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.
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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)
Ferguson, J.E.: The Heavy Elements: Environment Impact and Health Effects. Pergamon Press, Oxford (1990)
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)
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)
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)
Hernandez-Cruz, L., Lapidus, G.T., Carrillo-Romo, F.: Modelling of nickel permeation through a supported liquid membrane. Hydrometallurgy 48(3), 265–276 (1998)
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)
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)
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)
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)
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)
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)
Danesi, P.R.: Separation of metal species by supported liquid membranes. Sep. Sci. Technol. 19(11–12), 857–894 (1984)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Gutsche, C.D., Nam, K.C.: Calixarenes. 22. Synthesis, properties, and metal complexation of aminocalixarenes. J. Am. Chem. Soc. 110(18), 6153–6162 (1988)
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)
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)
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)
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)
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)
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We would like to thank the Scientific and Technological Research Council of Turkey (TUBITAK Grant Number 215Z570) for financial support of this work.
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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
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DOI: https://doi.org/10.1007/s10847-018-0831-z