Polymeric separation media: Binding of α,β-unsaturated carbonyl compounds to insoluble resins through michael additions or chelation of derivatives

Four different types of crosslinked polymers have been prepared for use in the binding of α-β-unsaturated compounds. The polymers have been tested in their reactions with unsaturated ketones, aldehydes, esters, acids, nitriles and/or lactones. The first three polymers were prepared by chemical modification of crosslinked polystyrene and contained amine, thiol, or sulfinate functional groups. They react with the unsaturated compounds through Michael additions. Simple procedures for the cleavage of the bound molecules from their solid support have been devised. All the nucleophilic polymers performed satisfactorily in the removal of allergenic α-methylene-γ-butyrolactones from a natural oil. The sulfinate resin is particularly attractive in view of its ability to be used repeatedly without requiring a regeneration step. The design of the fourth polymer which contained iminodiacetate copper groups allowed its use in ligand chromatography for the purification of amine-modified costus oil. The polymer is also very effective and recyclable.