Proton-ionizable acyclic dibenzopolyethers and their polymers for use in selective lead(II) separation

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Abstract
2,2′-[1,2-Ethanediylbis(oxy)]bisbenzoic acid (1), 2,2′-[oxybis(1,2-ethanediyloxy)]bisbenzoic acid (2), 1,2-[2′-(acetoxy)phenoxy] ethane (3), and 1,5-[2′-(acetoxy)phenoxy]-3-oxopentane (4) have been prepared for use in selective Pb(II) separation. The extraction of Pb(II) and Cu(II) from buffered aqueous solutions of varying pH into chloroform by 1–4 is examined in relation to their molecular structure. Compound 1 with an ethylene glycol spacer unit exhibits excellent extraction selectivity for Pb(II) over Cu(II). Lengthening the spacer group to a diethylene glycol unit diminishes the extraction efficiency and selectivity. For 3 and 4, extraction was inefficient due to low lipophilicity and solubility of the ligands in chloroform. Condensation polymerization of compounds 3 and 4 with formaldehyde in formic acid provides stable chelating resins 5 and 6 which contain both ion-exchange and polyether binding sites for metal complexation. Resin 5 with an ethylene glycol spacer group is found to be an effective chelating resin for Pb(II) separation. The sorption mechanism and selectivity are studied and compared with the commercially available iminodiacetic acid resin CR-10.