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Synthetic method of methyl hypophosphorous acid monoalkyl ester

A technology of monoalkyl methyl hypophosphite and methyl hypophosphorous acid is applied in the field of synthesis of monoalkyl methyl hypophosphite to achieve the effect of less control points

Inactive Publication Date: 2018-11-06
SICHUAN FOURSTAR BIOTECH RANDD CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The present invention aims to solve the problem that in the current synthesis process of monoalkyl methylphosphinate, it is necessary to first synthesize methyl phosphorus dichloride to generate monoalkyl methylphosphinate

Method used

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  • Synthetic method of methyl hypophosphorous acid monoalkyl ester

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] First, 100 g of ammonium hypophosphite (1.20 mol) and 253 mL of hexamethyldisilazane (1.20 mol) were mixed, stirred at 110 °C for 2 h under nitrogen protection, then cooled to 0 °C, and 1200 mL of new Distill dichloromethane, then add 60.6 g of methyl chloride (1.20 mol), stir at room temperature for 12 hours, filter to remove the yellow precipitate, first distill the filtrate under normal pressure to recover the solvent dichloromethane, then distill under reduced pressure to recover hexamethyldisilazide Alkanes, the distillation bottom liquid is 91.2 g methyl hypophosphorous acid (1.14 mol).

[0034] Add 91.2 g (1.14 mol) of methyl hypophosphorous acid and 313 mL (3.42 mol) of n-butanol into a 1 L three-neck flask, and then add 6.0 g of anhydrous CuSO 4 , stirred and reacted at 110-120°C, during the reaction process, the water produced by the reaction was continuously separated out, and after 8 hours, the reaction solution was rectified under reduced pressure to obtain...

Embodiment 2

[0036] First, mix 100 g of sodium hypophosphite (1.14 mol) and 105 mL of piperidine (1.14 mol), under nitrogen protection, stir at 110 °C for 2 h, then cool down to 0 °C, add 1200 mL of freshly distilled toluene to the reaction solution, and then add 57.6 g of methyl chloride (1.14 mol), stirred at room temperature for 12 h, filtered to remove the white precipitate, and the filtrate was distilled at normal pressure to recover the solvent dichloromethane, then distilled under reduced pressure to recover piperidine, and the distillation bottom liquid was 86.4 g of methyl methine Phosphoric acid (1.08 mol).

[0037]Add 86.4 g (1.08 mol) of methyl hypophosphorous acid and 297 mL (3.24 mol) of n-butanol into a 1 L three-necked flask, then add 3.0 g of strong acidic ion exchange resin, stir and react at 110-120 °C, and keep stirring during the reaction process. The water produced by the reaction was separated, and after 8 h, the reaction liquid was rectified under reduced pressure t...

Embodiment 3

[0039] First, mix 100 g of potassium hypophosphite (0.96 mol) and 78 mL of pyridine (0.96 mol), under nitrogen protection, stir at 110 °C for 2 h, then cool down to 0 °C, add 1200 mL of freshly distilled cyclohexane to the reaction solution, and then Add 48.5 g of methyl chloride (0.96 mol), stir at room temperature for 12 h, and filter to remove the white precipitate. The filtrate is distilled at normal pressure to recover the solvent methylene chloride, and then distilled under reduced pressure to recover pyridine. The bottom liquid of the distillation is 72.8 g of methyl chloride. Phosphoric acid (0.91 mol).

[0040] Add 72.8 g (0.91 mol) of methyl hypophosphorous acid and 251 mL (2.73 mol) of n-butanol into a 1 L three-necked flask, then add 6.0 g of ZnO, and stir the reaction at 110-120 °C. After 8 hours, the reaction solution was rectified under reduced pressure to obtain 117.3 g of mono-n-butyl methylphosphinate (0.86 mol), and recovered n-butanol (163 mL, 1.78 mol).

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Abstract

The invention discloses a synthetic method of methyl hypophosphorous acid monoalkyl ester and belongs to the technical field of organic synthesis. The invention aims at the problems of low MDP (methylenediphosphonic acid) synthetic yield, strict reaction condition and the like, according to the synthetic method provided by the invention, the methyl hypophosphorous acid monoalkyl ester is producedthrough synthesis of methyl hypophosphorous acid, and the synthesis of MDP is avoided. According to the synthetic method provided by the invention, a common reagent is adopted, methylation is performed firstly, and then esterification is performed to produce the methyl hypophosphorous acid monoalkyl ester. Control points in the entire process are less, technical problems of low yield and the likein a MDP synthesis process can be avoided, a completely new synthetic route of the methyl hypophosphorous acid monoalkyl ester is created, and industrial production is easier to achieved.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing monoalkyl methylphosphinate. Background technique [0002] Since the global large-scale commercial planting of genetically modified crops in 1996, it has had a huge impact on the world's pesticide industry and market. Since about 90% of the global planting area of ​​genetically modified crops is planted with glyphosate-resistant crops, the large-scale and repeated use of glyphosate has led to the occurrence and development of resistant weeds. Paraquat, the second largest herbicide in the world after glyphosate, has no antidote, resulting in a large number of non-productive poisoning deaths, and its liquid formulation is facing restrictions, so paraquat will withdraw from the market. For this reason, glufosinate-ammonium, the third largest herbicide after glyphosate and paraquat, has gained huge room for development. [0003] On May 17, 2017, the State ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/32
CPCC07F9/3217
Inventor 李舟何路涛王长江彭舟
Owner SICHUAN FOURSTAR BIOTECH RANDD CORP
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