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A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes as Liquid-Phase Extraction Agents for Some Toxic Ions

Yıl 2020, Cilt: 10 Sayı: 1, 418 - 426, 01.03.2020

Ömer Güngör

https://doi.org/10.21597/jist.610489

Öz

The liquid-phase extraction performance of phthalonitrile (3 and 4) and isoindoline (5 and 6) substituted calix[4]aren derivatives was studied towards (i) some selected divalent heavy metal cations (i.e Co2+, Ni2+, Cu2+, Cd2+, Hg2+, and Pb2+), (ii) dichromate (Cr2O72-/HCr2O7-), and (iii) arsenate (H2AsO4−/HAsO42−). In general, extraction yield was observed to be higher in the case of compounds 3 and 5 (cone conformation) when compared to 4 and 6 (1,3-alternate conformation). This indicated a somehow positive effect of cone conformation on the extraction performance rather than 1,3-alternate conformation. The stoichiometric ratio between the compound 3 and 4 with mercury picrate was estimated through job’s plot analysis method.

Anahtar Kelimeler

Heavy metal liquid-liquid extraction dichromate arsenate calixarenes.

Kaynakça

  • Akkuş GU, Al E, Korcan SE, 2015. Selective extraction of toxic heavy metals and biological activity studies using pyrimidylthioamide functionalised calix [4] arene. Supramolecular Chemistry, 27: 522–526.
  • Antonio M.T, Corredor L, Leret ML, 2003. Study of the activity of several brain enzymes like markers of the neurotoxicity induced by perinatal exposure to lead and/or cadmium. Toxicology Letters, 143: 331-340.
  • Asfari MZ, Böhmer V, Harrowfield J, Vicens, J, 2007. Calixarenes 2001. Editors: Zouhair Asfari, VolkerBöhmer, Jack Harrowfield, Jacques Vicens. Kluwer academic publishers, New york, Boston, Dordrecht, London, Moscow.
  • Bayrakci M, Ertul S, Yilmaz M, 2009. Synthesis of Di-Substituted Calix[4]arene-based Receptors for Extraction of Chromate and Arsenate Anions. Tetrahedron, 65 (38): 7963–7968.
  • Elçin S, Deligöz, H, 2015. Internal charge transfer based Hg-sensing Azocalix[4]arene Mono anthracenate derivatives. Sensors and Actuators B., 211: 83–92.
  • Ersoz M, 2007. Transport of mercury through liquid membranes containing calixarene carriers. Advances in Colloid and Interface Science, 134: 96-104.
  • Flor de María R, García-Sosa I, 2012. Stoichiometric Ratio in Calixarene Complexes, Stoichiometry and Research - The Importance of Quantity in Biomedicine, Dr Alessio Innocenti (Ed.), ISBN: 978-953-51-0198-7, InTech, Available from: http://www.intechopen.com/books/stoichiometry-and-researchthe-importance-of-quantity-in-biomedicine/stoichiometric-ratio-in-calixarene-complexes.
  • Förstner U, Wittmann GTW, 2012. Metal pollution in the aquatic environment. Berlin Heidelberg New York Tokyo. ISBN: 13:978-3-540-12856-4.
  • Gungor O, Memon S, Yilmaz M, Roundhill DM, 2005.Synthesis of alkyl nitrile and alkyl benzonitrile derivatives of calix[4]arene and their polymer supported analogues: A comparative study in two-phase extraction systems. Reactive & Functional Polymers, 63: 1–9.
  • Güngör Ö, 2018. Liquid phase extraction of azo dyes by novel calixarenes bearing phthalonitrile and diiminoisoindoline groups. Seperation Science and Tech., 53: 896–902.
  • Habuda-Stanic M, Kalajdzic B, Kules M, Velic NS, 2008. Arsenite and Arsenate Sorption by Hydrous ´ Ferric Oxide/Polymeric Material. Desalination, 229 (1): 1–9.
  • Hall AH, 2002. Chronic Arsenic Poisoning. Toxicology Letters, 128 (1): 69–72.
  • Hering JG, Chen PY, Wilkie JA, Elimelech M, 1997. Arsenic removal from drinking water during coagulation. J. Environ. Eng., 123 (8): 800–807.
  • IPCS 2001. Environmental Health Criteria 224, Arsenic and Arsenic Compounds, 2nd ed., World Health Organization, Geneva, Switzerland.
  • Kinga S, 2016. Calixarenes and Beyond, Editors: Placido Neri · Jonathan L. Sessler Mei-Xiang Wang . Chapter 38, pp. 1011-1036. ISBN: 978-3-319-31867-7.
  • Lidsky TI, Schneider JS, 2003. Lead neurotoxicity in children: basic mechanisms and clinical correlates. Brain, 126, 5-19.
  • Memon FN, Memon S, Minhas FT, 2016. Calix [4] arene-mediated uphill transport of methyl red through bulk liquid membrane: kinetics of operational variables. Desalination and Water Treatment, 57: 8358–8371.
