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Investigation of extraction properties of calix[4]arene dinitro derivative supported in merrifield resin towards phenolic species in aqueous media

Year 2020, Volume: 8 Issue: 1, 60 - 70, 05.03.2020
https://doi.org/10.36306/konjes.577216

Abstract

This article describes the preparation of calix[4]arene dinitro derivative supported in Merrifield resin (DNC[4]MR) and the investigation of its extraction properties towards some phenolic species such as phenol (PHE), p-chlorophenol (PCP), m-nitrophenol (MNP) and p-nitrophenol (PNP) which are important organic contaminants in aqueous media. Synthesized compounds were characterized by FT-IR analysis. According to results, % extraction values of phenolic species above mentioned were found 24,3, 40,5, 62,4 ve 65,9 %, respectively. Additionally, the extraction properties of DNK[4]MR were investigated towards phenolic species towards different concentrations. Finally, the extraction properties of DNK[4]MR were also evaluated for different concentrations of the ligand. Extraction equilibrium constants were calculated by log D vs. log [L] graphs. Consequently, according to both literature and this study, calixarene derivatives which have a unique three-dimensional structure and hydrogen bonding capabilities can be useful for removal of phenolic species from aqueous media.

References

  • Abay, İ., Denizli, A., Bişkin, E. ve Salih, B., 2005, Removal and pre-concentration of phenolic species onto β-cyclodextrin modified poly(hydroxyethylmethacrylate–ethyleneglycoldimethacrylate) microbeads, Chemosphere, 61 (9), 1263-1272.
  • Akpinar, M., Temel, F., Tabakci, B., Ozcelik, E. ve Tabakci, M., 2019, A phenyl glycinol appended calix[4]arene film for chiral detection of ascorbic acid on gold surface, Analytical Biochemistry, 583, 113373.
  • Al-Asheh, S., Banat, F. ve Abu-Aitah, L., 2003, Adsorption of phenol using different types of activated bentonites, Separation and Purification Technology, 33 (1), 1-10.
  • Aladağlı, V., Temel, F. ve Tabakcı, M., 2015, Removal of p-nitrophenol from aqueous solutions using aminopropyl silica gel-immobilized calix[4]arene polymer (C[4]APS), Anadolu University Journal of Science and Technology-A Applied Sciences and Engineering, 16 (2), 155.
  • Azzouz, A., Kailasa, S. K., Lee, S. S., J. Rascón, A., Ballesteros, E., Zhang, M. ve Kim, K.-H., 2018, Review of nanomaterials as sorbents in solid-phase extraction for environmental samples, TrAC Trends in Analytical Chemistry, 108, 347-369.
  • Banat, F. A., Al-Bashir, B., Al-Asheh, S. ve Hayajneh, O., 2000, Adsorption of phenol by bentonite, Environmental Pollution, 107 (3), 391-398.
  • Brinda L., A., Balasubramanian, A. ve Venkatesan, S., 2013, Extraction of phenol and chlorophenols using ionic liquid [Bmim]+[BF4]− dissolved in tributyl phosphate, CLEAN – Soil, Air, Water, 41 (4), 349-355.
  • Castillo, M., Puig, D. ve Barcelo´, D., 1997, Determination of priority phenolic compounds in water and industrial effluents by polymeric liquid-solid extraction cartridges using automated sample preparation with extraction columns and liquid chromatography use of liquid-solid extraction cartridges for stabilization of phenols, Journal of Chromatography A, 778 (1), 301-311.
  • Caturla, F., Martín-Martínez, J. M., Molina-Sabio, M., Rodriguez-Reinoso, F. ve Torregrosa, R., 1988, Adsorption of substituted phenols on activated carbon, Journal of Colloid and Interface Science, 124 (2), 528-534.
  • Cesari, L., Canabady-Rochelle, L. ve Mutelet, F., 2017, Extraction of phenolic compounds from aqueous solution using choline bis(trifluoromethylsulfonyl)imide, Fluid Phase Equilibria, 446, 28-35.
  • Chaouchi, S. ve Hamdaoui, O., 2014, Extraction of priority pollutant 4-nitrophenol from water by emulsion liquid membrane: emulsion stability, effect of operational conditions and membrane reuse, Journal of Dispersion Science and Technology, 35 (9), 1278-1288.
  • Dolaksiz, Y. E., Temel, F. ve Tabakci, M., 2018, Adsorption of phenolic compounds onto calix[4]arene-bonded silica gels from aqueous solutions, Reactive and Functional Polymers, 126, 27-35.
  • Erdemir, S., Tabakci, B. ve Tabakci, M., 2016, A highly selective fluorescent sensor based on calix[4]arene appended benzothiazole units for Cu2+, S2− and HSO4− ions in aqueous solution, Sensors and Actuators B: Chemical, 228, 109-116.
  • Gutsche, C. D. ve Iqbal, M., 1990, p-tert-Butylcalix[4]arene, Organic Syntheses, 68, 234.
