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Preparation method for R-2-(4- hydroxyphenoxy) propionate

A technology of hydroxyphenoxy and R-2-, which is applied in the field of preparation of R-2-(4-hydroxyphenoxy) propionate, can solve the problem of low optical purity of the product, and reduce production cost, Small environmental pollution and strong splitting specificity

Active Publication Date: 2014-06-11
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The optical purity of the product is not very high because the reaction process is prone to racemization

Method used

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  • Preparation method for R-2-(4- hydroxyphenoxy) propionate
  • Preparation method for R-2-(4- hydroxyphenoxy) propionate
  • Preparation method for R-2-(4- hydroxyphenoxy) propionate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Slant medium: NaNO 3 2g, K 2 HPO 4 1g, KCl 5g, FeSO 4 0.01g, MgSO 4 0.5g, 30g sucrose, 15g agar, constant volume to 1L, natural pH, sterilized at 121°C for 20 minutes, cooled to make a slope after sterilization, inoculated with Aspergillus oryzae WZ007 (CCTCC No: M206105), cultured at 30°C for 3 days, as Slope activated seeds;

[0025] Liquid fermentation medium: glucose 20g, peptone 20g, sucrose 10g, urea 3g, NaCl 5g, k 2 HPO 4 2g, MgSO 4 1g,, (NH 4 ) 2 SO 4 5g, dilute to 1L, pH natural. The filling volume is 80ml of 500ml triangular flask, sterilized at 121°C for 20 minutes, cooled after sterilization, inoculated with slant seeds, cultivated at 30°C for 48 hours, filtered to obtain mycelium, and dried to obtain 4.2g of enzyme powder.

Embodiment 2

[0027] 0.1 g of Aspergillus oryzae WZ007 enzyme powder prepared by the method in Example 1 was added to 10 ml of phosphate buffer solution containing 20 g / L racemic 2-(4-hydroxyphenoxy) ethyl propionate, and added dropwise during the reaction The 1mol / L sodium hydroxide solution was maintained at about 7.0, and at 30°C, after 2 hours of reaction, the reaction conversion rate was 53.2%. After the reaction was completed, filter and remove the bacterial cells, add an equal amount of ethyl acetate to extract twice, then combine the extracts, and distill under reduced pressure at 0.1 MPa to obtain R-2-(4-hydroxyphenoxy) ethyl propionate. The enantiomeric excess value of R-2-(4-hydroxyphenoxy)propionate is 98.2%, and the yield is 90.2%. The liquid phase of ethyl 2-(4-hydroxyphenoxy)propionate before and after the reaction process For chromatogram see figure 1 .

Embodiment 3

[0029] According to the method of Example 2, racemic 2-(4-hydroxyphenoxy) propionate with different R group structures was added as the reaction substrate, and other conditions remained unchanged. The reaction conversion and substrate enantiomeric excess values ​​of this reaction are shown in Table 1. The results in Table 1 show that, in terms of reaction conversion rate and substrate enantiomeric excess value, the R group is isopropyl group is better than other groups.

[0030] Table 1: Enzyme conversion results of different substrate structures

[0031]

[0032] Example 3:

[0033] According to the method in Example 2, the transformed reaction solution was reacted, and the bacterial cells obtained by filtration were rinsed with a buffer solution and then added with a new reaction substrate to continue the reaction. Repeat this process and reuse it 5 times. The obtained enzymatic hydrolysis results are shown in Table 2. After using Aspergillus oryzae WZ007 enzyme powder...

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Abstract

The invention provides a preparation method for R-2-(4- hydroxyphenoxy) propionate shown as formula (II). The method includes the following steps that with racemized 2-(4- hydroxyphenoxy) propionate as reaction substrate and under the action of microbial ester hydrolase, selective hydrolysis reaction is carried out, so that the R-2-(4- hydroxyphenoxy) propionate is prepared; and the microbial ester hydrolase comes from Aspergillus oryzae (CCTCC No: M206105). The preparation method has the advantages that the resolution specificity is high, the resolution rate is high, the production cost is greatly reduced, the preparation method is easy to operate, environmental pollution is less, and the preparation method is suitable for industrialized production.

Description

(1) Technical field [0001] The invention relates to a preparation method of R-2-(4-hydroxyphenoxy) propionate. (2) Background technology [0002] Aryloxyphenoxypropionate (Aryloxyph enox y propionate, APP for short) herbicides are a class of well-known highly active herbicides developed on the basis of the 2,4-D structure in the 1970s. Herbicides have the characteristics of high efficiency, low toxicity, and safety to subsequent crops. There are many chiral varieties of such herbicides. Since dipropa-yl was found to have herbicidal activity in 1975, 20 varieties have been commercialized so far, such as Jingpidi-prop, Jingwenshade, Jingaifen, and alkyne Grass esters and puma, etc., have become a class of herbicides that are developing rapidly. These herbicides have two optical isomers, the activity of which is almost entirely concentrated in the R isomer, and the S isomer has no activity or very low activity. Among them, R-2-(4-hydroxyphenoxy)propionate is an important int...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P41/00C12P7/62C12N9/18C12R1/69
Inventor 郑建永汪钊章银军
Owner ZHEJIANG UNIV OF TECH
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