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N-(diethylthiophosphoryl)-aza[18]crown-6: synthesis and ability of solvent extraction toward lead(II), zinc(II) and cadmium(II) metal cations

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EN
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EN
This work presents the synthesis of a strongly hydrophobic, functionalized monaza crown ether, i.e., lariat ether, namely N-(diethylthiophosphoryl)-aza[18]crown-6 and its application as ion extractant in solvent extraction systems. The synthesis of thiophosphorylated aza[18]crown-6 was performed with good yield. Separation systems have been successfully developed to extract Pb(II), Cd(II) and Zn(II) into organic phase, i.e., chloroform with the crown ethers: aza[18]crown-6 and N-(diethylthiophosphoryl)-aza[18] crown-6 as extractants. The selectivity order in both crown ethers was Pb(II) >> Cd(II) > Zn(II). The obtained results suggest that N-(diethylthiophosphoryl)-aza[18]crown-6 can be used for the selective removal of Pb(II) at lower pH values than aza[18]crown-6.
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autor
  • Institute of Chemistry, Environmental Protection, and Biotechnology Jan Dlugosz University of Czestochowa Armii Krajowej 13, 42-200 Czestochowa, Poland
  • Institute of Organic Chemistry, NASU, Kiev, Ukraine
Bibliografia
  • [1] Sgarlata C., Arena G., Longo E., Zhang D.M., Yang Y.F., Bartsch R.A., 2008. Heavy metal separation with polymer inclusion membranes. J. Membr. Sci. 323, 444-451.
  • [2] Aguilar J.C., Miguel E.R.D.S., Gyves J.D., Bartsch R.A., Kim M., 2001. Design, synthesis and evaluation of diazadibenzocrown ethers as Pb2+ extractants and carriers in plasticized cellulose triacetate membranes. Talanta 54, 1195-1209.
  • [3] Kim J., Ahn T.H., Lee M., Leong A.J., Lindoy L.F., Rumbel B.W., Skelton B.W., Strixner T., Wei G., White A.H., 2002. Metal ion recognition. The interaction of cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II), silver(I) and lead(II) with Nbenzylated macrocycles incorporating O2N2-, O3N2- and O2N3-donor sets. J. Chem. Soc. Dalton Trans. 21, 3993-3998.
  • [4] Cho M.H., Chun H.S., Kim J.H., Rhee C.H., Kim S.J., 1991. Study on Separation of Heavy Metal Ions in A Neutral Macrocycle-Mediated Emulsion Liquid Membrane System. Bull. Korean Chem.Soc. 12, 474-477.
  • [5] Cho M.H., Seon-Woo K.H., Heo M.Y., Lee I.C., Yoon C.J., Kim S.J., 1988. Studies on the macrocycles mediated transport in bulk liquid membrane system of transport metal ions. Bull. Korean Chem. Soc. 9, 292-295.
  • [6] Shamsipur M., Mashhadizadeh M.H., Azimi A., 2002. Highly selective and efficient transport of mercury(II) ions across a bulk liquid membrane containing tetrathia-12-crown-4 as a specific ion carrier. Sep. Purif. Technol. 27, 155-161.
  • [7] Gherrou A., Kerdjoudj H., Molinari R., Seta P., Drioli E., 2004. Fixed sites plasticized cellulose triacetate membranes containing crown ethers for silver(I), copper(II) and gold(III) ions transport. J. Membr. Sci. 228, 149-157.
  • [8] Ulewicz M., Kozłowski C., Walkowiak W., 2004. Removal of Zn(II), Cd(II) and Cu(II) ions by polymer inclusion membrane with side-armed diphosphaza-16-crown-6-ethers. Physicochem. Probl. Miner. Process. 38, 131-138.
  • [9] Ulewicz M., Sadowska K., Biernat J.F., Szczygelska-Tao J., 2009. Selectivity of Pb(II) transport across polymer inclusion membranes doped with imidazole azothiacrown ethers. J. Membr. Sci. 344, 32-38.
  • [10] Ulewicz M., Sadowska K., Biernat J.F., 2007. Selective transport of Pb(II) across polymer inclusion membrane using imidazole azocrown ethers as carriers. Physicochem. Probl. Miner. Process. 41, 133-143.
  • [11] Ulewicz M., Walkowiak W., 2006. Removal of Zn(II), Cd(II) and Pb(II) using polymer inclusion membrane transport with proton ionizable DB-16-C-5 crown ethers. Physicochem. Probl. Miner. Process. 40, 185-194.
  • [12] Luboch E., Wagner-Wysiecka E., Fainerman-Melnikova M., Lindoy L.F., Biernat J.F., 2006. Pyrrole azocrown ethers. Synthesis, complexation, selective lead transport and ion-selective membrane electrode studies. Supramol. Chem. 18, 593--601.
  • [13] Hayashi R., Hayashita T., Yoshikawa T., Hiratani K., Bartsch R.A., 2003. Design of a polymer inclusion membrane having proton-ionizable polyether carriers and their separation function for lead ion. Bunseki Kagaku 52, 755-762.
  • [14] Lee S.Ch., Lamb J.D., Cho M.H., Rhee Ch.H., Kim J.S., 2000. A lipophilic acyclic polyether dicarboxylic acid as Pb2+ carrier in polymer inclusion and bulk liquid membranes. Sep. Sci. Technol., 35, 767-778.
  • [15] Kim J.S., Kim S.K., Cho M.H., Lee S.H., Kim J.Y., Kwon S.-G., Lee E.-H., 2001. Permeation of Silver Ion through Polymeric CTA Membrane Containing Acyclic Polyether Bearing Amide and Amine Eng-Group. Bull. Korean Chem. Soc. 22, 1076-1080.
  • [16] Maeda H., Furuyoshi S., Nakatsuji Y., Okahara M., 1983. Synthesis of Monoaza Crown Ethers from N,N-Di[oligo(oxyalkylene)]amines and Oligoethylene Glycol Di(p-toluenesulfonates) or Corresponding Dichlorides. Bull. Chem. Soc. Jpn. 56, 212-218.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-565a448b-f2f9-42bf-86f3-a2b6a97a389c
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