Study of the synthesis of chitosan derivatives containing benzo‐21‐crown‐7 and their adsorption properties for metal ions

Abstract

AbstractThree new chitosan crown ethers, N‐Schiff base‐type chitosan crown ethers (I, III), and N‐secondary amino type chitosan crown ether (II) were prepared. N‐Schiff base‐type chitosan crown ethers (I, III) were synthesized by the reaction of 4′‐formylbenzo‐21‐crown‐7 with chitosan or crosslinked chitosan. N‐Secondary amino type chitosan‐crown ether (II) was prepared through the reaction of N‐Schiff base type chitosan crown ether (I) with sodium brohydride. Their structures were characterized by elemental analysis, infrared spectra analysis, X‐ray diffraction analysis, and solid‐state 13C NMR analysis. In the infrared spectra, characteristic peaks of CN stretch vibration appeared at 1636 cm−1 for I and 1652 cm−1 for II; characteristic peaks of NH stretch vibration appeared at 1570 cm−1 in II. The X‐ray diffraction analysis showed that the peaks at 2θ = 10° and 28° disappeared in chitosan derivatives I and III, respectively; the peak at 2θ = 10° disappeared and the peak at 2θ = 28° decreased in chitosan‐crown ether II; and the peak at 2θ = 20° decreased in all chitosan derivatives. In the solid‐state 13C NMR, characteristic aromatic carbon appeared at 129 ppm in all chitosan derivatives, and the characteristic peaks of carbon in CN groups appeared at 151 ppm in chitosan crown ethers I and III. The adsorption and selectivity properties of I, II, and III for Pd2+, Au3+, Pt4+, Ag+, Cu2+, and Hg2+ were studied. Experimental results showed these adsorbents not only had good adsorption capacities for noble metal ions Pd2+, Au3+, Pt4+, and Ag+, but also high selectivity for the adsorption of Pd2+ with the coexistence of Cu2+ and Hg2+. Chitosan‐crown ether II only adsorbs Hg2+ and does not adsorbs Cu2+ in an aqueous system containing Pd2+, Cu2+, and Hg2+. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 83: 1886–1891, 2002