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Preparation method of coronene

A compound and addition technology, applied in the preparation of organic compounds, chemical instruments and methods, hydrocarbon production from oxygen-containing organic compounds, etc., can solve the problems of harsh conditions, expensive raw materials, and complicated operations, and achieve mild reaction conditions and raw materials. Easy-to-obtain, simple-to-craft effects

Active Publication Date: 2016-07-27
FUYANG XINYIHUA MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The invention provides a preparation method of coronene, which solves the technical problems of expensive raw materials, harsh conditions, cumbersome operation and low yield in the prior art

Method used

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  • Preparation method of coronene
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preparation example Construction

[0032] According to the preparation method of coronene of the present invention, the method comprises:

[0033] Addition step: carry out an addition reaction with 1 equivalent of the compound represented by the formula I and 2.2 to 3.0 equivalents of the compound represented by the formula II in the presence of a base, and hydrolyze the reaction product into the compound represented by the formula III;

[0034] Ring-closing step: compound shown in formula III carries out ring-closing reaction in the presence of acid, and is converted into coronene shown in formula IV;

[0035] .

[0036] According to the preparation method of coronene of the present invention, the Chinese name of the compound shown in formula I is 9,10-dihydroanthracene; the Chinese name of the compound shown in formula II is 1,5-diethoxypentane-1,4- Dien-3-one; the Chinese name of the compound represented by formula IV is coronene.

[0037] The Chinese alias of corona benzene is cocoon, and the molecular ...

Embodiment approach

[0044] According to an embodiment of the present invention, in the addition step:

[0045] When the base is sodium hydride and the solvent is dimethyl sulfoxide, the reaction temperature is 50-80° C. and the reaction time is 5-7 hours.

[0046] According to the preparation method of coronene of the present invention, when the reaction temperature and the reaction time are selected in the above-mentioned numerical range, the amount of by-products produced by the reaction is reduced to the minimum, the purity of the product is increased, and the yield of the product is improved; the reaction temperature is 50~80 ℃ , the reaction conditions are mild, easy to control, and simple to operate.

[0047] The specific process of the addition step is as follows: add 1 equivalent of the compound represented by formula I, 2.2 to 3.0 equivalents of the compound represented by formula II and a solvent into the reactor and stir evenly, and slowly add 2.4 to 3.2 equivalents of alkali to the st...

Embodiment 1

[0061] According to the preparation method of coronene of the present invention, firstly, an addition step is performed, and 18g (0.1mol, 1eq) of the compound represented by formula I, 38g (0.22mol, 2.2eq) of the compound represented by formula II and 300ml of dimethyl sulfoxide are added. In the reactor and stirring evenly, 9.6g (0.24mol, 2.4eq) of 60% sodium hydride was slowly added to the stirring reactor, after the addition, the temperature was slowly raised to 50 °C for 5 h, cooled to 20 °C, and the reaction 10ml of methanol and 300ml of water were added to the solution for hydrolysis, 200ml of dichloromethane was added to the reaction solution for liquid separation, the aqueous phase obtained by the separation was extracted with dichloromethane, the organic phases obtained by extraction were combined, washed twice with water and saturated The solution is washed once with brine to obtain a dichloromethane solution containing the compound represented by formula III. Then c...

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Abstract

The invention discloses a preparation method of coronene. The preparation method comprises the following steps: addition: subjecting 1 equivalent of compound shown in a formula I and 2.2-3.0 equivalent of compound shown in a formula II to addition reaction in the presence of alkali and converting a reaction product to a compound shown in a formula III through hydrolysis; ring closing: subjecting the compound shown in the formula III to ring closing reaction in the presence of acid and converting a reaction product to coronene shown in a formula IV, wherein the formulas I, II, III and IV are shown in the specification. The preparation method has the beneficial effects that the preparation method is simple in process and is easy to operate; the required raw materials are available and are low in costs; the yield is as high as 80-91%; therefore the preparation method is suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of organic fluorescent material synthesis, in particular to a preparation method of coronene. Background technique [0002] Coronene is an organic fluorescent material. The maximum absorption wavelength of coronene is 255nm, the maximum emission wavelength is 520nm, and it has high quantum efficiency. Therefore, coronene can be used in ultraviolet-charge-coupled devices and radar. [0003] At present, the preparation method of coronene mainly includes the following three kinds: [0004] The first one is the preparation method disclosed in J.Org.Chem.1996,61,1136-1139 by JoostT.M.vanDijk, the chemical reaction equation of this method is as follows: [0005] [0006] In this method, it needs to be cooled to -60°C, which is not easy to operate, has many reaction steps and is cumbersome to operate, so it is not suitable for large-scale production; [0007] The second is the preparation method disclosed in J.Org.Chem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/20C07C15/20
CPCC07C1/20C07C41/30C07C15/20C07C43/1787
Inventor 王占奇王雪岚
Owner FUYANG XINYIHUA MATERIAL TECH
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