Synthetic method for glufosinate ammonium

A synthetic method, glufosinate-ammonium technology, applied in the field of pesticides, can solve the problems of defective safety, high price, high cost, etc., and achieve the effects of high safety, reduced post-processing steps, and mild reaction conditions

Inactive Publication Date: 2019-01-18
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the potassium tert-butoxide and isobutyl nitrite used in the oximation reaction are expensive and difficult

Method used

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  • Synthetic method for glufosinate ammonium
  • Synthetic method for glufosinate ammonium
  • Synthetic method for glufosinate ammonium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation method of intermediate II α-bromo-γ-butyrolactone:

[0035] Under ice bath, slowly add 330mL liquid bromine dropwise to the mixture of 500g γ-butyrolactone and 31g red phosphorus in a three-neck flask, then raise the temperature to 70°C, and continue to dropwise add 330mL liquid bromine. After the dropwise addition, the temperature was raised to 80° C. for 3 h. Stop heating until cooling, and continue blowing air to blow away excess liquid bromine and generated hydrogen bromide. Then the temperature was raised to 80°C, and 100 mL of water was slowly added dropwise, and 700 mL of water was added after the reaction eased, and refluxed for 4 hours. After cooling, the layers were separated, the aqueous layer was extracted with dichloromethane, the organic layers were combined, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product (b.p.120-125°C / 1.6kPa), which was purified by...

Embodiment 2

[0036] Embodiment 2: the preparation method of intermediate IIα-bromo-γ-butyrolactone:

[0037] Under ice bath, slowly add 330mL liquid bromine dropwise to the mixture of 500g γ-butyrolactone and 31g red phosphorus in a three-neck flask, then raise the temperature to 70°C, and continue to dropwise add 250mL liquid bromine. After the dropwise addition, the temperature was raised to 80° C. for 3 h. Stop heating until cooling, and continue blowing air to blow away excess liquid bromine and generated hydrogen bromide. Then the temperature was raised to 80°C, and 100 mL of water was slowly added dropwise, and 750 mL of water was added after the reaction eased, and refluxed for 4 hours. After cooling, the layers were separated, the aqueous layer was extracted with dichloromethane, the organic layers were combined, and dried over anhydrous magnesium sulfate. The crude product was obtained after distilling off the solvent under reduced pressure, which was purified by distillation un...

Embodiment 3

[0038] Embodiment 3: the preparation method of intermediate II α-bromo-γ-butyrolactone:

[0039] Under ice bath, slowly add 330mL liquid bromine dropwise to the mixture of 500g γ-butyrolactone and 31g red phosphorus in a three-neck flask, then raise the temperature to 70°C, and continue to dropwise add 150mL liquid bromine. After the dropwise addition, the temperature was raised to 80° C. for 3 h. Stop heating until cooling, and continue blowing air to blow away excess liquid bromine and generated hydrogen bromide. Then the temperature was raised to 80°C, and 100 mL of water was slowly added dropwise, and 750 mL of water was added after the reaction eased, and refluxed for 4 hours. After cooling, the layers were separated, the aqueous layer was extracted with dichloromethane, the organic layers were combined, and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the crude product was obtained, which was purified by distillation ...

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Abstract

The invention relates to a synthetic method for glufosinate ammonium. The synthetic method comprises the following steps: single-bromine substitution, amination, amino protection, chlorination ring opening, Arbuzov reaction and acidizing hydrolysis ammoniation; the single-bromine substitution means triggering alpha-site single-bromine substitution betweengamma-butyrolactone I and bromine under theexistence of catalyst and performing reduced pressure distillation, thereby acquiring a pure intermediate II alpha-bromine-gamma-butyrolactone; phosphorus tribromide is served as the catalyst; amination means triggering amination reaction between alpha-bromine-gamma-butyrolactone II and ammonium hydroxide, and then adding hydrochloric acid and reflowing, thereby acquiring an intermediate IIIalpha-amino-gamma-butyrolactone hydrochloride. The invention has the beneficial effects: 1) low-costgamma-butyrolactone is taken as a raw material, is subjected to single-bromine substitution with bromineand then is subjected to amination reaction with ammonium hydroxide; the adopted raw materials are low-cost and easily acquired; reaction conditions are mild; operation is simple and convenient; safety is high; amplifying production is feasible; reaction yield is high; product purity is high; cost is greatly lowered; the synthetic method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a synthesis method of glufosinate-ammonium. Background technique [0002] Glufosinate-ammonium (glufosinate-ammonium), the chemical name is 4-[hydroxy (methyl) phosphono]-DL-alanine, the structure is as follows: [0003] [0004] Glufosinate (glufosinate) is a high-efficiency, low-toxicity, broad-spectrum contact-killing organophosphorus herbicide, which was first developed and produced by Hearst Company (later owned by Bayer Company). It is a glutamine synthetase inhibitor, which leads to nitrogen metabolism disorder in plants, excessive accumulation of ammonia, disintegration of chloroplasts, inhibition of photosynthesis and death of plants. In the early years, Hearst successfully introduced glufosinate-ammonium resistance genes into more than 20 crops such as rice, wheat, and corn. Glufosinate-ammonium is the second most resistant herbicide in the world after glyphosat...

Claims

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Application Information

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IPC IPC(8): C07F9/30
CPCC07F9/301
Inventor 贾丽慧陈云峰陈长安
Owner WUHAN INSTITUTE OF TECHNOLOGY
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