High-efficiency preparation method for 2.3.6.7-tetramethyl anthracene and application thereof in preparation of triptycene and derivatives thereof

A tetramethylanthracene, high-efficiency technology, applied in the application field of preparing triptycene and its derivatives, can solve the problems of endangering human health, harsh preparation conditions, and affecting the rapid development of triptycene synthesis chemistry, and achieves high feasibility , The preparation technology is simple, and the effect of promoting rapid development

Active Publication Date: 2019-04-16
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Triptycene is synthesized in one step through the addition reaction of benzyne and anthracene, while the preparation of 2,3,6,7-tetramethylanthracene is generally carried out by o-xylene and benzyl alcohol or dichloromethane in anhydrous trioxidation Under the catalysis of aluminum, it is formed after heating up, but the preparation conditions of this preparation method are relatively harsh, the yield is low, and there are chlorine-containing volatile organic compounds in the reaction raw materials, which seriously endanger human health and destroy the ecological environment. The industrial production of 2,3,6,7-tetramethylanthracene has influenced the rapid development of the synthetic chemistry of tripterene

Method used

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  • High-efficiency preparation method for 2.3.6.7-tetramethyl anthracene and application thereof in preparation of triptycene and derivatives thereof
  • High-efficiency preparation method for 2.3.6.7-tetramethyl anthracene and application thereof in preparation of triptycene and derivatives thereof
  • High-efficiency preparation method for 2.3.6.7-tetramethyl anthracene and application thereof in preparation of triptycene and derivatives thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] At room temperature, divide 8.2g (grams) of ferric trichloride into a 100ml three-necked flask equipped with 6ml (milliliters) of o-xylene and a mechanical stirrer, and slowly add 13ml (milliliters) of dimethoxymethane.

[0024] After the addition is complete, stir at room temperature for 1 hour (hour), and then react in a water bath at 70° C. for 4 hours. After the water bath is completed, drop the ice bath to below 5°C, pour about 40mL of 3mol / L sulfuric acid ice-water mixed solution, stir at room temperature for 30 minutes, pour out the upper layer containing salt, add 50mL of xylene, heat, stir and reflux for 0.5h, and cool to Suction filtration at room temperature, the filter cake was washed 3 times with xylene to obtain a black-green solid, which was dried under an infrared lamp in a fume hood, and extracted with xylene for 48 hours to obtain white needles 2,3,6, 4.7 g of 7-tetramethylanthracene crystals, yield 80.3%, melting point 299°C, purity 99.8%.

[0025] ...

Embodiment 2

[0029] At room temperature, divide 16.4g (grams) of ferric chloride into three additions into a 250ml three-necked flask equipped with 12ml (milliliters) of o-xylene and a mechanical stirrer, and slowly add 26ml (milliliters) of dimethoxymethane.

[0030] After the addition is complete, stir at room temperature for 1 hour (hour), and then react in a water bath at 70° C. for 4 hours. After the water bath is completed, drop the ice bath to below 5°C, pour about 80mL of 3mol / L sulfuric acid ice-water mixed solution, stir at room temperature for 30 minutes, pour out the upper layer containing salt, add 100mL of xylene, heat, stir and reflux for 0.5h, and cool to Suction filtration at room temperature, the filter cake was washed 3 times with xylene to obtain a black-green solid, which was dried under an infrared lamp in a fume hood, and extracted with xylene for 48 hours to obtain white needles 2,3,6, 9.5 g of 7-tetramethylanthracene crystals, yield 81.2%, melting point 299°C, pur...

Embodiment 3

[0032] At room temperature, divide 8.2g (grams) of ferric trichloride into a 100ml three-necked flask equipped with 6ml (milliliters) of o-xylene and a mechanical stirrer, and slowly add 13ml (milliliters) of dimethoxymethane.

[0033] After the addition is complete, stir at room temperature for 1 hour (hour), and then react in a water bath at 80° C. for 4 hours. After the water bath is completed, lower the ice bath to below 5°C, pour about 40mL of 3mol / L sulfuric acid ice-water mixed solution, stir at room temperature for 30 minutes, pour out the upper layer containing salt, add 50mL of xylene, heat, stir and reflux for 1h, and cool to room temperature , filtered with suction, and the filter cake was washed 3 times with xylene to obtain a black-green solid, which was dried under an infrared lamp in a fume hood and extracted with xylene for 48 hours to obtain white needles 2,3,6,7 - 4.9 g of tetramethylanthracene crystals, the yield is 83.8%, the melting point is 299° C., and...

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Abstract

The invention relates to the field of functional polymer materials, in particular to a high-efficiency preparation method for 2.3.6.7-tetramethyl anthracene and application thereof in preparation of triptycene and derivatives thereof. The high-efficiency preparation method for 2.3.6.7-tetramethyl anthracene is composed of the following steps: dissolving dimethoxymethane into o-xylene, adding ferric chloride reagent, continuously reacting and heating and stirring; cooling to room temperature, adding dilute sulfuric acid and dimethylbenzene for reflux under ice bath, and performing air pump filtration; drying with infrared lamp after air pump filtration, and purifying to obtain 2.3.6.7-tetramethyl anthracene. Compared with the prior art, the high-efficiency preparation method for 2.3.6.7-tetramethyl anthracene has the advantages of simple preparation process, high yield and high purity; by using dimethoxymethane as raw material, the method replaces chlorinated volatile organic compound which harms human health and destroy ecological environment; and by adopting ferric chloride as catalyst, the reaction can be more stably promoted and controlled, the industrial production of productsis facilitated, and the method has important industrial practical application value.

Description

technical field [0001] The invention relates to the field of functional polymer materials, in particular to a high-efficiency preparation method of 2,3,6,7-tetramethylanthracene and its application in the preparation of triptycene and its derivatives. Background technique [0002] Anthracene is an organic molecule with high fluorescence and planar large π bond structure. Anthracene and its derivatives basically use the more active 9,10-position hydrogen to undergo reactions such as bromomethylation, hydroformylation, and bromination, and then react with other compounds to form functional materials. However, the limited active reaction sites of anthracene restrict the types of anthracenyl derivatives and the expansion of material properties of anthracenyl derivatives. By increasing the reactive sites of anthracene, especially the 2,3,6,7-positions, the planar large π-bond structure, high rigidity and high fluorescence of anthracene will be further utilized, and it will becom...

Claims

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Application Information

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IPC IPC(8): C07C15/28C07C1/20C07C7/00C07C2/72C07C15/20
CPCC07C1/20C07C2/72C07C7/00C07C15/28C07C15/20
Inventor 程琳徐鹏飞李佩瑾
Owner HUAQIAO UNIVERSITY
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