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Method for preparing dextro-trans-DE chrysanthemic acid through enzymolysis

A technology for enzymatic hydrolysis and chrysanthemic acid, which is applied in the fields of organic chemistry, separation/purification of carboxylic acid compounds, organic chemistry, etc., can solve the problems such as the preparation process of dextro-trans DE chrysanthemic acid that has not been found in research, and achieve stable control. , The effect of shortening the enzymatic hydrolysis reaction time and the small size of the production equipment

Pending Publication Date: 2021-07-20
JIANGSU YOUJIA CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no research on the preparation process of right-handed trans-DE chrysanthemic acid has been found in the continuous flow mode of microchannel reactor

Method used

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  • Method for preparing dextro-trans-DE chrysanthemic acid through enzymolysis
  • Method for preparing dextro-trans-DE chrysanthemic acid through enzymolysis
  • Method for preparing dextro-trans-DE chrysanthemic acid through enzymolysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Microchannel reactor: PDMS microchannel chip, the channel diameter is 300 μm, the length is 1000 mm, and the heat exchange medium is heat transfer oil.

[0034] (2) Preparation of D-trans DE chrysanthemic acid:

[0035] Microchannel reactor preparation: Control the residence time of the reaction system in each module by adjusting the flow rate of the delivery pump and the length of the microchannel. The residence time in the mixing module is 30 seconds, and the residence time in the reaction module is 60 seconds. The reaction is controlled by the external heat transfer oil system The temperature of each module of the device, the temperature of the mixing module is 35°C, and the temperature of the reaction module is 35°C.

[0036] EYN045 esterase 0.1g is dissolved in 10g water to obtain 10.1g esterase liquid, 2% ammonia water 100g, chrysanthemum acid ethyl ester (cis / trans=10 / 90) 10g, above-mentioned raw material adopts high-pressure metering pump in proportion respe...

Embodiment 2

[0038] (1) Microchannel reactor: stainless steel microchannel chip, channel diameter 500μm, length 1000mm, heat transfer medium is heat transfer oil.

[0039] (2) Preparation of D-trans DE chrysanthemic acid:

[0040] Microchannel reactor preparation: Control the residence time of the reaction system in each module by adjusting the flow rate of the delivery pump and the length of the microchannel. The residence time in the mixing module is 30 seconds, and the residence time in the reaction module is 80 seconds. The reaction is controlled by the external heat transfer oil system The temperature of each module of the device, the temperature of the mixing module is 40°C, and the temperature of the reaction module is 40°C.

[0041] EYN045 esterase 0.2g is dissolved in 20g water to obtain 20.2g esterase liquid, 2% ammonia water 200g, chrysanthemum acid ethyl ester (cis / trans=10 / 90) 20g, above-mentioned raw material adopts high-pressure metering pump respectively in proportion, at 0...

Embodiment 3

[0043] (1) Microchannel reactor: stainless steel microchannel chip, channel diameter 300μm, length 1000mm, heat transfer medium is heat transfer oil.

[0044] (2) Preparation of D-trans DE chrysanthemic acid:

[0045] Microchannel reactor preparation: Control the residence time of the reaction system in each module by adjusting the flow rate of the delivery pump and the length of the microchannel. The residence time in the mixing module is 30 seconds, and the residence time in the reaction module is 60 seconds. The reaction is controlled by the external heat transfer oil system The temperature of each module of the device, the temperature of the mixing module is 40°C, and the temperature of the reaction module is 40°C.

[0046] EYN045 esterase 0.1g is dissolved in 10g water to obtain 10.1g esterase liquid, 2% ammonia water 100g, chrysanthemum acid ethyl ester (cis / trans=10 / 90) 10g, above-mentioned raw material adopts high-pressure metering pump in proportion respectively, at 0.5...

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Abstract

The invention discloses a method for preparing dextro-trans-DE chrysanthemic acid through enzymolysis. DE chrysanthemic acid ester, a buffer solution and a chrysanthemate enzyme solution are preheated and then subjected to an enzymolysis reaction in a microchannel reactor, and the dextro-trans-DE chrysanthemic acid compound is obtained after the enzymolysis product is sequentially subjected to ultrafiltration, acidification and other steps. The method disclosed by the invention has the characteristics of low cost, low energy consumption, few three wastes, continuity and controllability, high resolution efficiency and the like, and has excellent industrialization prospects and economic benefits.

Description

technical field [0001] The invention relates to a method for preparing dextro-trans DE chrysanthemic acid by enzymatic hydrolysis, and belongs to the technical field of chemical synthesis. Background technique [0002] DE chrysanthemum acid (chrysanthemic acid), chemical name 2,2-dimethyl-3-(2-methyl-1-propenyl) cyclopropanecarboxylic acid, is an important intermediate for the synthesis of pyrethroid insecticides. [0003] The hydrolysis of racemic chrysanthemic acid esters yields the four isomers of chrysanthemic acid. Studies have shown that the pyrethrins formed by the four isomers of chrysanthemic acid and a certain structure of chrysanthemum alcohol have great differences in their insecticidal properties, and the pyrethrins formed by (+)-trans-chrysanthemum acid usually have the highest insecticidal activity , (+)-cis-chrysanthemic acid followed by the other two effects are small. Therefore, it is of great significance to study the separation of four stereoisomers of ...

Claims

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Application Information

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IPC IPC(8): C12P7/40C07C61/37C07C51/42
CPCC07B2200/07C07C51/42C12P7/40C07C2601/02C07C61/37
Inventor 王振锋吴必俊余金建程炎
Owner JIANGSU YOUJIA CHEM
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