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A kind of method for preparing glufosinate-ammonium

A technology of glufosinate-ammonium and methyl phosphinate, which is applied in the fields of chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc. Industrial production is difficult and the reaction route is long, etc., to achieve the effects of reduced production costs, stable properties, and easy operation

Inactive Publication Date: 2016-02-17
CHONGQING UNISPLENDOUR CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Among the above routes, the raw material of route 1 is easily available in the market, but the Grignard reaction requires anaerobic and anhydrous conditions, which is difficult in industrial production, and the yield of the Michael addition step is only 60%, and the total yield is not high. high
Route 2 has a short reaction process and a relatively high yield. It is a relatively mature process for the synthesis of glufosinate-ammonium in China at present. It has two disadvantages: one is that the methylphosphonite diester is active and difficult to store
But above-mentioned these two kinds of methods reaction routes are all relatively long, it is more difficult in industrialized production

Method used

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Examples

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Effect test

Embodiment 2

[0037] Example 2 Preparation of isobutyl methylphosphinate

[0038] Add 300.0 mL of cyclohexane and 148.0 g (2.0 mol) of isobutanol to a 1000 mL four-necked flask, pass ammonia gas at a flow rate of 50 mL / min, stir and cool, and add 117.0 g (1.0 mol) dropwise at -10°C. A solution of methyl phosphorous dichloride and 250.0 mL cyclohexane. After dripping, react for 2 hours, filter, and remove the solvent under reduced pressure to obtain 134.2 g of a colorless liquid with a content of 96.3% of isobutyl methylphosphinate and a yield of 95.0%.

Embodiment 3

[0039] Example 3 Preparation of n-hexyl methylphosphinate

[0040] Add 400.0 mL of cyclohexane and 204.3 g (2.0 mol) of n-hexanol to a 1000 mL four-necked flask, pass ammonia gas at a flow rate of 60 mL / min, stir and cool, and add 117.0 g (1.0 mol) methyl at 0°C. A solution of phosphorus dichloride and 200.0 mL cyclohexane. After dripping, react for 3 hours, filter, and remove the solvent under reduced pressure to obtain 157.9 g of a colorless liquid, the content of n-hexyl methylphosphinate is 96.4%, and the yield is 92.8%.

[0041] The final product prepared in the following examples of the present invention is in the form of glufosinate ammonium salt, molecular formula C 5 H 18 N 3 O 4 P, the molecular weight is 215.19, the structural formula is as follows:

[0042]

Embodiment 4

[0043] Example 4 Preparation of glufosinate-ammonium

[0044] Add 55.0g (0.5mol) of ethyl methylphosphinate prepared in Example 1 to a 250ml four-neck flask under the protection of nitrogen, heat to 115°C, and add DL-2-hydroxy-3-butene dropwise A mixture of 66.3 g (0.5 mol) ethyl ester and 3.0 g n-butyric acid. The dropping time is controlled for about 2hr, and the dropping temperature is controlled at 115-120°C. After the addition, the reaction was kept for 30 minutes.

[0045] The reaction solution was cooled to about 80°C, and 37% hydrochloric acid was slowly added dropwise until the pH value reached 4, and then heated to reflux for 2hr. The acidified liquid was cooled to 40°C, the pH was adjusted to 12 with 25% ammonia water, and the reaction was kept warm for 2 hours.

[0046] The above materials are dehydrated under reduced pressure until the water content of the solution drops to 10%. Then dissolve with 300g of methanol, filter to remove impurities such as ammonium chlorid...

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Abstract

The invention belongs to the field of chemical synthesis, and in particular relates to a novel method for preparing herbicide, namely glufosinate-ammonium. The method comprises the following steps: conducting addition reaction on methyl phosphonic acid ester compounds and DL-2-hydroxy-3-crotonic acid ester compounds to obtain hydroxybutyric acid ester derivatives, and conducting acidification and ammonification reaction on the hydroxybutyric acid ester derivatives to obtain a glufosinate-ammonium compound. The method can avoid using high-toxic cyanide and obviously shortens a reaction route, so that the reaction steps of a process for preparing glufosinate-ammonium are reduced, the operation is simpler and more convenient, and many times of recrystallization is not needed for removing ammonium salt. The cost is reduced, and the method is completely suitable for large-scale production.

Description

Technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a preparation method of the herbicide glufosinate-ammonium, in particular to a method for synthesizing glufosinate-ammonium by DL-2-hydroxy-3-butenoate compound. Background technique [0002] Glufosinafe (Glufosinafe) is a high-efficiency, low-toxicity, non-selective herbicide first developed by Hoechest, and its trade name is Basta. Its molecular formula is: C 5 H 12 NO 4 P; Molecular weight: 181.1; Structural formula: [0003] [0004] The chemical name of glufosinate-ammonium: 4-[hydroxy(methyl)phosphono]-DL-homoalanine; CAS number: [151276-47-22]. Glufosinate-ammonium is easily soluble in water, has low solubility in organic solvents, and is stable to light. It is easily hydrolyzed in water with pH=5-9; the melting point of glufosinate-ammonium is 229-231℃ for DL ​​type and 214-216℃ for L type. Because glufosinate-ammonium is only conducted in the leaves and does not...

Claims

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Application Information

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IPC IPC(8): C07F9/30
Inventor 王飞朱丽利刘丹万霞姚如杰郑道敏
Owner CHONGQING UNISPLENDOUR CHEM
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