Abstract
In this study, we have reported the synthesis of new amino-substituted p-tert-butylcalix[4]arene (3) and its application for the removal of two carcinogenic azo dyes, i.e., Chicago Sky Blue (CSB) and Tropaeolin 000 (TP) from aqueous environment. The newly synthesized calix–ligand 3 is characterized by FT-IR and 1H NMR spectroscopy as well as elemental analysis. The extraction efficiency of newly calix–ligand 3 for CSB and TP dyes from aqueous media was evaluated through liquid–liquid extraction experiments. The newly synthesized calix–ligand 3 showed outstanding extraction percentage and maximum percent extraction, i.e., 97 and 96 % of CSB and TP dyes was achieved at pH 9, respectively. During the extraction process, effect of various parameters was monitored and found that extraction is highly dependent on pH and salinity. Moreover, cyclic structure, cavity size, functional groups of the calixarene derivative, hydrophobicity, and the ionic property of guest molecules also affect the extraction efficiency. The comparative data prop up calix–ligand 3 as an effective extractant for both CSB and TP dyes.
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Ahmad, A. L., Puasa, S. W., & Zulkali, M. M. D. (2006). Micellar-enhanced ultrafiltration for removal of reactive dyes from an aqueous solution. Desalination, 191, 153–161.
Akceylan, E., Bahadir, M., & Yilmaz, M. (2009). Removal efficiency of a calix[4]arene-based polymer for water-soluble carcinogenic direct azo dyes and aromatic amines. Journal of Hazardous Materials, 162, 960–966.
Ali, H. (2010). Biodegradation of synthetic dyes—a review. Water, Air, & Soil Pollution, 213, 251–273.
Anbia, M., & Salehi, S. (2012). Removal of acid dyes from aqueous media by adsorption onto amino-functionalized nanoporous silica SBA-3. Dyes and Pigments, 94, 1–9.
Golka, K., Kopps, S., & Myslak, Z. W. (2004). Carcinogenicity of azo colorants: influence of solubility and bioavailability. Toxicology Letters, 151, 203–210.
Grierson, S. (1989). Dyeing and dyestuffs. Aylesbury: Shire Album 229, Shire Publications Ltd.
Gungor, O., Memon, S., Yilmaz, A., & Yilmaz, M. (2008). Evaluation of the performance of calix[8]arene derivatives as liquid phase extraction material for the removal of azo dyes. Journal of Hazardous Materials, 158, 202–207.
Gupta, V. K., & Suhas. (2009). Application of low-cost adsorbents for dye removal—a review. Journal of Environmental Management, 90, 2313–2342.
Gutsche, C. D., & Lin, L. G. (1986). The synthesis of functionalized, calixarenes. Tetrahedron, 42, 1633–1640.
Harrelkas, F., Paulo, A., Alves, M. M., El, K. L., Zahraa, O., Pons, M. N., et al. (2008). Photocatalytic and combined anaerobic–photocatalytic treatment of textile dyes. Chemosphere, 72, 1816–1822.
Harrelkas, F., Azizi, A., Yaacoubi, A., Benhammou, A., & Pons, M. N. (2009). Treatment of textile dye effluents using coagulation–flocculation coupled with membrane processes or adsorption on powdered activated carbon. Desalination, 235, 330–339.
Jain, R., & Shrivastava, M. (2008). Adsorptive studies of hazardous dye Tropaeoline 000 from an aqueous phase on to coconut-husk. Journal of Hazardous Materials, 158, 549–556.
Kalyani, D. C., Telke, A. A., Dhanve, R. S., & Jadhav, J. P. (2009). Eco-friendly biodegradation and detoxification of Reactive Red 2 textile dye by newly isolated Pseudomonas sp. SUK1. Journal of Hazardous Materials, 163, 735–742.
Kamboh, M. A., Solangi, I. B., Sherazi, S. T. H., & Memon, S. (2011a). Sorption of congo red onto p-tert-butylcalix[4]arene based silica resin. Journal of the Iranian Chemical Society, 8, 272–279.
Kamboh, M. A., Solangi, I. B., Sherazi, S. T. H., & Memon, S. (2011b). A highly efficient calix[4]arene based resin for the removal of azo-dyes. Desalination, 268, 83–89.
Kamboh, M. A., Solangi, I. B., Sherazi, S. T. H., & Memon, S. (2011c). Synthesis and application of p-tert-butylcalix[8]arene immobilized material for the removal of azo dyes. Journal of Hazardous Materials, 186, 651–655.
Karagoz, B., Bayramoglu, G., Altintas, N., Bicak, & Arica, M. Y. (2011). Amine functional monodisperse microbeads via precipitation polymerization of N-vinyl formamide: immobilized laccase for benzidine based dyes degradation. Bioresource Technology, 102, 6783–6790.
