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Industrial synthesis method of picene

A technology of benzaldehyde and alkyl, applied in chemical instruments and methods, compounds containing elements of Group 3/13 of the periodic table, preparation of carbon-based compounds, etc., to achieve the effects of high safety, reduced pollution and less impurities

Pending Publication Date: 2022-05-13
西安欧得光电材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The invention uses 2-bromophenanthrene and o-bromobenzaldehyde as basic raw materials, and can realize the green industrialized mass production of perylene by using commonly used classic reactions, and can obtain high-purity products with a content of 99.9% without sublimation, effectively solving the problem of existing Problems in the industrial synthetic method of perimid, the four steps of the present invention are combined with the method of producing peregrine so far and have not been reported so far

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  • Industrial synthesis method of picene
  • Industrial synthesis method of picene
  • Industrial synthesis method of picene

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specific Embodiment approach

[0042] The present invention is described below in conjunction with specific examples, and used raw material, solvent and catalyst are conventional commercially available products, and following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention.

[0043] A kind of industrial synthesis method of peregrine, is characterized in that, comprises the following steps:

[0044] Step 1: The substrate 2-bromophenanthrene is placed in a low temperature state, and the alkyl derivative of lithium and tributyl borate are subjected to a substitution reaction to obtain the intermediate 2-phenanthrene boronic acid, the 2-bromophenanthrene, the lithium The molar ratio of the alkyl derivative and the tributyl borate is 1:1-2:1-2;

[0045]Step 2: use the intermediate 2-phenanthrene boronic acid and o-bromobenzaldehyde obtained in step 1 to carry out Suzuki coupling reaction to obtain 2-(phenanthrene-2-yl)benzaldehyde, the 2-phe...

Embodiment 1

[0068] The invention discloses a method for the industrial synthesis of peregrine, specifically, the method comprises the following steps:

[0069] Add 2.400kg of the substrate 2-bromophenanthrene (molecular weight 257.13, 9.334mol), THF 200L into a 500L reaction kettle, use liquid nitrogen to lower the temperature of the system to -78℃~-100℃, and control the temperature from -78℃~- 100°C, then add 5.14L (2mol / L, 10.28mol) of n-butyllithium and 2.58kg of tributyl borate (molecular weight: 230.152, 11.211mol) dropwise in sequence to carry out the substitution reaction, stop the reaction when the reaction is complete, and the reaction liquid will heat up naturally To room temperature 20°C-25°C, distill THF off, pour the reaction solution into hydrochloric acid water, solid precipitates, filter to obtain intermediate 2-phenanthreneboronic acid crude product;

[0070] Obtain intermediate 2-phenanthrene boronic acid crude product with step 1 and contain 2-phenanthrene boronic acid ...

Embodiment 2

[0075] The invention discloses a method for the industrial synthesis of peregrine, specifically, the method comprises the following steps:

[0076] Add 2.400kg of the substrate 2-bromophenanthrene (molecular weight 257.13, 9.334mol), THF 200L into a 500L reaction kettle, use liquid nitrogen to lower the temperature of the system to -78℃~-100℃, and control the temperature from -78℃~- 100°C, then add 9.664L (2mol / L, 18.668mol) of n-butyllithium and 4.296kg (molecular weight: 230.152, 18.668mol) of tributyl borate dropwise in order to carry out the substitution reaction, stop the reaction when the reaction is complete, and the reaction liquid will heat up naturally To room temperature 20 ℃ ~ 25 ℃, THF was evaporated, the reaction solution was poured into hydrochloric acid water, the solid precipitated, filtered to obtain the intermediate 2-phenanthrene boric acid crude product;

[0077] Obtain intermediate 2-phenanthrene boronic acid crude product with step 1 and contain 2-phenanth...

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Abstract

The invention discloses an industrial synthesis method of picene, which comprises the following steps: by taking 2-bromophenanthrene and o-bromobenzaldehyde as basic raw materials, carrying out substitution reaction on the 2-bromophenanthrene to obtain an intermediate 2-phenanthreneboronic acid, synthesizing 2-(phenanthrene-2-yl) benzaldehyde through Suzuki coupling reaction, carrying out Wittig reaction to obtain (E)-2-(2-(2-methoxyvinyl) phenyl) phenanthrene, and carrying out dehydration ring-closure reaction to obtain the picene. The method provided by the invention is simple to operate, realizes industrial batch production of picene, is green, and can obtain a high-purity product with the content of 99.9% without sublimation.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing superconducting properties of hydrocarbon compounds, and in particular to an industrial synthesis method for peregrine. Background technique [0002] An important organic intermediate, the molecular formula is C 22 h 14 , is an aromatic compound in which a benzene ring is condensed and linked into a W-type, and belongs to a type of hydrocarbon compound. [0003] Since A.F.Herbard reported in 1991 that alkali metal doped fullerenes (A X C 60 ) superconductivity, other graphite and hydrocarbon compounds have also been used in the research of superconductivity, and perylene belongs to hydrocarbon compounds with simple structure, which is the first case in superconducting materials. The energy band gap of peracene is 3.3eV, which is larger than that of pentacene at 1.8eV, and the ionization energy of peracene at 5.5eV is also greater than that...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/20C07C15/20
CPCC07C1/20C07C41/30C07C45/68C07F5/025C07C15/20C07C43/166C07C47/546
Inventor 任莺歌杨松彬李涛郭红梅郭随林
Owner 西安欧得光电材料有限公司
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