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Immobilization of novel the semicarbazone derivatives of calix[4]arene onto magnetite nanoparticles for removal of Cr(VI) ion

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Abstract

A series of novel the semicarbazone derivatives of calix[4]arene have been synthesized and then immobilized onto amino functionalized magnetic nanoparticles. Magnetic Fe3O4 nanoparticles were prepared by the chemical co-precipitation of Fe(III) and Fe(II) ions and the nanoparticles were modified directly by 3-aminopropyltriethoxy silane (APTES) to introduce reactive amine groups onto the particles’ surface. The characterization of the prepared compounds was made by FT-IR, elemental analysis, TGA/DTG and NMR techniques. The sorption properties of the new calix[4]arene based magnetic sorbents toward Cr(VI) ion were also studied. The results showed that the prepared magnetic nanoparticles were effective sorbents for the removal of Cr(VI) ion. Also, Langmuir and Freundlich isotherm models were applied for Cr(VI) ion sorption by using MN-C2 and it was found that the experimental data confirmed to Langmiur isotherm model.

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References

  1. Matthews, S.E., Beer, P.D.: Calixarene-based anion receptors. Supramol. Chem. 17(6), 411–435 (2005)

    Article  CAS  Google Scholar 

  2. Yilmaz, M., Memon, S., Tabakci, M., Bartsch, R.A.: In: Bregg, R.K. (ed.) New Frontiers in Polymer Research, p. 125. Nova Science Publishers, Hauppauge NY (2006)

  3. Tabakci, M., Ersoz, M., Yilmaz, M.: A calix[4]arene-containing polysiloxane resin for removal of heavy metals and dichromate anion. J Macromol Sci Pure Appl Chem 43, 57–64 (2006)

    Article  CAS  Google Scholar 

  4. Memon, S., Tabakci, M., Roundhill, D.M., Yilmaz, M.: Synthesis and evaluation of the Cr(VI) extraction ability of amino/nitrile calix[4]arenes immobilized onto a polymeric backbone. React. Funct. Polym. 66, 1342–1349 (2006)

    Article  CAS  Google Scholar 

  5. Gokel, G.: Crown ethers, cryptands. In: Stoddart, J.F. (ed.) Monographs in Supramolecular Chemistry. Royal Society of Chemistry, London (1991)

    Google Scholar 

  6. Van Veggel, F.C.J.M., Verboom, W., Reinhoudt, D.N.: Metallomacrocycles: supramolecular chemistry with hard and soft metal cations in action. Chem. Rev. 94, 279–299 (1994)

    Article  CAS  Google Scholar 

  7. Hamdi, A., Nam, K.C., Ryu, B.J., Kim, J.S., Vicens, J.: Anion complexation. A ditriphenylphosphonium calix[4]arene derivative as a novel receptor for anions. Tetrahedron Lett. 45, 4689–4962 (2004)

    Article  CAS  Google Scholar 

  8. Gutsche, C.D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge (1998)

    Google Scholar 

  9. Asfari, Z., Bohmer, V., Harrowfield, Mc.B., Vincens, J.: Calixarenes. Kluwer Academic Publishers, Dordrecht (2001)

    Google Scholar 

  10. Vicens, J., Bohmer, V.: Calixarenes: A Versatile Class of Macrocyclic Compounds. Topics in Inclusion Science, pp. 149–172. Kluwer Academic Publishers, Dordrecht (1991)

    Google Scholar 

  11. Memon, S., Roundhill, D.M., Yilmaz, M.: Remediation and Liquid–Liquid Phase Transfer Extraction of Chromium(VI). A Review. Collect Czech Chem. Commun. 69, 1231–1250 (2004)

    Article  CAS  Google Scholar 

  12. Dozol, J.F., Rouquette, H., Ungaro, R., Casnati, A.: Chem. Abs. 122, 239730n, (CEA) International Patent WO 94/24138 (1995)

  13. Demirel, A., Dogan, A., Canel, E., Memon, S., Yilmaz, M., Kilic, E.: Hydrogen ion-selective poly(vinyl chloride) membrane electrode based on a p-tert-butylcalix[4]arene-oxacrown-4. Talanta 62, 123 (2004)

    Article  CAS  Google Scholar 

  14. Ertul, S., Bugdayci, M., Yilmaz, M.: Removal of chromate and phosphate anion from aqueous solutions using calix[4]aren receptors containing proton switchable units. J. Hazard. Mater. 181, 1059–1065 (2010)

