Synthesis of Sol-Gel Silicas functionalized with Schiff Base Ligands
Keywords:
Schiff base functionalized silicas, Sol-gel method, Extraction of metal ionsAbstract
Schiff bases containing azomethine linkage in their structure are good ligands and show great metal binding ability. In last few years sol-gel method is found very attractive for synthesis of gels due to its low cost, low operating temperature and ease of synthesis. This work presents the synthesis of Schiff base functionalized gels through sol-gel method and their use in extraction of metal ions from aqueous medium at room temperature and appropriate pH. Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM) and X-ray diffraction (XRD) analyses of both blank and functionalized gels are presented. The analyses data show successful incorporation of the Schiff base in sol-gel matrix. Metal removal data show high efficiency of Schiff base functionalized gels.
References
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[2] S. C. Bell, G. L. Conklin and S. J. Childress. The separation of ketimine isomers, Journal of the American Chemical Society, Vol. 85, pp. 2868-2869, 1963.
[3] H. Schiff. On some phenolic derivatives of aldehydes, Annals of Chemistry, Vol. 131, pp.118, 1864.
[4] Dr. M. Fogiel. Staff of Research and Education Association, The Organic Problem Solver, Education Association, New York, 1987.
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[7] J. Hine and C. Y. Yeh. Equilibrium in formation and conformational isomerization of imines derived from isobutyraldehyde and saturated aliphatic primary amines, Journal of the American Chemical Society, Vol. 89, pp. 2669-2676, 1967.
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[12] A. O. De Souza, F.C.S.Galetti, C.L. Silva, B. Bicalho, M.M. Parma and S.F. Fonseca. Antimycobacterial and cytotoxicity activity of synthetic and natural compounds, Quim Nova, Vol. 30(7), pp. 1563-1566, 2007.
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[19] A. Llobet, A. E. Martell and M. A. Mart??nez. Cu (I) and Cu (II) dinuclear complexes of a new hexaaza schiff base dinucleating macrocyclic ligand and their oxygenation chemistry, Journal of Molecular Catalysis Chemical, Vol. 129, pp. 19-26, 1998.
[20] T. Katsuki. Unique asymmetric catalysis of cis-? metal complexes of salen and its related Schiff-base ligands. Chemical Society Reviews, Vol. 33, pp. 437-444, 2004.
[21] Lozana, P. G. Lassahn, C. Zhang, B. Wu, C. Janiak, G. Rheinwald. Dinuclear nickel (II) and palladium (II) complexes in combination with different co-catalysts as highly active catalysts for the vinyl/addition polymerization of norbornene, Zeitschrift für Naturforschung, Vol. 58, pp. 1152-1164, 2003.
[22] R. Soomro, M. J. Ahmed, N. Memon and H. Khan. A simple and selective spectrophotometric method for the determination of trace gold in real, environmental, biological, geological and soil samples using bis (salicylaldehyde) orthophenylenediamine, Analytical Chemistry Insights, Vol. 3, pp. ACI-S977, 2008.
[23] M. J. Ahmed and M. N. Uddin. A simple spectrophotometric method for the determination of cobalt in industrial, environmental, biological and soil samples using bis (salicylaldehyde) orthophenylenediamine, Chemosphere, Vol. 67, pp. 2020-2027, 2007.
[24] G. K. Krishnapillai and S. J. Konnully. Removal of Fe (III) using a polystyrene anchored Schiff base, Environmental Chemistry Letters, Vol. 5, pp. 19-21, 2007.
[25] Z. H. Chohan, M. H. Youssoufi, A. Jarrahpour and T. B. Hadda. Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: indolenyl sulfonamide derivatives, European Journal of Medicinal Chemistry, Vol. 45(3), pp. 1189-1199, 2009.
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[27] M. Shingare and D. Ingle. Synthesis of pyrimidine schiff-bases as anticancer agents, Journal of the Indian Chemical Society, Vol. 53, pp. 1036-1037, 1976.
[28] P. Pathak, V. Jolly and K. Sharma. Synthesis and biological activities of some new substituted arylazo schiff bases, Oriental Journal of Chemistry, Vol. 16, pp. 161-162, 2000.
