Process for preparing phosphine oxamate and its derivatives

A technology for glufosinate and derivatives is applied in the field of preparing glufosinate and derivatives thereof, which can solve the problems of increasing reaction by-products, difficult-to-separate impurities, increasing production costs and the like, and achieves saving production costs, high yield, high purity effect

Inactive Publication Date: 2006-11-08
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this route shortens the reaction steps, there are more difficult-to-separate impurities in the glufosinate product when the acid anhydride is used as the condensation agent
In addition

Method used

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  • Process for preparing phosphine oxamate and its derivatives
  • Process for preparing phosphine oxamate and its derivatives
  • Process for preparing phosphine oxamate and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 5.61 g of freshly distilled acrolein (0.10 mol) were added to 6.00 g of acetic acid (0.10 mol) and added dropwise to 13.61 g of diethyl methylphosphonite (0.10 mol) at room temperature. After stirring for 2 h, it was added dropwise to 4.9 g of sodium cyanide (0.10 mol), 10.7 g of ammonium chloride (0.20 mol) in 50 ml of 25% ammonia solution, and the solution was brown. After stirring for 2h, it was added dropwise to 200ml of 37% hydrochloric acid without separation, and heated to reflux for 2h. Use a rotary evaporator at 50-60°C to basically evaporate the water to dryness to obtain a light yellow viscous substance. Add 125ml of methanol to dissolve, and filter to remove the solid ammonium chloride to obtain the filtrate. Methanol was distilled off, 15ml of distilled water was added, and the pH was adjusted to 3.0-3.5 with 5N sodium hydroxide solution. Add 40ml of methanol and place it at low temperature to precipitate 17.7g of white crystals. The product was analyzed...

Embodiment 2

[0039] 5.61 g of freshly distilled acrolein (0.10 mol) were added to 6.00 g of acetic acid (0.10 mol) and added dropwise to 13.61 g of diethyl methylphosphonite (0.10 mol) at room temperature. After stirring for 2 h, it was added dropwise to 4.9 g of sodium cyanide (0.10 mol), 10.7 g of ammonium chloride (0.20 mol) in 50 ml of 25% ammonia solution, and the solution was brown. After stirring for 2h, it was added dropwise to 200ml of 20% sodium hydroxide solution without separation, and heated to reflux for 2h. Use 5N sodium hydroxide solution to adjust the pH to 3.0-3.5, and then use a rotary evaporator at 50-60°C to basically evaporate the water to dryness to obtain a light yellow viscous substance. Add 125ml of methanol to dissolve, and filter to remove the solid sodium chloride to obtain the filtrate. Methanol was distilled off, 15ml of distilled water was added to dissolve, then 40ml of methanol was added, and placed at low temperature, 16.4g of white crystals were precipi...

Embodiment 3

[0041]5.61 g of freshly distilled acrolein (0.10 mol) was mixed with 6.00 g of acetic acid (0.10 mol) at room temperature to form a solution. This solution was added dropwise to a solution of 13.61 g of diethyl methylphosphonite (0.10 mol) and 4.6 g of ethanol (0.10 mol). After the mixture was stirred at room temperature for 2 h, it was added dropwise to 4.9 g of sodium cyanide (0.10 mol), 10.7 g of ammonium chloride (0.20 mol) in 50 ml of 25% ammonia solution, and the solution was brown. After stirring for 2 h, the crude aminonitrile was added dropwise to 200 ml of 37% hydrochloric acid. The mixture was heated to reflux for 3.5h. Use a rotary evaporator at 50-60°C to basically evaporate the water to dryness to obtain a light yellow viscous substance. Add 125ml of methanol to dissolve, and filter to remove the solid ammonium chloride to obtain the filtrate. Methanol was distilled off, 15ml of distilled water was added, and the pH was adjusted to 3.0-3.5 with 5N sodium hydro...

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Abstract

The present invention relates to preparation process of phosphine oxamate and its derivatives, and is especially preparation process through Michael addition reaction of methyl phosphinate and acrylaldehyde. The present invention features the condensing agent for the reaction of proper weak acid and the three step reaction for preparing phosphine oxamate product. Adopting weak acid as the condensing agent can obtain high yield and high purity of phosphine oxamate product. Adopting weak acid as the condensing agent to replace anhydride and using no alcohol can lower the production cost.

Description

technical field [0001] The invention relates to a method for preparing glufosinate and its derivatives, in particular to a method for preparing glufosinate and its derivatives by using a suitable weak acid as a condensation agent. Background technique [0002] How to prepare glufosinate (Yan Haichang, He Hongdong, Pesticides, 2002, 41 (9), 46-48) how to have many document reports at present, but ubiquitous reaction steps are many, reaction yield is on the low side and production cost is on the high side question. The glufosinate synthesis route (CN1267-305A) developed by Hoechst Company recently takes methyl phosphonite as raw material, uses acid anhydride as condensation agent, and reacts with acrolein in the presence of alcohol, then carries out Strecker reaction and acid hydrolysis reaction Preparation of glufosinate. Although this route shortens the reaction steps, there are more difficult-to-separate impurities in the glufosinate product when acid anhydrides are used ...

Claims

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Application Information

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IPC IPC(8): C07F9/28C07F9/48
Inventor 李啸风邵生富沈国平张骏陈奇文黄红波
Owner ZHEJIANG UNIV
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