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Method for separation and refining of L-glufosinate-ammonium and salts thereof

A purification method and glufosinate-ammonium technology are applied in the field of separation and purification of L-form and D-form, which can solve the problems of high cost, residue, complicated separation of chiral isomers, etc., and achieve the effect of solving difficult purification and low cost.

Active Publication Date: 2016-12-07
YONGNONG BIOSCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, whether it is the asymmetric hydrogenation method of keto acid or the synthesis of L-glufosinate-ammonium from natural chiral raw materials, the D-isomer will inevitably be produced and remain in the L-isomer product
Often the separation of such chiral isomers is complex or costly

Method used

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  • Method for separation and refining of L-glufosinate-ammonium and salts thereof
  • Method for separation and refining of L-glufosinate-ammonium and salts thereof
  • Method for separation and refining of L-glufosinate-ammonium and salts thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 200ml of water into a 500ml three-necked bottle, and add hydrochloric acid dropwise to adjust the pH to 1.9. Add 100 grams of L-body glufosinate-ammonium crude product (L:D=92.7:7.3), heat up to 45°C, and keep warm at 45-50°C for 2 hours.

[0041] Cool down to normal temperature (20°C), filter, and separate to obtain a low-L body component solid, which weighs 18 grams after drying, and the measured L:D is 66:34; the filtrate is concentrated and dehydrated, and 800ml of methanol is added, stirred, cooled, filtered, and dried Weighing 81.5 grams, analysis L:D=98.5:1.5.

Embodiment 2

[0043] Add 150ml of water into a 500ml three-necked flask, and add sulfuric acid dropwise to adjust the pH to 1.9. Add 100 g of crude L-glufosinate-ammonium (L:D=86.0:14.0), raise the temperature to 45° C., and keep stirring for 2 hours.

[0044] Cool down to normal temperature, filter and separate to obtain the low-L body component solid, dry weight 34.5 grams, measure L:D=65:35; concentrate and dehydrate the filtrate, add 700ml of methanol, stir, cool down, filter to obtain 65.0 grams of solid, measure L: D's result was 97:3.

Embodiment 3

[0046] Add 32 grams (L: D = 65: 35) of the crude product obtained from one separation into a 500 ml three-necked flask, add 60 ml of acidic water with pH = 1.9, repeat the operation as in Example 1 to separate, and dehydrate the filtrate with methanol After treatment, 21.0 g of the racemate solid was obtained by separation, and the measured L:D=50.5:49.5; 10.8 g of the L-rich component was obtained, and the measured L:D result was 92.5:7.5.

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Abstract

The invention discloses a method for separation and refining of L-glufosinate-ammonium and salts thereof. An L-glufosinate-ammonium acquisition method includes: adding crude glufosinate-ammonium into acid water solution, heating for dissolving, cooling for solid precipitation, filtering for separating solids, and subjecting filtrate to aftertreatment to obtain refined L-glufosinate-ammonium, wherein the content of L-glufosinate-ammonium in the crude glufosinate-ammonium is larger than 52%, and the pH value of the acid water solution is 1.2-4.0. According to different solubility of different glufosinate-ammonium isomers in specific-acidity water solution, purification and separation of free amino acids or hydrochlorides of L-glufosinate-ammonium are realized, chiral isomer separation is realized by low cost, high-content biological activity is obtained, and the problem of difficulty in purification of L-glufosinate-ammonium obtained by chemical synthesis is solved.

Description

technical field [0001] The invention relates to the field of separation of chiral isomers of compounds, in particular to a separation and purification technology of L-form and D-form of glufosinate-ammonium free amino acid or hydrochloride. Background technique [0002] Glufosinate-ammonium (glufosinate-ammonium) was developed and produced by Hearst AG (now Bayer AG) in Germany. Its chemical name is 4-{hydroxyl (methyl)phosphono}-DL-homoalanine, and its other name is glufosinate-ammonium. Salt, etc., are glutamine synthesis inhibitors, non-selective contact herbicides. Studies have shown that its herbicidal activity is limited to the L-isomer. Although the commercial product is a DL mixture, the D-isomer does not have biological herbicidal activity, so the biological activity of L-glufosinate-ammonium is 2 times that of the DL racemate at the same concentration. times. [0003] The development and commercialization of L-glufosinate-ammonium salt was first completed by the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30
CPCC07F9/301
Inventor 黄耀师吴克孟毛春晖滕忠华陈军化赵学庆
Owner YONGNONG BIOSCI
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