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3, 3', 4, 4'-oxydiphthalic dianhydride and 9-oxo(oxa)fluorene dianhydride composition, preparation method and application thereof

A technology of biphenyl ether dianhydride and fluorene dianhydride, which is applied in the field of organic synthesis, can solve problems such as tensile resistance, heat resistance, and insufficient mechanical strength, and achieve the effects of small waste discharge, large application prospects, and simple operation

Active Publication Date: 2016-11-09
河北海力香料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the polyimide prepared from 3,3',4,4'-biphenyl ether dianhydride as raw material has deficiencies in properties such as tensile resistance, heat resistance, and mechanical strength.

Method used

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  • 3, 3', 4, 4'-oxydiphthalic dianhydride and 9-oxo(oxa)fluorene dianhydride composition, preparation method and application thereof
  • 3, 3', 4, 4'-oxydiphthalic dianhydride and 9-oxo(oxa)fluorene dianhydride composition, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 1000 g of N,N-dimethylformamide containing 2% water, 250 g of N-methyl-4-nitrophthalimide, 8 g of sodium nitrite and 12 g of sodium nitrate into a 2L autoclave, Raise the temperature to above 165°C and keep it warm for the reaction. The reaction pressure is maintained at 0.05-0.1MPa. After 16 hours of reaction, the temperature is lowered to 60-70°C. The material is transferred to the distillation bottle, and the solvent is recovered. 400 g of water was added to the liquid, crystallized, and filtered to obtain light yellow intermediate compound bis(N-methylphthalimide) ether represented by formula I and compound represented by formula II.

[0033] Put the above-mentioned intermediate, 100g of sodium hydroxide, and 400g of water into the reaction flask, stir and heat up to 100°C for reflux reaction for 12 hours, then add 335g of hydrochloric acid with a mass concentration of 30% for crystallization, cool down to 40-90°C, and filter to obtain the formula III The crude ...

Embodiment 2

[0037] Add 48kg of N,N-dimethylformamide, 2kg of water, 15kg of N-methyl-4-nitrophthalimide, 0.2kg of potassium nitrite, and 0.5kg of copper nitrate into a 100L reaction kettle , stir well to make it evenly mixed, then raise the temperature to 170°C and keep it warm for reaction, the reaction pressure is maintained at 0.15-0.25MPa, and the reaction ends in about 12 hours. After recovering about 38 kg of solvent, 25 kg of water was added thereto, crystallized, and filtered to obtain light yellow intermediate compound bis(N-methylphthalimide) ether represented by formula I and compound represented by formula II.

[0038] Put the above intermediate, 6 kg of sodium hydroxide, and 24 kg of water into the reaction kettle, stir and raise the temperature to 100°C for reflux reaction for 14 hours, then add 20kg of 30% hydrochloric acid for crystallization, cool down to 40-90°C, and filter to obtain the formula III The crude product of the compound 4,4'-diphenyl ether tetracarboxylic ac...

Embodiment 3

[0042]Add 49kg of N,N-dimethylformamide, 1kg of water, 15kg of N-methyl-4-nitrophthalimide, 0.2kg of potassium nitrite, and 0.5kg of sodium nitrate into a 100L reaction kettle , stir well to make it evenly mixed, then raise the temperature to 156-160°C and keep it warm for reaction, the reaction pressure is maintained at 0.05-0.15MPa, and the reaction is completed in about 13 hours. After recovering about 38 kg of solvent, 25 kg of water was added thereto, crystallized, and filtered to obtain light yellow intermediate compound bis(N-methylphthalimide) ether represented by formula I and compound represented by formula II.

[0043] Put the above-mentioned intermediate, 8.5kg potassium hydroxide, and 24 kg water into the reactor, stir and heat up to 100°C for reflux reaction for 14 hours, then add 17kg of 50% sulfuric acid for crystallization, cool down to 40-90°C, and filter to obtain the formula III The crude product of the compound 4,4'-diphenyl ether tetracarboxylic acid and ...

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Abstract

Relating to the technical field of organic synthesis, the invention discloses a 3, 3', 4, 4'-oxydiphthalic dianhydride and 9-oxo(oxa)fluorene dianhydride composition, a preparation method and application thereof. The composition includes 3, 3, 4', 4'-oxydiphthalic dianhydride and 9-oxo(oxa)fluorene dianhydride in a mass ratio of 70-95:5-30. The composition provided by the invention can be prepared into high performance polyimide, which is far superior to polyimide synthesized purely from 3, 3', 4, 4'-oxydiphthalic dianhydride as the raw material in the aspects of tensile strength, heat resistance, mechanical strength and other performance. Through selection of an etherification reaction catalyst and a solvent, the invention provides a preparation method of the3, 3', 4, 4'-oxydiphthalic dianhydride and 9-oxo(oxa)fluorene dianhydride composition, and the method has the characteristics of simple operation, high product purity, low emission of "three wastes", and easy industrialization, thus having great application prospects.

Description

technical field [0001] The invention relates to the technical field of organic synthesis. Background technique [0002] 3,3’,4,4’-Biphenyl ether dianhydride is an extremely useful chemical intermediate for the preparation of polyimide materials. The polyimide synthesized with it as raw material has excellent thermal processing performance, high temperature resistance up to 400°C and high insulation performance. It has been widely used in aviation, aerospace, microelectronics, nano, liquid crystal, separation membrane, laser and other fields, and has been listed as one of the most promising engineering plastics in the 21st century. [0003] The methods for synthesizing 3,3',4,4'-biphenyl ether dianhydride mainly include the condensation method of halogenated phthalic anhydride and hydroxyphthalic anhydride, the method of halogenated phthalic anhydride and N-methyl-4-nitrophthalimide Law. [0004] The halogenated phthalic anhydride and hydroxyphthalic anhydride method uses ...

Claims

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Application Information

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IPC IPC(8): C08G73/10C07D493/14C07D307/89
CPCC07D307/89C07D493/14C08G73/10
Inventor 李文革张云堂杨桓邵帅郭少康时红粉
Owner 河北海力香料股份有限公司
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