Method for preparing 1,3-acetone dicarboxylic acid diester and an intermediate thereof by using citric acid to catalyze oxidization of 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, environmental pollution, etc., and achieve short reaction time and environmental friendliness , mild effect

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 low yield and environmental pollution problems of the existing 1,3-acetone dicarboxylic acid diester and its intermediate 1,3-acetone dicarboxylic acid preparation method, the invention provides citric acid acid catalyzed hydrogen peroxide A method for preparing 1,3-acetone dicarboxylic acid diester and its intermediates by oxidation, while increasing the yield, with less pollution but greater production efficiency improvement

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 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 to dissolve the citric acid, and add 1ml of 98% sulfuric acid (0.018mol) dropwise therein. When the temperature was raised to 55°C, 136g (1.2mol) of 30% aqueous hydrogen peroxide solution was added dropwise. Bubbles were observed to pop out quickly and evenly. With the addition of aqueous hydrogen peroxide solution, the reaction temperature gradually increased. After completion, react at 85°C for 2 hours, evaporate water under reduced pressure to dissolve citric acid, cool, crystallize, filter with suction, wash with ice water, and dry to obtain 141g (0.97 mol) of the product 1,3-acetonedicarboxylic acid. The yield is 97%, the purity is 97%, and the melting point is 135°C (decomposition).

Embodiment 2

[0032] Add 210g (1mol) of citric acid monohydrate in a 500ml round bottom flask equipped with a reflux condenser, stirrer, and thermometer, add 60ml of water to dissolve the citric acid, and add 5ml of 98% sulfuric acid (0.09mol) dropwise therein, Raise the temperature to 50°C, and start to add 170g (1.5mol) of 30% hydrogen peroxide solution dropwise. It was observed that bubbles popped out quickly and evenly. With the addition of hydrogen peroxide solution, the reaction temperature gradually increased. After the addition, react at 90°C for 1 hour, evaporate the water under reduced pressure to dissolve the citric acid, cool, crystallize, filter with suction, wash with ice water, and dry to obtain 139g (0.95 mol) of the product 1,3-acetonedicarboxylic acid , The yield is 95%, the purity is 95%, and the melting point is 135°C (decomposition).

Embodiment 3

[0034] Add citric acid monohydrate 210g (1mol) in the 500ml round bottom flask that reflux condenser, stirrer, thermometer are housed, add 50ml water and make citric acid dissolve, and dropwise 10ml 98% sulfuric acid (0.18mol) wherein, Raise the temperature to 55°C. At this time, 136 g (1.2 mol) of 30% aqueous hydrogen peroxide solution was added dropwise. It was observed that bubbles popped out quickly and uniformly. With the addition of aqueous hydrogen peroxide solution, the reaction temperature gradually increased. After the addition, react at 85°C for 1 hour, evaporate the water under reduced pressure to dissolve the citric acid, cool, crystallize, filter with suction, wash with ice water, and dry to obtain 141g (0.97 mol) of the product 1,3-acetonedicarboxylic acid , the yield is 97%, the purity is 97%, and the melting point is 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 using citric acid to catalyze oxidization of hydrogen peroxide. The method comprises the steps of: with at least one medium-strong acid as a catalyst and 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 used for efficiently preparing the 1,3-acetone dicarboxylic acid diester and the intermediate thereof, and is high in yield, small in pollution and short in reaction time; and 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 catalyzing hydrogen peroxide oxidation with citric acid. 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 citri...

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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