  • Gutsche, C. D., 1998, Calixarenes revisited, Royal Society of Chemistry, p. 1-9.
  • He, X., Wu, Z., Sun, Z., Wei, X., Wu, Z., Ge, X. ve Cravotto, G., 2018, A novel hybrid of β-cyclodextrin grafted onto activated carbon for rapid adsorption of naphthalene from aqueous solution, Journal of Molecular Liquids, 255, 160-167.
  • Li, J.-M., Meng, X.-G., Hu, C.-W. ve Du, J., 2009, Adsorption of phenol, p-chlorophenol and p-nitrophenol onto functional chitosan, Bioresource Technology, 100 (3), 1168-1173.
  • Memon, S., Akceylan, E., Sap, B., Tabakci, M., Roundhill, D. M. ve Yilmaz, M., 2003, Polymer supported calix[4]arene derivatives for the extraction of metals and dichromate anions, Journal of Polymers and the Environment, 11 (2), 67-74.
  • Memon, S., Tabakci, M., Roundhill, D. M. ve Yilmaz, M., 2006, Synthesis and evaluation of the Cr(VI) extraction ability of amino/nitrile calix[4]arenes immobilized onto a polymeric backbone, Reactive and Functional Polymers, 66 (11), 1342-1349.
  • Nayak, P. S. ve Singh, B. K., 2007, Removal of phenol from aqueous solutions by sorption on low cost clay, Desalination, 207 (1), 71-79.
  • Ozcelik, E., Temel, F., Erdemir, S., Tabakci, B. ve Tabakci, M., 2019a, QCM sensors coated with calix[4]arenes bearing sensitive chiral moieties for chiral discrimination of 1-phenylethylamine enantiomers, Journal of Inclusion Phenomena and Macrocyclic Chemistry.
  • Ozcelik, E., Temel, F. ve Tabakcı, M., 2019b, Kaliksaren türevi immobilize edilmiş merrifield reçinesi ile kaplı QCM sensöründe sulu ortamda 4-nitrofenol algılanması, Konya Mühendislik Bilimleri Dergisi, 7 (3), 595-603.
  • Pedersen, C. J., 1968, Ionic complexes of macrocyclic polyethers, Federation Proceedings, 27 (6), 1305-1309.
  • Rawajfih, Z. ve Nsour, N., 2006, Characteristics of phenol and chlorinated phenols sorption onto surfactant-modified bentonite, Journal of Colloid and Interface Science, 298 (1), 39-49.
  • Tabakci, M., Memon, S., Yilmaz, M. ve Max Roundhill, D., 2004, Synthesis and evaluation of extraction ability of calix[4]-crown-6 cone conformer and its oligomeric analogue, Reactive and Functional Polymers, 58 (1), 27-34.
  • Tabakci, M., Tabakci, B. ve Beduk, A. D., 2012, Synthesis and application of an efficient calix[4]arene-based anion receptor bearing imidazole groups for Cr(VI) anionic species, Tetrahedron, 68 (22), 4182-4186.
  • Tabakcı, M., 2008, Immobilization of calix[6]arene bearing carboxylic acid and amide groups on aminopropyl silica gel and its sorption properties for Cr(VI), Journal of Inclusion Phenomena and Macrocyclic Chemistry, 61 (1), 53-60.
  • Temel, F. ve Tabakcı, M., 2016, Calix[4]arene coated QCM sensors for detection of VOC emissions: Methylene chloride sensing studies, Talanta, 153, 221-227.
  • Temel, F., Erdemir, S., Ozcelik, E., Tabakci, B. ve Tabakci, M., 2019a, Rapid and real-time detection of arginine enantiomers by QCM sensor having a calix[4]arene receptor bearing asymmetric centers, Talanta, 204, 172-181.
  • Temel, F., Erdemir, S., Tabakci, B., Akpinar, M. ve Tabakci, M., 2019b, Selective chiral recognition of alanine enantiomers by chiral calix[4]arene coated quartz crystal microbalance sensors, Analytical and Bioanalytical Chemistry.
  • Temel, F., 2020a, One novel calix[4]arene based QCM sensor for sensitive, selective and high performance-sensing of formaldehyde at room temperature, Talanta, 211, 120725.
  • Temel, F., 2020b, Real-time and selective recognition of erythromycin by self-assembly of calix[4]arene on QCM sensor, Journal of Molecular Liquids, 297, 111818.
  • Temel, F., Turkyilmaz, M. ve Kucukcongar, S., 2020, Removal of methylene blue from aqueous solutions by silica gel supported calix[4]arene cage: Investigation of adsorption properties, European Polymer Journal, 125, 109540.
  • Wei, W., Yin, X.-B. ve He, X.-W., 2008, pH-mediated dual-cloud point extraction as a preconcentration and clean-up technique for capillary electrophoresis determination of phenol and m-nitrophenol, Journal of Chromatography A, 1202 (2), 212-215.
  • Yilmaz, A., Tabakci, B. ve Tabakci, M., 2009, New diamino derivatives of p-tert-butylcalix[4]arene for oxyanion recognition: synthesis and complexation studies, Supramolecular Chemistry, 21 (6), 435-441.
  • Zhu, L., Chen, B. ve Shen, X., 2000, Sorption of phenol, p-nitrophenol, and aniline to dual-cation organobentonites from water, Environmental Science & Technology, 34 (3), 468-475.

