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Synthesis method for 2,3,6,7-triptycene tetracarboxylic dianhydride

A technology of pterylene tetracarboxylic dianhydride and pterylene tetracarboxylic acid, which is applied in the field of functional polymer materials to achieve the effects of prolonging feeding time, high product purity and avoiding side reactions

Inactive Publication Date: 2012-08-01
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, there are few reports on the polyimide with the three benzene ring planes in triptycene as the main chain direction due to the difficulty in the synthesis of monomers.

Method used

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  • Synthesis method for 2,3,6,7-triptycene tetracarboxylic dianhydride
  • Synthesis method for 2,3,6,7-triptycene tetracarboxylic dianhydride
  • Synthesis method for 2,3,6,7-triptycene tetracarboxylic dianhydride

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Embodiment 1

[0033] A kind of synthetic method of 2,3,6,7-triptycenetetracarboxylic dianhydride of the present embodiment comprises the following steps: under conditions of ice-salt bath and vigorous stirring, 35g (grams) of aluminum trichloride is divided into three additions Place 80ml (milliliters) of o-xylene in a 250ml three-necked flask equipped with a mechanical stirrer, slowly add 8g (grams) of benzyl alcohol dropwise through a constant pressure funnel, and keep the system temperature at -5°C during the addition. After the addition is complete, stir at room temperature for 0.5h (hour), and then react in an oil bath at 115°C for 4h. Thereafter, the mixed reactant was settled in 500ml of 5% hydrochloric acid ice water, and after standing still, it was filtered with suction, and the filter cake was washed with 50ml of water, 100ml of ethyl acetate, 50ml of saturated sodium bicarbonate, and 50ml of water, and vacuum-dried to obtain 8.5g of white 2,3,6,7-Tetramethylanthracene is a solid...

Embodiment 2

[0046] A kind of synthetic method of 2,3,6,7-triptycene tetracarboxylic dianhydride of the present embodiment comprises the following steps: under ice-salt bath and vigorous stirring condition, put 120ml (milliliters) o-xylene and 70ml (milliliter) in the 250ml three-necked flask of dichloromethane, add 60g (gram) aluminum trichloride in four times, guarantee system temperature 0 ℃ during the addition process. After the addition is complete, react at room temperature for 0.5 h (hour), and then react in a water bath at 65° C. for 4 h. Afterwards, the mixed reactant was slowly dispersed in 300ml of 5% hydrochloric acid ice-water mixed solution. During the pouring process, vigorous stirring was required. After standing still, suction filtration, the filter cake was washed with anhydrous acetone, dried, and o-xylene was recrystallized to obtain white 20 g of flaky 2,3,6,7-tetramethylanthracene solid, melting point is 299°C. figure 1 It is the 1H-NMR chart of 2,3,6,7-tetramethylan...

Embodiment 3

[0060] A kind of synthetic method of 2,3,6,7-triptycene tetracarboxylic dianhydride of the present embodiment comprises the following steps: under conditions of ice-salt bath and vigorous stirring, 40g (grams) of aluminum trichloride is divided into three additions Place 80ml (milliliters) of o-xylene in a 250ml three-necked flask equipped with a mechanical stirrer, slowly add 10g (grams) of benzyl alcohol dropwise through a constant pressure funnel, and keep the system temperature at about -5°C during the addition. After the addition is complete, stir at room temperature for 15 minutes (minutes), and then react in an oil bath at 115° C. for 3.5 hours (hours). Thereafter, the mixed reactant was settled in 65ml of 5% hydrochloric acid ice water, and after standing still, it was suction filtered, and the filter cake was washed with 65ml of water, 125ml of ethyl acetate, 65ml of saturated sodium bicarbonate, and 65ml of water, and vacuum-dried to obtain 9.8g of white 2,3,6,7-Tetr...

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Abstract

The invention discloses a synthesis method for 2,3,6,7-triptycene tetracarboxylic dianhydride. The method comprises the following steps of: 1) preparing 2,3,6,7-tetramethylanthracene from o-xylene and benzyl alcohol or methylene chloride under the catalysis of anhydrous aluminum trichloride; 2) diazotizing the 2,3,6,7-tetramethylanthracene, anthranilic acid and amyl nitrite to generate a crude product 2,3,6,7-tetramethyl triptycene; 3) performing chromatographic separation on the crude product 2,3,6,7-tetramethyl triptycene, and flushing the separated 2,3,6,7-tetramethyl triptycene by using a mixed eluting agent to obtain 2,3,6,7-tetramethyl triptycene; 4) oxidizing the 2,3,6,7-tetramethyl triptycene in a mixed solvent consisting of potassium permanganate, pyridine and water under a reflux condition to generate 2,3,6,7-triptycene tetracarboxylic acid; and 5) refluxing and dehydrating the 2,3,6,7-triptycene tetracarboxylic acid in acetic anhydride to generate the 2,3,6,7-triptycene tetracarboxylic dianhydride. The method has the characteristics of readily available and low-cost raw materials, high yield and high product purity.

Description

technical field [0001] The invention relates to a synthesis method of 2,3,6,7-triptycene tetracarboxylic dianhydride, which belongs to the field of functional polymer materials. Background technique [0002] Aromatic polyimide, as a class of important structural and functional materials, has a wide range of applications in microelectronics technology, aerospace and other aspects. Due to the very stable aromatic heterocyclic structure in polyimide molecules, it reflects other Polymer materials have incomparable excellent performance, but the contradiction between high performance and processability greatly limits its application. Nowadays, the more common method for synthesizing linear polyarimides is the polycondensation reaction between dianhydride and diamine monomers. It is of great significance to expand the application of polyimide to develop new dianhydride monomers from monomer molecular design. [0003] In recent years, triptycene-based conjugated polymers, aromati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08
Inventor 程琳刘嘉川徐华胜
Owner HUAQIAO UNIVERSITY
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