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Relationship between chemical structure and extraction efficiency toward palladium with ketonic derivatives of p-tert-octylcalix[4]arene in nitric acid media

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Abstract

A p-tert-octylcalix[4]arene derivative with four phenyl ketonic side arms has been synthesized as a solvent extraction reagent for precious metal ions in order to compare the extraction behavior with that of the corresponding methyl ketonic derivative of p-tert-octylcalix[4]arene in nitric acid media. The extraction efficiency of the phenyl ketonic derivative for palladium was superior to that of the methyl ketonic one over the whole nitric acid concentration range. Silver and platinum were also moderately extracted by the phenyl ketonic derivative in low nitric acid concentration. The results demonstrated that the extraction behavior of the ligands towards precious metals is related to several structural factors, such as the flexibility of the side arms, the electric charge on the carbonyl oxygen atoms and the lipophilic properties. This work also determined the extraction mechanism of palladium with the phenyl ketonic derivative of p-tert-octylcalix[4]arene based on slope analysis and the peak shift for the FT-IR spectra of the ligand before and after the metal loading. Stripping from the organic phase after forward extraction was performed to separate palladium and silver.

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Acknowledgments

This was financially supported by “The Environment Research and Technology Development Fund, No. 3 K-123022, from the Ministry of the Environment, Government of Japan”.

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Correspondence to Keisuke Ohto.

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The present paper is dedicated to Prof. Jack Harrowfield and Dr. Jacques Vicens on the celebration of their 70th birthday.

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Kim, J.Y., Morisada, S., Kawakita, H. et al. Relationship between chemical structure and extraction efficiency toward palladium with ketonic derivatives of p-tert-octylcalix[4]arene in nitric acid media. J Incl Phenom Macrocycl Chem 82, 25–32 (2015). https://doi.org/10.1007/s10847-014-0467-6

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  • DOI: https://doi.org/10.1007/s10847-014-0467-6

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