MERRIFIELD REÇİNESİNE DESTEKLENMİŞ KALİKS[4]AREN DİNİTRO TÜREVİNİN SULU ORTAMDAKİ FENOLİK TÜRLERE KARŞI EKSTRAKSİYON ÖZELLİKLERİNİN İNCELENMESİ

Year 2020, Volume: 8 Issue: 1, 60 - 70, 05.03.2020
https://doi.org/10.36306/konjes.577216

Abstract

Bu çalışmada, Merrifield reçinesine desteklenmiş kaliks[4]aren dinitro türevi (DNK[4]MR) hazırlanarak, sulu ortamda bulunan önemli organik kirleticilerden olan fenol (FEN), p-klorofenol (PKF), m-nitrofenol (MNF) ve p-nitrofenol (PNF) gibi bazı fenolik türlere karşı ekstraksiyon özellikleri incelendi. Sentezlenen bileşiklerin, FT-IR analizleri ile karakterizasyonları gerçekleştirildi. Sonuçlara göre, yukarıda bahsi geçen fenolik türlere karşı sırasıyla % 24,3, 40,5, 62,4 ve 65,9 ekstraksiyon verileri elde edildi. Ayrıca, farklı fenolik tür konsantrasyonlarına karşı DNK[4]MR'nin ekstraksiyon özellikleri incelendi. Son olarak, DNK[4]MR'nin fenolik türlere karşı ekstraksiyon kabiliyetlerinin ayrıntılı bir şekilde incelenmesi için farklı konsantrasyonlarda ligand çözeltileri hazırlanarak log D'ye karşı log [L] grafiği çizilerek etkileşim sonucu oluşan ekstraksiyon denge sabitleri (Kex) hesaplandı. Hem literatür bilgileri hem de yapılan bu çalışmanın sonuçlarına göre, kaliksaren türevlerinin kendisine özgü üç boyutlu yapısı ve hidrojen bağı yapabilme kabiliyetleri sayesinde, fenolik türlerin sulu ortamlardan uzaklaştırılması konusunda oldukça kullanışlı olabileceklerini göstermiştir.

