Hydroxylation-Depolymerization of Oxyphenylene-Based Super Engineering Plastics To Regenerate Arenols

[Image: see text] Super engineering plastics, high-performance thermoplastic resins, show high thermal stability and mechanical strength as well as chemical resistance. On the other hand, chemical recycling for these plastics has not been developed due to their stability. This study describes depolymerization of oxyphenylene super engineering plastics via carbon–oxygen main chain cleaving hydroxylation reaction with an alkali hydroxide nucleophile. This method is conducted with cesium hydroxide as a hydroxy source and calcium hydride as a dehydration agent in 1,3-dimethyl-2-imidazolidinone, which provides hydroxylated monomers effectively. In the case of polysulfone, both 4,4′-sulfonyldiphenol (bisphenol S) and 4,4′-(propane-2,2-diyl)diphenol (bisphenol A) were obtained in high yields. Other super engineering plastics such as polyethersulfone, polyphenylsulfone, and polyetheretherketone were also applicable to this depolymerization.