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Method for preparing dextral cis-permethrinic acid

A technology of cis-cis permethrin and permethrin, which is applied in the field of preparation of d-cis permethrin, can solve the problem of low ee value of d-cis permethrin and poor production practical applicability Large size, lack of sources of chemical resolution agents, etc., to avoid steps such as crystallization and purification, improve single selectivity of hydrolysis, and low production cost

Inactive Publication Date: 2021-02-02
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] The preparation of D-cis permethrin by selective hydrolysis of permethrin with biological enzymes has not been reported in the literature so far.
[0006] However, the ee value of D-cis-permethrin obtained by the traditional chemical resolution method is generally low and cannot be directly used for the synthesis of pyrethroid products. Other chemical or physical crystallization purification processes are required to improve the ee value. , increasing the manufacturing steps, the practical application of production is not great
And the source of chemical resolution agent is becoming more and more scarce, and the cause of high pollution in the production process has been gradually eliminated. Therefore, the research and development of an economical and convenient biocatalytic resolution method to prepare D-cis permethrin has become a new important way.

Method used

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  • Method for preparing dextral cis-permethrinic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] A preparation method of D-cis permethrin: 200g of methyl permethrin (cis / trans = 50 / 50), 1000g of water, 1g of CEYR205 esterase (US Sigma) are put into a 1000ml four-neck bottle , stirred and reacted at 40°C for 48hr, during the reaction process, 10% sodium hydroxide was used to adjust the pH of the system to 4-8. Hydrochloric acid was used to adjust the pH of the system to 2, and the solvent toluene was added to extract the organic phase, and the solvent was desolvated from the extract to obtain about 44.7 g of the desired product D-cis permethrin. The content of gas chromatography capillary column analysis was 99.52%. The content of dextrocis-isomer was 99.21% according to the property column analysis.

Embodiment 2

[0025] A preparation method of D-cis permethrin: 200g of ethyl permethrin (cis / trans=70 / 30), 1000g of water, 1g of CEYR205 esterase (US Sigma) are put into a 1000ml four-neck bottle , stirred and reacted for 48hr at 40°C, the reaction process was adjusted to PH4-8 with 10% sodium hydroxide, the reaction was completed with the separation of the oil and water layers in Example 1, and the water layer was acidified, extracted, and precipitated to obtain D-cis permethrin. 58.8g, the gas chromatography capillary column analysis content is 99.42%, the gas chromatography chiral column analysis dextrocis body content is 99.01%.

Embodiment 3

[0027] A kind of preparation method of D-cis permethrin: 200g of permethrin methyl ester (cis / trans = 80 / 20), 1000g of 1% ammonia water, 1g of CEYR205 esterase are put into 1000ml four-neck bottle Sigma), stirred and reacted at 40°C for 48hr, the reaction was completed with the separation of the oil and water layers in Example 1, and the water layer was acidified, extracted, and desolvated to obtain about 71.3g of D-cis permethrin, and the gas chromatography capillary column analysis content was 99.43%. According to gas chromatography chiral column analysis, the content of the right-handed cis-isomer was 99.09%.

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Abstract

The invention discloses a method for preparing dextral cis-permethrinic acid. The method comprises the step of selectively hydrolyzing racemic permethrinic acid ester in an aqueous solution in the presence of biocatalyst esterase to obtain dextral cis-permethrinic acid with an ee value being more than 99 percent. According to the method, the hydrolysis single selectivity of racemic permethrinic acid ester is improved by selecting proper esterase, the ee value of the finally obtained dextral cis-permethrin is greater than 99%, the dextral cis-permethrinic acid can be directly used for producting and manufacturing various sanitary or agricultural pyrethroid products, can avoid the steps of crystallization and purification of low ee value intermediates and the like, and enables the productionprocess to be simplified.

Description

technical field [0001] The invention relates to a preparation method of D-cis permethrin, in particular to a method for preparing chiral D-cis permethrin through a biological resolution method. Background technique [0002] Permethrinic acid (also known as DV chrysanthemum acid, English name Permethrinic acid), that is, 2.2-dimethyl-3-(2.2-dichlorovinyl) cyclopropanecarboxylic acid, is a synthetic agricultural pyrethroid pesticide acid part important intermediates. 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, and there are four isomers of permethrin. [0005] The preparation of D-cis permethrin by selective hydrolysis of permethrin with biological enzymes has not been reported in the literature so far. [0006] However, the ee value of D-cis-permethrin obtained by the traditional chemical resolution method is gen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/40C12P41/00
CPCC12P7/40C12P41/005
Inventor 冯广军姜友法王宝林王振锋吴必俊余金建程炎
Owner JIANGSU YANGNONG CHEM
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