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A kind of preparation method of 3-(methyl alkoxy phosphoryl) propionate compound

A technology of methyl alkoxyphosphoryl and methyl phosphonite dialkyl, which is applied in the field of compound preparation and can solve harsh problems

Inactive Publication Date: 2016-02-03
CHONGQING UNISPLENDOUR CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The advantage of this method is that the yield is high, and the post-treatment is simple. The disadvantage is that the reaction is carried out under anhydrous and oxygen-free conditions, which is relatively harsh, and only two compounds with the same alkoxy group can be synthesized.

Method used

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  • A kind of preparation method of 3-(methyl alkoxy phosphoryl) propionate compound
  • A kind of preparation method of 3-(methyl alkoxy phosphoryl) propionate compound
  • A kind of preparation method of 3-(methyl alkoxy phosphoryl) propionate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a four-necked round-bottomed flask equipped with stirring, a thermometer and a constant pressure dropping funnel, add 204 g (1.5 mol) of diethyl methylphosphinate and 300 mL of absolute ethanol, and then add 99 % of ethyl acrylate 152g (1.505mol), cool the material in the flask to 5°C, control the temperature not to exceed 20°C, add ethyl acrylate dropwise, keep warm for 2h after the dropwise addition; sampling, GC analysis results show that methylphosphonous acid The content of diethyl ester was 0.53%, and the content of ethyl acrylate was 0.86%. The solvent and 307.2g of light yellow product ethyl 3-(methylethoxyphosphoryl)propionate were obtained by distillation under reduced pressure, with a content of 97.3% and a yield of 95.8%.

[0021] The product structure detection data are as follows, which proves the structural formula of the product obtained in the present embodiment:

[0022] 1 HNMR (600MHz, CDCl 3 ): δ4.16(q, 2H), 4.07(q, 2H), 2.65-2.68(m, 2H), 2.04-2...

Embodiment 2

[0024] In a four-necked round-bottomed flask equipped with stirring, a thermometer and a constant pressure dropping funnel, add 204 g (1.5 mol) of diethyl methylphosphinate and 300 mL of acetic acid, and then add 99% diethyl methylphosphonite into the constant pressure dropping funnel Ethyl acrylate 152g (1.505mol), cool the material in the flask to 5°C, control the temperature not to exceed 20°C, add ethyl acrylate dropwise, keep warm for 2h after the dropwise addition; sampling, GC analysis results show that diethyl phosphinate The ester content is 0.63%, the ethyl acrylate content is 0.94%; the solvent and 305.8g light yellow product ethyl 3-(methylethoxyphosphoryl) propionate are obtained by distillation under reduced pressure, the content is 97.6%, and the yield is 95.6%.

Embodiment 3

[0026] In a four-necked round-bottomed flask equipped with stirring, a thermometer and a constant pressure dropping funnel, add 204 g (1.5 mol) of diethyl methylphosphinate and 300 mL of absolute ethanol, and then add 99 % of methyl acrylate 131g (1.505mol), cool the material in the flask to 5°C, control the temperature not to exceed 20°C, add methyl acrylate dropwise, keep warm for 2h after the dropwise addition; sampling, GC analysis results show that methyl phosphonous acid The content of diethyl ester was 0.47%, the content of methyl acrylate was 0.92%; the solvent and 287.4g of light yellow product 3-(methylethoxyphosphoryl) methyl propionate were obtained by distillation under reduced pressure, the content was 97.5%, and the yield was 96.3%.

[0027] The product structure detection data are as follows, which proves the structural formula of the product obtained in the present embodiment:

[0028] 1 HNMR (600MHz, CDCl 3 ): δ4.07(q, 2H), 3.67(s, 3H), 2.65-2.68(m, 2H), 2....

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Abstract

The invention discloses a method for preparing 3-(methyl alkoxy phosphoryl group) propionate compound. Methyl phosphorous acid dialkyl and acrylate are taken as the raw material, and the reaction is carried out in a nonaqueous secondary solvent so as to obtain the 3-(methyl alkoxy phosphoryl group) propionate. According to the method, the Methyl phosphorous acid dialkyl and acrylate are taken as the raw material, the reaction solvent is the nonaqueous secondary solvent such as alcohol, carboxylic acid, and the like, besides being used as the solvent, the nonaqueous secondary solvent also can be reacted with alkyl anions generated in the reaction process so as to generate corresponding ether or carboxylic ester, the two alkoxy in the 3-(methyl alkoxy phosphoryl group) propionate are from methyl phosphorous acid and dialkyl and acrylate respectively, therefore, the method can be used for synthetizing the 3-(methyl alkoxy phosphoryl group) propionate with different alkoxy according to requirements, the reaction does not need to be carried out under anhydrous and anaerobic condition, the content of the product prepared by the method is more than 98%, and the yield of the product is over 95%.

Description

technical field [0001] The invention relates to a method for preparing a compound, in particular to a method for preparing a 3-(methylalkoxyphosphoryl) propionate compound. Background technique [0002] 3-(Methylalkoxyphosphoryl)propionate compound is an important pesticide intermediate, which can be used in the synthesis of L-glufosinate-ammonium. [0003] J.Org.Chem.,1991,56,1783-1788 reported a preparation method of ethyl 3-(methylethoxyphosphoryl)propionate, using ethyl acrylate and methylethoxyphosphoric acid as raw materials , sodium ethylate as a catalyst, the reaction to obtain ethyl 3-(methylethoxyphosphoryl) propionate, the reaction equation is as follows: [0004] [0005] The yield is 81.4%. After the reaction, it is necessary to treat the catalyst and separate by-products, and the operation is relatively cumbersome. [0006] The patent literature with the publication number CN101665514A reports a synthesis method of 3-(methylalkoxyphosphoryl) propionate com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/32
Inventor 丁永良张飞吴传隆屈洋刘佳何咏梅李静李双龙
Owner CHONGQING UNISPLENDOUR CHEM