A new chelating matrix, SiNP, has been prepared by immobilizing 1.5-dimethyl-1 H-pyrazole-3-carbaldehyde on silica gel modified with 3-aminopropyl-trimethoxysilane. This new chelating material was well characterized by elemental analysis, FT-IR spectroscopy, cross polarization magic angle spinning solid state 13C-NMR, nitrogen adsorption-desorption isotherm, BET surface area, BJH pore size, and scanning electron microscopy (SEM). The new product exhibits good chemical and thermal stability as determined by thermogravimetry curves (TGA). The new prepared material was used as an adsorbent for the solid-phase extraction (SPE) of Pb(II), Cd(II), Cu(II) and Zn(II) from aqueous solutions using a batch method, prior to their determination by flame atomic adsorption spectrometry. The adsorption capacity was investigated using kinetics and pH effects. Common coexisting ions did not interfere with separation and determination.
References
[1]
Babel, S.; Kurniawan, T.A. Low-cost adsorbents for heavy metal uptake from contaminated water: A review. J. Haz. Mater. 2003, 97, 219–243, doi:10.1016/S0304-3894(02)00263-7.
[2]
Saeed, M.M.; Ahmed, M. Retention, kinetics and thermodynamics pro-file of cadmium adsorption from iodide medium onto polyurethane foam and its separation from zinc bulk. Anal. Chem. Acta 2004, 525, 289–297, doi:10.1016/j.aca.2004.08.011.
[3]
Sanchez, L.R.B.; de La Riva, B.S.V.; Fernandez, J.M.C.; Pereiro, R.; Medel, A.S. Determination of lead and mercury in sea water by preconcentration in a flow injection system followed by atomic adsorption spectrometry detection. Talanta 2001, 55, 1071–1078, doi:10.1016/S0039-9140(01)00523-9.
[4]
Silbergeld, E. The Elimination of Lead from Gasoline: Impacts of Lead in Gasoline on Human Health, and the Costs and Benefits of Elimination Lead Additives, Draft Paper; The World Bank: Washington, DC, USA, 1996; p. 3.
[5]
Solé, E.; Ballbriga, A.; Dominguez, C. Lead exposure in children: Levels in blood, prevalence of intoxication and related factors. BioMetals 1998, 11, 189–197, doi:10.1023/A:1009253611000.
[6]
Goswami, A.; Singh, A.K. Silica gel functionalized with resacetophenone: Synthesis of a new chelating matrix and its application as metal ion collector for their flame atomic absorption spectrometric determination. Anal. Chim. Acta 2002, 454, 229–240, doi:10.1016/S0003-2670(01)01552-5.
[7]
Melek, E.; Tuzen, M.; Soylak, M. Flame atomic absorption spectrometric determination of cadmium(II) and lead(II) after their solid phase extraction as dibenzyldithiocarbamate chelates on Dowex Optipore V-493. Anal. Chim. Acta 2006, 578, 213–219, doi:10.1016/j.aca.2006.07.003.
[8]
Jiang, N.; Chang, X.J.; Zheng, H.; He, Q.; Hu, Z. Selective solid-phase extraction of nickel (II) using a surface-imprinted silica gel sorbent. Anal. Chim. Acta 2006, 577, 225–231, doi:10.1016/j.aca.2006.06.049.
[9]
Duan, T.C.; Song, X.J.; Jin, D.; Li, H.F.; Xu, J.W.; Chen, H.T. Preliminary results on the determination of ultratrace amounts of cadmium in tea samples using a flow injection on-line solid phase extraction separation and preconcentration technique to couple with a sequential injection hydride generation atomic fluorescence spectrometry. Talanta 2005, 67, 968–974, doi:10.1016/j.talanta.2005.04.017.
[10]
Suvardhan, K.; Suresh Kumar, K.; Rekha, D.; Jayaraj, B.; Krishnamurthy, N.G.; Chiranjeevi, P. Preconcentration and solid-phase extraction of beryllium, lead, nickel, and bismuth from various water samples using 2-propylpiperidine-1-carbodithioate with flame atomic absorption spectrometry (FAAS). Talanta 2006, 68, 735–740, doi:10.1016/j.talanta.2005.05.020.
[11]
Wan, Z.; Xu, Z.R.; Wang, J.H. Flow injection on-line solid phase extraction for ultra-trace lead screening with hydride generation atomic fluorescence spectrometry. Analyst 2006, 131, 141–147, doi:10.1039/b511829h.
[12]
Fang, J.; Iang, Y.J.; Yan, X.P.; Ni, Z.M. Selective quantification of trace palladium in road dusts and roadside soils by displacement solid-phase extraction online coupled with electrothermal atomic absorption spectrometry. Environ. Sci. Technol. 2005, 39, 288–292, doi:10.1021/es049303+.
