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Removal of p-Nitrophenol from Aqueous Solutions by Calixarene based Graphene Oxide

Year 2021, Volume: 9 , 79 - 90, 30.12.2021
https://doi.org/10.36306/konjes.1013091

Abstract

In this study, calix[4]arene-based graphene oxide (GO-Epoxy-C[4]CN) was synthesized using graphene oxide (GO), which was obtained from graphite powder by the Hummers method. After GO preparation, it was reacted by (3-glycidyloxypropyl)trimethoxysilane (GPTMS) to get its epoxy (GO-Epoxy). Then, GO-Epoxy-C[4]CN was obtained by immobilization of p-tert-butylcalix[4]arene nitrile derivative onto the GO-Epoxy. Characterizations of synthesized compounds were performed by 1H NMR and FTIR analysis. The obtained new adsorbent (GO-Epoxy-C[4]CN) was used for the removal of p-nitrophenol (PNP) from wastewater. First of all, comparison studies were carried out using adsorbent and starting compounds, and it was observed that it provided a very high efficiency with 81% adsorption efficiency compared to the others. Then, the effect of pH and concentration on adsorption was investigated. Hence, it was seen that the adsorption was more compatible with the Langmuir isotherm.

References

  • Abbas, M. N., Al-Madhhachi, A.-S. T. ve Esmael, S. A., 2019, Quantifying soil erodibility parameters due to wastewater chemicals International Journal of Hydrology Science and Technology, 9 (5), 550-568.
  • Akceylan, E., Erdemir, S., Özçelik, E. ve Tabakcı, B., 2021, Bazı fenolik kirliliklerin imidazol türevli kaliks[4]aren içeren manyetik nanopartiküller kullanarak sulu çözeltilerden uzaklaştırılması, Konya Journal of Engineering Sciences, 9 (2), 442-454.
  • 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.
  • Aydın, M. E. ve Özcan, S., 2005, Konya yeraltı sularında klorlu fenoller, Selçuk Üniversitesi Mühendislik, Bilim Ve Teknoloji Dergisi, 20 (1), 9-18.
  • Bai, L., Tajikfar, A., Tamjidi, S., Foroutan, R. ve Esmaeili, H., 2021, Synthesis of MnFe2O4@graphene oxide catalyst for biodiesel production from waste edible oil, Renewable Energy, 170, 426-437.
  • Batur, E., Baytar, O., Kutluay, S., Horoz, S. ve Şahin, Ö., 2021, A comprehensive new study on the removal of Pb (II) from aqueous solution by şırnak coal-derived char, Environ Technol, 42 (3), 505-520.
  • 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.
  • Collins, E. M., McKervey, M. A., Madigan, E., Moran, M. B., Owens, M., Ferguson, G. ve Harris, S. J., 1991, Chemically modified calix[4]arenes. Regioselective synthesis of 1,3-(distal) derivatives and related compounds. X-Ray crystal structure of a diphenol-dinitrile, Journal of the Chemical Society, Perkin Transactions 1 (12), 3137-3142.
  • Çiplak, Z., Yildiz, N. ve Çalimli, A., 2015, Investigation of Graphene/Ag Nanocomposites Synthesis Parameters for Two Different Synthesis Methods, Fullerenes, Nanotubes and Carbon Nanostructures, 23 (4), 361-370.
  • Dogan, M., Temel, F. ve Tabakci, M., 2020, High-Performance Adsorption of 4-Nitrophenol onto Calix[6]arene-Tethered Silica from Aqueous Solutions, Journal of Inorganic and Organometallic Polymers and Materials, 30 (10), 4191-4202.
  • 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.
  • Dun, Y. ve Zuo, Y., 2017, Preparation and characterization of a GPTMS/graphene coating on AA-2024 alloy, Applied Surface Science, 416, 492-502.
  • Gutsche, C. D. ve Iqbal, M., 1990, p-tert-butylcalix[4]arene, Organic Syntheses, 68, 234. Hummers, W. S. ve Offeman, R. E., 1958, Preparation of Graphitic Oxide, Journal of the American Chemical Society, 80 (6), 1339-1339.
