Hydrogenation of High Molecular Weight Bisphenol A Type Epoxy Resin BE503 in a Functional and Greener Solvent Mixture Using a Rh Catalyst Supported on Carbon Black

Abstract

A functional greener solvent mixture containing water, isopropyl alcohol (IPA) and ethyl acetate with the ratio 10:20:70 (wt%) was found to accelerate hydrogenation of bisphenol A type epoxy resin BE503 with a molecular weight of 1500 through an on-water mechanism, and led to an increased H2 availability, due to high solubility of H2 in IPA. Different carbon-based supports were tested and VulcanXC72 was found as the best support among the tested carbon-based ones as it possessed the highest amount of electron deficient promoter, RhOx. The catalyst, Rh5/VulcanXC72-polyol, synthesized by the microwave assisted polyol method, yielded a 100% hydrogenation of aromatic rings with an epoxy ring opening below 20.0% at 50 °C and a H2 pressure of 1000 psi in 2.25 h. Intrinsic activation energies for the hydrogenation of aromatic rings and epoxy ring opening were experimentally estimated and a mechanism for the hydrogenation of BE503 was proposed, wherein the hydrogenation of aromatic rings and epoxy ring opening in BE503 proceeded simultaneously in parallel and in-series with parallel being the major pathway.