Synthesis method of tetracarboxylic dianhydride with fluorinated rigid structure

A technology of tetracarboxylic dianhydride and rigid structure, which is applied in organic chemistry and other fields, and can solve problems such as bone and tooth deformity and toxicity

Inactive Publication Date: 2020-06-19
浙江中科玖源新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Both hydrogen fluoride and its aqueous solution are toxic and can easily deform bones and teeth. Hydrofluoric acid can penetrate the skin and be absorbed by mucous membranes, respiratory tract, and gastrointestinal tract, causing irreversible burns

Method used

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  • Synthesis method of tetracarboxylic dianhydride with fluorinated rigid structure
  • Synthesis method of tetracarboxylic dianhydride with fluorinated rigid structure
  • Synthesis method of tetracarboxylic dianhydride with fluorinated rigid structure

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Experimental program
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Effect test

Embodiment 1

[0041] A kind of tetracarboxylic dianhydride with fluorinated rigid structure, its structural formula is as follows:

[0042]

[0043] The tetracarboxylic dianhydride synthetic method shown in this structural formula comprises:

[0044] S1. Under nitrogen atmosphere and ice bath conditions, add 30g 1,1,1-trifluoroacetone (0.268mol) into 350mL dichloromethane and stir until completely dissolved, then add 66g 3,4-dimethylphenol ( 0.536mol) and 40g trifluoromethanesulfonic acid (0.268mol) were stirred until completely dissolved, stirred and reacted at room temperature for 24 hours, after the reaction was finished, the reaction solution was slowly poured into deionized water, the organic phase was extracted and rotary evaporated to obtain a solid, vacuum Dry overnight to obtain 38g 9-methyl-9-(trifluoromethyl)-2,3,6,7-tetramethyloxanthene (yield: 44%), and its hydrogen spectrogram refers to figure 1 shown;

[0045] S2, 20g 9-methyl-9-(trifluoromethyl)-2,3,6,7-tetramethylxanth...

Embodiment 2

[0048] A kind of tetracarboxylic dianhydride with fluorinated rigid structure, its structural formula is as follows:

[0049]

[0050] The tetracarboxylic dianhydride synthetic method shown in this structural formula comprises:

[0051]S1. Under nitrogen atmosphere and ice bath conditions, add 30g of hexafluoroacetone (0.181mol) into 350mL of dichloromethane and stir until completely dissolved, then add 44g of 3,4-dimethylphenol (0.362mol) and 28g of tris Fluoromethanesulfonic acid (0.181mol) was stirred until it was completely dissolved, and the reaction was stirred at room temperature for 24 hours. After the reaction, the reaction solution was slowly poured into deionized water, and the organic phase was extracted and rotary evaporated to obtain a solid, which was dried overnight in vacuum to obtain 24 g of 9 - bis(trifluoromethyl)-2,3,6,7-tetramethylxanthene (yield: 36%);

[0052] S2. Add 20g of 9-bis(trifluoromethyl)-2,3,6,7-tetramethylxanthene (0.053mol) to a mixture ...

Embodiment 3

[0055] A kind of tetracarboxylic dianhydride with fluorinated rigid structure, its structural formula is as follows:

[0056]

[0057] The tetracarboxylic dianhydride synthetic method shown in this structural formula comprises:

[0058] S1. Under nitrogen atmosphere and ice bath conditions, add 30g 2,2,2-trifluoroacetophenone (0.172mol) into 350mL dichloromethane and stir until completely dissolved, then add 42g 3,4-dimethyl Phenol (0.344mol) and 20g trifluoroacetic acid (0.172mol) were stirred until completely dissolved, stirred and reacted at room temperature for 24 hours, after the reaction was completed, the reaction solution was slowly poured into deionized water, the organic phase was extracted and rotary evaporated to obtain a solid, vacuum Dry overnight to obtain 43 g of 9-phenyl-9-(trifluoromethyl)-2,3,6,7-tetramethylxanthene (yield: 64%);

[0059] S2, 20g 9-phenyl-9-(trifluoromethyl)-2,3,6,7-tetramethylxanthene (0.053mol) was added to a mixture of pyridine:water ...

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Abstract

The invention provides a synthesis method of tetracarboxylic dianhydride with a fluorinated rigid structure. According to the method, trifluoromethanesulfonic acid, trifluoroacetic acid and/or sulfuric acid is adopted to replace hydrofluoric acid to serve as a catalyst to achieve conversion from 3,4-dimethylphenol or 3,3',4,4'-tetramethyldiphenyl ether to xanthene tetracarboxylic dianhydride, so that the whole synthesis method has the advantages of being efficient, safe and controllable.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of tetracarboxylic dianhydride with a fluorinated rigid structure. Background technique [0002] Tetracarboxylic dianhydrides with fluorinated rigid structures can be directly used as monomers in the preparation of high-performance polymers, especially in the synthesis of polyimides, which have a wide range of applications. [0003] In the synthesis process of this type of tetracarboxylic dianhydride, the U.S. Patent Publication "5051520 (published on September 24, 1991)" involves the use of 3,4-dimethylphenol or 3,3',4,4'- Tetramethyldiphenyl ether and fluorine-containing ketones undergo an addition condensation reaction under the condition of an acid catalyst, but the acid catalyst used is hydrofluoric acid. Hydrofluoric acid (HF) is an aqueous solution of hydrogen fluoride gas, a colorless, fuming corrosive liquid with a strong pungent odor. It i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/14
CPCC07D493/14
Inventor 李南文许辉
Owner 浙江中科玖源新材料有限公司
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