Skip to main content
Log in

Utilization of transport efficacy of novel calix[4]arene-embedded polymer inclusion membrane towards trace metals

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

In this study, 25,27-bis(3-mercaptopropoxyl)-26,28-dihydroxy calix[4]arene was successfully synthesized from the reaction of calix[4]arene-dialkylbromide derivative with thiourea. The structure of 25,27-bis(3-mercaptopropoxyl)-26,28-dihydroxy calix[4]arene was fully characterized using 1HNMR, 13CNMR and elemental analysis techniques. The obtained mercapto-substituted calix[4]arene derivative was employed as an additive material along with cellulose triacetate (CTA) and 2-nitrophenyl octyl ether (o-NPOE) for the preparation of a novel polymer inclusion membrane (C@PIM). The structure and surface morphology of mercapto-substituted calix[4]arene-embedded polymer inclusion membrane was determined using thermogravimetric analysis, scanning electron microscopy and elemental analysis techniques. Donnan dialysis system was also used to assess the transport efficacy of C@PIM towards Pb(II), Zn(II), Cu(II), Ni(II), Cd(II) and Co(II) ions. The results show that new C@PIM exhibited 99% transport efficacy but also selectivity toward Ni(II) and other ions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Habibi, S., Nematollahzadeh, A., Mousavi, S.A.: Nano-scale modification of polysulfone membrane matrix and the surface for the separation of chromium ions from water. Chem. Eng. J. 267, 306–316 (2015)

    Article  CAS  Google Scholar 

  2. Ferguson, J.E.: The Heavy Elements: Environment Impact and Health Effects. Pergamon Press, Oxford (1990)

    Google Scholar 

  3. Koseoglu, T.S., Kir, E., Ozkorucuklu, S.P., Karamizrak, E.: Preparation and characterization of P2FAn/PVDF composite cation-exchange membranes for the removal of Cr(III) and Cu(II) by Donnan dialysis. React. Funct. Polym. 70(11), 900–907 (2010)

    Article  CAS  Google Scholar 

  4. Kolev, S.D., Argiropoulos, G., Cattrall, R.W., Hamilton, I.C., Paimin, R.: Mathematical modelling of membrane extraction of gold(III) from hydrochloric acid solutions. J. Membr. Sci. 137(1–2), 261–269 (1997)

    Article  CAS  Google Scholar 

  5. Chitra, K.R., Gaikwad, A.G., Surender, G.D., Damodaran, A.D.: Studies on ion transport of some rare earth elements through solvating extractants immobilised on supported liquid membrane. J. Membr. Sci. 125(2), 257–268 (1997)

    Article  CAS  Google Scholar 

  6. Hernandez-Cruz, L., Lapidus, G.T., Carrillo-Romo, F.: Modelling of nickel permeation through a supported liquid membrane. Hydrometallurgy 48(3), 265–276 (1998)

    Article  CAS  Google Scholar 

  7. Alguacil, F.J., Coedo, A.G., Dorado, M.T., Padilla, I.: Phosphine oxide mediate transport: modelling of mass transfer in supported liquid membrane transport of gold (III) using Cyanex 923. Chem. Eng. Sci. 56(10), 3115–3122 (2001)

    Article  CAS  Google Scholar 

  8. Almeida, M.I.G.S., Cattrall, R.W., Kolev, S.D.: Recent trends in extraction and transport of metal ions using polymer inclusion membranes (PIMs). J. Membr. Sci. 415, 9–23 (2012)

    Article  CAS  Google Scholar 

  9. Almeida, M.I.G.S., Chan, C., Pettigrove, V.J., Cattrall, R.W., Kolev, S.D.: Development of a passive sampler for zinc(II) in urban pond waters using a polymer inclusion membrane. Environ. Pollut. 193, 233–239 (2014)

    Article  CAS  PubMed  Google Scholar 

  10. Belkhouche, N.E., Didi, M.A., Romero, R., Jonsson, J.A., Villemin, D.: Study of new organophosphorus derivates carriers on the selective recovery of M(II) and M(III) metals, using supported liquid membrane extraction. J. Memb. Sci. 284(1–2), 398–405 (2006)

    Article  CAS  Google Scholar 

  11. Benzal, G., Kumar, A., Delshams, A., Sastre, A.M.: Mathematical modelling and simulation of cotransport phenomena through flat sheet-supported liquid membranes. Hydrometallurgy 74(1–2), 117–130 (2004)

    Article  CAS  Google Scholar 

  12. Canet, L., Seta, P.: Extraction and separation of metal cations in solution by supported liquid membrane using lasalocid A as carrier. Pure Appl. Chem. 73(12), 2039–2046 (2001)

    Article  CAS  Google Scholar 

  13. Danesi, P.R.: Separation of metal species by supported liquid membranes. Sep. Sci. Technol. 19(11–12), 857–894 (1984)

    Article  CAS  Google Scholar 

  14. Garcia-Rodriguez, A., Matamoros, V., Kolev, S.D., Fontas, C.: Development of a polymer inclusion membrane (PIM) for the preconcentration of antibiotics in environmental water samples. J. Membr. Sci. 492, 32–39 (2015)

