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2, 3, 6, 7-tetramethyl-9,10-o-naphthylanthracene and synthetic method thereof

A technology of o-naphthyl anthracene and synthesis method, applied in 2 fields, can solve the problems of few dianhydride monomers, complicated synthesis, etc., and achieve the effects of good solubility and stability, simple preparation, high synthesis yield and purity

Active Publication Date: 2013-08-28
HUAQIAO UNIVERSITY
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  • Abstract
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  • Application Information

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Problems solved by technology

The research on the synthesis of diamine monomers is common and relatively mature. On the contrary, there are few types of dianhydride monomers that can be used to synthesize aromatic polyimides, and the synthesis is complicated.
[0004] However, polyimides based on triptycene tetracarboxylic dianhydride and its derivatives have rarely been reported.

Method used

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  • 2, 3, 6, 7-tetramethyl-9,10-o-naphthylanthracene and synthetic method thereof
  • 2, 3, 6, 7-tetramethyl-9,10-o-naphthylanthracene and synthetic method thereof
  • 2, 3, 6, 7-tetramethyl-9,10-o-naphthylanthracene and synthetic method thereof

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preparation example Construction

[0036] The present invention also relates to a synthesis method of 2,3,6,7-tetramethyl-9,10-o-naphthyl anthracene, comprising the following steps:

[0037] Step 10, o-xylene and dichloromethane react under the catalysis of aluminum trichloride, and generate 2,3,6,7-tetramethylanthracene by heating up through Friedel-Crafts reaction;

[0038] Step 20, 2,3,6,7-tetramethylanthracene and 1,4-epoxy-1,4-dihydronaphthalene are heated to reflux in an organic solvent to undergo a Diels-Alder reaction to generate 2,3,6,7- Tetramethyl-9,10-o-(1,4-epoxynaphthyl)anthracene crude product;

[0039] Step 30. The crude 2,3,6,7-tetramethyl-9,10-o-(1,4-epoxynaphthyl)anthracene is separated by column chromatography and washed with a mixed eluent to obtain 2,3,6, 7-Tetramethyl-9,10-o-(1,4-epoxynaphthyl)anthracene;

[0040] Step 40. 2,3,6,7-tetramethyl-9,10-o-(1,4-epoxynaphthyl)anthracene is dehydrated under acetic acid / acetic anhydride under reflux to obtain 2,3,6,7 -Tetramethyl-9,10-o-naphthyl...

Embodiment 1

[0051] The synthesis method of 2,3,6,7-tetramethyl-9,10-o-naphthylanthracene in this embodiment is as follows: Measure 120ml o-xylene and 65ml dichloromethane and mix together, and cool in an ice bath To 0-5°C, add solid aluminum trichloride in batches under vigorous stirring. After the addition, react at 0-5°C for 1 hour, then rise to room temperature for 1 hour, and then react at 60°C for 5 hours. After the reaction, the above reaction solution was poured into glacial hydrochloric acid aqueous solution, stirred, static, filtered and recrystallized with toluene to obtain 22g of white to yellow needle-like crystals of 2,3,6,7-tetramethylanthracene, melting point 299°C.

[0052] 6.50g (27.8mmol) of 2,3,6,7-tetramethylanthracene and 2.00g (13.9mmol) of 1,4-epoxy-1,4-dihydronaphthalene were added to a 250ml three-necked flask, and Add 100ml of xylene, then heat to reflux, monitor the end of the reaction with TLC, and reflux for 120h. After the reaction, the reaction bottle was c...

Embodiment 2

[0069] The synthesis method of 2,3,6,7-tetramethyl-9,10-o-naphthylanthracene of the present embodiment is as follows: Measure 120ml o-xylene and 75ml dichloromethane and mix together, and cool in an ice bath To 0-5°C, add solid aluminum trichloride in batches under vigorous stirring. After the addition, react at 0-5°C for 1 hour, then rise to room temperature for 1 hour, and then react at 70°C for 3 hours. After the reaction, the above reaction solution was poured into glacial hydrochloric acid aqueous solution, stirred, static, filtered and recrystallized with toluene to obtain 21 g of white to yellow needle-like crystals of 2,3,6,7-tetramethylanthracene, melting point 299°C.

[0070] 6.50g (27.8mmol) of 2,3,6,7-tetramethylanthracene and 2.00g (13.9mmol) of 1,4-epoxy-1,4-dihydronaphthalene were added to a 250ml three-necked flask, and Add 100ml of toluene, then heat to reflux, monitor the end of the reaction with TLC, and reflux for 120h. After the reaction, the reaction bot...

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Abstract

The invention provides 2, 3, 6, 7-tetramethyl-9,10-o-naphthylanthracene and a synthetic method thereof. The synthetic method comprises: synthesizing 2,3,6,7-tetramethylanthracene from o-xylene and dichloromethane, performing a cycloaddition reaction on the 2,3,6,7-tetramethylanthracene and an epoxy compound, purifying by a column chromatography, carrying out acidic dehydration, removing reverse reaction products, and performing separation on columns to obtain the high-purity 2, 3, 6, 7-tetramethyl-9,10-o-naphthylanthracene. The triptycene derivatives disclosed by the invention is simple to prepare, low in raw material price, high in synthesis rate, and high in purity; and the synthetic method is simple in reaction conditions, mild and small in pollution.

Description

【Technical field】 [0001] The present invention relates to 2,3,6,7-tetramethyl-9,10-o-naphthyl anthracene and its synthesis method. 【Background technique】 [0002] As an excellent structural and functional material, aromatic polyimide has been widely used in aerospace, machinery, microelectronics, electrical, chemical and other fields. However, the contradiction between the excellent performance and the defect of processability limits its development and application. Currently, linear polyimides are synthesized by dehydration condensation between diamine and dianhydride monomers. The research on the synthesis of diamine monomers is common and relatively mature. On the contrary, there are few types of dianhydride monomers that can be used to synthesize aromatic polyimides, and the synthesis is complicated. Therefore, the synthesis of new dianhydride monomers through molecular design is of great significance for expanding the application of polyimides. [0003] In recent yea...

Claims

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Application Information

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IPC IPC(8): C07C15/20C07C5/48
Inventor 程琳崔洋洋
Owner HUAQIAO UNIVERSITY
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