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Method for synthesizing alpha-aminophosphonate through water phase cleaning

An amino phosphonate and clean technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve the problems of catalysts that do not have large-scale industrial applications, catalysts that cannot be recycled, and catalyst preparation Complex process and other issues, to achieve the effect of large-scale industrial production, stable to water, and short reaction time

Inactive Publication Date: 2012-01-18
YANCHENG TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods have one or more of the following disadvantages: the preparation process of the catalyst is complicated and the cost is high; the catalyst cannot be recycled, and its discharge causes the cost of three wastes treatment; the equipment is severely corroded; the operation process is complicated; only suitable for laboratories Or small-scale operations, do not have large-scale industrial applications, etc.
However, the biggest problem of water phase reaction is that many organic materials have low solubility in water, the materials cannot be fully contacted, and the reaction yield is low. One of the ways to solve the problem is to add cationic, anionic, and nonionic surfactants to promote the production of materials. contact to increase the yield of the reaction

Method used

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  • Method for synthesizing alpha-aminophosphonate through water phase cleaning
  • Method for synthesizing alpha-aminophosphonate through water phase cleaning
  • Method for synthesizing alpha-aminophosphonate through water phase cleaning

Examples

Experimental program
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Effect test

Embodiment 1

[0021] In a 25mL round bottom flask, add 10mmol (1.06g) of benzaldehyde, 10mmol (0.93g) of aniline, 11mmol (1.83g) of triethyl phosphite, 1mmol of Tween-20 and 15ml of water in sequence, and mix at 60°C under normal pressure Stir for 30 minutes, filter and wash with cold water, and recrystallize from ethanol to obtain pure diethyl α-anilino-benzylphosphonate with a yield of 91%.

Embodiment 2

[0023] In a 25mL round bottom flask, add 10mmol (1.36g) p-methoxybenzaldehyde, 10mmol (1.38g) 4-nitroaniline, 12mmol (1.32g) trimethyl phosphite, 0.5mmol Tween-20, 5mL of water, mixed and stirred at 70°C for 60 minutes, filtered and washed with cold water, recrystallized from methanol to obtain pure dimethyl α-(4-nitroanilino)-(4-methoxyphenyl)methylphosphonate Product, yield 86%.

Embodiment 3

[0025] In a 25mL round bottom flask, add 10mmol (1.06g) benzaldehyde, 10mmol (0.93g) aniline, 20mmol (2.76g) diethyl phosphite, 0.1mmol Tween-20, 0.1mmol Tween-60 and 1.5ml water in sequence , mixed and stirred at 60° C. under normal pressure for 45 minutes, filtered and washed with cold water, and recrystallized from ethanol to obtain pure diethyl α-anilino-benzylphosphonate with a yield of 90%.

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Abstract

The invention discloses a method for synthesizing alpha-aminophosphonate through water phase cleaning. Aromatic aldehyde, amine and phosphite ester are used as raw materials, non-ionic surface active agents are used as catalysts, water replaces organic solvents to be used as reaction media, the heating and stirring reaction is carried out at ordinary pressure, and the synthesis of the target compound is realized. Compared with the prior art, the method has the advantages that (1) Tween-20 and Tween-60 non-ionic surface active agents are adopted, raw material resources are wide, the preparation is convenient, and safety and reliability are realized; (2) the catalytic activity is high, the use consumption is little, the stability on the water is realized, the catalysts are not inactivated, and the cyclic use can be realized; and (3) a water phase reaction method is adopted, the environment pollution caused by the organic solvent use is avoided, in addition, the post treatment is convenient, the reaction is safe and stable, the industrial amplification is easy, and energy saving and emission reduction effects are obvious. The method belongs to an efficient and environment-friendly method for synthesizing alpha-aminophosphonate compounds, and the large-scale industrial production is favorably realized.

Description

A technical field [0001] The invention relates to a method for synthesizing α-aminophosphonate through clean water phase, which belongs to the technical field of chemical material preparation. This method is suitable for the occasions where aromatic aldehydes, amines and phosphites are used as raw materials, water is used instead of organic solvents as reaction medium, and the target compound is realized by heating and stirring reaction under normal pressure. Two background technology [0002] α-phosphoramidate compounds have good anti-plant virus, inhibitory enzyme activity, anti-tumor, herbicide, bactericidal and other important biological activities, and have a wide range of uses in biochemistry and medicinal chemistry, such as being used as a polymerization inhibitor Antibiotics, antibiotics and pharmacological media, herbicides, hapten-catalyzed antibodies, etc., and also an important substrate for the synthesis of phosphono-peptides, so its synthesis method has attract...

Claims

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Application Information

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IPC IPC(8): C07F9/40
Inventor 方东倪春节曹严芳
Owner YANCHENG TEACHERS UNIV
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