    Article  CAS  Google Scholar 

  15. Memon, S., Yilmaz, A., Roundhill, D.M., Yilmaz, M.: Synthesis of polymeric calix[4]arene dinitrile and diamino-derivatives: exploration of their extraction properties towards dichromate anion. J. Macromol. Sci. Pure. 41, 433–447 (2004)

    Article  Google Scholar 

  16. Tabakci, M., Memon, S., Yilmaz, M., Roundhill, D.M.: Synthesis and extraction studies of a versatile calix[4]arene-based ‘proton-switchable extractant’ for toxic metals and dichromate anions. J. Incl. Phenom. Macrocycl. Chem. 45, 267–270 (2003)

    Article  Google Scholar 

  17. Ediz, O., Tabakci, M., Memon, S., Yilmaz, M., Roundhill, D.M.: A convenient approach towards the synthesis of a “proton switchable” chromium(VI) extractant based on calix[4]arene. Supramol. Chem. 16, 199–204 (2004)

    Article  CAS  Google Scholar 

  18. Bayrakci, M., Ertul, S., Sahin, O., Yilmaz, M.: Synthesis of two new p-tert-butylcalix[4]arene β-ketoimin derivatives for extraction of dichromate anion. J. Incl. Phenom. Macrocycl. Chem. 63, 241–247 (2009)

    Article  CAS  Google Scholar 

  19. Gungor, O., Memon, S., Yilmaz, M., Roundhill, D.M.: Synthesis of alkyl nitrile and alkyl benzonitrile derivatives of calix[4]arene and their polymer supported analogues: a comparative study in two-phase extraction systems. React. Funct. Polym. 63, 1–9 (2005)

    Article  CAS  Google Scholar 

  20. Gupta, A.K., Gupta, M.: Synthesis and surface engineering of iron oxide nanoparticles for biomedical applications. Biomaterials 26, 3995–4021 (2005)

    Article  CAS  Google Scholar 

  21. Krizzova, J., Spanova, A., Rittich, B., Horak, D.: Magnetic hydrophilic methacrylate-based polymer microspheres for genomic DNA isolation. J. Chromatogr. A 1064, 247–253 (2005)

    Article  Google Scholar 

  22. Ito, A., Shinkai, M., Honda, H., Kobayashi, T.: Medical application of functionalized magnetic nanoparticles. J. Biosci. Bioeng. 100, 1 (2005)

    Article  CAS  Google Scholar 

  23. Mornet, S., Vasseur, S., Grasset, F., Goglio, G., Demourgues, A., Portier, J., Pollert, E., Duguet, E.: Magnetic nanoparticle design for medical applications. Prog. Solid State Chem. 34, 237–247 (2006)

    Article  CAS  Google Scholar 

  24. Neuberger, T., Schopf, B., Hofmann, H., Hofmann, M., von Rechenberg, B.: Superparamagnetic nanoparticles for biomedical applications: possibilities and limitations of a new drug delivery system. J. Magn. Magn. Mater. 293, 483 (2005)

    Article  CAS  Google Scholar 

  25. del Campo, A., Sen, T., Lellouche, J.P., Bruce, I.J.: Multifunctional magnetite and silica–magnetite nanoparticles: synthesis, surface activation and applications in life sciences. J. Magn. Magn. Mater. 293, 33–40 (2005)

    Article  Google Scholar 

  26. Saiyed, Z.M., Sharma, S., Godawat, R., Telang, S.D., Ramchand, C.N.: Activity and stability of alkaline phosphatase (ALP) immobilized onto magnetic nanoparticles (Fe3O4). J. Biotechnol. 131, 240–244 (2007)

    Article  CAS  Google Scholar 

  27. Ozcan, F., Ersoz, M., Yilmaz, M.: Preparation and application of calix[4]arene-grafted magnetite nanoparticles for removal of dichromate anions. Mater. Sci. Eng. C 29, 2378–2383 (2009)

    Article  CAS  Google Scholar 

  28. Sayin, S., Ozcan, F., Yilmaz, M.: Synthesis and evaluation of chromate and arsenate anions extraction ability of a N-methylglucamine derivative of calix[4]arene immobilized onto magnetic nanoparticles. J. Hazard. Mater. 178, 312–319 (2010)