  • Mendonça Fábrega, F, BorgesMansur M, 2007. Liquid–liquid extraction of mercury (II) from hydrochloric acid solutions by Aliquat 336. Hydrometallurgy, 87: 83-90.
  • Mishra SP, Tiwari D, Dubey R, Mishra M, 1998. Biosorptive behaviour of casein for Zn2+, Hg2+ and Cr3+: effects of physico-chemical treatments. Bioresour. Technol., 63: 1–5.
  • Neri P, Sessler JL, Wang M, 2016. Editors. Calixarenes and Beyond. Springer. ISBN: 978-3-319-31867-7. Pedersen CJ, 1968. Federation Proceedings. 27: 1305–1309.
  • Qian CL, Dong-su BI, 2007. Toxicity effect of Hg2+ and Cr (VI) on alga growth in eutrophic water. Agric. Sci. Technol., 8: 25–28.
  • Qureshi I, Memon S, 2012. Synthesis and Application of Calixarene-based Functional Material for Arsenic Removal from Water. Applied Water Science, 2 (3): 177–86.
  • Roundhill MD, 1995. Metal Complexes of Calixarenes. Book Editor: Kenneth D. Karlin. Progress in Inorganic Chemistry, Volume 43. ISBN:9780470166444.
  • Roundhill MD, Solangi B, Memon S, Bhanger MI, Yilmaz M, 2009. The Liquid-Liquid Extraction of Toxic Metals (Cd, Hg and Pb) by Calixarenes. Pak. J. Anal. Environ. Chem., 10: 1-13.
  • Samanta I, Bandyopadhyay S, 2017. Toxicity, in: Pet Bird Diseases and Care. Springer, 253–262. ISBN: 978-981-10-3674-3.
  • Sayin S, Engin M.S, Eymur S, Çay S, 2018. Synthesis and Characterization of 1-(2-Furoyl) Piperazine Calix [4] arene for the Preconcentration of Metal Ions. Analytical Letters, 51: 111–118.
  • Shahabuddin M, Roundhill DM, Mustafa Y, 2004. Remediation and liquid-liquid phase transfer extraction of chromium (VI). A Review, Collect. Czech. Chem. Commun., 69: 1231-1250.
  • Tabakci B, Alici O, Karatas I, 2013. 4-tert-butylcalix [4] arene having nitrile pendant groups as Hg2+ selective receptors. Talanta, 106: 92–96.
  • Tabakcı M, Memon S, Yılmaz M, Roundhill DM, 2003. Novel copper(II) complexes of p-tert-butylcalix[4]arene diamide derivatives: synthesis, antimicrobial and DNA cleavage activities. J. Incl.Phenom. and Macrocyclic Chem., 45: 267-270.
  • Tabakci M, Memon S, Yilmaz M, Roundhill DM, 2004. Synthesis and evaluation of extraction ability of calix [4]-crown-6 cone conformer and its oligomeric analogue. React. Funct. Polymer, 58: 27–34.
  • Talanov VS, Talanova GG, Gorbunova M.G, Bartsch RA, 2002. Novel caesium-selective, 1, 3-alternate calix[4]arene-bis (crown-6-ethers) with proton-ionizable groups for enhanced extraction efficiency. Journal of the Chemical Society: Perkin Transactions 2, 2: 209-215.
  • Talanova GG, Elkarim NSA, Talanov VS, Bartsch RA, 1999. A calixarene-based fluorogenic reagent for selective mercury (II) recognition. Anal. Chemistry, 71: 3106–3109.
  • Valenzuela O, Germolec D, Borja-Aburto V, Contreras-Ruiz J, Garcia-Vargas G, Delrazo L, 2007. Chronic arsenic exposure increases TGFalpha concentration in bladder urothelial cells of Mexican populations environmentally exposed to inorganic arsenic. Toxicol. Appl. Pharmacol., 222 (3): 264–70.
  • Viraraghavan T, Subramanian KS, Aruldoss JA, 1999. Arsenic in drinking waterproblems and solutions. Water Science and Technology, 40 (2): 69–76.
  • Visser AE, Swatloski RP, Griffin ST, Hartman DH, Rogers RD, 2001. Liquid/liquid extraction of metal ions in room temperature ionic liquids. Separation Science and Technology, 36 (6): 785–804.
  • World Health Organization (WHO). Arsenic in Drinking Water (Geneva: United Nations, 2001).
  • Yilmaz A, Tabakci B, Akceylan E, Yilmaz M, 2007. Synthesis and dichromate anion extraction ability of p-tert-butylcalix[4]arene diamide derivatives with different binding sites. Tetrahedron, 63: 5000-5005.
  • Yolcubal I, Akyol NH, 2008. Adsorption and transport of arsenate in carbonate-rich soils: coupled effects of nonlinear and rate-limited sorption. Chemosphere, 73 (8): 1300–1307.
  • Yordanov AT, Mague, JT, Roundhill DM, 1995. Synthesis of heavy metal ion selective calix[4]arenes having sulfur containing lower-rim functionalities. Inorg. Chemistry, 34: 5084– 5087.
  • Yordanov AT, Wolf NJ, Georgiev EM, Koch HF, Falana OM, Roundhil DM, 1999. Derivatized Calix[4]arenes as Selective Phase Transfer Extractants for Heavy Metal and Oxyion Salts. Comments on Inorganic Chemistry, 20: 163–175.
  • Yusof AM, Malek NANN, 2009. Removal of Cr(VI) and As(V) from aqueous solutions by HDTMA-modified zeolite Y. Journal of Hazardous Materials, 162 (2): 1019–1024.

