Synthesis and Characterization of Polymer Metal Chelates Derived from Poly(2,2,3,3-tetra methyleneaminecyclopropyl)phenyl Acrylate

Abstract

The new method for the synthesis of p-(2,2,3,3-tetracyanocyclopropyl)phenyl acrylate (P-TCP) was applied. In this method, p-acryloyloxybenzaldehyde was reacted with malononitrile and cyanogen bromide at 0°C in short time. Then, the P-TCP monomer was polymerized by free-radical polymerization to obtain a poly-(2,2,3,3-tetracyanocyclopropyl)phenyl acrylate with multicyanocyclopropane functionalities in the pendant group. The nitrile functions in pendant groups of the prepared polymer were reduced to primary amines using NaBH4 and NiCl2 salts at 65°C in dry ethanol for the preparation of poly(2,2,3,3-tetra methyleneaminecyclopropyl)phenyl acrylate (PTAP) as a new polymer. The PTAP was soluble in acetone and ethylacetate. The PTAP was examined for the removal of Cu(II), Ni(II), Zn(II), and Cr(III) ions from aqueous solutions under noncompetitive and competitive conditions at various pH. The adsorption rate was high (<60 min). The complexation of selected heavy metal ions by the PTAP is strongly dependent on the pH of medium and the adsorption of all selected metal ions was more favorable at the pH 7. Also the maximum sorption of the PTAP for selected metal ions under competitive conditions belongs to Cu(II) at pH 7. The kd value is calculated for the prepared chelating polymer, and the result indicates approximately high values in the case of Cu(II) ion. The synthesized polymer and its metal chelates were characterized by FT-IR, 1H NMR, thermogravimetric analysis, gravimetry, UV–vis spectroscopy, and atomic absorption spectrometry.