  • Johra, F. T., Lee, J.-W. ve Jung, W.-G., 2014, Facile and safe graphene preparation on solution based platform, Journal of Industrial and Engineering Chemistry, 20 (5), 2883-2887.
  • Liao, C., Zhao, X.-R., Jiang, X.-Y., Teng, J. ve Yu, J.-G., 2020, Hydrothermal fabrication of novel three-dimensional graphene oxide-pentaerythritol composites with abundant oxygen-containing groups as efficient adsorbents, Microchemical Journal, 152, 104288.
  • Lu, M., Cheng, Y., Pan, S.-l. ve Wei, G.-y., 2016, Batch adsorption of p-nitrophenol by ZSM-11: equilibrium, kinetic, and thermodynamic studies, Desalination and Water Treatment, 57 (7), 3029-3036.
  • Mahugo-Santana, C., Sosa-Ferrera, Z., Torres-Padrón, M. E. ve Santana-Rodríguez, J. J., 2010, Analytical methodologies for the determination of nitroimidazole residues in biological and environmental liquid samples: A review, Anal Chim Acta, 665 (2), 113-122.
  • Özçelik, E., Temel, F. ve Tabakcı, M., 2019, Kaliksaren türevi immobilize edilmiş merrifield reçinesi ile kaplı qcm sensöründe sulu ortamda 4-nitrofenol algılanması, Konya Mühendislik Bilimleri Dergisi, 7 (3), 595-603.
  • Peng, Y., Fu, S., Liu, H. ve Lucia, L. A., 2016, Accurately Determining Esterase Activity via the Isosbestic Point of p-Nitrophenol, 2016, 11 (4), 13.
  • Rezania, S., Kamboh, M. A., Arian, S. S., Alrefaei, A. F., Alkhamis, H. H., Albeshr, M. F., Cho, J., Barghi, A. ve Amiri, I. S., 2021, Nitrile-calixarene grafted magnetic graphene oxide for removal of arsenic from aqueous media: Isotherm, kinetic and thermodynamic studies, Chemosphere, 268, 129348.
  • Saxena, S., Tyson, T. A., Shukla, S., Negusse, E., Chen, H. ve Bai, J., 2011, Investigation of structural and electronic properties of graphene oxide, Applied Physics Letters, 99 (1), 013104.
  • Tabakci, 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., 2020, Merrifield Reçinesine Desteklenmiş Kaliks[4]aren Dinitro Türevinin Sulu Ortamdaki Fenolik Türlere Karşı Ekstraksiyon Özelliklerinin İncelenmesi, Konya Mühendislik Bilimleri Dergisi, 8 (1), 60-70.
  • 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.
  • Tor, A., Aydin, M. E., Aydin, S., Tabakci, M. ve Beduk, F., 2013, Removal of lindane from an aqueous solution by using aminopropyl silica gel-immobilized calix[6]arene, J Hazard Mater, 262, 656-663.
  • Wang, H., Li, Z., Zhang, F., Wang, Y., Zhang, X., Wang, J. ve He, X., 2021, Comparison of Ti/Ti4O7, Ti/Ti4O7-PbO2-Ce, and Ti/Ti4O7 nanotube array anodes for electro-oxidation of p-nitrophenol and real wastewater, Separation and Purification Technology, 266, 118600.
  • Yadav, N., Narayan Maddheshiaya, D., Rawat, S. ve Singh, J., 2020, Adsorption and equilibrium studies of phenol and para-nitrophenol by magnetic activated carbon synthesised from cauliflower waste, Environmental Engineering Research, 25 (5), 742-752.
  • Yao, Y.-X., Li, H.-B., Liu, J.-Y., Tan, X.-L., Yu, J.-G. ve Peng, Z.-G., 2014, Removal and Adsorption of p-Nitrophenol from Aqueous Solutions Using Carbon Nanotubes and Their Composites, Journal of Nanomaterials, 2014, 571745.
  • Zaaba, N. I., Foo, K. L., Hashim, U., Tan, S. J., Liu, W.-W. ve Voon, C. H., 2017, Synthesis of Graphene Oxide using Modified Hummers Method: Solvent Influence, Procedia Engineering, 184, 469-477.
  • Zhao, R., Li, Y., Ji, J., Wang, Q., Li, G., Wu, T. ve Zhang, B., 2021, Efficient removal of phenol and p-nitrophenol using nitrogen-doped reduced graphene oxide, Colloids and Surfaces A: Physicochemical and Engineering Aspects, 611, 125866.

p-NİTRO FENOLÜN KALİKSAREN TEMELLİ GRAFEN OKSİT İLE SULU ÇÖZELTİLERDEN UZAKLAŞTIRILMASI

Year 2021, Volume: 9 , 79 - 90, 30.12.2021
https://doi.org/10.36306/konjes.1013091