A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes as Liquid-Phase Extraction Agents for Some Toxic Ions

Yıl 2020, Cilt: 10 Sayı: 1, 418 - 426, 01.03.2020

Ömer Güngör

https://doi.org/10.21597/jist.610489

Öz

The liquid-phase extraction performance of phthalonitrile (3 and 4) and isoindoline (5 and 6) substituted calix[4]aren derivatives was studied towards (i) some selected divalent heavy metal cations (i.e Co2+, Ni2+, Cu2+, Cd2+, Hg2+, and Pb2+), (ii) dichromate (Cr2O72-/HCr2O7-), and (iii) arsenate (H2AsO4−/HAsO42−). In general, extraction yield was observed to be higher in the case of compounds 3 and 5 (cone conformation) when compared to 4 and 6 (1,3-alternate conformation). This indicated a somehow positive effect of cone conformation on the extraction performance rather than 1,3-alternate conformation. The stoichiometric ratio between the compound 3 and 4 with mercury picrate was estimated through job’s plot analysis method.

Anahtar Kelimeler

Heavy metal liquid-liquid extraction dichromate arsenate calixarenes

Kaynakça

  • Akkuş GU, Al E, Korcan SE, 2015. Selective extraction of toxic heavy metals and biological activity studies using pyrimidylthioamide functionalised calix [4] arene. Supramolecular Chemistry, 27: 522–526.
  • Antonio M.T, Corredor L, Leret ML, 2003. Study of the activity of several brain enzymes like markers of the neurotoxicity induced by perinatal exposure to lead and/or cadmium. Toxicology Letters, 143: 331-340.
  • Asfari MZ, Böhmer V, Harrowfield J, Vicens, J, 2007. Calixarenes 2001. Editors: Zouhair Asfari, VolkerBöhmer, Jack Harrowfield, Jacques Vicens. Kluwer academic publishers, New york, Boston, Dordrecht, London, Moscow.
  • Bayrakci M, Ertul S, Yilmaz M, 2009. Synthesis of Di-Substituted Calix[4]arene-based Receptors for Extraction of Chromate and Arsenate Anions. Tetrahedron, 65 (38): 7963–7968.
  • Elçin S, Deligöz, H, 2015. Internal charge transfer based Hg-sensing Azocalix[4]arene Mono anthracenate derivatives. Sensors and Actuators B., 211: 83–92.
  • Ersoz M, 2007. Transport of mercury through liquid membranes containing calixarene carriers. Advances in Colloid and Interface Science, 134: 96-104.
  • Flor de María R, García-Sosa I, 2012. Stoichiometric Ratio in Calixarene Complexes, Stoichiometry and Research - The Importance of Quantity in Biomedicine, Dr Alessio Innocenti (Ed.), ISBN: 978-953-51-0198-7, InTech, Available from: http://www.intechopen.com/books/stoichiometry-and-researchthe-importance-of-quantity-in-biomedicine/stoichiometric-ratio-in-calixarene-complexes.
  • Förstner U, Wittmann GTW, 2012. Metal pollution in the aquatic environment. Berlin Heidelberg New York Tokyo. ISBN: 13:978-3-540-12856-4.
  • Gungor O, Memon S, Yilmaz M, Roundhill DM, 2005.Synthesis of alkyl nitrile and alkyl benzonitrile derivatives of calix[4]arene and their polymer supported analogues: A comparative study in two-phase extraction systems. Reactive & Functional Polymers, 63: 1–9.
