Degradation of Polyacrylates by One-Pot Sequential Dehydrodecarboxylation and Ozonolysis

We establish a synthetically convenient method to degrade polyacrylate homopolymers. Carboxylic acids are installed along the polymer backbone by partial hydrolysis of the ester side chains, and then, in a one-pot sequential procedure, the carboxylic acids are converted into alkenes and oxidatively cleaved. This process enables the robustness and properties of polyacrylates to be maintained during their usable lifetime. The ability to tune the degree of degradation was demonstrated by varying the carboxylic acid content of the polymers. This method is compatible with a wide range of polymers prepared from vinyl monomers through copolymerization of acrylic acid with different monomers including acrylates, acrylamides, and styrenics.

Automated summary

We have developed a convenient method for degrading polyacrylate homopolymers. Carboxylic acids are introduced into the polymer backbone through hydrolysis of the ester side chains, and then converted into alkenes and oxidatively cleaved in a one-pot sequential procedure. This method allows the robustness and properties of polyacrylates to be maintained during their usable lifetime. The degree of degradation can be tuned by varying the carboxylic acid content of the polymers. This method is compatible with a wide range of polymers prepared from vinyl monomers through copolymerization with different monomers including acrylates, acrylamides, and styrenics.