The preparation and properties of chelates of transition metal ions with the homopolymer and copolymers of p‐vinylbenzoylacetone

Abstract

Abstractp‐Vinylbenzoylacetone (VBA) was prepared by the condensation of p‐vinylacetophenone and ethyl acetate. This monomer was homopolymerized and copolymerized with acrylamide or maleic anhydride to produce polymers which would chelate substantial amounts of transition metal ions such as Cu2+, Ni2+, Co2+, Eu3+, and VO2+. In the case of the Cu2+ and Ni2+ chelates, about 80–90% of the metal ion could be eluted by dilute mineral acids. The resulting eluted products apparently have a somewhat porous structure because they are capable of rechelating these ions from water solution, even though the solid homopolymer which had not been chelated and eluted is too hydrophobic to chelate very much metal ion from water solution. The eluted Cu2+ chelate readily reaccepted Cu2+ ions from water solution and discriminated against Ni2+ almost completely. However, the eluted Ni2+ chelate would reaccept both Cu2+ and Ni2+ ions, but exhibited a strong preference for Cu2+ ions in competitive batch experiments. The VO2+ chelate was an effective heterogeneous phase catalyst for the epoxidation of allyl alcohols such as geraniol with tert‐butylhyroperoxide. The chelate was stable under these oxidative conditions and could be recovered unchanged and reused.