4-Phenylethynylphthalic anhydride (PEPA)

CAS Number 119389-05-8

Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

4-Phenylethynylphthalic anhydride (PEPA) MSDS

4-Phenylethynylphthalic anhydride (PEPA) CAS 119389-05-8

A phthalic anhydride intermediate

For the synthesis of polyimides as end-capping reagent in application of gas separation membranes and high-performance polymers

Overview
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4-Phenylethynylphthalic anhydride (PEPA), CAS number 119389-05-8, a phthalic anhydride derivative, has a phenylethynyl substituent at 4-position. 4-Phenylethynylphthalic anhydride is commonly used as an end-capping reagent for polyimides synthesis and modification, such as TriA-X polyimides. The diphenylacetylene end-capping moiety undergoes thermally induced radical curing process for crosslinked polyimides. The crosslink further improves the thermal stability of the polyimides (5% decomposition temperature T_d5 = 591.3 °C). Diphenylacetylene also reacts with tetraphenylcyclopentadienone forming a fully conjugated hexaphenylbenzene under Diels-Alder reaction.

PEPA can also be introduced as an imide pedant onto a polymer backbone that has free amines. The modified polymer membranes show improved gas permeability in application of gas separation.

General Information

CAS Number	119389-05-8
Chemical Formula	C₁₆H₈O₃
Full Name	4-Phenylethynylphthalic anhydride
Molecular Weight	248.23 g/mol
Synonyms	5-(Phenylethynyl)isobenzofuran-1,3-dione, 5-(Phenylethynyl)-2-benzofuran-1,3-dione
Classification / Family	Anhydride building block, Separation membranes, High-performance polymers

Chemical Structure

Product Details

Purity	>99%
Melting Point	T_m = 152 °C
Appearance	Pale yellow to yellow powder/crystal

MSDS Documentation

4-Phenylethynylphthalic anhydride (PEPA) MSDS Sheet

Literature and Reviews

Diels–Alder cycloaddition polymerization of highly aromatic polyimides and their multiblock copolymers, D. Cristurean et al., Polym. Chem., 12, 3160(2021); DOI: 10.1039/d1py00314c.
Improved melt processabilities of thermosetting polyimide matrix resins for high temperature carbon fiber composite applications, H.-Y. Zhang et al., Polymers, 14, 965(2022); DOI: 10.3390/polym14050965.
Liquid crystalline thermosetting (LCT) composites based triboelectric nanogenerator with intrinsic flame retardancy, M. Qadeer et al., Adv. Mater. Technol., 7(10), 2200002(2022); DOI: 10.1002/admt.202200002.
Preparation and properties of modified phenylethynyl terminated polyimide with neodymium oxide, P. Zhang et al., Materials 15, 4148(2022); DOI: 10.3390/ma15124148.
Synthesis, properties and gas separation performance of poly(arylene ether sulfone) containing imide pendant groups, Y. Yu et al., RSC Adv., 7, 42468(2017); DOI: 10.1039/c7ra07355k.

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