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The synthetic method of 2-methacryloyloxyethyl phosphorylcholine

A technology of methacryloyloxyethylphosphorylcholine and hydroxyethyl methacrylate, which is applied in the field of synthesis of 2-methacryloyloxyethylphosphorylcholine, and can solve the problem of long route and high yield. Low yield and other problems, to achieve the effect of high product yield, simple and feasible process, cheap and easy-to-obtain raw materials and auxiliary materials

Inactive Publication Date: 2015-12-23
CHONGQING TECH & BUSINESS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention is used to solve the problems of long route and low yield in the existing 2-methacryloyloxyethyl phosphorylcholine synthesis method

Method used

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  • The synthetic method of 2-methacryloyloxyethyl phosphorylcholine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Step a, synthesis of 2-chloro-2 oxo-1,3,2-dioxaphospholane

[0019] Get 161 grams (1.05 moles) of phosphorus oxychloride and 100 milliliters of benzene in a dry there-necked flask, o Add 0.5 gram of cuprous chloride under ℃, then dropwise add 62 grams (1 mole) of ethylene glycol, keep the temperature at 5 o Below C, after the dropwise addition, at 5 o Stir for 1 hour below C, then react at 40°C for 0.5 hour, and rectify the reaction solution to obtain 2-chloro-2oxo-1,3,2-dioxaphospholane product with a yield of 95% and product purity Up to 99%.

[0020] Step b, synthesis of 2-methacryloyloxyethyl phosphorylcholine

[0021] Take 26 g of hydroxyethyl methacrylate (0.2 mol), 35.5 g of trimethylamine (0.6 mol), 100 ml of tetrahydrofuran, and 100 ml of acetonitrile in a dry pressure reaction bottle, at -20 o 28.5 g of 2-chloro-2-oxo-1,3,2-dioxaphospholane (0.2 mol) was slowly added dropwise at C, and after the dropwise addition was completed, the reaction was maintained ...

Embodiment 2

[0023] Step a, synthesis of 2-chloro-2 oxo-1,3,2-dioxaphospholanes

[0024] Take 62 grams (1 mole) of ethylene glycol and 100 milliliters of benzene in a dry three-necked flask, o Add 0.5 gram of cuprous chloride under ℃, then dropwise add 161 grams (1.05 moles) of phosphorus oxychloride, keep the temperature at 5 o Below C, after the dropwise addition, at 5 o Stir at below C for 1 hour, then react at 40°C for 0.5 hour, and rectify the reaction solution to obtain 2-chloro-2oxo-1,3,2-dioxaphospholane product with a yield of 93% and product purity Up to 99%.

[0025] Step b, synthesis of 2-methacryloyloxyethyl phosphorylcholine

[0026] Take 130 grams of hydroxyethyl methacrylate (1 mole), 177.5 grams of trimethylamine (3 moles), 500 milliliters of tetrahydrofuran and 500 milliliters of acetonitrile in a dry pressure reaction bottle, at -20 o 142.5 g of 2-chloro-2-oxo-1,3,2-dioxaphospholane (1 mole) was slowly added dropwise at C, and after the dropwise addition was complete...

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Abstract

The invention discloses a 2-methacroyloxyethyl phosphorylcholine synthesizing method. The 2-methacroyloxyethyl phosphorylcholine synthesizing method comprises the following steps that ethanediol reacts with phosphorus oxychloride in the presence of catalysts to obtain 2-chlorine-2oxo-1, 3, 2-dioxaphospholane, and 2-methacroyloxyethyl phosphorylcholine is obtained by one-pot reaction of the 2-chlorine-2oxo-1, 3, 2-dioxaphospholane, hydroxyethyl methylacrylate and trimethylamine in a stress reaction flask. The 2-methacroyloxyethyl phosphorylcholine synthesizing method is simple in synthetic route, novel, simple and convenient in process, high in product yield and purity, and suitable for industrial production; the catalysts are low in price and easy to obtain; the environment is not affected.

Description

technical field [0001] The invention relates to a method for synthesizing 2-methacryloyloxyethyl phosphorylcholine. Background technique [0002] 2-Methacryloyloxyethylphosphorylcholine polymer is widely used in tissue engineering, artificial organs, immobilized enzymes, blood purification, biosensors, Daily chemicals and other aspects have been deeply researched and widely used. A large number of research results have shown that homopolymers and copolymers with 2-methacryloyloxyethylphosphorylcholine as monomers exhibit good blood compatibility and can effectively inhibit protein in the blood. These results have important implications for the construction of biocompatible long-circulating drug delivery carriers. [0003] The synthetic routes of 2-methacryloxyethyl phosphorylcholine reported in the literature are as follows: In 1978, Kadoma et al. used hydroxyethyl bromide and phosphorus oxychloride as raw materials to successfully synthesize 2-methacryloyl bromide and pho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/10
Inventor 蒋和雁
Owner CHONGQING TECH & BUSINESS UNIV