%.

[0032] (2) Cyclization: Add 1000kg of adduct, 2000kg of solvent N, N-dimethylformamide to the reaction kettle, control the temperature at -15°C, add 4000kg of sodium tert-amylate catalyst dropwise into the kettle, and finish adding in 30 minutes. Keep warm for 15 minutes after the dropwise addition, and take a sample for analysis. The content of the adduct is required to be 0.5...

Embodiment 2

[0036] (1) addition: the same as (1) addition step in Example 1.

[0037] (2) Cyclization: Add 1000kg of adduct to the reaction kettle, 2000kg of solvent N,N-dimethylacetamide, control the temperature at -15°C, add 4000kg of potassium tert-amylate catalyst dropwise into the kettle, and finish adding dropwise in 30 minutes. Keep warm for 15 minutes after the dropwise addition, and take a sample for analysis. The content of the adduct is required to be 0.5-1.0%. After passing the test, evaporate the solvent to dryness under negative pressure, add water to wash the cyclized product, and separate the lower layer of the cyclized product. The effective content is 94%, and the cis-trans ratio is 7.1:1. , yield 81.5%.

[0038] (3) Saponification: Add 5000kg of cyclized product, 9000kg of ethylene glycol, and 20kg of phase transfer catalyst tetrabutylammonium bromide into the reactor, stir and heat up to 90°C, and start to add 48% (w / w) KOH aqueous solution dropwise for 3 hours. After...

Embodiment 3

[0041] (1) addition: the same as (1) addition step in Example 1.

[0042] (2) Cyclization: Add 1000kg of adduct, 2000kg of solvent N,N-dimethylformamide to the reactor, control the temperature at -15°C, add 4000kg of sodium isoamyloxide catalyst dropwise into the kettle, and finish adding dropwise in 30 minutes. Keep warm for 15 minutes after the dropwise addition, and take a sample for analysis. The content of the adduct is required to be 0.5-1.0%. After passing the test, evaporate the solvent to dryness under negative pressure, add water to wash the cyclized product, and separate the lower cyclized product. The effective content is 92%, and the cis-trans ratio is 6.0:1 , yield 79.7%

[0043] (3) Saponification: Add 5000kg of cyclized product, 9000kg of n-butanol, 20kg of phase transfer catalyst tetrabutylammonium chloride into the reactor, stir and heat up to 90°C, start to add 48% (w / w) KOH aqueous solution dropwise for 3 hours After the addition, keep the temperature at 9...

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Abstract

The invention discloses a production process of lambda-cyhalothric acid and belongs to the field of organic synthesizing. The lambda-cyhalothric acid is produced by dimethyl-4-pentenoic acid methyl ester, trifluorotrichloroethane and potassium 2-methyl-2-butoxide through addition, cyclization, saponification, acidification and refining. The production process has the advantages that the potassium2-methyl-2-butoxide used as the catalyst of cyclization reaction is high in selectivity and can increase cyclic compound cis-trans ratio; ethylene glycol is used as the solvent in the saponification process for the first time, a used staged heat preservation method can greatly lower the generation of side reaction, increase main content and increase reaction yield, reaction cycle can be shortenedgreatly, and productivity can be increased.

Description

technical field [0001] The invention relates to a compound preparation method, in particular to a method for synthesizing permethrin, which is a compound used as a pesticide intermediate, and belongs to the field of organic synthesis. technical background [0002] Chrysanthemum acid, also known as Kung Fu acid in domestic custom, chemical name is 3-(2-chloro-3,3,3-trifluoropropen-1-yl)-2,2-dimethylcyclopropanecarboxylic acid, It is a common intermediate of many pyrethroid species. Zeneca was the first to successfully develop and put into industrial production for the production of Kungfuthrin, Tefluthrin and Uranus, etc. [0003] There are 3 methods for the synthetic process of permethrin reported in the literature at present, but what are selected at home and abroad all is the industrialized route with the pyrethrinate as the starting raw material, i.e. the pyrethrinate (methyl ester and ethyl ester) first Addition reaction with trifluorotrichloroethane (F113A), followed ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C61/40C07C51/02C07C27/02C07C67/333C07C69/747C07C67/347C07C69/635
CPCC07C67/347C07B2200/09C07C51/02C07C51/412C07C67/333C07C69/635C07C69/747C07C61/40
Inventor 奚胜虎张永忠周太炎陈锡铭季红进
Owner LIANYUNGANG CCA CHEM CO LTD
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