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Preparation method for glufosinate

A technology of glufosinate-ammonium and ammonium carbonate is applied in the new preparation field of herbicide glufosinate-ammonium, which can solve the problems of harsh reaction conditions, expensive raw materials, low reaction yield and the like, and achieves the effects of mild conditions, easy detection and high purity

Active Publication Date: 2012-07-18
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The yield of the process is stable and the conditions are mild, but the ammonium chloride in the reaction brings a big problem of three wastes. At the same time, it is difficult to separate the ammonium chloride mixed in the product from the product glufosinate-ammonium, and the removal process is cumbersome, which greatly affects the purity and quality of the product. Cost of production
In addition, the intermediate product cyanide compound has a high boiling point and no obvious ultraviolet absorption. It is difficult to track and detect the reaction process with gas chromatography and liquid chromatography, which is not conducive to intermediate control in the production process.
[0008] Other chemical synthesis methods such as high-pressure catalytic synthesis, low-temperature directional synthesis, Abu Zov synthesis, Gabriel-diethyl malonate synthesis, chiral synthesis and other methods all have the following one or more shortcomings: 1) Reaction conditions Harsh, 2) expensive raw materials, 3) disadvantages such as low reaction yield, not suitable for industrial production

Method used

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  • Preparation method for glufosinate
  • Preparation method for glufosinate
  • Preparation method for glufosinate

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1: the preparation of 5-(2-(methylethoxyphosphono) ethyl) hydantoin

[0028]

[0029] Add 25.2 g (0.1 mol) of ethyl (3-acetoxy-3-ethoxy) propylmethylphosphinate, 5.9 g (0.12 mol) of NaCN, and 100 ml of ethanol in succession into a 500 ml three-necked flask, and feed nitrogen After stirring at room temperature for 15 min, 100 ml of an aqueous solution containing 21.0 g (0.25 mol) of ammonium carbonate was added dropwise, and the temperature was raised to 70° C. for 3 h. The solvent and ammonium carbonate were removed by rotary evaporation at 80°C, and 100mL of ethanol was added to dissolve, filtered, and precipitated to obtain 24.5g of crude product 5-(2-(methylethoxyphosphono)ethyl)hydantoin. 87.2%, yield 91.3%. 1 H NMR (500MHz, DMSO): δ: 1.203-1.233 (m, 3H); δ: 1.409 (d, J=13.8Hz, 3H) δ: 1.653-1.888 (m, 4H); δ: 3.901-3.962 (m , 2H); δ: 4.081 (t, J=5.6Hz, 1H) δ: 7.988 (s, 1H); δ: 10.681 (s, 1H).

Embodiment 2

[0030] Embodiment 2: the preparation of 5-(2-(methylethoxyphosphono) ethyl) hydantoin

[0031] Add 25.2 g (0.1 mol) of ethyl (3-acetoxy-3-ethoxy) propylmethylphosphinate, 5.9 g (0.12 mol) of NaCN, and 100 ml of ethanol in succession into a 500 ml three-necked flask, and feed nitrogen After stirring at room temperature for 15 min, 100 ml of an aqueous solution containing 21.0 g (0.25 mol) of ammonium carbonate was added dropwise, and the temperature was raised to 70° C. for 1.5 h. The solvent and ammonium carbonate were removed by rotary evaporation at 80°C, and 100mL of ethanol was added to dissolve, filtered, and precipitated to obtain 23.5g of crude product 5-(2-(methylethoxyphosphono)ethyl)hydantoin, the content 79.1%, yield 79.4%.

Embodiment 3

[0032] Embodiment 3: the preparation of 5-(2-(methylethoxyphosphono) ethyl) hydantoin

[0033] Add 25.2 g (0.1 mol) of ethyl (3-acetoxy-3-ethoxy) propylmethylphosphinate, 5.9 g (0.12 mol) of NaCN, and 100 ml of ethanol in succession into a 500 ml three-necked flask, and feed nitrogen After stirring at room temperature for 15 min, 100 ml of an aqueous solution containing 21.0 g (0.25 mol) of ammonium carbonate was added dropwise, and the temperature was raised to 40° C. for 3 h. The solvent and ammonium carbonate were removed by rotary evaporation at 80°C, and 100mL of ethanol was added to dissolve, filtered, and precipitated to obtain 11.5g of crude product 5-(2-(methylethoxyphosphono)ethyl)hydantoin. 76.2%, yield 37.4%.

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Abstract

The invention relates to a new preparation method for herbicide glufosinate. The method comprises the following steps of: performing Bucherer-Bergs cyclization reaction on a methylphosphonate derivative type compound (II), ammonium carbonate and cyanide serving as raw materials to obtain a compound shown by a formula (III); and then hydrolyzing to prepare glufosinate compound shown by a formula (I). According to the preparation method, hemiacetal or acetal is used as a raw material, and the Bucherer-Bergs cyclization reaction is performed to obtain a glycolylurea derivative, so that high yield, easiness for detection and mild condition are guaranteed; and after glycolylurea is cyclihydrolyzed, a product has high purity, and ammonium salt can be removed without multiple recrystallization processes.

Description

(1) Technical field [0001] The invention relates to a new preparation method of the herbicide glufosinate-ammonium, in particular to a method for preparing glufosinate-ammonium by Bucherer-Bergs reaction ring closure and hydrolysis of methyl phosphonate derivative compounds, ammonium carbonate and cyanide. (2) Technical background [0002] Glufosinate (glufosinate) is a highly efficient, low toxicity, non-selective (killing) organophosphorus herbicide with partial systemic action. Its original drug is white to light yellow crystalline powder, easily soluble in water, difficult to Soluble in organic solvents, stable to light; easily hydrolyzed in aqueous solution with pH=5-9. Its synthesis methods include fermentation and chemical synthesis. [0003] Compound II can be prepared by reacting diethyl methylphosphonite with acrolein, the reaction conditions are mild and the yield is high. (WO 79 / 00405, CN 1858054A, US6359162) [0004] [0005] The relatively mature technolo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30
Inventor 杜晓华李以名徐振元
Owner ZHEJIANG UNIV OF TECH
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