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4-phenylacetylene benzoic anhydride preparation method

A technology of phenylacetylene phthalic anhydride and phenylacetylene, which is applied in the field of preparation of 4-phenylacetylene phthalic anhydride, can solve the problems of restricting the development of PI resin and the high price of the final product, and achieve the effects of low price, simple preparation method and high yield

Inactive Publication Date: 2004-11-10
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the 4-phenylacetylene phthalic anhydride described in the U.S. patent is synthesized by 4-bromophthalic anhydride as a basic raw material. Because its raw material is not commercialized, the final product price is more expensive, which limits the further development of PI resin

Method used

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Embodiment 1

[0018] Under nitrogen protection, 4-chlorophthalic anhydride (182.56g, 1mol), phenylacetylene (102.13g, 1mol), palladium dichloride (0.018g 0.1mmol), triphenylphosphine (0.1g 0.4mmol), chlorine Cuprous chloride (0.02g 0.2mmol) was dissolved in N,N'-dimethylacetamide (1800ml) and triethylamine (1000ml), heated to 80°C, after the reaction was carried out for 6h, the filtrate was poured into a large amount of water, The precipitate was collected and fully washed with water. After drying, it was heated and vacuum sublimated to obtain pale yellow 4-phenylacetylene phthalic anhydride (174 g 0.7 mol) with a yield of 70%.

Embodiment 2

[0020] Under nitrogen protection, 4-chlorophthalic anhydride (182.56g, 1mol), phenylacetylene (102.13g, 1mol), palladium dichloride (0.07g, 0.4mmol), triphenylphosphine (0.06g, 0.24mmol) 1. Cuprous chloride (0.6g, 0.6mmol) was dissolved in N,N'-dimethylformamide (1200ml) and triethylamine (500ml), heated to 60°C, after the reaction was carried out for 20h, the filtrate was poured into The precipitate was collected and washed in a large amount of water, and after being fully dried, it was sublimated under vacuum by heating to obtain 4-phenylacetylene phthalic anhydride (149 g, 0.6 mol) with a yield of 60%.

Embodiment 3

[0022] Under nitrogen protection, 4-chlorophthalic anhydride (182.56g, 1mol), phenylacetylene (102.13g, 1mol), palladium dichloride (0.18g, 1mmol), triphenylphosphine (1g, 4mmol), chloride Cuprous (0.1g, 10mmol) was dissolved in N-methyl-2-pyrrolidone (600ml) and triethylamine (500ml), heated to 80°C, and after 12 hours of reaction, the filtrate was poured into a large amount of water, and the precipitate was collected And washed, fully dried, heated and vacuum sublimated to obtain pale yellow 4-phenylacetylene phthalic anhydride (179 g, 0.72 mol) with a yield of 72%.

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Abstract

The invention relates to a process for preparing 4-phenylacetylene- benzoic anhydride from 4-chlorophthalic anhydride as raw material, at the presence of 4 (triphenylphosphine) fertilizer as catalyst, copper chloride as catalyst promoter, and tertiary amine as absorbent of reaction by-product through coupling reaction in nonprotonic solvent with phenylacetylene.

Description

technical field [0001] The invention belongs to the preparation method of 4-phenylacetylene phthalic anhydride. Background technique [0002] Thermosetting polyimides (PIs) are a class of matrix resins for advanced composite materials, which have high thermal oxidation resistance, mechanical properties and high glass transition temperature, and have important applications in the field of aerospace materials. Among them, the polyimide composite material with norbornene as the end-capping agent has been successfully used in the manufacture of aerospace vehicles, but its heat resistance level and other properties cannot fully meet the requirements, so a new higher heat-resistant end-capping material was developed Agents are one of the current research hotspots. U.S. NASA invented 4-phenylacetylene phthalic anhydride capping agent (US patent, 5681967) in the mid-nineties, and found that it has higher heat resistance and solvent resistance. Based on this end-capping agent, they...

Claims

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Application Information

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IPC IPC(8): C07D307/89
Inventor 王震高连勋丁孟贤
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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