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Preparation method of glufosinate-ammonium

A technology of glufosinate-ammonium and phosphonic-aldehyde, which is applied in the field of pesticide chemistry, can solve problems such as few examples and no research reports on glufosinate-ammonium, and achieve the effects of avoiding waste water, good environmental friendliness, and short process

Active Publication Date: 2020-04-17
NANJING REDSUN BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Since Arbuzov made an in-depth explanation of the mechanism of the Michaelis–Arbuzov reaction at the beginning of the last century, the research on this phosphate compound has become common. Through R-PCl 2 (R = alkyl, phenyl, thienyl, etc.) or (RO) 3 The reaction of P as a substrate to prepare phosphate esters via cyclophosphoheterocycles has also been reported, but there are not many examples of its real application as a follow-up technology.
And there is no relevant research report on the preparation of glufosinate-ammonium by this technology

Method used

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  • Preparation method of glufosinate-ammonium
  • Preparation method of glufosinate-ammonium

Examples

Experimental program
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Embodiment 1

[0038] Add 12.0 g of methyl phosphine dichloride dropwise to the mixed solution of acrolein (6.2 g) and acetic anhydride (11.5 g), and maintain the reaction at -5 to 0 ° C. After the dropwise addition, maintain the temperature and continue the reaction for 1 h. Then place the reaction solution at 20-30°C for 2 hours to end the reaction; use a rotary evaporator (temperature 50-70°C, vacuum degree above -0.09MPpa) to remove the low-boiling by-product acetyl chloride After removing unreacted acrolein and acetic anhydride, add 5.1g of water, fully stir and hydrolyze at a temperature of 20-40°C for 1h; add sodium cyanide (5.5g) and ammonium chloride (11.8g) dropwise to the obtained hydrolyzate , ammonia water (45mL, 20%), stirred and reacted at 20-40°C for 4h, and the excess ammonia water was removed by rotary evaporation to obtain the intermediate aminonitrile solution; the obtained aminonitrile solution was refluxed with 300mL hydrochloric acid (35%) for hydrolysis After 4 hours,...

Embodiment 2

[0041] Add 24.2g of methyl phosphine dichloride dropwise to the mixed solution of acrolein (12.9g) and acetic anhydride (24.5g), maintain the reaction at -5~0°C, after the dropwise addition, keep the temperature and continue the reaction for 1.5h , then place the reaction solution at 20-30°C for 2.5h to end the reaction; use a rotary evaporator (temperature 50-70°C, vacuum degree above -0.09MPpa) to remove low-boiling by-products After acetyl chloride, unreacted acrolein and acetic anhydride, add 10.2g of water, fully stir and hydrolyze at 20-40°C for 1 hour; add sodium cyanide (11.1g), ammonium chloride (23.9 g), a mixed solution of ammonia water (90mL, 20%), stirred and reacted at 20-40°C for 4h, and the excess ammonia water was removed by rotary evaporation to obtain the intermediate aminonitrile solution; the aminonitrile solution was hydrolyzed with 500mL hydrochloric acid (35%) under reflux After 4 hours, the excess hydrochloric acid was removed by rotary evaporation, th...

Embodiment 3

[0043] Add 36.1g of methyl phosphine dichloride dropwise to the mixed solution of acrolein (19.1g) and acetic anhydride (34.6g), maintain the reaction at -5~0°C, after the dropwise addition, keep the temperature and continue the reaction for 2h, Then put the reaction solution at 20-30°C for 3h to end the reaction; use a rotary evaporator (temperature 50-70°C, vacuum above -0.09MPpa) to remove the low-boiling by-product B After acid chloride, unreacted acrolein and acetic anhydride, add 16.1g of water, and fully stir and hydrolyze at a temperature of 20-40°C for 1.5h; add sodium cyanide (16.5g), ammonium chloride (35.9 g), a mixed solution of ammonia water (140mL, 20%), stirred and reacted at 20-40°C for 4h, and the excess ammonia water was removed by rotary evaporation to obtain the intermediate aminonitrile solution; the aminonitrile solution was hydrolyzed with 800mL hydrochloric acid (35%) under reflux After 4 hours, the excess hydrochloric acid was removed by rotary evapor...

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Abstract

The invention discloses a preparation method of glufosinate-ammonium. According to the method, methyl phosphine dichloride is used as a raw material, and reacts with acrolein under the action of acetic anhydride to obtain an unsaturated phosphine-containing heterocyclic ring represented by a formula I; a hydrolysis reaction is performed to obtain a phosphine aldehyde intermediate represented by aformula II; the phosphine aldehyde intermediate is subjected to a strecker reaction to obtain an amino nitrile intermediate; and the amino nitrile intermediate is sequentially subjected to a hydrolysis reaction and a salifying reaction to obtain glufosinate-ammonium. According to the invention, the preparation method is short in technological process, and particularly can directly obtain the phosphine aldehyde intermediate without diethyl methylphosphite, so that the production cost of glufosinate-ammonium can be greatly reduced, and the further commercial popularization of glufosinate-ammonium is facilitated; and the method has good environmental friendliness, avoids the wastewater generated by the Grignard reaction in the traditional method, and also has no great potential safety hazard.

Description

technical field [0001] The invention belongs to the field of pesticide chemistry and relates to a preparation method of glufosinate-ammonium. Background technique [0002] Glufosinate-ammonium mainly contains the following synthetic routes: [0003] Route A: Methyl phosphine dichloride reacts with n-butanol (or isobutanol) to prepare methyl monobutyl phosphinate (MPE), and then reacts with 1-cyano-2-propenyl acetate (ACA) in Addition reaction under the action of a catalyst, the addition product is ammonified with ammonia water to obtain an aminonitrile intermediate, which is hydrolyzed under the action of hydrochloric acid to obtain glufosinate-ammonium acid, and then continues to undergo a series of post-treatments to obtain glufosinate-ammonium. [0004] [0005] Route B: the reaction of methyl phosphine dichloride and ethanol to prepare diethyl methyl phosphonite, then diethyl methyl phosphonite reacts with acrolein, ethanol, acetic anhydride, and the resulting produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30
CPCC07F9/301
Inventor 王福军岳瑞宽薛谊陈新春蒋剑华陈洪龙
Owner NANJING REDSUN BIOCHEM CO LTD
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