  • Güngör Ö, 2018. Liquid phase extraction of azo dyes by novel calixarenes bearing phthalonitrile and diiminoisoindoline groups. Seperation Science and Tech., 53: 896–902.
  • Habuda-Stanic M, Kalajdzic B, Kules M, Velic NS, 2008. Arsenite and Arsenate Sorption by Hydrous ´ Ferric Oxide/Polymeric Material. Desalination, 229 (1): 1–9.
  • Hall AH, 2002. Chronic Arsenic Poisoning. Toxicology Letters, 128 (1): 69–72.
  • Hering JG, Chen PY, Wilkie JA, Elimelech M, 1997. Arsenic removal from drinking water during coagulation. J. Environ. Eng., 123 (8): 800–807.
  • IPCS 2001. Environmental Health Criteria 224, Arsenic and Arsenic Compounds, 2nd ed., World Health Organization, Geneva, Switzerland.
  • Kinga S, 2016. Calixarenes and Beyond, Editors: Placido Neri · Jonathan L. Sessler Mei-Xiang Wang . Chapter 38, pp. 1011-1036. ISBN: 978-3-319-31867-7.
  • Lidsky TI, Schneider JS, 2003. Lead neurotoxicity in children: basic mechanisms and clinical correlates. Brain, 126, 5-19.
  • Memon FN, Memon S, Minhas FT, 2016. Calix [4] arene-mediated uphill transport of methyl red through bulk liquid membrane: kinetics of operational variables. Desalination and Water Treatment, 57: 8358–8371.
  • Mendonça Fábrega, F, BorgesMansur M, 2007. Liquid–liquid extraction of mercury (II) from hydrochloric acid solutions by Aliquat 336. Hydrometallurgy, 87: 83-90.
  • Mishra SP, Tiwari D, Dubey R, Mishra M, 1998. Biosorptive behaviour of casein for Zn2+, Hg2+ and Cr3+: effects of physico-chemical treatments. Bioresour. Technol., 63: 1–5.
  • Neri P, Sessler JL, Wang M, 2016. Editors. Calixarenes and Beyond. Springer. ISBN: 978-3-319-31867-7. Pedersen CJ, 1968. Federation Proceedings. 27: 1305–1309.
  • Qian CL, Dong-su BI, 2007. Toxicity effect of Hg2+ and Cr (VI) on alga growth in eutrophic water. Agric. Sci. Technol., 8: 25–28.
  • Qureshi I, Memon S, 2012. Synthesis and Application of Calixarene-based Functional Material for Arsenic Removal from Water. Applied Water Science, 2 (3): 177–86.
  • Roundhill MD, 1995. Metal Complexes of Calixarenes. Book Editor: Kenneth D. Karlin. Progress in Inorganic Chemistry, Volume 43. ISBN:9780470166444.
  • Roundhill MD, Solangi B, Memon S, Bhanger MI, Yilmaz M, 2009. The Liquid-Liquid Extraction of Toxic Metals (Cd, Hg and Pb) by Calixarenes. Pak. J. Anal. Environ. Chem., 10: 1-13.
  • Samanta I, Bandyopadhyay S, 2017. Toxicity, in: Pet Bird Diseases and Care. Springer, 253–262. ISBN: 978-981-10-3674-3.
  • Sayin S, Engin M.S, Eymur S, Çay S, 2018. Synthesis and Characterization of 1-(2-Furoyl) Piperazine Calix [4] arene for the Preconcentration of Metal Ions. Analytical Letters, 51: 111–118.
  • Shahabuddin M, Roundhill DM, Mustafa Y, 2004. Remediation and liquid-liquid phase transfer extraction of chromium (VI). A Review, Collect. Czech. Chem. Commun., 69: 1231-1250.
