A heterocyclic ethynyl phthalic anhydride derivative, its synthesis method and application

The synthesis of heterocyclic acetylenic anhydride derivatives via the oxidative coupling reaction of acetylenic anhydride with five-membered heterocyclic compounds solves the problem of high-temperature synthesis of phenylacetylenic anhydride and achieves high-yield and environmentally friendly preparation of polyimide end-capping agents.

CN119039282BActive Publication Date: 2026-07-14DALIAN NEW SUNSHINE MATERIAL TECH CO LTD

Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
DALIAN NEW SUNSHINE MATERIAL TECH CO LTD
Filing Date
2024-08-19
Publication Date
2026-07-14

AI Technical Summary

Technical Problem

Existing methods for synthesizing phenylacetylene phthalic anhydride require high temperatures, have poor processability and low material stability, and are not environmentally friendly with low yields.

Method used

Heterocyclic acetylenic anhydride derivatives were synthesized by oxidative coupling reaction of acetylenic phthalic anhydride with five-membered heterocyclic compounds. Palladium and copper catalysts, organic bases and oxygen atmosphere were used. The reaction temperature was 40-80℃ and the reaction time was 8-24 hours. The post-processing was simple.

Benefits of technology

A method for synthesizing heterocyclic ethynyl phthalic anhydride derivatives at lower temperatures was achieved with high yield, simple operation, and atom economy. Water was produced as a byproduct, which reduced the crosslinking temperature and production cost of the material.

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Abstract

The application belongs to the field of organic synthesis, and relates to a synthesis method of a material intermediate, in particular to a heterocyclic ethynyl anhydride derivative, a synthesis method and application thereof. The structure of the heterocyclic ethynyl anhydride derivative is shown in formula I: the heterocyclic ethynyl anhydride derivative shown in formula I is obtained by oxidative coupling reaction of ethynyl anhydride and a five-membered heterocyclic compound, and the derivative can be used as a capping agent of polyimide. The heterocyclic ethynyl anhydride capping agent of the polyimide containing a heterocyclic ring is synthesized for the first time, the synthesis method has good selectivity, high yield, mild conditions, conforms to atomic economy, and is easy to realize industrial production.
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