[29] A. T. Chaviara, P. C. Christidis, A. Papageorgiou, E. Chrysogelou, D. HadjipavlouLitina and C. Bolos. In vivo anticancer, anti-inflammatory, and toxicity studies of mixed-ligand Cu (II) complexes of dien and its Schiff dibases with heterocyclic aldehydes and 2-amino-2-thiazoline Crystal structure of (Cu(dien)(Br)(2a-2tzn)](Br)(H 2 O), Journal of Inorganic Biochemistry, Vol. 99, pp. 2102-2109, 2005.
[30] M. Baseer, V. Jadhav, R. Phule, Y. Archana and Y. Vibhute. Synthesis and antibacterial activity of some new schiff bases, Oriental Journal of Chemistry, Vol. 16, pp. 553-556, 2000.
[31] Z. H. Chohan, Hassan, H. Pervez, A. Rauf, A. Scozzafava and C. T. Supuran. Isatin-derived antibacterial and antifungal compounds and their transition metal complexes, Journal of Enzyme Inhibition and Medicinal Chemistry, Vol. 17(2), 2000.
[32] S. Pandeya, D. Sriram, G. Nath, and E. DeClercq. Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4?-chlorophenyl) thiazol-2-yl] thiosemicarbazide, European Journal of Pharmaceutical Sciences, Vol. 9, pp. 25-31, 1999.
[33] S. Sridhar, S. Pandeya, and E. De Clercq. Synthesis and anti-HIV activity of some isatin derivatives, Bollettino Chimico Farmaceutico, Vol. 140, pp. 302-305, 2001.
[34] I. Cohen, N. Rist and C. Duponchel. Synthesis and antituberculosis activity of thiocarboxamide derivatives of schiff bases, Journal of Pharmaceutical Sciences, Vol. 66, pp. 1332-1334, 1977.
[35] W. Singh and B. Dash. Synthesis of some new schiff bases containing thiazole and oxazole nuclei and their fungicidal activity, Pesticides, Vol. 22, pp. 33-37, 1988.
[36] R. Pignatello, A. Panico, P. Mazzone, M. Pinizzotto, A.Garozzo and P. Fumeri. Schiff bases of N-hydroxy-N-aminoguanidines as antiviral, antibacterial and anticancer agents, European Journal of Medicinal Chemistry, Vol. 29, pp. 781-785, 1994.
[37] L. Guofa, S. Tongshun and Z. Yongnian. Infrared and Raman spectra of complexes about rare earth nitrate with schiff base from o-vanillin and 1-naphthylamine, Journal of Molecular Structure, Vol. 412, pp. 75-81, 1997.
[38] Das, T. Choudhury, G. Das, D. Chowdhury and B. Choudhury. Comparative studies on largicidal activity of some schiff bases with Correspondian Amines. Chemistry Environmental Review, Vol. 3, pp. 19-23, 1994.
[39] F. Sparatore, G. Pirisino, M. Alamanni, P. Manca-Dimich and M. Satta. Azomethine derivatives with anti-inflammatory activity, Bollettino chimico farmaceutico, Vol. 117, pp. 638-651, 1978.
[40] J. Wen and G. L. Wilkes. Organic/inorganic hybrid network materials by the sol-gel approach, Chemistry of Materials, Vol. 8, pp. 1667-1681, 1996.
[41] S. E. Bailey, T. J. Olin, R. M. Bricka, and D. D. Adrian. A review of potentially low-cost sorbents for heavy metals, Water Research, Vol. 33, pp. 2469-2479, 1999.
[42] Cochrane, S. Lu, S. Gibb and I. Villaescusa. A comparison of low-cost biosorbents and commercial sorbents for the removal of copper from aqueous media, Journal of Hazardous Materials, Vol. 137, pp. 198-206, 2006.
[43] G. Nakhla, A. Lugowski, J. Patel and V. Rivest. Combined biological and membrane treatment of food-processing wastewater to achieve dry-ditch criteria: pilot and full-scale performance, Bioresource technology, Vol. 97, pp. 1-14, 2006.
[44] B. E. Reed, W. Lin, M. R. Matsumoto and J. N. Jensen. Physicochemical processes, Water environment research, Vol. 69, pp. 444-462, 1997.
[45] G. V. Myasoedova, S. B. Savvin and E. Blasius. Chelating sorbents in analytical chemistry. Critical Reviews in Analyticl Chemistry, Vol. 17, pp. 1-63, 1986.
[46] G. Myasoedova and S. Savvin. New chelating sorbents and their analytical application, Zhurnal Analiticheskoj Khimii, Vol. 37(3), pp. 499-519, 1982.