    Article  CAS  Google Scholar 

  15. Gherasim, C.V., Bourceanu, G., Olariu, R.I., Arsene, C.: A novel polymer inclusion membrane applied in chromium(VI) separation from aqueous solutions. J. Hazard. Mater. 197, 244–253 (2011)

    Article  CAS  PubMed  Google Scholar 

  16. Gherrou, A., Kerdjoudj, H.: Cyanide as a copper leaching agent for the remediation of fouling of a supported liquid membrane by formamidine disulphide in thiourea medium. Desalination 158(1–3), 195–200 (2003)

    Article  CAS  Google Scholar 

  17. Sgarlata, C., Arena, G., Longo, E., Zhang, D.M., Yang, Y.F., Bartsch, R.A.: Heavy metal separation with polymer inclusion membranes. J. Membr. Sci. 323(2), 444–451 (2008)

    Article  CAS  Google Scholar 

  18. Nghiem, L.D., Mornane, P., Potter, I.D., Perera, J.M., Cattrall, R.W., Kolev, S.D.: Extraction and transport of metal ions and small organic compounds using polymer inclusion membranes (PIMs). J. Membr. Sci. 281(1–2), 7–41 (2006)

    Article  CAS  Google Scholar 

  19. Vazquez, M.I., Romero, V., Fontas, C., Antico, E., Benavente, J.: Polymer inclusion membranes (PIMs) with the ionic liquid (IL) aliquat 336 as extractant: effect of base polymer and IL concentration on their physical-chemical and elastic characteristics. J. Membr. Sci. 455, 312–319 (2014)

    Article  CAS  Google Scholar 

  20. Cooper, C.A., Lin, Y.S., Gonzalez, M.: Separation properties of surface modified silica supported liquid membranes for divalent metal removal/recovery. J. Membr. Sci. 229(1–2), 11–25 (2004)

    Article  CAS  Google Scholar 

  21. Bagheri, M., Mashhadizadeh, M.H., Razee, S.: Solid phase extraction of gold by sorption on octadecyl silica membrane disks modified with pentathia-15-crown-5 and determination by AAS. Talanta 60(4), 839–844 (2003)

    Article  CAS  PubMed  Google Scholar 

  22. Bozkurt, S., Yilmaz, M., Sirit, A.: Chiral calix[4]arenes bearing amino alcohol functionality as membrane carriers for transport of chiral amino acid methylesters and mandelic acid. Chirality 24(2), 129–136 (2012)

    Article  CAS  PubMed  Google Scholar 

  23. Nisola, G.M., Cho, E., Beltran, A.B., Han, M., Kim, Y., Chung, W.J.: Dye/water separation through supported liquid membrane extraction. Chemosphere 80(8), 894–900 (2010)

    Article  CAS  PubMed  Google Scholar 

  24. Rovira, M., Sastre, A.M.: Modelling of mass transfer in facilitated supported liquid-membrane transport of palladium(II) using di-(2-ethylhexyl) thiophosphoric acid. J. Membr. Sci. 149(2), 241–250 (1998)

    Article  CAS  Google Scholar 

  25. Gutsche, C.D., Nam, K.C.: Calixarenes. 22. Synthesis, properties, and metal complexation of aminocalixarenes. J. Am. Chem. Soc. 110(18), 6153–6162 (1988)

    Article  CAS  PubMed  Google Scholar 

  26. Vanloon, J.D., Arduini, A., Coppi, L., Verboom, W., Pochini, A., Ungaro, R., Harkema, S., Reinhoudt, D.N.: Selective functionalization of calix[4]arenes at the upper rim. J. Org. Chem. 55(21), 5639–5646 (1990)

    Article  CAS  Google Scholar 

  27. Demirtas, H.N., Bozkurt, S., Durmaz, M., Yilmaz, M., Sirit, A.: Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives. Tetrahedron 65(15), 3014–3018 (2009)

    Article  CAS  Google Scholar 

  28. Kurzatkowska, K., Sayin, S., Yilmaz, M., Radecka, H., Radecki, J.: Calix[4]arene derivatives as dopamine hosts in electrochemical sensors. Sens. Actuators B 218, 111–121 (2015)

    Article  CAS  Google Scholar 

  29. Akin, S., Gulen, M., Sayin, S., Azak, H., Yildiz, H.B., Sonmezoglu, S.: Modification of photoelectrode with thiol-functionalized calix[4]arenes as interface energy barrier for high efficiency in dye-sensitized solar cells. J Power Sources 307, 796–805 (2016)

    Article  CAS  Google Scholar 

  30. Zawierucha, I., Kozlowski, C., Malina, G.: Removal of toxic metal ions from landfill leachate by complementary sorption and transport across polymer inclusion membranes. Waste Manage. 33(10), 2129–2136 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We would like to thank the Scientific and Technological Research Council of Turkey (TUBITAK Grant Number 215Z570) for financial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mehmet Soner Engin.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Engin, M.S., Sayin, S. & Cay, S. Utilization of transport efficacy of novel calix[4]arene-embedded polymer inclusion membrane towards trace metals. J Incl Phenom Macrocycl Chem 92, 173–179 (2018). https://doi.org/10.1007/s10847-018-0831-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-018-0831-z

Keywords

Navigation