Synthetic method of 4,4'-(hexafluoroisopropylidene)diphthalic anhydride

A technology of diphthalic anhydride and hexafluoroisopropylidene, which is applied in the field of synthesis of 4,4'-diphthalic anhydride, can solve the problems of cumbersome operation, high amount of oxidant, and poor dehydration effect. Achieve the effects of lowering the reaction temperature, simplifying the operation steps and improving the efficiency

Active Publication Date: 2017-01-25
SHANDONG HUAXIA SHENZHOU NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to make up for the shortcomings of the existing methods such as complicated operation, high oxidant consumption, po

Method used

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  • Synthetic method of 4,4'-(hexafluoroisopropylidene)diphthalic anhydride

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0026] Specific example 1:

[0027] In a 2000mL three-necked flask, add 14.40g 4,4'-(hexafluoroisopropylidene) di-o-xylene and pyridine (200mL) / water (100mL) mixed solvent, heat to 100℃, and then add permanganese 38.0 g of potassium acid was reacted for 3 hours. After the reaction, a small amount of ethanol was added dropwise to remove unreacted potassium permanganate. After the mixture was filtered, the filtrate was evaporated to remove pyridine, then the pH was adjusted to 1, the water was evaporated to dryness, 320mL of acetone was added to heat to dissolve the organic matter, the insoluble matter was filtered off, and the filtrate was evaporated to dryness to obtain the crude product hexafluorotetraacid with a yield of 80.0%.

[0028] A mixed solvent of 4.80g hexafluorotetraacid, 8mL acetic anhydride and 8mL xylene was added to a 150mL flask, and reacted for 40 minutes at 140°C. After the reaction is completed, it is naturally cooled, filtered to obtain a crude product of hexa...

Example Embodiment

[0029] Specific example 2:

[0030] In a 2000mL three-necked flask, add 14.40g 4,4'-(hexafluoroisopropylidene) di-o-xylene and pyridine (200mL) / water (100mL) mixed solvent, heat to 100℃, and then add permanganese 50.0 g of potassium acid, reacted for 4 hours, after the reaction, a small amount of ethanol was added dropwise to remove unreacted potassium permanganate. After the mixture was filtered, the filtrate was evaporated to remove the pyridine, then the pH was adjusted to 1, the water was evaporated to dryness, 320 mL of acetone was added to heat to dissolve the organic matter, the insoluble matter was filtered off, and the filtrate was evaporated to dryness to obtain the crude product hexafluorotetraacid with a yield of 62.0%.

[0031] A mixed solvent of 4.80 g hexafluorotetraacid, 12 mL acetic anhydride, and 12 mL xylene was added to a 150 mL flask, and reacted for 40 minutes at 110°C. After the reaction, the crude product hexafluorodianhydride (6FDA) was obtained by natural...

Example Embodiment

[0032] Specific example 3:

[0033] In a 2000mL three-necked flask, add 14.40g 4,4'-(hexafluoroisopropylidene) di-o-xylene and pyridine (200mL) / water (100mL) mixed solvent, heat to 130℃, then add permanganese 50.0 g of potassium acid, reacted for 2 hours. After the reaction, a small amount of ethanol was added dropwise to remove unreacted potassium permanganate. After the mixture was filtered, the filtrate was evaporated to remove pyridine, then the pH was adjusted to 1, the water was evaporated to dryness, 320mL of acetone was added to heat to dissolve the organic matter, the insoluble matter was filtered off, the filtrate was evaporated to dryness to obtain the crude product hexafluorotetraacid with a yield of 40.0%.

[0034] A mixed solvent of 4.80 g hexafluorotetraacid, 12 mL acetic anhydride, and 12 mL xylene was added to a 150 mL flask, and reacted at 130° C. for 1 hour. After the reaction, the crude product hexafluorodianhydride (6FDA) is obtained by natural cooling, filtra...

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Abstract

The invention belongs to the technical field of organic synthesis and particularly relates to a synthetic method of 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, comprising the steps of (1) thermally oxidizing 4,4'-(hexafluoroisopropylidene)di-o-xylene under the action of potassium permanganate to obtain hexafluorotetracid; (2) adding the hexafluorotetracid into a mixed solvent of xylene and acetic anhydride, heating and stirring, and post-processing after reaction is over. Less potassium permanganate is added in the oxidizing reaction with less frequency, reaction time is shortened, and operation steps are simplified; the use of inorganic bases is avoided, oxidizing property of potassium permanganate can be improved, and the cost is reduced; dehydration process is modified, reaction temperature is lowered, reaction time is shortened, and hexafluorotetracid can be more efficiently converted into hexafluorodianhydride, with the purity up to 99.5%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 4,4'-(hexafluoroisopropylidene) diphthalic anhydride. Background technique [0002] Fluorine-containing polyimide has excellent comprehensive properties and is widely used in aerospace, aviation, microelectronics, electronic appliances, gas separation and other fields. The structural properties of fluorine-containing monomers ultimately affect the performance of fluorine-containing polyimides. The types of fluorine-containing monomers are limited, the preparation conditions are harsh, the process is complicated, and the cost is high, which limits the promotion and application of fluorine-containing polyimide materials. 4,4'-(hexafluoroisopropylidene) diphthalic anhydride (6FDA) is the most widely used dianhydride monomer for the synthesis of fluorine-containing polyimides, and it is also the monomer with the highest degree of industria...

Claims

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Application Information

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IPC IPC(8): C07D307/89
CPCC07D307/89
Inventor 王汉利王磊孟祥青
Owner SHANDONG HUAXIA SHENZHOU NEW MATERIAL
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