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Preparation method of 3-carboxymethyl-1,2,4-cyclopentanetricarboxylic acid-1,4:2,3-dianhydride

A technology of cyclopentanetricarboxylic acid and tricarboxylic acid cyclopentaneacetic acid, applied in the field of fine chemicals, can solve the problems of low product purity, low yield, severe reaction and exothermic operation and runaway operation

Inactive Publication Date: 2019-03-22
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process does not require the addition of metal catalysts, and the post-treatment operation is simple, avoiding the problems of rapid temperature rise, violent exothermic operation, out-of-control operation, low product purity, and low yield.

Method used

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  • Preparation method of 3-carboxymethyl-1,2,4-cyclopentanetricarboxylic acid-1,4:2,3-dianhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Put 132.20g (1.00mol) of dicyclopentadiene, 600.00g of methanol solvent, and 150.00g of distilled water in a bubble reactor, and at low temperature, continuously feed ozone gas from the bottom of the bubble reactor to control the reaction temperature After 4 hours of reaction, the raw materials were detected by the gas phase to be completely reacted, and the prepared crude product was directly carried out to the next reaction without any treatment.

[0020] Place the reaction solution of the previous step in a reactor with a fractionation device, add 250.00g (2.20mol) of 30% hydrogen peroxide in batches, control the reaction temperature at 60°C, and extract 400.00g by vacuum distillation during the reaction The solvent was mixed, and the reaction was completed after 8 hours. Distilled under reduced pressure to obtain 244.60 g of a colorless transparent viscous liquid with a yield of 94.10%, which was 2,3,5-tricarboxylic acid cyclopentaneacetic acid.

[0021] Put 244.60g...

Embodiment 2

[0023] Put 132.20g (1.00mol) of dicyclopentadiene, 600.00g of ethanol solvent, and 150.00g of distilled water in the bubble reactor, and at low temperature, continuously feed ozone gas from the bottom of the bubble reactor to control the reaction temperature After 5 hours of reaction, the gas phase detection of the raw material reaction was complete, and the prepared crude product was directly carried out to the next reaction without any treatment.

[0024] Place the reaction solution in the previous step in a reactor with a fractionation device, add 272.00g (2.40mol) of hydrogen peroxide with a concentration of 30% in batches, control the reaction temperature at 80°C, and extract 400.00g by vacuum distillation during the reaction The solvent was mixed, and the reaction was completed after 7 hours. Distilled under reduced pressure to obtain 241.20 g of a colorless transparent viscous liquid with a yield of 92.70%, which was 2,3,5-tricarboxylic acid cyclopentaneacetic acid.

[...

Embodiment 3

[0027] Place 132.20g (1.00mol) of dicyclopentadiene, 600g formic acid solvent, and 150g distilled water in a bubble reactor, and at low temperature, continuously feed ozone gas from the bottom of the bubble reactor to control the reaction temperature to 0 ℃, after 6 hours of reaction, the gas phase detection of the raw material reaction was complete, and the prepared crude product was directly carried out to the next reaction without any treatment.

[0028] Place the reaction solution in the previous step in a reactor with a fractionation device, add 295.00g (2.60mol) of 30% hydrogen peroxide in batches, control the reaction temperature to 100°C, and extract 400.00g by vacuum distillation during the reaction The solvent was mixed, and the reaction was completed after 5 hours. Distilled under reduced pressure to obtain 234.80 g of light yellow transparent viscous liquid with a yield of 90.24%, which was 2,3,5-tricarboxylic acid cyclopentaneacetic acid.

[0029] Put 234.80g (0.9...

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Abstract

The invention discloses a preparation method of 3-carboxymethyl-1,2,4-cyclopentanetricarboxylic acid-1,4:2,3-dianhydride and belongs to the field of preparation methods of fine chemicals. The main technical scheme is that dicyclopentadiene is taken as a starting material and subjected to oxidation reaction with ozone and hydrogen peroxide sequentially, intermediate product 2,3,5-tricarboxylic acidcyclopentane acetic acid is obtained, finally, acetic anhydride is taken as a dehydrating agent, and dehydration ring closing is performed for synthesizing the target product 3-carboxymethyl-1,2,4-cyclopentanetricarboxylic acid-1,4:2,3-dianhydride. The method in the scheme has the advantages of being mild in reaction condition, safe to operate, high in product purity and yield, pollution-free andthe like, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of 3-carboxymethyl-1,2,4-cyclopentanetricarboxylic acid-1,4:2,3-dianhydride. Background technique [0002] 2,3,5-tricarboxylic acid cyclopentaneacetic acid and its downstream product 3-carboxymethyl-1,2,4-cyclopentanetricarboxylic acid-1,4:2,3-dianhydride are an important Chemical raw materials, n-butanol ester of 2,3,5-tricarboxylic acid cyclopentaneacetic acid can be used in lubricants, downstream products 3-carboxymethyl-1,2,4-cyclopentanetricarboxylic acid-1, 4: 2,3-dianhydride is one of the raw materials for preparing polyimide materials. The polyimide material synthesized from the dianhydride monomer and other diamine monomers has high solubility and thermoplasticity due to the asymmetry of the alicyclic structure and large volume, and is a low-temperature curing orientation with excellent performance. It is widely used in photosensitive mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08
CPCC07D493/08
Inventor 冯柏成李春阳金岩侯喜超葛平宇
Owner QINGDAO UNIV OF SCI & TECH
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