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Method for preparing 1,3-acetone dicarboxylic acid diester and intermediate thereof by oxidizing citric acid and hydrogen peroxide

A technology of acetone dicarboxylic acid and hydrogen peroxide, which is applied in the direction of carboxylate preparation, carboxylate preparation, chemical instruments and methods, etc., can solve the problems of low yield and environmental pollution, and achieve no environmental pollution, no cost and no environment Pollution, producing easily controlled effects

Active Publication Date: 2013-09-11
CHONGQING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problem of low yield and environmental pollution caused by the existing 1,3-acetone dicarboxylic acid diester and its intermediate preparation method, the present invention provides 1,3-acetone dicarboxylic acid di The method of ester and its intermediate is a kind of efficient green synthetic method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 210g (1mol) of citric acid monohydrate into a 500ml round bottom flask equipped with a reflux condenser, a stirrer, and a thermometer, add 50ml of water, raise the temperature to 55°C, and start adding 30% aqueous hydrogen peroxide solution dropwise 136g (1.2mol), observed that bubbles evenly emerged, with the addition of aqueous hydrogen peroxide solution, the reaction temperature gradually increased, after the addition was completed, reacted at 95°C for 3 hours, evaporated to dryness under reduced pressure and weighed 141g (0.97 mol) of the product 1,3-acetonedicarboxylic acid was obtained, with a yield of 96%, a purity of 97%, and a melting point of 135°C (decomposition).

Embodiment 2

[0029] Add 210g (1mol) of citric acid monohydrate into a 500ml round bottom flask equipped with a reflux condenser, stirrer, and thermometer, add 60ml of water, raise the temperature to 65°C, and start adding 30% hydrogen peroxide aqueous solution dropwise 125g (1.1mol), it was observed that bubbles came out evenly, with the addition of aqueous hydrogen peroxide solution, the reaction temperature gradually increased, after the addition was completed, it was reacted at 95°C for 2.5 hours, evaporated to dryness under reduced pressure and weighed 142g (0.97 mol) of the product 1,3-acetonedicarboxylic acid was obtained, with a yield of 97%, a purity of 96%, and a melting point of 135°C (decomposition).

Embodiment 3

[0031] Add 210g (1mol) of citric acid monohydrate into a 500ml round-bottomed flask equipped with a reflux condenser, a stirrer, and a thermometer, add 60ml of water, raise the temperature to 50°C, and start adding 170g of 30% hydrogen peroxide dropwise (1.5mol) solution, it was observed that bubbles came out evenly. With the addition of hydrogen peroxide solution, the reaction temperature gradually increased. After the dropwise addition was completed, it was reacted at 90°C for 4 hours, evaporated to dryness under reduced pressure, and weighed 139g (0.95 mol) of the product 1,3-acetonedicarboxylic acid was obtained, with a yield of 95%, a purity of 95%, and a melting point of 135°C (decomposition).

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Abstract

The invention discloses a method for preparing 1,3-acetone dicarboxylic acid diester and an intermediate thereof by oxidizing citric acid and hydrogen peroxide. The method comprises the steps of: with hydrogen peroxide as an oxidizing agent, oxidizing citric acid in a water solution of citric acid at 0-100 DEG C to obtain 1,3-acetone dicarboxylic acid; and enabling the obtained 1,3-acetone dicarboxylic acid to be subjected to an esterification reaction with low-level fatty alcohol to obtain the 1,3-acetone dicarboxylic acid diester. The method disclosed by the invention is good in selectivity, high in transformation rate, free of environmental pollution and convenient for post treatment, thereby being an environment-friendly synthesis method; the method is a new synthesis method further satisfying atom economy rules; and moreover, the method is suitable for large-scale industrial production and the economic efficiency is greatly improved.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a method for preparing 1,3-acetone dicarboxylic acid diester and an intermediate thereof by oxidation of citric acid hydroperoxide. Background technique [0002] 1,3-Acetone dicarboxylic acid diester and its intermediates 1,3-Acetone dicarboxylic acid is an important organic synthesis and pharmaceutical intermediates, which can be used to synthesize endo-nortropine, glazone, benztropine, radium strontium nitrate and other drugs. Therefore, the research on the synthesis methodology of 1,3-acetone dicarboxylic acid diester and its intermediate 1,3-acetone dicarboxylic acid has an important application prospect. [0003] 1,3-acetone dicarboxylic acid diester is mainly obtained by the esterification reaction of 1,3-acetone dicarboxylic acid (1,3-acetone dicarboxylic acid) with alcohol, while 1,3-acetone dicarboxylic acid is mainly obtained from citric acid oxidative...

Claims

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Application Information

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IPC IPC(8): C07C59/347C07C51/373C07C69/716C07C67/08
Inventor 陈义文陈静衡林森
Owner CHONGQING UNIV OF POSTS & TELECOMM
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