Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Highly CO2-soluble 5-Amido-8-hydroxyquinoline Chelating Agents for Extraction of Metals in Sc-CO2

  • Chang, Fei (Department of Chemistry and Advanced Materials and Industrial Liaison Research Institute, College of Environment and Applied Chemistry, Kyung Hee University) ;
  • Park, Seo-Hun (Department of Chemistry and Advanced Materials and Industrial Liaison Research Institute, College of Environment and Applied Chemistry, Kyung Hee University) ;
  • Kim, Hakwon (Department of Chemistry and Advanced Materials and Industrial Liaison Research Institute, College of Environment and Applied Chemistry, Kyung Hee University)
  • Published : 2008.07.20
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Abstract

Novel $CO_2$-soluble 8-hydroxyquinoline (8-HQ) chelating agents were synthesized and evaluated for solubility and metal ion extraction ability in supercritical $CO_2\;(Sc-CO_2)$. Among them, secondary amide-containing 8- HQ derivatives cannot be dispersed well into Sc-$CO_2$, but tertiary amide-containing derivatives can dissolve completely in Sc-$CO_2$ even at low CO2 pressures, perhaps owing to the predominant intermolecular interaction between the chelating agent and the $CO_2$ molecule. Based on 8-HQ chelating agent solubility data, we investigated the extraction of metal ions ($Co^{2+}$, $Cu^{2+}$, $Sr^{2+}$, $Cd^{2+}$, and $Zn^{2+}$) using two highly $CO_2$-soluble 8-HQ derivatives (4d, 4e) in Sc-$CO_2$. The extraction efficiency of tertiary amide-containing 8-HQ ligands, both fluorinated and non-fluorinated forms, was dramatically increased in the presence of diethyl amine (organic base). We suggest that diethyl amine could play an important synergistic role in the stronger metal binding ability of 8-HQ through an in situ deprotonation reaction in Sc-$CO_2$ medium.

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