Organocatalytic amidation of poly(ethylene terephthalate)

Abstract

Petrochemicals Research Institute, King Abdulaziz City for Science and Technology, Riyadh, Saudi Arabia Recent advance in technology regarding biomass transformation has enabled poly(ethylene terephthalate) (PET), a widely used thermoplastic, to be regarded as a bio-based polymer. The escalating production of PET today is, however, still leading to a global concern over the treatment of PET waste products and its destructive impact to the environment. Thus the recycling should be addressed more seriously. We previously reported that a potent organic catalyst, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), affects the depolymerization of PET by ethylene glycol efficiently, comparable to conventional metal catalysts. Now, we apply this organocatalysis in amidation of PET to develop a spectrum of terephthalamides possessing diverse functionalities. Both experimental and computational studies proved that TBD was quite effective in the amidation of PET allowing the corresponding terephthalamides from even arylamines. The terephthalamides are often employed as a building block of high performance materials such as additives, modifiers, and monomers. Considering the PET waste as a feedstock for such useful materials can be another solution to the existing environmental concerns and the management of limited petroleum sources.