Advanced chemical recycling of poly(ethylene terephthalate) through organocatalytic aminolysisElectronic supplementary information (ESI) available: Experimental details and Cartesian coordinates for optimized structures. See DOI: 10.1039/c2py20793a

We report the effective organocatalysis of the aminolytic depolymerization of waste poly(ethylene terephthalate) (PET) using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) producing a broad range of crystalline terephthalamides. This diverse set of monomers possesses great potential as building blocks for high performance materials with desirable thermal and mechanical properties deriving from the terephthalic moiety and amide hydrogen bonding. Further, a computational study established mechanistic insight into self-catalyzed and organocatalyzed aminolysis of terephthalic esters, suggesting that the bifunctionality of TBD particularly concerning activation of the carbonyl group differentiates TBD from other organic bases. A diverse set of terephthalimide monomers have been efficiently formed by the TBD-catalyzed degradation of PET with various amines.