Preparation method of glufosinate-ammonium intermediate

An intermediate, glufosinate-ammonium technology, which is applied in the field of synthesis of organic compounds, can solve the problems of flammable hydrogen cyanide gas, highly toxic, and highly toxic, and achieve reduced risk, strong nucleophilic ability, and improved reaction yield. rate effect

Inactive Publication Date: 2019-06-14
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Glufosinate-ammonium cyanide is a key intermediate for the synthesis of glufosinate-ammonium. The reported synthesis method of this intermediate is the addition reaction of methyl phosphite and acrolein, and then with sodium cyanide and ammonia/chloride...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 13.6 g of diethyl methylphosphonite (0.1 mol) and 30 ml of ethanol to the reaction flask, under the protection of nitrogen, add 5.6 g of newly distilled acrolein (0.1 mol) dropwise at 25°C, React for 2 hours. Then, ethanol and remaining acrylic acid are recovered by distillation under reduced pressure. 10 g of 5% hydrochloric acid was added to the residue at 25°C to continue the reaction. After 2 hours, ethanol produced by hydrolysis was distilled off under reduced pressure to obtain 15.4 g of phosphonaldehyde. Add 15.4 g of phosphoraldehyde obtained dropwise to 4.9 g of sodium cyanide (0.1 mol), 8 g of ammonium chloride (0.15 mol) in 50 ml of 25% ammonia solution, the temperature of the addition is controlled at 25 °C, and the addition is complete Afterwards, the reaction was continued for 3 hours. After the reaction was completed, ethyl acetate was extracted, the organic phases were combined, and vacuum distillation obtained 16.8 g of glufosinate-ammonium cyanam...

Embodiment 2

[0021] Add 13.6 g of diethyl methylphosphonite (0.1 mol) and 30 ml of ethanol to the reaction flask, under the protection of nitrogen, add 5.6 g of newly distilled acrolein (0.1 mol) dropwise at 25°C, React for 2 hours. Then, ethanol and remaining acrylic acid are recovered by distillation under reduced pressure. 10 g of 5% hydrochloric acid was added to the residue at 25°C to continue the reaction. After 2 hours, ethanol produced by hydrolysis was distilled off under reduced pressure to obtain 15.4 g of phosphonaldehyde. Add 15.4 g of phosphoraldehyde obtained dropwise to 9.9 g of trimethylsilylcyanide (0.1mol), 8 g of ammonium chloride (0.15mol) in 50 ml of 25% ammonia solution, dropwise at a temperature of 25°C, and dropwise After the addition was completed, the reaction was continued for 3 hours. After the reaction was completed, ethyl acetate was extracted, the organic phases were combined, and distilled under reduced pressure to obtain 17 g of glufosinate-ammonium cyan...

Embodiment 3

[0023] Add 13.6 g of diethyl methylphosphonite (0.1 mol) and 30 ml of ethanol to the reaction flask, under the protection of nitrogen, add 6.7 g of newly distilled acrolein (0.12 mol) dropwise at 25 °C, React for 2 hours. Then, ethanol and remaining acrylic acid are recovered by distillation under reduced pressure. 10 g of 5% hydrochloric acid was added to the residue at 25°C to continue the reaction. After 2 hours, ethanol produced by hydrolysis was distilled off under reduced pressure to obtain 15.8 g of phosphonaldehyde. Add 15.8 g of phosphoraldehyde obtained dropwise to 9.9 g of trimethylsilylcyanide (0.1mol), 8 g of ammonium chloride (0.15mol) in 50 ml of 25% ammonia solution, dropwise at a temperature of 25°C, and dropwise After the addition was completed, the reaction was continued for 3 hours. After the reaction, ethyl acetate was extracted, and the organic phases were combined and distilled under reduced pressure to obtain 17.4 g of glufosinate-ammonium cyanamide, ...

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PUM

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Abstract

The invention relates to a preparation method of a glufosinate-ammonium intermediate. The preparation method comprises the following steps: with diethyl methylphosphite as a starting raw material, firstly carrying out a Michael reaction of diethyl methylphosphite and acrolein, and then carrying out a Streckker reaction on a product without treatment and trimethylsilyl cyanide and an ammonia watersolution of ammonium chloride to obtain the glufosinate-ammonium key intermediate, namely glufosinate-ammonium cyanamide. Compared with a traditional synthesis method, the method has the advantages that sodium cyanide is replaced by trimethylsilyl cyanide, the toxicity is greatly reduced, the operation safety is improved, meanwhile, the nucleophilic capacity is high, the reaction is facilitated, and the yield is high.

Description

technical field [0001] The invention relates to the synthesis of organic compounds, in particular to a preparation method of glufosinate-ammonium. Background technique [0002] Glufosinate-ammonium was successfully developed by Hearst Company in the 1980s (later owned by Bayer Company). It is a non-conductive herbicide with high efficiency, low toxicity and environmental friendliness. It is easy to degrade in soil and is harmful to crops. Safe, not easy to drift, wide weeding spectrum, high activity, less dosage, less pressure on the environment, it is the world's largest tonnage pesticide variety. Especially with the rapid development of transgenic technology, the planting of transgenic herbicide-tolerant crops has intensified in recent years, and the use of herbicide-tolerant crops has increased significantly. Glufosinate-ammonium is an excellent herbicide that kills herbicides and is very suitable as a resistance gene. At present, glufosinate-ammonium has become the seco...

Claims

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Application Information

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IPC IPC(8): C07F9/32
Inventor 于国权孙霞林马长庆丁华平
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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