Synthetic method of high-quality acetonedicarboxylic acid and acetonedicarboxylate

A technology of acetone dicarboxylate and acetone dicarboxylate, which is applied in the field of synthesis of high-quality acetone dicarboxylate and acetone dicarboxylate, to achieve the effects of light equipment corrosion, low environmental pressure, and easy purification

Inactive Publication Date: 2015-11-25
SHANDONG FANGMING PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, sulfuryl chloride or oleum corrodes equipment seriously, and produces a l

Method used

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  • Synthetic method of high-quality acetonedicarboxylic acid and acetonedicarboxylate
  • Synthetic method of high-quality acetonedicarboxylic acid and acetonedicarboxylate
  • Synthetic method of high-quality acetonedicarboxylic acid and acetonedicarboxylate

Examples

Experimental program
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Effect test

Embodiment 1

[0010] Example 1. In a 250ml three-neck flask, add 50g (0.5mol) of concentrated hydrochloric acid (chemically pure, content 36.5%), stir well, raise the temperature to 30°C, add 42.9g (0.436mol) of epichlorohydrin dropwise, The dropwise addition was completed in about 45 minutes, and the reaction was incubated for another 2 hours. After the reaction was completed, the mixture was left to stand for separation, and the organic phase was separated into 1,3-dichloropropanol, which was dehydrated with anhydrous sodium carbonate at room temperature.

[0011] In a 250ml three-necked flask, add 138.8 grams of 30% sodium cyanide aqueous solution (0.85mol), raise the temperature to reflux, slowly add the organic phase of the step reaction dropwise, and the dropwise addition is completed in about 1 hour, and keep the temperature for 2 hours, cool to room temperature, and divide The organic phase is 1,3-dinitrile propanol, and washed with 30ml*3 water.

[0012] In a 250ml three-necked fl...

Embodiment 2

[0015] Example 2. In a 250ml three-necked flask, add hydrobromic acid and 50 grams (0.5mol) of concentrated hydrochloric acid (chemically pure, content 36.5%), and stir well, raise the temperature to 30°C, and dropwise add 42.9 grams of epichlorohydrin ( 0.436mol), the dropwise addition was completed in about 45 minutes, and then incubated for 2 hours. After the reaction was completed, the mixture was left to stand for separation, and the organic phase was separated into 1,3-dichloropropanol, which was dehydrated with anhydrous sodium carbonate at room temperature.

[0016] In a 250ml three-necked flask, add 138.8 grams of 30% sodium cyanide aqueous solution (0.85mol), raise the temperature to reflux, slowly add the organic phase of the step reaction dropwise, and the dropwise addition is completed in about 1 hour, and keep the temperature for 2 hours, cool to room temperature, and divide The organic phase is 1,3-dinitrile propanol, and washed with 30ml*3 water.

[0017] In a...

Embodiment 3

[0020] Example 3. In a 250ml three-necked flask, add hydrofluoric acid and 50 grams (0.5mol) of concentrated hydrochloric acid (chemically pure, content 36.5%), and stir well, raise the temperature to 30°C, and dropwise add 42.9 grams of epichlorohydrin ( 0.436mol), the dropwise addition was completed in about 45 minutes, and then incubated for 2 hours. After the reaction was completed, the mixture was left to stand for separation, and the organic phase was separated into 1,3-dichloropropanol, which was dehydrated with anhydrous sodium carbonate at room temperature.

[0021] In a 250ml three-necked flask, add 138.8 grams of 30% sodium cyanide aqueous solution (0.85mol), raise the temperature to reflux, slowly add the organic phase of the step reaction dropwise, and the dropwise addition is completed in about 1 hour, and keep the temperature for 2 hours, cool to room temperature, and divide The organic phase is 1,3-dinitrile propanol, and washed with 30ml*3 water.

[0022] In ...

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Abstract

The invention discloses a synthetic method of high-quality acetonedicarboxylic acid and acetonedicarboxylate. The method comprises the following steps: epoxyhalopropane used as an initial raw material and halogen hydride undergo addition to synthesize 1,3-dihalopropanol; 1,3-dihalopropanol reacts with hydrocyanate to generate 3-hydroxy-1,5-pentanedinitrile; the cyan group of 3-hydroxy-1,5-pentanedinitrile is hydrolyzed to form a carboxyl group in order to generate 3-hydroxy-1,5-glutaric acid; 3-hydroxy-1,5-glutaric acid is oxidized by an oxidant to generate acetonedicarboxylic acid; and acetonedicarboxylic acid and alcohol or a hydroxy group-containing organic compound undergo esterification to obtain acetonedicarboxylate. The route of the method is longer than original technological routes, the reaction selectivity of every step is very high, and easy purification is realized, so the content of the finally synthesized acetonedicarboxylic acid and acetonedicarboxylate reaches 99.5% or more, and the single impurity content is smaller than 0.1%. The method has the advantages of light device corrosion, few three wastes, and small environment protection pressure.

Description

technical field [0001] The invention relates to a method for synthesizing high-quality acetone dicarboxylic acid and acetone dicarboxylate, belonging to the field of pharmaceutical and chemical synthesis. Background technique [0002] Acetone dicarboxylate and acetone dicarboxylate are important intermediates of anti-inflammatory analgesic Zomepirac Sodium and osteoporosis strontium ranelate. The traditional production method is to oxidize anhydrous citric acid with sulfuryl chloride or oleum to produce acetone dicarboxylate and acetone dicarboxylate. The content of acetone dicarboxylate is difficult to exceed 97.5%, and the content of more than two impurities exceeds 1.0%. Moreover, sulfuryl chloride or oleum severely corrodes equipment and produces a large amount of waste acid, which puts great pressure on environmental protection. Such as literature: BoehringerSohnC.H.DE1160814.1964 and Cai Yunming etc. Pharmaceutical Industry, 198314:3. The process route is as follows: ...

Claims

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Application Information

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IPC IPC(8): C07C59/347C07C51/373C07C69/716C07C67/08
Inventor 张立余洪智韩涛范兴山
Owner SHANDONG FANGMING PHARMACEUTICAL CO LTD
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