  • Tabakci B, Alici O, Karatas I, 2013. 4-tert-butylcalix [4] arene having nitrile pendant groups as Hg2+ selective receptors. Talanta, 106: 92–96.
  • Tabakcı M, Memon S, Yılmaz M, Roundhill DM, 2003. Novel copper(II) complexes of p-tert-butylcalix[4]arene diamide derivatives: synthesis, antimicrobial and DNA cleavage activities. J. Incl.Phenom. and Macrocyclic Chem., 45: 267-270.
  • Tabakci M, Memon S, Yilmaz M, Roundhill DM, 2004. Synthesis and evaluation of extraction ability of calix [4]-crown-6 cone conformer and its oligomeric analogue. React. Funct. Polymer, 58: 27–34.
  • Talanov VS, Talanova GG, Gorbunova M.G, Bartsch RA, 2002. Novel caesium-selective, 1, 3-alternate calix[4]arene-bis (crown-6-ethers) with proton-ionizable groups for enhanced extraction efficiency. Journal of the Chemical Society: Perkin Transactions 2, 2: 209-215.
  • Talanova GG, Elkarim NSA, Talanov VS, Bartsch RA, 1999. A calixarene-based fluorogenic reagent for selective mercury (II) recognition. Anal. Chemistry, 71: 3106–3109.
  • Valenzuela O, Germolec D, Borja-Aburto V, Contreras-Ruiz J, Garcia-Vargas G, Delrazo L, 2007. Chronic arsenic exposure increases TGFalpha concentration in bladder urothelial cells of Mexican populations environmentally exposed to inorganic arsenic. Toxicol. Appl. Pharmacol., 222 (3): 264–70.
  • Viraraghavan T, Subramanian KS, Aruldoss JA, 1999. Arsenic in drinking waterproblems and solutions. Water Science and Technology, 40 (2): 69–76.
  • Visser AE, Swatloski RP, Griffin ST, Hartman DH, Rogers RD, 2001. Liquid/liquid extraction of metal ions in room temperature ionic liquids. Separation Science and Technology, 36 (6): 785–804.
  • World Health Organization (WHO). Arsenic in Drinking Water (Geneva: United Nations, 2001).
  • Yilmaz A, Tabakci B, Akceylan E, Yilmaz M, 2007. Synthesis and dichromate anion extraction ability of p-tert-butylcalix[4]arene diamide derivatives with different binding sites. Tetrahedron, 63: 5000-5005.
  • Yolcubal I, Akyol NH, 2008. Adsorption and transport of arsenate in carbonate-rich soils: coupled effects of nonlinear and rate-limited sorption. Chemosphere, 73 (8): 1300–1307.
  • Yordanov AT, Mague, JT, Roundhill DM, 1995. Synthesis of heavy metal ion selective calix[4]arenes having sulfur containing lower-rim functionalities. Inorg. Chemistry, 34: 5084– 5087.
  • Yordanov AT, Wolf NJ, Georgiev EM, Koch HF, Falana OM, Roundhil DM, 1999. Derivatized Calix[4]arenes as Selective Phase Transfer Extractants for Heavy Metal and Oxyion Salts. Comments on Inorganic Chemistry, 20: 163–175.
  • Yusof AM, Malek NANN, 2009. Removal of Cr(VI) and As(V) from aqueous solutions by HDTMA-modified zeolite Y. Journal of Hazardous Materials, 162 (2): 1019–1024.
Toplam 41 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