References

  • Abay, İ., Denizli, A., Bişkin, E. ve Salih, B., 2005, Removal and pre-concentration of phenolic species onto β-cyclodextrin modified poly(hydroxyethylmethacrylate–ethyleneglycoldimethacrylate) microbeads, Chemosphere, 61 (9), 1263-1272.
  • Akpinar, M., Temel, F., Tabakci, B., Ozcelik, E. ve Tabakci, M., 2019, A phenyl glycinol appended calix[4]arene film for chiral detection of ascorbic acid on gold surface, Analytical Biochemistry, 583, 113373.
  • Al-Asheh, S., Banat, F. ve Abu-Aitah, L., 2003, Adsorption of phenol using different types of activated bentonites, Separation and Purification Technology, 33 (1), 1-10.
  • Aladağlı, V., Temel, F. ve Tabakcı, M., 2015, Removal of p-nitrophenol from aqueous solutions using aminopropyl silica gel-immobilized calix[4]arene polymer (C[4]APS), Anadolu University Journal of Science and Technology-A Applied Sciences and Engineering, 16 (2), 155.
  • Azzouz, A., Kailasa, S. K., Lee, S. S., J. Rascón, A., Ballesteros, E., Zhang, M. ve Kim, K.-H., 2018, Review of nanomaterials as sorbents in solid-phase extraction for environmental samples, TrAC Trends in Analytical Chemistry, 108, 347-369.
  • Banat, F. A., Al-Bashir, B., Al-Asheh, S. ve Hayajneh, O., 2000, Adsorption of phenol by bentonite, Environmental Pollution, 107 (3), 391-398.
  • Brinda L., A., Balasubramanian, A. ve Venkatesan, S., 2013, Extraction of phenol and chlorophenols using ionic liquid [Bmim]+[BF4]− dissolved in tributyl phosphate, CLEAN – Soil, Air, Water, 41 (4), 349-355.
  • Castillo, M., Puig, D. ve Barcelo´, D., 1997, Determination of priority phenolic compounds in water and industrial effluents by polymeric liquid-solid extraction cartridges using automated sample preparation with extraction columns and liquid chromatography use of liquid-solid extraction cartridges for stabilization of phenols, Journal of Chromatography A, 778 (1), 301-311.
  • Caturla, F., Martín-Martínez, J. M., Molina-Sabio, M., Rodriguez-Reinoso, F. ve Torregrosa, R., 1988, Adsorption of substituted phenols on activated carbon, Journal of Colloid and Interface Science, 124 (2), 528-534.
  • Cesari, L., Canabady-Rochelle, L. ve Mutelet, F., 2017, Extraction of phenolic compounds from aqueous solution using choline bis(trifluoromethylsulfonyl)imide, Fluid Phase Equilibria, 446, 28-35.
  • Chaouchi, S. ve Hamdaoui, O., 2014, Extraction of priority pollutant 4-nitrophenol from water by emulsion liquid membrane: emulsion stability, effect of operational conditions and membrane reuse, Journal of Dispersion Science and Technology, 35 (9), 1278-1288.
  • Dolaksiz, Y. E., Temel, F. ve Tabakci, M., 2018, Adsorption of phenolic compounds onto calix[4]arene-bonded silica gels from aqueous solutions, Reactive and Functional Polymers, 126, 27-35.
  • Erdemir, S., Tabakci, B. ve Tabakci, M., 2016, A highly selective fluorescent sensor based on calix[4]arene appended benzothiazole units for Cu2+, S2− and HSO4− ions in aqueous solution, Sensors and Actuators B: Chemical, 228, 109-116.
  • Gutsche, C. D. ve Iqbal, M., 1990, p-tert-Butylcalix[4]arene, Organic Syntheses, 68, 234.
  • Gutsche, C. D., 1998, Calixarenes revisited, Royal Society of Chemistry, p. 1-9.
  • He, X., Wu, Z., Sun, Z., Wei, X., Wu, Z., Ge, X. ve Cravotto, G., 2018, A novel hybrid of β-cyclodextrin grafted onto activated carbon for rapid adsorption of naphthalene from aqueous solution, Journal of Molecular Liquids, 255, 160-167.
  • Li, J.-M., Meng, X.-G., Hu, C.-W. ve Du, J., 2009, Adsorption of phenol, p-chlorophenol and p-nitrophenol onto functional chitosan, Bioresource Technology, 100 (3), 1168-1173.
  • Memon, S., Akceylan, E., Sap, B., Tabakci, M., Roundhill, D. M. ve Yilmaz, M., 2003, Polymer supported calix[4]arene derivatives for the extraction of metals and dichromate anions, Journal of Polymers and the Environment, 11 (2), 67-74.
  • Memon, S., Tabakci, M., Roundhill, D. M. ve Yilmaz, M., 2006, Synthesis and evaluation of the Cr(VI) extraction ability of amino/nitrile calix[4]arenes immobilized onto a polymeric backbone, Reactive and Functional Polymers, 66 (11), 1342-1349.
