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Preparation method of 9,9-bis(trifluoromethyl)-2,3,6,7-xanthene tetracarboxylic dianhydride

A technology of xanthene tetracarboxylic acid and tetramethylxanthene, which is applied in the field of xanthene derivatives, can solve the problems that the catalyst trifluoromethanesulfonic acid is not easy to obtain, is not suitable for large-scale industrial production, and is harmful to human body and environment. Achieve good product purity, environmental friendliness, and reduce solvent waste

Active Publication Date: 2022-01-11
CHANGZHOU SUNLIGHT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The main shortcomings of the above literatures include: (1) the yields are low, less than 30% in the first two steps; (2) the hydrofluoric acid used in literature 1 is a highly toxic substance, which is harmful to the human body and the environment; (3) The catalyst trifluoromethanesulfonic acid used in Document 2 is not easy to obtain and is not suitable for large-scale industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0030] The preparation method of the 9,9-bis(trifluoromethyl)-2,3,6,7-oxanthene tetracarboxylic dianhydride of this embodiment is as follows:

[0031] ①Add 200mL of 1,3-dichlorobenzene, 45.2g (0.2mol) of 3,3',4,4'-tetramethyldiphenyl ether and 26.7g (0.2mol) of anhydrous trichloride to the reaction bottle Aluminum, then lower the temperature to -30~-35°C, add 33.2g (0.2mol) of hexafluoroacetone dropwise, and raise the temperature to 35±2°C for 12 hours after the drop.

[0032] After the reaction, the temperature was lowered to 0-5°C, and 350mL of ice water was added dropwise, then 36mL of 30wt% hydrochloric acid was added dropwise, stirred, and the layers were separated. The organic layer was washed twice with water and dried with anhydrous sodium sulfate.

[0033] ②Put the dried organic layer in step ① into a high-pressure reactor lined with tetrafluoroethylene, add 400g of water, 1.5g of dimethylaminopyridine, and 90mL of 65wt% nitric acid (1.3mol), close the reactor, and he...

Embodiment 2）

[0037] The preparation method of the 9,9-bis(trifluoromethyl)-2,3,6,7-oxanthene tetracarboxylic dianhydride of this embodiment is as follows:

[0038] ①Add 200mL of 1,2-dichloroethane, 45.2g (0.2mol) of 3,3',4,4'-tetramethyldiphenyl ether and 29.3g (0.22mol) of anhydrous trichloride into the reaction flask Aluminum, then lower the temperature to -30~-35°C, add 36.5g (0.22mol) hexafluoroacetone dropwise, and raise the temperature to 35±2°C for 15 hours after the dropwise reaction.

[0039] After the reaction was completed, the temperature was lowered to 0-5°C, 320 mL of ice water was added dropwise, and then 36 mL of 30 wt % hydrochloric acid was added dropwise, stirred, separated into layers, the organic layer was washed twice with water and dried with anhydrous sodium sulfate.

[0040] ②Put the dried organic layer in step ① into a high-pressure reactor lined with tetrafluoroethylene, add 400g of water, 1.5g of dimethylaminopyridine, and 90mL of 65wt% nitric acid (1.3mol), clo...

Embodiment 3）

[0044] The preparation method of the 9,9-bis(trifluoromethyl)-2,3,6,7-oxanthene tetracarboxylic dianhydride of this embodiment is as follows:

[0045] ①Add 200mL of carbon disulfide, 45.2g (0.2mol) of 3,3',4,4'-tetramethyldiphenyl ether and 40g (0.3mol) of anhydrous aluminum trichloride to the reaction bottle, then cool down to -30~ -35°C, add 34.9g (0.21mol) hexafluoroacetone dropwise, and raise the temperature to 35±2°C to react for 14h after dropping.

[0046]After the reaction, lower the temperature to 0-5°C, add 300mL of ice water dropwise, then add 36mL of 30wt% hydrochloric acid dropwise, stir, separate layers, wash the organic layer twice with water and dry with anhydrous sodium sulfate.

[0047] ②Put the dried organic layer in step ① into a high-pressure reactor lined with tetrafluoroethylene, add 400g of water, 1.5g of dimethylaminopyridine, and 100mL of 68wt% nitric acid (1.5mol), close the reactor, and first raise the temperature to 115±2°C, react for 2h, then rai...

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Abstract

The invention discloses a preparation method of 9,9-bis (trifluoromethyl)-2,3,6,7-xanthene tetracarboxylic dianhydride, which comprises the following steps: by taking 3,3',4,4'-tetramethyl diphenyl ether as an initial raw material, condensing with hexafluoroacetone under the catalysis of a Lewis acid to obtain 9,9-bis(trifluoromethyl)-2,3,6,7-tetramethyl xanthene, oxidizing with nitric acid to obtain 9,9-bis(trifluoromethyl)-2,3,6,7-xanthene tetracarboxylic acid, and finally, dehydrating into anhydride to obtain the 9,9-bis(trifluoromethyl)-2,3,6,7-xanthene tetracarboxylic dianhydride. According to the method, the Lewis acid is adopted as a condensation reaction catalyst, nitric acid is adopted as an oxidizing agent, and high reaction yield can be obviously obtained. The Lewis acid adopted in the condensation reaction is low in price, easy to obtain and more environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of xanthene derivatives, and specifically relates to a preparation method of 9,9-bis(trifluoromethyl)-2,3,6,7-oxanthene tetracarboxylic dianhydride. Background technique [0002] In recent years, with the rapid development of electronic information industries such as display devices, as a substitute for glass substrates, the industrial application of polyimide paste materials for flexible OLED display substrates has gradually become a research and development hotspot in the industry. Aromatic fluorine-containing polyimide has outstanding heat resistance, electronic insulation, flame resistance, good mechanical properties and optical properties, and can well meet the optical, electrical and mechanical properties of flexible OLED display substrates. The harsh and comprehensive requirements put forward by other aspects have good application prospects. [0003] 9,9-bis(trifluoromethyl)-2,3,6,7-oxanthene tetraca...

Claims

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Application Information

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IPC IPC(8): C07D493/14
CPCC07D493/14
Inventor 胡国宜胡锦平吴建华张培锋
Owner CHANGZHOU SUNLIGHT PHARMA
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