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Grignard reaction-based method for preparing phenylphosphonic acid trimethoxy silane

A technology of phenylphosphonic acid trimethoxysilane and tetramethoxysilane, which is applied in the field of preparation of phenylphosphonic acid trimethoxysilane, can solve the problem that the keying success rate cannot be guaranteed, the proton conductivity is not high, the content of phosphonic acid Stability limitations and other issues, to achieve the effect of less side reactions, stable phosphonic acid content, and fast reaction speed

Inactive Publication Date: 2014-10-08
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the inserted phosphonic acid groups are keyed in at a later stage, the success rate of keying cannot be guaranteed, which limits the stability of the phosphonic acid content of the corresponding proton exchange membrane, resulting in the presence of protons in the high temperature proton exchange membrane at high temperature and low humidity. The defect of low conductivity

Method used

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  • Grignard reaction-based method for preparing phenylphosphonic acid trimethoxy silane
  • Grignard reaction-based method for preparing phenylphosphonic acid trimethoxy silane
  • Grignard reaction-based method for preparing phenylphosphonic acid trimethoxy silane

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Effect test

Embodiment 1

[0022] The preparation method of the phenylphosphonic acid trimethoxysilane based on Grignard reaction, it comprises the steps:

[0023] 1) Under the condition of anhydrous and nitrogen protection, add 3g of dry magnesium powder and 2g into the flask, and add 10mL of anhydrous ether and 5mL of m-chlorophenylphosphonic acid, heat the solution for a few minutes and make the solution slightly boil, and wait for the reaction After the reflux of anhydrous ether in the medium was evaporated, add 15mL m-chlorophenylphosphonic acid and 15mL anhydrous ether dropwise, continue to react for 1h after the dropwise addition, then slowly heat and recover anhydrous ether, until the reaction temperature reaches 80°C, Stop the reaction to obtain the Grignard reagent of m-chlorophenylphosphonic acid; wherein the average temperature rise rate of slow heating is 10° C. / min;

[0024] 2) Under the conditions of anhydrous and nitrogen protection, the prepared Grignard reagent of m-chlorophenylphospho...

Embodiment 2

[0026] The preparation method of the phenylphosphonic acid trimethoxysilane based on Grignard reaction, it comprises the steps:

[0027] 1) Under the condition of anhydrous and nitrogen protection, add 3g of dry magnesium powder and several grains of iodine into the flask, and add 10mL of anhydrous ether and 5mL of m-chlorophenylphosphonic acid, heat the solution for a few minutes to slightly boil, After the reflux of anhydrous ether in the reaction is evaporated, add 15mL of m-chlorophenylphosphonic acid and 15mL of anhydrous ether dropwise; ℃, stop the reaction, and obtain the Grignard reagent of m-chlorophenylphosphonic acid; wherein the average temperature rise rate of slow heating is 7°C / min;

[0028] 2) Under the conditions of anhydrous and nitrogen protection, cool and stir the Grignard reagent of m-chlorophenylphosphonic acid on an ice-water bath, and at the same time, add 9.5mL tetramethoxysilane and 10mL anhydrous ether dropwise with a dropping funnel Control the ra...

Embodiment 3

[0030] The preparation method of the phenylphosphonic acid trimethoxysilane based on Grignard reaction, it comprises the steps:

[0031] 1) Under the condition of anhydrous and nitrogen protection, add 3g of dry magnesium powder and several grains of iodine into the flask, and add 10mL of anhydrous ether and 5mL of m-chlorophenylphosphonic acid, heat the solution for a few minutes to slightly boil, After the reflux of anhydrous ether disappears during the reaction, add 15mL of m-chlorophenylphosphonic acid and 15mL of anhydrous ether dropwise; after the dropwise addition, continue the reaction for 1 hour, then heat slowly and recover anhydrous ether until the reaction temperature reaches 80°C , stop the reaction to obtain the Grignard reagent of m-chlorophenylphosphonic acid; wherein the average temperature rise rate of slow heating is 10° C. / min;

[0032]2) Under the conditions of anhydrous and nitrogen protection, cool and stir the Grignard reagent of m-chlorophenylphosphoni...

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Abstract

The invention discloses a grignard reaction-based method for preparing phenylphosphonic acid trimethoxy silane. The method comprises the following steps: 1) adding dry magnesium powder and iodine to an absolute ether under water-free and oxygen-free conditions, and adding an m-Chlorophenyl phosphonic acid to participate into reaction, so as to obtain a grignard reagent of the m-Chlorophenyl phosphonic acid; 2) dropwise adding an anhydrous diethyl ether solution of tetramethoxysilane to the grignard reagent of the m-Chlorophenyl phosphonic acid under the water-free and oxygen-free conditions at 0-5 DEG C, carrying out micro-boiling, so that a reaction mixture flows back, then cooling on an ice-water bath, separating out an ether layer, washing and drying, and then obtaining a crude product ether solution; collecting a fraction at 137-141 DEG C, so as to obtain the phenylphosphonic acid trimethoxy silane. The phenylphosphonic acid trimethoxy silane prepared by the method has the advantages of fast reaction speed, low temperature, high yield, fewer side effects and stable phosphonic acid content, can be applied to a proton exchange membrane, and is especially applicable to a high-temperature proton exchange membrane.

Description

technical field [0001] The invention belongs to the technical field of fuel cells, and relates to a preparation method of phenylphosphonic acid trimethoxysilane based on Grignard reaction. Background technique [0002] Proton exchange membrane fuel cell (PEMFC) is a clean, high-efficiency, green and environmentally friendly power generation device, which has a wide range of applications in stationary or mobile fuel cell power generation systems. As an important part of the proton exchange membrane fuel cell, the proton exchange membrane plays a dual role of separating fuel and oxidant and conducting protons. With the rapid development of the development and application of PEMFC in recent years, the research and achievements of proton exchange membranes are also emerging. So far, the most prominent is the perfluorosulfonic acid proton exchange membrane (i.e. Nafion membrane) of DuPont of the United States, which has the advantages of high proton conductivity and good chemica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/38H01M8/10H01M8/1233H01M8/124
CPCY02E60/521Y02E60/50
Inventor 沈春晖许多铎孔更金郑磊张鹏凡袁兵阳
Owner WUHAN UNIV OF TECH
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