Abstract

Bu çalışmada, kaliks[4]aren temelli grafen oksit (GO-Epoksi-C[4]CN), öncelikle grafit tozundan Hummers metodu kullanarak grafen oksitin (GO) sentezlenmesi ve (3-glisidoksipropil)trimetoksisilan (GPTMS) ile etkileştirilerek epoksi ucundan p-ter-bütilkaliks[4]aren dinitril türevinin bağlanması ile elde edildi. Sentezlenen bileşiklerin karakterizasyonları, 1H NMR ve FTIR analizleri ile gerçekleştirildi. Elde edilen yeni adsorban (GO-Epoksi-C[4]CN), atık sulardan p-nitro fenolün (PNF) giderilmesi için kullanıldı. Öncelikle, adsorban ve başlangıç bileşikleri kullanılarak karşılaştırma çalışmaları gerçekleştirildi ve % 81 adsorpsiyon verimi ile diğerlerine göre oldukça yüksek bir verim sağladığı gözlendi. Çalışmanın devamında, pH ve konsantrasyonun adsorpsiyona etkisi incelendi. Konsantrasyon çalışmalarından elde edilen bulgular ışığında adsorpsiyonun Langmuir izotermiyle daha uyumlu olduğu görüldü.

Thanks

Bu çalışma, 10-12 Haziran 2021 tarihleri arasında Konya Teknik Üniversitesi Kimya Mühendisliği Bölümünde gerçekleştirilen 14. Ulusal Kimya Mühendisliği Kongresinde sunulmuş ve ek çalışmalarla bu makaleye dönüştürülmüştür. Bu çalışma için, Konya Teknik Üniversitesi'ne sağlamış olduğu imkanlardan dolayı teşekkür ederiz.