[47] Chow and H. Gesser. Preconcentration of Trace Metals from Aquatic Environmental Samples, Hazard Assessment of Chemicals: Current Developments, Vol. 1, 1981.
[48] R. S. Murthy, J. Holzbecher and D. E. Ryan. Trace element preconcentration from aqueous solutions on a solid phase. Reviews in Analytical Chemistry, Vol. 6, pp. 113-150, 1982.
[49] C. Xiong and C. Yao. Study on the adsorption of cadmium (II) from aqueous solution by D152 resin, Journal of Hazardous Materials, Vol. 166, pp. 815-820, 2009.
[50] N. V. Deorkar and L. L. Tavlarides. Zinc, cadmium and lead separation from aqueous streams using solid-phase extractants, Industrial and Engineering Chemistry Research, Vol. 36, pp. 399-406, 1997.
[51] M. Nadeem, I. Tan, M. Haq, S. Shahid, S. Shah and G. McKay. Sorption of lead ions from aqueous solution by chickpea leaves, stems and fruit peelings, Adsorption Science and Technology, Vol. 24, pp. 269-282, 2006.
[2] S. C. Bell, G. L. Conklin and S. J. Childress. The separation of ketimine isomers, Journal of the American Chemical Society, Vol. 85, pp. 2868-2869, 1963.
[3] H. Schiff. On some phenolic derivatives of aldehydes, Annals of Chemistry, Vol. 131, pp.118, 1864.
[4] Dr. M. Fogiel. Staff of Research and Education Association, The Organic Problem Solver, Education Association, New York, 1987.
[5] R. A. Mekheimer, A. M. A. Hameed and K. U. Sadek. First synthesis and isolation of the e-and z-isomers of some new Schiff bases Reactions of 6-azido-5-formyl-2-pyridone with aromatic amines, Molecules, Vol. 13, pp. 195-203, 2008.
[6] K. N. Campbell, H. Sommers and B. K. Campbell. Organohalogenated persistent organic pollutants in American captured in eastern Canada, Journal of American Chemical Society, Vol. 66, p. 6682, 1994.
[7] J. Hine and C. Y. Yeh. Equilibrium in formation and conformational isomerization of imines derived from isobutyraldehyde and saturated aliphatic primary amines, Journal of the American Chemical Society, Vol. 89, pp. 2669-2676, 1967.
[8] C. Sandorfy. The chemistry of the carbon-nitrogen double bond, 1970.
[9] H. Weingarten, J. P. Chupp and W. A. White. Ketimine syntheses use of titanium tetrachloride in a new procedure for their preparation, The Journal of Organic Chemistry, Vol. 32, pp. 3246-3249, 1967.
[10] R. Bonnett and T. Emerson. 834 Optical rotatory dispersion Part XXII, Steroidal azomethines, Journal of the Chemical Society, pp. 4508-4511, 1965.
[11] M.B. Smith and J. March. Advanced Organic Chemistry, 5th edition 1994.
[12] A. O. De Souza, F.C.S.Galetti, C.L. Silva, B. Bicalho, M.M. Parma and S.F. Fonseca. Antimycobacterial and cytotoxicity activity of synthetic and natural compounds, Quim Nova, Vol. 30(7), pp. 1563-1566, 2007.
[13] A. N. Mazidji, B. Koopman and G. Bitton. Chelating resin versus ion-exchange resin for heavy metal removal in toxicity fractionation, Water Science Tecnology, Vol. 26, p. 189, 1982.
[14] Nilchi, M. R. Hadjmohammadi, S. R. Garmarodi and R. Saberi and J. Hazard. Mater Studies on the adsorption behavior of trace amounts of 90Sr2+, 140La3+, 60Co2+, Ni2+ and Zr4+ cations on synthesized inorganic ion exchangers, Journal of hazardous materials, Vol. 167, pp. 531-535, 2009.
[15] G. V. Myasoedova and S. B. Savvin. Chelating sorbents in analytical chemistry. Critical Review Analytical Chemistry, Vol. 171, 1986.
[16] G. Myasoedova and S. Savvin. New chelating sorbents and their analytical application, Zhurnal Analiticheskoj Khimii, Vol. 37, pp. 499-519, 1982.
[17] A. Chow and H. Gesser. Preconcentration of trace metals from aquatic environmental samples, Hazard Assessment of Chemicals: Current Developments, Vol. 1, 1981.
