Preparation method of dextro trans-chrysanthemic acid

A technology for the first chrysanthemic acid ester and chrysanthemic acid, which is applied in the field of preparation of the first dextrorotatory trans chrysanthemic acid, can solve the problems of increasing manufacturing steps, and the practical application of production is not large, so as to facilitate recycling and improve hydrolysis The effect of single selectivity and convenient use

Inactive Publication Date: 2018-09-04
JIANGSU YANGNONG CHEM +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the D-trans chrysanthemic acid with an ee value of 80% cannot be directly used in the synthesis of pyrethroid products. It is necessary to use other chemical or physical crystallization purification processes to improve the ee value, which increases the manufacturing steps and is not practical for production. Big

Method used

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  • Preparation method of dextro trans-chrysanthemic acid

Examples

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Comparison scheme
Effect test

Embodiment 1

[0020] A preparation method of the first dextrorotatory trans-type chrysanthemic acid: 200 g of ethyl chrysanthemic acid (cis / trans = 10 / 90), 1000 g of 1% ammonia water, and 1 g of EYN045 esterase (US Sigma) were put into a 1000 ml four-neck bottle , stirred and reacted at 40°C for 48 hours, after the reaction, the oil-water layer was separated (centrifugation or ultrafiltration membrane separation was used to recover the enzyme and the raw material was recycled), the water layer was split and concentrated hydrochloric acid was added to adjust the pH of the system to 2, and the solvent toluene was added to extract the dextrorotational For trans chrysanthemic acid, the solvent is removed by precipitation of the extract to obtain about 67.5 g of the desired product, the first dextrorotatory chrysanthemic acid, the gas chromatography capillary column analysis content is 99.52%, and the gas chromatography chiral column analysis dextrorotation trans isomer content is 99.21%.

Embodiment 2

[0022] A preparation method for the first dextrorotatory trans-type chrysanthemic acid: 200 g of methyl chrysanthemic acid (cis / trans = 10 / 90), 1000 g of 1% ammonia solution, 1 g of EYN045 esterase (US Sigma ), stirred and reacted at 40°C for 48hr, after the reaction was completed, the oil-water layer was separated according to the operation in Example 1, and the water layer was acidified, extracted, and desolvated to obtain about 68.9g of D-trans chrysanthemic acid, and the gas chromatography capillary column analysis content was 99.42% , gas chromatography chiral column analysis of the right-handed trans-isomer content was 99.01%.

Embodiment 3

[0024] A preparation method of the first dextrorotatory trans-type chrysanthemic acid: 200 g of isopropyl chrysanthemic acid (cis / trans = 10 / 90), 1000 g of 1% ammonia solution, and 1 g of EYN045 esterase are put into a 1000 ml four-necked bottle. Sigma), stirred and reacted at 40°C for 48hr, after the reaction was completed, the oil-water layer was separated according to the operation in Example 1, and the water layer was acidified, extracted, and desolvated to obtain about 65g of D-trans chrysanthemic acid, and the gas chromatography capillary column analysis content was 99.55% , gas chromatography chiral column analysis of the right-handed trans-isomer content was 99.51%.

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Abstract

The invention discloses a preparation method of dextro trans-chrysanthemic acid. The method includes: in ammonia water or an aqueous solution of organic amine with a carbon atom number of less than 6,subjecting racemic chrysanthemic acid ester to selective hydrolysis in the presence of biocatalyst esterase to obtain dextro trans-chrysanthemic acid with an ee value of greater than 99%. The methodprovided by the invention selects a specific buffer system to change the biotic environment of esterase, improves the hydrolysis single selectivity of racemic chrysanthemic acid ester, the finally obtained dextro trans-chrysanthemic acid has an ee value of greater than 99%, and can be directly used for the production and manufacturing of various sanitary pyrethroids, crystallization purification of the low ee value intermediate and other steps can be avoided, and the production process is simplified.

Description

technical field [0001] The invention relates to a preparation method of the first right-handed trans chrysanthemic acid, in particular to a method for preparing the first chiral right-handed trans chrysanthemic acid by a biological resolution method. Background technique [0002] The first chrysanthemum acid (English name Chrysanthemic acid), that is, 2.2-dimethyl-3-(2-methyl-1-propenyl) cyclopropanecarboxylic acid, is an important intermediate for the synthesis of pyrethroid hygienic pesticides. body. The structure is as follows: [0003] [0004] Because there are two chiral carbon atoms on its cyclopropane ring, there are two configurations of left and right rotation, plus two cis and trans isomers, the first chrysanthemic acid has four isomers in total. As the acid moiety of pyrethroid pesticides, the first chrysanthemic acid of different isomers has a large difference in insecticidal activity, among which the right-handed trans first chrysanthemic acid shows high b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/40
CPCC12P7/40
Inventor 周其奎姜友法王宝林冯广军王振锋吴必俊
Owner JIANGSU YANGNONG CHEM
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