References

  • Abbas, M. N., Al-Madhhachi, A.-S. T. ve Esmael, S. A., 2019, Quantifying soil erodibility parameters due to wastewater chemicals International Journal of Hydrology Science and Technology, 9 (5), 550-568.
  • Akceylan, E., Erdemir, S., Özçelik, E. ve Tabakcı, B., 2021, Bazı fenolik kirliliklerin imidazol türevli kaliks[4]aren içeren manyetik nanopartiküller kullanarak sulu çözeltilerden uzaklaştırılması, Konya Journal of Engineering Sciences, 9 (2), 442-454.
  • 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.
  • Aydın, M. E. ve Özcan, S., 2005, Konya yeraltı sularında klorlu fenoller, Selçuk Üniversitesi Mühendislik, Bilim Ve Teknoloji Dergisi, 20 (1), 9-18.
  • Bai, L., Tajikfar, A., Tamjidi, S., Foroutan, R. ve Esmaeili, H., 2021, Synthesis of MnFe2O4@graphene oxide catalyst for biodiesel production from waste edible oil, Renewable Energy, 170, 426-437.
  • Batur, E., Baytar, O., Kutluay, S., Horoz, S. ve Şahin, Ö., 2021, A comprehensive new study on the removal of Pb (II) from aqueous solution by şırnak coal-derived char, Environ Technol, 42 (3), 505-520.
  • 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.
  • Collins, E. M., McKervey, M. A., Madigan, E., Moran, M. B., Owens, M., Ferguson, G. ve Harris, S. J., 1991, Chemically modified calix[4]arenes. Regioselective synthesis of 1,3-(distal) derivatives and related compounds. X-Ray crystal structure of a diphenol-dinitrile, Journal of the Chemical Society, Perkin Transactions 1 (12), 3137-3142.
  • Çiplak, Z., Yildiz, N. ve Çalimli, A., 2015, Investigation of Graphene/Ag Nanocomposites Synthesis Parameters for Two Different Synthesis Methods, Fullerenes, Nanotubes and Carbon Nanostructures, 23 (4), 361-370.
  • Dogan, M., Temel, F. ve Tabakci, M., 2020, High-Performance Adsorption of 4-Nitrophenol onto Calix[6]arene-Tethered Silica from Aqueous Solutions, Journal of Inorganic and Organometallic Polymers and Materials, 30 (10), 4191-4202.
  • 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.
  • Dun, Y. ve Zuo, Y., 2017, Preparation and characterization of a GPTMS/graphene coating on AA-2024 alloy, Applied Surface Science, 416, 492-502.
  • Gutsche, C. D. ve Iqbal, M., 1990, p-tert-butylcalix[4]arene, Organic Syntheses, 68, 234. Hummers, W. S. ve Offeman, R. E., 1958, Preparation of Graphitic Oxide, Journal of the American Chemical Society, 80 (6), 1339-1339.
  • Johra, F. T., Lee, J.-W. ve Jung, W.-G., 2014, Facile and safe graphene preparation on solution based platform, Journal of Industrial and Engineering Chemistry, 20 (5), 2883-2887.
  • Liao, C., Zhao, X.-R., Jiang, X.-Y., Teng, J. ve Yu, J.-G., 2020, Hydrothermal fabrication of novel three-dimensional graphene oxide-pentaerythritol composites with abundant oxygen-containing groups as efficient adsorbents, Microchemical Journal, 152, 104288.
  • Lu, M., Cheng, Y., Pan, S.-l. ve Wei, G.-y., 2016, Batch adsorption of p-nitrophenol by ZSM-11: equilibrium, kinetic, and thermodynamic studies, Desalination and Water Treatment, 57 (7), 3029-3036.
  • Mahugo-Santana, C., Sosa-Ferrera, Z., Torres-Padrón, M. E. ve Santana-Rodríguez, J. J., 2010, Analytical methodologies for the determination of nitroimidazole residues in biological and environmental liquid samples: A review, Anal Chim Acta, 665 (2), 113-122.
  • Özçelik, E., Temel, F. ve Tabakcı, M., 2019, Kaliksaren türevi immobilize edilmiş merrifield reçinesi ile kaplı qcm sensöründe sulu ortamda 4-nitrofenol algılanması, Konya Mühendislik Bilimleri Dergisi, 7 (3), 595-603.
  • Peng, Y., Fu, S., Liu, H. ve Lucia, L. A., 2016, Accurately Determining Esterase Activity via the Isosbestic Point of p-Nitrophenol, 2016, 11 (4), 13.
  • Rezania, S., Kamboh, M. A., Arian, S. S., Alrefaei, A. F., Alkhamis, H. H., Albeshr, M. F., Cho, J., Barghi, A. ve Amiri, I. S., 2021, Nitrile-calixarene grafted magnetic graphene oxide for removal of arsenic from aqueous media: Isotherm, kinetic and thermodynamic studies, Chemosphere, 268, 129348.
  • Saxena, S., Tyson, T. A., Shukla, S., Negusse, E., Chen, H. ve Bai, J., 2011, Investigation of structural and electronic properties of graphene oxide, Applied Physics Letters, 99 (1), 013104.
  • Tabakci, 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., 2020, Merrifield Reçinesine Desteklenmiş Kaliks[4]aren Dinitro Türevinin Sulu Ortamdaki Fenolik Türlere Karşı Ekstraksiyon Özelliklerinin İncelenmesi, Konya Mühendislik Bilimleri Dergisi, 8 (1), 60-70.
  • 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.
  • Tor, A., Aydin, M. E., Aydin, S., Tabakci, M. ve Beduk, F., 2013, Removal of lindane from an aqueous solution by using aminopropyl silica gel-immobilized calix[6]arene, J Hazard Mater, 262, 656-663.
  • Wang, H., Li, Z., Zhang, F., Wang, Y., Zhang, X., Wang, J. ve He, X., 2021, Comparison of Ti/Ti4O7, Ti/Ti4O7-PbO2-Ce, and Ti/Ti4O7 nanotube array anodes for electro-oxidation of p-nitrophenol and real wastewater, Separation and Purification Technology, 266, 118600.
  • Yadav, N., Narayan Maddheshiaya, D., Rawat, S. ve Singh, J., 2020, Adsorption and equilibrium studies of phenol and para-nitrophenol by magnetic activated carbon synthesised from cauliflower waste, Environmental Engineering Research, 25 (5), 742-752.
  • Yao, Y.-X., Li, H.-B., Liu, J.-Y., Tan, X.-L., Yu, J.-G. ve Peng, Z.-G., 2014, Removal and Adsorption of p-Nitrophenol from Aqueous Solutions Using Carbon Nanotubes and Their Composites, Journal of Nanomaterials, 2014, 571745.
  • Zaaba, N. I., Foo, K. L., Hashim, U., Tan, S. J., Liu, W.-W. ve Voon, C. H., 2017, Synthesis of Graphene Oxide using Modified Hummers Method: Solvent Influence, Procedia Engineering, 184, 469-477.
  • Zhao, R., Li, Y., Ji, J., Wang, Q., Li, G., Wu, T. ve Zhang, B., 2021, Efficient removal of phenol and p-nitrophenol using nitrogen-doped reduced graphene oxide, Colloids and Surfaces A: Physicochemical and Engineering Aspects, 611, 125866.
There are 30 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Research Article
Authors

Fatih Çengel 0000-0002-1665-1487

Farabi Temel 0000-0002-5502-8647

Publication Date December 30, 2021
Submission Date October 22, 2021
Acceptance Date November 11, 2021
Published in Issue Year 2021 Volume: 9

Cite

IEEE F. Çengel and F. Temel, “p-NİTRO FENOLÜN KALİKSAREN TEMELLİ GRAFEN OKSİT İLE SULU ÇÖZELTİLERDEN UZAKLAŞTIRILMASI”, KONJES, vol. 9, pp. 79–90, 2021, doi: 10.36306/konjes.1013091.