[18] J. G. Cory and A. H. Cory. International Encylopedia of Pharmacology and Therapeutics, Pergamon Press, New York, 1989.
[19] A. Llobet, A. E. Martell and M. A. Mart??nez. Cu (I) and Cu (II) dinuclear complexes of a new hexaaza schiff base dinucleating macrocyclic ligand and their oxygenation chemistry, Journal of Molecular Catalysis Chemical, Vol. 129, pp. 19-26, 1998.
[20] T. Katsuki. Unique asymmetric catalysis of cis-? metal complexes of salen and its related Schiff-base ligands. Chemical Society Reviews, Vol. 33, pp. 437-444, 2004.
[21] Lozana, P. G. Lassahn, C. Zhang, B. Wu, C. Janiak, G. Rheinwald. Dinuclear nickel (II) and palladium (II) complexes in combination with different co-catalysts as highly active catalysts for the vinyl/addition polymerization of norbornene, Zeitschrift für Naturforschung, Vol. 58, pp. 1152-1164, 2003.
[22] R. Soomro, M. J. Ahmed, N. Memon and H. Khan. A simple and selective spectrophotometric method for the determination of trace gold in real, environmental, biological, geological and soil samples using bis (salicylaldehyde) orthophenylenediamine, Analytical Chemistry Insights, Vol. 3, pp. ACI-S977, 2008.
[23] M. J. Ahmed and M. N. Uddin. A simple spectrophotometric method for the determination of cobalt in industrial, environmental, biological and soil samples using bis (salicylaldehyde) orthophenylenediamine, Chemosphere, Vol. 67, pp. 2020-2027, 2007.
[24] G. K. Krishnapillai and S. J. Konnully. Removal of Fe (III) using a polystyrene anchored Schiff base, Environmental Chemistry Letters, Vol. 5, pp. 19-21, 2007.
[25] Z. H. Chohan, M. H. Youssoufi, A. Jarrahpour and T. B. Hadda. Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: indolenyl sulfonamide derivatives, European Journal of Medicinal Chemistry, Vol. 45(3), pp. 1189-1199, 2009.
[26] L. Gibson, W. Kerr, A. Nordon, J. Reglinski, C. Robertson, L. Turnbull. On-site determination of formaldehyde a low cost measurement device for museum environments, Analytica Chimica Acta, Vol. 623, pp. 109-116, 2008.
[27] M. Shingare and D. Ingle. Synthesis of pyrimidine schiff-bases as anticancer agents, Journal of the Indian Chemical Society, Vol. 53, pp. 1036-1037, 1976.
[28] P. Pathak, V. Jolly and K. Sharma. Synthesis and biological activities of some new substituted arylazo schiff bases, Oriental Journal of Chemistry, Vol. 16, pp. 161-162, 2000.
[29] A. T. Chaviara, P. C. Christidis, A. Papageorgiou, E. Chrysogelou, D. HadjipavlouLitina and C. Bolos. In vivo anticancer, anti-inflammatory, and toxicity studies of mixed-ligand Cu (II) complexes of dien and its Schiff dibases with heterocyclic aldehydes and 2-amino-2-thiazoline Crystal structure of (Cu(dien)(Br)(2a-2tzn)](Br)(H 2 O), Journal of Inorganic Biochemistry, Vol. 99, pp. 2102-2109, 2005.
[30] M. Baseer, V. Jadhav, R. Phule, Y. Archana and Y. Vibhute. Synthesis and antibacterial activity of some new schiff bases, Oriental Journal of Chemistry, Vol. 16, pp. 553-556, 2000.
[31] Z. H. Chohan, Hassan, H. Pervez, A. Rauf, A. Scozzafava and C. T. Supuran. Isatin-derived antibacterial and antifungal compounds and their transition metal complexes, Journal of Enzyme Inhibition and Medicinal Chemistry, Vol. 17(2), 2000.
[32] S. Pandeya, D. Sriram, G. Nath, and E. DeClercq. Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4?-chlorophenyl) thiazol-2-yl] thiosemicarbazide, European Journal of Pharmaceutical Sciences, Vol. 9, pp. 25-31, 1999.
[33] S. Sridhar, S. Pandeya, and E. De Clercq. Synthesis and anti-HIV activity of some isatin derivatives, Bollettino Chimico Farmaceutico, Vol. 140, pp. 302-305, 2001.
