Coordination-Insertion Polymerization of Vinyl (1-acetoxy ethyl) ether Utilizing Palladium Catalysts

Abstract

Our society’s copious generation of plastic waste necessitates progress toward environmentally sustainable plastics. However, catalytic inefficiency of ethylene copolymerization with polar monomers is a major obstacle to the production of biodegradable polymers. This work utilizes palladium phosphine-phosphonic diamide (PPDA) catalysts in conjunction with a novel vinyl (1-acetoxy ethyl) ether comonomer as a protecting group to circumvent points of catalytic arrest in ethylene copolymerization. While it remains uncertain whether the proposed mechanistic improvements compensate for unfavorable electronic and steric properties of vinyl (1-acetoxy ethyl) ether, this work has demonstrated the utility of ligand design. Catalytic activity and polymer characteristics were improved in comparison to classic palladium-phosphine sulfonate catalysts, illustrating the effects of strong ligand donicity. In addition, the post- production de-acetylation of the copolymer was investigated. However, the unexpected evolution of some products suggests that thermolysis may not be an ideal method of functionalization, and other pathways should be pursued.