Extraction of metal picrates by lipophilic hexamide and hexamine derivatives of azacrown [18]-N6

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To determine the metal ion complexing ability of high molecular weight macrocyclic polyamines and polyamides, lipophilic derivatives of azacrown [18]-N6 (hexacyclen) were prepared. Transition and heavy metal picrates, but not alkali and alkaline earth picrates, were extracted from water into chloroform and transported from water through chloroform into a second water phase by the hexa-4-dodecyloxybenzoyl and hexa-3,4-bis-dodecyloxybenzoyl amide derivatives1 and2 and by the hexa-4-dodecyloxybenzyl amine derivative3 of [18]-N6 (hexacyclen). The relative amounts of picrates extracted by hexamine3 from a pH 5 aqueous solution were Cu2+∼Ag+∼Pb2+> Hg2+>Zn2+>Co2+>Ni2+∼Cd2+. Using a pH 7 receiving phase, none of the metal ions were transported rapidly through chloroform, and only Co2+, Cu2+, and Pb2+, were transported rapidly into a pH 11 aqueous phase. The hexamide2, but not hexamide1, extracted significant amounts of the picrates of Cu2+, Ag+, and Hg2+, and transported Cu2+ and Ag+ but not Hg2+.