Lariat Ether Carboxylic Acids, O-Benzylhydroxamates and Hydroxamic Acids with Fluorinated Substituents: Synthesis, Metal Ion Complexation and Solubility in Supercritical Carbon Dioxide

A series of lariat ether carboxylic acids, O-benzylhydroxamates, and hydroxamic acids with fluorine-containing substituents is prepared. In general, the presence of fluorine-containing substituents is found to increase the solubility of the lariat ethers in supercritical carbon dioxide. Efficiencies of the fluorine-containing lariat ether carboxylic and hydroxamic acids are compared with those for non-fluorinated analogs in solvent extraction of lanthanide ions from aqueous solutions into chloroform. Responses of the fluorine-containing lariat ether O-benzylhydroxamates towards alkali metal cations in solvent polymeric membrane electrodes are compared with those analogous non-fluorinated compounds.