Kazakova, E. K., Morozova, J. E., Mironova, D. A., & Konovalov, A. I. (2012). Sorption of azo dyes from aqueous solutions by tetradodecyloxybenzylcalix[4]resorcinarene derivatives. Journal of Inclusion Phenomena and Macrocyclic Chemistry. doi:10.1007/s10847-011-0075-7.
Kurniawan, A., Sutiono, H., Indraswati, N., & Ismadji, S. (2012). Removal of basic dyes in binary system by adsorption using rarasaponin–bentonite: revisited of extended Langmuir model. Chemical Engineering Journal, 189, 264–274.
Muthuraman, G. (2011). Extractive removal of astacryl blue BG and astacryl golden yellow dyes from aqueous solutions by liquid–liquid extraction. Desalination, 277, 308–312.
Ozmen, E. Y., Erdemir, S., Yilmaz, M., & Bahadir, M. (2007). Removal of carcinogenic direct azo dyes from aqueous solutions using calix[n]arene derivatives. Clean, 35, 612–616.
Przystaś, W., Godlewska, E. Z., & Sota, E. G. (2012). Biological removal of azo and triphenylmethane dyes and toxicity of process by-products. Water, Air, & Soil Pollution, 223, 1581–1592.
Río, A. I. D., Fernández, J., Molina, J., Bonastre, J., & Cases, F. (2011). Electrochemical treatment of a synthetic wastewater containing a sulphonated azo dye. Determination of naphthalenesulphonic compounds produced as main by-products. Desalination, 273, 428–435.
Santos, V. P., Pereira, M. F. R., Faria, P. C. C., & Orfao, J. J. M. (2009). Decolorisation of dye solutions by oxidation with H2O2 in the presence of modified activated carbons. Journal of Hazardous Materials, 162, 736–742.
Saratale, R. G., Saratale, G. D., Chang, J. S., & Govindwar, S. P. (2011). Bacterial decolorization and degradation of azo dyes: a review. Journal of the Taiwan Institute of Chemical Engineers, 42, 138–157.
Sayin, S., & Yilmaz, M. (2011). Synthesis of a new calixarene derivative and its immobilization onto magnetic nanoparticle surfaces for excellent extractants toward Cr(VI), As(V), and U(VI). Journal of Chemical & Engineering Data, 56, 2020–2029.
Sayin, S., Ozcan, F., Memon, S., & Yilmaz, M. (2010). Synthesis and oxoanions (dichromate/arsenate) sorption study of N-methylglucamine derivative of calix[4]arene immobilized onto poly[(phenyl glycidyl ether)-co-formaldehyde]. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 67, 385–391.
Shobhana, K., Menon, R. V., Patel, J. G., & Panchal. (2011). The synthesis and characterization of calix[4]arene based azo dyes. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 67, 73–79.
Sponza, D. T. (2006). Toxicity studies in a chemical dye production industry in Turkey. Journal of Hazardous Materials, A138, 438–447.
Verma, A. K., Raghukumar, C., Parvatkar, R. R., & Naik, C. G. (2012). A rapid two-step bioremediation of the anthraquinone dye, Reactive Blue 4 by a marine-derived fungus. Water, Air, & Soil Pollution, 223, 3499–3509.
Vijayaraghavan, R., Vedaraman, N., Surianarayanan, M., & MacFarlane, D. R. (2006). Extraction and recovery of azo dyes into an ionic liquid. Talanta, 69, 1059–1062.
Welham, A. (2000). The theory of dyeing (and the secret of life). Journal of the Society of Dyers and Colourists, 116, 140–143.
Yilmaz, M., Memon, S., Tabakci, M., & Bartsch, R. A. (2006). Design of polymer appended calixarenes as ion carriers. In R. K. Bregg (Ed.), New frontiers in polymer research (pp. 125–172). Commack: Nova.
Yilmaz, A., Yilmaz, E., Yilmaz, M., & Bartsch, R. A. (2007). Removal of azo dyes from aqueous solutions using calix[4]arene and β-cyclodextrin. Dyes and Pigments, 74, 54–59.
Yilmaz, E., Memon, S., & Yilmaz, M. (2010). Removal of direct azo dyes and aromatic amines from aqueous solutions using two β-cyclodextrin-based polymers. Journal of Hazardous Materials, 174, 592–597.
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We would like to thank The Scientific and Technological Research Council of Turkey (2216 Research Fellowship Programme For Foreign Citizens) and the Research Foundation of Selcuk University (BAP) for the financial support of this work.
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Kamboh, M.A., Akoz, E., Memon, S. et al. Synthesis of Amino-Substituted p-tert-Butylcalix[4]arene for the Removal of Chicago Sky Blue and Tropaeolin 000 Azo Dyes from Aqueous Environment. Water Air Soil Pollut 224, 1424 (2013). https://doi.org/10.1007/s11270-012-1424-x
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DOI: https://doi.org/10.1007/s11270-012-1424-x