[34] I. Cohen, N. Rist and C. Duponchel. Synthesis and antituberculosis activity of thiocarboxamide derivatives of schiff bases, Journal of Pharmaceutical Sciences, Vol. 66, pp. 1332-1334, 1977.
[35] W. Singh and B. Dash. Synthesis of some new schiff bases containing thiazole and oxazole nuclei and their fungicidal activity, Pesticides, Vol. 22, pp. 33-37, 1988.
[36] R. Pignatello, A. Panico, P. Mazzone, M. Pinizzotto, A.Garozzo and P. Fumeri. Schiff bases of N-hydroxy-N-aminoguanidines as antiviral, antibacterial and anticancer agents, European Journal of Medicinal Chemistry, Vol. 29, pp. 781-785, 1994.
[37] L. Guofa, S. Tongshun and Z. Yongnian. Infrared and Raman spectra of complexes about rare earth nitrate with schiff base from o-vanillin and 1-naphthylamine, Journal of Molecular Structure, Vol. 412, pp. 75-81, 1997.
[38] Das, T. Choudhury, G. Das, D. Chowdhury and B. Choudhury. Comparative studies on largicidal activity of some schiff bases with Correspondian Amines. Chemistry Environmental Review, Vol. 3, pp. 19-23, 1994.
[39] F. Sparatore, G. Pirisino, M. Alamanni, P. Manca-Dimich and M. Satta. Azomethine derivatives with anti-inflammatory activity, Bollettino chimico farmaceutico, Vol. 117, pp. 638-651, 1978.
[40] J. Wen and G. L. Wilkes. Organic/inorganic hybrid network materials by the sol-gel approach, Chemistry of Materials, Vol. 8, pp. 1667-1681, 1996.
[41] S. E. Bailey, T. J. Olin, R. M. Bricka, and D. D. Adrian. A review of potentially low-cost sorbents for heavy metals, Water Research, Vol. 33, pp. 2469-2479, 1999.
[42] Cochrane, S. Lu, S. Gibb and I. Villaescusa. A comparison of low-cost biosorbents and commercial sorbents for the removal of copper from aqueous media, Journal of Hazardous Materials, Vol. 137, pp. 198-206, 2006.
[43] G. Nakhla, A. Lugowski, J. Patel and V. Rivest. Combined biological and membrane treatment of food-processing wastewater to achieve dry-ditch criteria: pilot and full-scale performance, Bioresource technology, Vol. 97, pp. 1-14, 2006.
[44] B. E. Reed, W. Lin, M. R. Matsumoto and J. N. Jensen. Physicochemical processes, Water environment research, Vol. 69, pp. 444-462, 1997.
[45] G. V. Myasoedova, S. B. Savvin and E. Blasius. Chelating sorbents in analytical chemistry. Critical Reviews in Analyticl Chemistry, Vol. 17, pp. 1-63, 1986.
[46] G. Myasoedova and S. Savvin. New chelating sorbents and their analytical application, Zhurnal Analiticheskoj Khimii, Vol. 37(3), pp. 499-519, 1982.
[47] Chow and H. Gesser. Preconcentration of Trace Metals from Aquatic Environmental Samples, Hazard Assessment of Chemicals: Current Developments, Vol. 1, 1981.
[48] R. S. Murthy, J. Holzbecher and D. E. Ryan. Trace element preconcentration from aqueous solutions on a solid phase. Reviews in Analytical Chemistry, Vol. 6, pp. 113-150, 1982.
[49] C. Xiong and C. Yao. Study on the adsorption of cadmium (II) from aqueous solution by D152 resin, Journal of Hazardous Materials, Vol. 166, pp. 815-820, 2009.
[50] N. V. Deorkar and L. L. Tavlarides. Zinc, cadmium and lead separation from aqueous streams using solid-phase extractants, Industrial and Engineering Chemistry Research, Vol. 36, pp. 399-406, 1997.
[51] M. Nadeem, I. Tan, M. Haq, S. Shahid, S. Shah and G. McKay. Sorption of lead ions from aqueous solution by chickpea leaves, stems and fruit peelings, Adsorption Science and Technology, Vol. 24, pp. 269-282, 2006.
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2018-01-22
How to Cite
Shazia Naheed. (2018). Synthesis of Sol-Gel Silicas functionalized with Schiff Base Ligands. University of Wah Journal of Science and Technology (UWJST), 2, 7–12. Retrieved from https://uwjst.org.pk/index.php/uwjst/article/view/10
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