Method for preparing 4,4,5,5-dinaphthalene tetracarboxylic acid dianhydride

A technology of binaphthyltetracarboxylic acid and dianhydride, which is applied in 4 fields, can solve problems such as mass production obstacles, and achieve the effects of simple route, high efficiency, and reduced reaction cost

Inactive Publication Date: 2009-04-01
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] This reaction needs to go through four steps to synthesize the target product, and the reaction method of Grignard reagent is use

Method used

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  • Method for preparing 4,4,5,5-dinaphthalene tetracarboxylic acid dianhydride
  • Method for preparing 4,4,5,5-dinaphthalene tetracarboxylic acid dianhydride
  • Method for preparing 4,4,5,5-dinaphthalene tetracarboxylic acid dianhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Atmospheric pressure (1.01*10 5 Pa), add 13.6g (0.05mol) 4-bromo-1,8-naphthalene anhydride, potassium hydroxide of 4 times the molar amount in the 500ml three-necked flask equipped with stirrer, condenser, thermometer, nitrogen feed inlet 11g (0.2mol), 3.4g (0.05mol) of reducing agent sodium formate of 1 times the molar amount, 200ml distilled water, heat to make the solid dissolve completely, then add 0.25g (Pd content 1.12×10 -4 mol) Pd / C (Pd content 5wt%, water content 5wt%), stirred and refluxed at 95° C. for 10 hours to complete the reaction. Suction filtration while hot after reaction finishes, remove catalyst and gac, add about 10ml of concentrated hydrochloric acid (12mol / l) to make precipitation completely in filtrate again, this moment, solution is acidic, and pH value is 2. Then filter to obtain a yellow solid, which was washed 5 times with distilled water to remove salt and acid in the solid, and then dried in a vacuum oven at 200°C for 10 hours to obtain a...

Embodiment 2

[0041] With the step of embodiment 1, the amount of Pd / C (Pd content 5wt%, moisture content 5wt%) is increased to 0.50g (Pd content 2.24*10 -4 mol), the yellow solid powder 6.2g was obtained after recrystallization, and the yield was 63%.

Embodiment 3

[0043] With the step of embodiment 1, the amount of Pd / C (Pd content 5wt%, moisture content 5wt%) is increased to 0.75g (Pd content 3.36*10 -4 mol), obtain yellow solid powder 5.9g after recrystallization, productive rate 59.8%, lower than the productive rate of implementing 1.

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Abstract

The invention relates to a preparation method widely used for preparing a 4, 4', 5, 5'-binaphthyl-tetracarboxylic dianhydride monomer of polyimide materials. The method is as follows: 4-halo-1, 8-anhydride naphthalene and potassium hydroxide which is 4 to 10 times of the molar volume of the 4-halo-1, 8-anhydride naphthalene are added with distilled water and heated for dissolving; then a Pd/C catalyst and a reducer are added, the temperature of a reaction system is controlled in a range between 80 and 120 DEG C and the reflux reaction is carried out for 3 to 40 hours; the Pd/C and impurities are filtered out and then hydrochloric acid or nitric acid is added into the filtrate for acidification so as to lead the pH value of the reaction system to be 1 to 3 and obtain yellow emulsion precipitation; the precipitation is washed by distilled water for 3 to 5 times and then is dried in a vacuum oven for 10 to 20 hours at the temperature of 180 to 200 DEG C so as to obtain yellow powder solids; then DMF is adopted for recrystallization so as to obtain the 4, 4', 5, 5'-binaphthyl-tetracarboxylic dianhydride monomer. The method of the invention is characterized by simple and convenient operation, being practical and having good effect.

Description

technical field [0001] The invention belongs to the technical field of polyimide preparation, in particular to a method for preparing 4,4',5,5'-binaphthyltetracarboxylic dianhydride monomers widely used in the preparation of polyimide materials. Background technique [0002] With the development of aerospace technology, all walks of life have an urgent demand for heat-resistant, high-strength, and lightweight structural materials. At this time, a class of polymers with aromatic heterocycles as the main structural unit came into being. Among them, polyimide has attracted people's attention because of its cost-effective advantages. For fully aromatic polyimide, its decomposition temperature is generally around 500°C, and it will not be brittle in liquid nitrogen at -269°C. It has good high and low temperature resistance, good mechanical properties, etc. Wait. In addition, according to incomplete statistics, there are 200-300 kinds of dianhydrides and diamines used to synthes...

Claims

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Application Information

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IPC IPC(8): C07D311/78
Inventor 党国栋李鹏陈春海周宏伟
Owner JILIN UNIV
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