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Preparation method of glufosinate and analogue of glufosinate

An analog, glufosinate-ammonium technology, which is applied in the field of preparation of glufosinate-ammonium and its analogs, can solve the problems of difficult glufosinate-ammonium separation and purification process, cumbersome purification process, a large amount of ammonium chloride, etc., and achieves high product purity and yield. High, less side effects

Inactive Publication Date: 2015-09-09
ANHUI COSTAR BIOCHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The synthesis route has mild conditions and stable yield, and is one of the more mature glufosinate-ammonium routes at present. The method is called the Strecker-Zelinsky synthesis method, but highly toxic cyanide is used. The environmental requirements are high, and a large amount of ammonium chloride will be produced in the reaction, which is difficult to separate from the product glufosinate-ammonium, and the purification process is cumbersome

Method used

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  • Preparation method of glufosinate and analogue of glufosinate
  • Preparation method of glufosinate and analogue of glufosinate
  • Preparation method of glufosinate and analogue of glufosinate

Examples

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Embodiment example 1

[0026] In a 500ml four-neck flask, add 5.8gKOH, 95g methyl phosphine dichloride, 180ml n-butyl ester, and the reaction temperature is 210°C. Small molecules are continuously separated during the reaction, and 200ml N-N-dimethylformamide is added after the reaction is completed. Liquid separation was carried out in a separatory funnel to obtain 108 g of intermediate (I), with a purity of 99.2%.

[0027] Add 220ml of formic acid to the intermediate (I), add 6.7g of catalyst KOH, put in 66.2g of 2-hydroxybutene-3-carbonitrile, slowly add 135ml of acetic anhydride into the constant pressure dropping funnel, and control the dropping time between 30min and 40min After the reaction was completed, the small molecules were distilled off under reduced pressure to obtain 88.6 g of intermediate (II) with a purity of 98.5%.

[0028] In the intermediate (II), add 66 g of n-butyl methylphosphonite, 88.6 g of 2-acetoxy-3-butenenitrile, add 0.20 g of benzoyl peroxide, and react for 2 hours at ...

Embodiment example 2

[0031] In a 500ml four-neck flask, add 4.2gKOH, 65g methyl phosphine dichloride, 120ml n-butyl ester, and the reaction temperature is 230°C. Small molecules are continuously separated during the reaction, and 150ml N-N-dimethylformamide is added after the reaction is completed. Liquid separation was carried out in a separatory funnel to obtain 78 g of intermediate (I) with a purity of 99.5%.

[0032] To the intermediate (I), add 180ml of formic acid, add 4.2g of catalyst KOH, put in 56.8g of 2-hydroxybutene-3-carbonitrile, slowly add 95ml of acetic anhydride into the constant pressure dropping funnel, and the dropping time is controlled within 30min~ After 40 minutes, the small molecules were distilled off under reduced pressure to obtain 66.6 g of intermediate (II) with a purity of 99.0%.

[0033] In the intermediate (II), add 66.6 g of n-butyl methylphosphonite, drop 78 g of 2-acetoxy-3-butenenitrile, add 0.20 g of benzoyl peroxide, and react for 2 hours at 70° C. After com...

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Abstract

The invention discloses a method used for synthesizing glufosinate and an analogue of glufosinate by taking methylphosphoric dichloride and 2-hydroxy butane-3-nitrile as initial raw materials. According to the method, esterification is carried out so as to obtain methyl phosphite ester (I) and 2-acetyloxy-3-butenenitrile (II), intermediate (3-acetyloxy-3-cyano-propyl)-methylphosphonate (III) is obtained via Michael free radical addition, and glufosinate and the analogue (IV) are obtained via ammoniation and hydrolysis. Synthetic route of the method is short; yield is high; by-product is less; product purity is high; and the method is suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of glufosinate-ammonium and its analogues, belonging to the field of organic chemical synthesis. Background technique [0002] Glufosinate-ammonium was successfully developed by Hoechst in the 1980s (later owned by Bayer). The common name is glufosinate, and the trade name is It is a racemic compound, which is a broad-spectrum contact herbicide. [0003] There are many reports on the synthesis of glufosinate-ammonium, mainly including Abuzov synthesis, high-pressure catalytic synthesis, Gabriel synthesis, Bucherer-Bergs (Bucherer-Bergs) synthesis, low-temperature directional synthesis, Si Chuck (Strecker)-Zelinsky synthesis, but there are certain defects and problems. Among them, the Abuzov synthesis method needs to introduce expensive trifluoroacetic acid for the protection and deprotection of the amino group, and the production cost is relatively high. The high-pressure catalytic synthesis method need...

Claims

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Application Information

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IPC IPC(8): C07F9/30
Inventor 杨红兵先斌陈锐张志宏
Owner ANHUI COSTAR BIOCHEM CO LTD
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