Ömer Güngör 0000-0002-3835-2920

Yayımlanma Tarihi 1 Mart 2020
Gönderilme Tarihi 25 Ağustos 2019
Kabul Tarihi 7 Kasım 2019
Yayımlandığı Sayı Yıl 2020 Cilt: 10 Sayı: 1

Kaynak Göster

APA Güngör, Ö. (2020). A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes as Liquid-Phase Extraction Agents for Some Toxic Ions. Journal of the Institute of Science and Technology, 10(1), 418-426. https://doi.org/10.21597/jist.610489
AMA Güngör Ö. A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes as Liquid-Phase Extraction Agents for Some Toxic Ions. Iğdır Üniv. Fen Bil Enst. Der. Mart 2020;10(1):418-426. doi:10.21597/jist.610489
Chicago Güngör, Ömer. “A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes As Liquid-Phase Extraction Agents for Some Toxic Ions”. Journal of the Institute of Science and Technology 10, sy. 1 (Mart 2020): 418-26. https://doi.org/10.21597/jist.610489.
EndNote Güngör Ö (01 Mart 2020) A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes as Liquid-Phase Extraction Agents for Some Toxic Ions. Journal of the Institute of Science and Technology 10 1 418–426.
IEEE Ö. Güngör, “A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes as Liquid-Phase Extraction Agents for Some Toxic Ions”, Iğdır Üniv. Fen Bil Enst. Der., c. 10, sy. 1, ss. 418–426, 2020, doi: 10.21597/jist.610489.
ISNAD Güngör, Ömer. “A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes As Liquid-Phase Extraction Agents for Some Toxic Ions”. Journal of the Institute of Science and Technology 10/1 (Mart 2020), 418-426. https://doi.org/10.21597/jist.610489.
JAMA Güngör Ö. A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes as Liquid-Phase Extraction Agents for Some Toxic Ions. Iğdır Üniv. Fen Bil Enst. Der. 2020;10:418–426.
MLA Güngör, Ömer. “A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes As Liquid-Phase Extraction Agents for Some Toxic Ions”. Journal of the Institute of Science and Technology, c. 10, sy. 1, 2020, ss. 418-26, doi:10.21597/jist.610489.
Vancouver Güngör Ö. A Study on The Usability of Some Phthalonitrile and Diiminoisoindoline Substituted Calixarenes as Liquid-Phase Extraction Agents for Some Toxic Ions. Iğdır Üniv. Fen Bil Enst. Der. 2020;10(1):418-26.
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