Synthesis method of high-purity 1-pyrenecarboxaldehyde

Abstract

The invention discloses a synthesis method of high-purity 1-pyrenecarboxaldehyde. The synthesis method is characterized in that pyrene is fed into an organic solvent; stirring is performed for dissolution; dichloromethyl methyl ether is injected and added into reaction liquid; the reaction liquid is cooled by ice-salt bath; then, a mixed solution of TiCI4 and dichloromethane is dropwise added; the reaction liquid is subjected to quenching reaction; after the quenching is completed, water is added; stirring is performed for layering; an organic phase is subjected to working procedures such as washing and drying; a crude product 1-pyrenecarboxaldehyde is obtained; the crude product 1-pyrenecarboxaldehyde is subjected to heating and backflow dissolution by organic solvents; active carbon is added for decoloration; through the working procedures of heat filtering, cooling crystallization and the like, the 1-pyrenecarboxaldehyde is obtained; the GC content is 99.5 percent; the total yield of the reaction is 80 percent or higher. The used synthesis raw materials are cheap, can be easily obtained, and are industrial products; the reaction conditions are mild; the risk is low; the operation is convenient; the reaction is easy to control; the synthesis method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method for high-purity 1-pyrene formaldehyde, which belongs to the technical field of synthesis of novel nanometer chemical material applications. Background technique [0002] Pyrene chemical derivatives are widely used in material science, and 1-pyrene formaldehyde, as a new type of pyrene derivative, will make great contributions to the research of new nanomaterials, and the compound contains a highly active aldehyde group Groups can be used as raw materials for the synthesis of other pyrene derivatives, such as 1-pyrenemethanol, 1-pyrenecarboxylic acid, 1-(bromomethyl)pyrene and other pyrene derivatives, and these compounds are popular researches in material science in recent years . In recent years, it has been reported that many scholars have begun to study the application of 1-formaldehyde in new materials. For example, researchers Gao Changyou and Wang Zhipeng of Zhejiang University in China have develope...

AI Technical Summary

Problems solved by technology

The classic approach is to utilize POCl 3 / DMF system for formylation reaction to introduce aldehyde groups, but the highly dangerous and highly toxic POCl is used 3 Raw materials, the reaction is difficult to control, and the yield reported in the literature is only about 30%, which is not suitable for industrialization (Dyes and Pigments, 2011, vol. 89, # 3 p. 199 – 211)

In addition, there are also literature reports on the synthesis method of 1-pyrene formaldehyde, using pyrene and dichloromethyl methyl ether, TiCl 4 and other reactions, but the process is cumbersome, the product purity and yield are not high, and highly toxic solvents such as benzene are used in the product purification process, which affects the environment and human health, and is not suitable for industrialization (Organic Preparations and Procedures International, 1997, vol . 29, # 3 p. 321–330)

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