  • Nayak, P. S. ve Singh, B. K., 2007, Removal of phenol from aqueous solutions by sorption on low cost clay, Desalination, 207 (1), 71-79.
  • Ozcelik, E., Temel, F., Erdemir, S., Tabakci, B. ve Tabakci, M., 2019a, QCM sensors coated with calix[4]arenes bearing sensitive chiral moieties for chiral discrimination of 1-phenylethylamine enantiomers, Journal of Inclusion Phenomena and Macrocyclic Chemistry.
  • Ozcelik, E., Temel, F. ve Tabakcı, M., 2019b, Kaliksaren türevi immobilize edilmiş merrifield reçinesi ile kaplı QCM sensöründe sulu ortamda 4-nitrofenol algılanması, Konya Mühendislik Bilimleri Dergisi, 7 (3), 595-603.
  • Pedersen, C. J., 1968, Ionic complexes of macrocyclic polyethers, Federation Proceedings, 27 (6), 1305-1309.
  • Rawajfih, Z. ve Nsour, N., 2006, Characteristics of phenol and chlorinated phenols sorption onto surfactant-modified bentonite, Journal of Colloid and Interface Science, 298 (1), 39-49.
  • Tabakci, M., Memon, S., Yilmaz, M. ve Max Roundhill, D., 2004, Synthesis and evaluation of extraction ability of calix[4]-crown-6 cone conformer and its oligomeric analogue, Reactive and Functional Polymers, 58 (1), 27-34.
  • Tabakci, M., Tabakci, B. ve Beduk, A. D., 2012, Synthesis and application of an efficient calix[4]arene-based anion receptor bearing imidazole groups for Cr(VI) anionic species, Tetrahedron, 68 (22), 4182-4186.
  • Tabakcı, M., 2008, Immobilization of calix[6]arene bearing carboxylic acid and amide groups on aminopropyl silica gel and its sorption properties for Cr(VI), Journal of Inclusion Phenomena and Macrocyclic Chemistry, 61 (1), 53-60.
  • Temel, F. ve Tabakcı, M., 2016, Calix[4]arene coated QCM sensors for detection of VOC emissions: Methylene chloride sensing studies, Talanta, 153, 221-227.
  • Temel, F., Erdemir, S., Ozcelik, E., Tabakci, B. ve Tabakci, M., 2019a, Rapid and real-time detection of arginine enantiomers by QCM sensor having a calix[4]arene receptor bearing asymmetric centers, Talanta, 204, 172-181.
  • Temel, F., Erdemir, S., Tabakci, B., Akpinar, M. ve Tabakci, M., 2019b, Selective chiral recognition of alanine enantiomers by chiral calix[4]arene coated quartz crystal microbalance sensors, Analytical and Bioanalytical Chemistry.
  • Temel, F., 2020a, One novel calix[4]arene based QCM sensor for sensitive, selective and high performance-sensing of formaldehyde at room temperature, Talanta, 211, 120725.
  • Temel, F., 2020b, Real-time and selective recognition of erythromycin by self-assembly of calix[4]arene on QCM sensor, Journal of Molecular Liquids, 297, 111818.
  • Temel, F., Turkyilmaz, M. ve Kucukcongar, S., 2020, Removal of methylene blue from aqueous solutions by silica gel supported calix[4]arene cage: Investigation of adsorption properties, European Polymer Journal, 125, 109540.
  • Wei, W., Yin, X.-B. ve He, X.-W., 2008, pH-mediated dual-cloud point extraction as a preconcentration and clean-up technique for capillary electrophoresis determination of phenol and m-nitrophenol, Journal of Chromatography A, 1202 (2), 212-215.
  • Yilmaz, A., Tabakci, B. ve Tabakci, M., 2009, New diamino derivatives of p-tert-butylcalix[4]arene for oxyanion recognition: synthesis and complexation studies, Supramolecular Chemistry, 21 (6), 435-441.
  • Zhu, L., Chen, B. ve Shen, X., 2000, Sorption of phenol, p-nitrophenol, and aniline to dual-cation organobentonites from water, Environmental Science & Technology, 34 (3), 468-475.
There are 36 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Research Article
Authors

Farabi Temel

Publication Date March 5, 2020
Submission Date June 12, 2019
Acceptance Date August 16, 2019
Published in Issue Year 2020 Volume: 8 Issue: 1

Cite

IEEE F. Temel, “MERRIFIELD REÇİNESİNE DESTEKLENMİŞ KALİKS[4]AREN DİNİTRO TÜREVİNİN SULU ORTAMDAKİ FENOLİK TÜRLERE KARŞI EKSTRAKSİYON ÖZELLİKLERİNİN İNCELENMESİ”, KONJES, vol. 8, no. 1, pp. 60–70, 2020, doi: 10.36306/konjes.577216.