    Article  CAS  Google Scholar 

  29. Sayin, S., Ozcan, F., Yilmaz, M., Tor, A., Memon, S., Cengeloglu, Y.: Synthesis of calix[4]arene-grafted magnetite nanoparticles and evaluation of their arsenate as well as dichromate removal efficiency. Clean-soil Air Water 38, 639–648 (2010)

    CAS  Google Scholar 

  30. Gutsche, C.D., Iqbal, M., Stewart, D.: Calixarenes. 19. Syntheses procedures for p-tert-butylcalix[4]arene. J. Org. Chem. 51, 742–745 (1986)

    Article  CAS  Google Scholar 

  31. Collins, M., McKervey, M.A., Madigan, E., Moran, M.B., Owens, M., Ferguson, G., Harris, S.J.: Chemically modified calix[4]arenes. Regioselective synthesis of 1,3-(distal) derivatives and related compounds. X-Ray crystal structure of a diphenol-dinitrile. J. Chem. Soc. Perkin. Trans. 1, 3137–3142 (1991)

    Article  Google Scholar 

  32. Chawla, H.M., Pant, N., Srivastava, B., Upreti, S.: Convenient direct synthesis of bisformylated calix[4]arenes via ipso substitution. Org. Lett. 8, 2237–2240 (2006)

    Article  CAS  Google Scholar 

  33. Niazi, A., Ghasemi, N., Goodarzi, M., Ebadi, A.: Simultaneous spectrophotometric determination of uranium and thorium using arsenazo III by H-point standard addition method and partial least squares regression. J. Chin. Chem. Soc. 54, 411–418 (2007)

    CAS  Google Scholar 

  34. Pedersen, C.J.: Ionic complexes of macrocyclic polyethers. Fed. Proc. Am. Soc. Exp. Biol. 27, 1305 (1968)

    CAS  Google Scholar 

  35. Bozkurt, S., Karakucuk, A., Sirit, A., Yilmaz, M.: Synthesis of two calix[4]arene diamide derivatives for extraction of chromium(VI). Tetrahedron 61, 10443–10448 (2005)

    Article  CAS  Google Scholar 

  36. Bayrakci, M., Ertul, S., Yilmaz, M.: Synthesis of di-substituted calix[4]arene-based receptors for extraction of chromate and arsenate anions. Tetrahedron 65, 7963–7968 (2009)

    Article  CAS  Google Scholar 

  37. Tabakci, M., Memon, S., Yilmaz, M.: Synthesis and extraction properties of new ‘proton-switchable’ tri- and tetra-substituted calix[4]arene derivatives bearing pyridinium units. Tetrahedron 63, 6861–6865 (2007)

    Article  CAS  Google Scholar 

  38. Bozkurt, S., Kocabas, E., Durmaz, M., Yilmaz, M., Sirit, A.: Synthesis and dichromate anion sorption of silica gel-immobilized calix[4]arenas. J. Hazard. Mater. 165, 974–979 (2009)

    Article  CAS  Google Scholar 

  39. Memon, G.Z., Bhanger, M.I., Akhtar, M.: The removal efficiency of chestnut shells for selected pesticides from aqueous solutions. J. Colloid Interface Sci. 315, 33–40 (2007)

    Article  CAS  Google Scholar 

  40. Selvi, K., Pattabhi, S., Kadirvelu, K.: Removal of Cr(VI) from aqueous solution by adsorption onto activated carbon. Bioresour. Technol. 80, 87–89 (2001)

    Article  CAS  Google Scholar 

  41. Garg, V.K., Gupta, R., Kumar, R., Gupta, R.K.: Adsorption of chromium from aqueous solution on treated sawdust. Bioresour. Technol. 92, 79–81 (2004)

    Article  CAS  Google Scholar 

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Acknowledgment

We thank the Scientific Research Projects Foundation of Selcuk University (SUBAP Grant Number 2009-09201148) for financial support of this work produced from a part of E. Akoz’s M.Sc. Thesis.

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  1. Department of Chemistry, Selcuk University, 42031, Konya, Turkey

    Enise Akoz, Serkan Erdemir & Mustafa Yilmaz

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  1. Enise Akoz
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  2. Serkan Erdemir
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  3. Mustafa Yilmaz
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Correspondence to Mustafa Yilmaz.

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Akoz, E., Erdemir, S. & Yilmaz, M. Immobilization of novel the semicarbazone derivatives of calix[4]arene onto magnetite nanoparticles for removal of Cr(VI) ion. J Incl Phenom Macrocycl Chem 73, 449–458 (2012). https://doi.org/10.1007/s10847-011-0083-7

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