From Plastic Waste to Pharmaceutical Precursors
PET Upcycling Through Ruthenium Catalyzed Semi-Hydrogenation
Pavel S. Kulyabin (University of St Andrews)
James Luk (University of St Andrews)
Evgeny A. Uslamin (TU Delft - ChemE/O&O groep)
Alexander A. Kolganov (TU Delft - ChemE/Inorganic Systems Engineering)
Garima Saini (University of St Andrews)
Raymundo Marcial-Hernandez (University of St Andrews)
Ketan Pancholi (Robert Gordon University)
Benjamin Kühne (Merck KGaA)
Evgeny A. Pidko (TU Delft - ChemE/Inorganic Systems Engineering)
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Abstract
We report here the upcycling of PET (polyethylene terephthalate) waste via semihydrogenation to make ethyl 4-(hydroxymethyl)benzoate. The reaction is catalyzed by a ruthenium pincer catalyst at 80 °C in bioderived solvents – a combination of 2-methyl THF and ethanol. A detailed mechanistic investigation through organometallic and kinetic studies, as well as chemical exchange saturation transfer (CEST) NMR spectroscopy, provides insights into the nature of active species and factors that promote and inhibit the catalytic hydrogenation of PET. Using this mechanistic knowledge, a record high turnover number of >30 000 was achieved for the hydrogenative depolymerization of end-of-life PET waste (e.g., bottles and textiles). The semihydrogenation product, ethyl 4-(hydroxymethyl)benzoate, was utilized to make precursors of various known pharmaceutical drugs, an agrochemical, as well as a new and recyclable polyester. A cradle-to-gate life cycle assessment demonstrated that using PET waste as a feedstock for EHMB production significantly reduces the environmental footprint compared to the conventional route from p-toluic acid.
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