Depolymerization of PET with n-Hexylamine, n-Octylamine, and 3-Amino-1-Propanol, Affording Terephthalamides

Abstract

The chemical conversion of plastic waste has been considered an important subject in terms of the circular economy, and the chemical recycling and upcycling of poly(ethylene terephthalate) (PET) has been considered one of the most important subjects. In this study, the depolymerization of PET with n-hexylamine, n-octylamine, and 3-amino-1-propanol has been explored in the presence of Cp*TiCl3 (Cp* = C5Me5). The reactions of PET with n-hexylamine and n-octylamine at 130 °C afforded the corresponding N,N′-di(n-alkyl) terephthalamides in high yields (>90%), and Cp*TiCl3 plays a role as the catalyst to facilitate the conversion in exclusive selectivity. The reaction of PET with 3-amino-1-propanol proceeded at 100 °C even in the absence of the Ti catalyst, affording N,N′-bis(3-hydroxy) terephthalamides in high yields. A unique contrast has been demonstrated between the depolymerization of PET by transesterification with alcohol and by aminolysis; the depolymerizations with these amines proceeded without the aid of a catalyst.