Organic acid glycidyl ester preparation method

A technology of glycidyl ester and glycidol, applied in the field of organic acid glycidyl ester preparation, can solve problems such as troublesome n-hexane recovery, influence product quality, etc., and achieve the effects of shortening reaction time, reducing production cost, and simplifying production process

Inactive Publication Date: 2013-07-17
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, triethylamine may be mixed into the product, which affects the quality of the product, and the recovery of n-hexane is also very troublesome

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 131mg of methyl p-iodobenzoate, 221mg of glycidol, and 2.7g of ethyl acetate solvent were sequentially added to a three-necked flask provided with a water separator and a thermometer, and then 60mg of 4-dimethylaminopyridine and 30mg of Add p-hydroxyanisole into the reaction kettle, control the reaction temperature at 60°C, and react for 2 hours. During the reaction, nitrogen gas is constantly blown in to remove the methanol produced by the reaction. The normal phase chromatography conditions are 200-300 mesh silica gel, p-iodobenzene The mass ratio of glycidyl formate crude product to silica gel is 1:30, the mobile phase is n-hexane / ether=4 / 1, the elution volume is 4 column volumes, the fraction containing glycidyl p-iodobenzoate is collected and evaporated to dryness to obtain 0.098g of glycidyl p-iodobenzoate pale yellow solid, the yield is 65%.

Embodiment 2

[0018] The 4-nitrobenzoic acid methyl ester of 90mg, the glycidol of 221mg, the ethyl acetate solvent of 2.7g are added in the three-necked flask that is provided with water trap and thermometer successively, then the 4-dimethylaminopyridine of 60mg and Add 30 mg of p-hydroxyanisole into the reaction kettle, control the reaction temperature at 50°C, and react for 2 hours. During the reaction, nitrogen gas is constantly blown in to remove the methanol produced by the reaction. The normal phase chromatography conditions are 200-300 mesh silica gel, 4 - The mass ratio of glycidyl nitrobenzoate to silica gel is 1:30, the mobile phase is n-hexane / ether = 4 / 1, the elution volume is 4 column volumes, and the 4-nitrobenzoic acid glycidyl ester is collected The fractions were evaporated to dryness to obtain 0.084g 4-nitrobenzoic acid glycidyl ester colorless liquid, the yield was 75%.

Embodiment 3

[0020] Add 43mg of methyl acrylate and 221mg of glycidol to a three-necked flask equipped with a water separator and a thermometer, then add 60mg of 4-dimethylaminopyridine and 30mg of p-hydroxyanisole into the reaction kettle, Control the reaction temperature at 60°C and react for 2 hours. During the reaction, nitrogen gas is constantly blown in to remove the methanol produced by the reaction. The normal phase chromatography conditions are 200-300 mesh silica gel, and the mass ratio of glycidyl acrylate to silica gel is 1:30. The mobile phase was n-hexane / ether=4 / 1, and the elution volume was 4 column volumes. The fractions containing glycidyl acrylate were collected and evaporated to dryness to obtain 0.047 g of glycidyl acrylate as a colorless liquid with a yield of 74%.

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Abstract

The invention relates to an organic acid glycidyl ester preparation method, and belongs to the field of organic synthesis. According to the method, a catalyst is utilized to catalyze the transesterification of organic ester and glycidol, wherein the organic ester is methyl acrylate, methyl benzoate, 4-nitrobenzoic acid methyl ester, methyl 4-iodobenzoate, 4-(methoxycarbonyl) phenylacetylene or methyl p-methoxy cinnamate; and the catalyst is 4dimethylaminopyridine. The invention has the beneficial effects that the 4dimethylaminopyridine serves as the catalyst, so that the reaction time is effectively shortened, and energy conservation and emission reduction are benefited.

Description

technical field [0001] The invention relates to a method for preparing glycidyl organic acid, which belongs to the field of organic synthesis. Background technique [0002] The transesterification reaction between esters and alcohols can use different types of catalysts. JP55011542 uses KOH as a condensation reaction catalyst, but this strong alkaline substance can make glycidol polymerize in a short time, resulting in potential dangers such as explosion. DE2423405 uses more basic lithium methoxide as a catalyst, which brings great danger to post-processing. The use of weakly basic catalysts has also been reported. For example, DE2525026 uses potassium cyanide as a catalyst, which can cause the appearance of addition by-products, which not only complicates the reaction process, but also reduces the purity of the product. JP55094381 used less toxic potassium acetate as a catalyst, but in the distillation process of post-treatment, the purity of the product was significantly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/00C07D303/16
Inventor 刘建辉宋珠草
Owner DALIAN UNIV OF TECH
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