[13]
Haginaka, J. Selectivty of affinity media in solide-phase extraction of analytes. Trends Anal. Chem. 2005, 24, 407–415, doi:10.1016/j.trac.2004.12.005.
[14]
Sarkar, A.R.; Datta, P.K.; Sarkar, M. Sorption recovery of metal ions using silica gel modified with salicyladoxime. Talanta 1996, 43, 1857–1862, doi:10.1016/0039-9140(96)01953-4.
[15]
Price, P.M.; Clark, J.H.; Macquarrie, D.J. Modified silicas for clean technology. J. Chem. Soc. Dalton Trans. 2000, 101–110, doi:10.1039/A905457J.
[16]
Grigoropoulou, G.; Stathi, P.; Karakassides, M.A.; Louloudi, M.; Deligibiannakis, Y. Functionalized SiO2 with N-,S-containing ligands for Pb(II) and Cd(II) adsorption. Colloids Surf. 2008, 320, 25–35, doi:10.1016/j.colsurfa.2008.01.007.
[17]
Fan, J.; Wu, C.; Peng, C.; Peng, P. Preparation of xylenol orange functionalized silica gel as a selective solid phase extractor and application for preconcentration-separtion of mercury from waters. J. Haz. Mater. 2007, 145, 323–330, doi:10.1016/j.jhazmat.2006.11.025.
[18]
Jamali, M.R.; Assadi, Y.; Shemirani, F.; Salavati-Niasari, M. Application of thiophene-2-carbaldehyde-modified mesoporous silica as a new sorbent for separation and preconcentration of palladium prior to inductively coupled plasma atomic emission spectrometric determination. Talanta 2007, 71, 1524–1529, doi:10.1016/j.talanta.2006.07.034.
[19]
Akhond, M.; Absalan, G.; Sheikhian, L.; Eskandari, M.M.; Sharghi, H. Di (n-propyl) thiuram disulfide bonded on silica gel as a new sorbent for separation, preconcentration, and measurement of silver ion from aqueous samples. Sep. Purif. Technol. 2006, 52, 53–59, doi:10.1016/j.seppur.2006.03.014.
[20]
Amarasekara, A.S.; Owereh, O.S.; Aghara, S.K. Synthesis of 4-acylpyrazolone Schiff base ligand grafted silica and selectivity in adsorption of lanthanides from aqueous solutions. J. Rare Eart. 2009, 27, 870–874, doi:10.1016/S1002-0721(08)60352-X.
[21]
Ngeontae, W.; Aeungmaitrepirom, W.; Tuntulani, T. Chemically modified silica gel with aminothioamidoanthraquinone for solid phase extraction and preconcentration of Pb(II), Cu(II), Ni(II), Co(II) and Cd(II). Talanta 2007, 71, 1075–1082, doi:10.1016/j.talanta.2006.05.094.
[22]
Goswami, A.; Singh, A.K. 1,8-Dihydroxyanthraquinone anchored on silica gel: Synthesis and application as solid phase extraction for lead(II), Zinc(II) and cadmium(II) prior to determination by flame atomic adsorption spectrometry. Talanta 2002, 58, 669–678.
[23]
Sadeghi, S.; Sheikhzadeh, E. Solid phase extraction using silica gel modified with murexide for preconcentration of uranium (VI) ions from water samples. J. Haz. Mater. 2009, 163, 861–868, doi:10.1016/j.jhazmat.2008.07.053.
[24]
Gubbuk, I.H.; Hatay, I.; Coskun, A.; Ersoz, M. Immobilization of oxime derivative on silica for the preparation of new adsorbent. J. Haz. Mater. 2009, 172, 1532–1537, doi:10.1016/j.jhazmat.2009.08.024.
[25]
Sharma, R.K.; Pandey, A.; Gulati, S.; Adholeya, A. An optimized procedure for preconcentration, determination and on-line recovery of palladium using highly selective diphenyldiketone-monothiosemicarbazone modified silica gel. J. Haz. Mater. 2012, 209, 285–292.
[26]
Mukherjee, R. Coordination chemistry with pyrazol-based chelating ligands: Molecular structural aspects. Coord. Chem. Rev. 2000, 203, 151–218, doi:10.1016/S0010-8545(99)00144-7.
[27]
Trofimenko, S. Recent advances in poly(pyrazolyl)borate (scorpionate) chemistry. Chem. Rev. 1993, 93, 943–980, doi:10.1021/cr00019a006.
[28]
Trofimenho, S. The coordination chemistry of pyrazole-derived ligands. Prog. Inorg. Chem. 1986, 34, 115–210, doi:10.1002/9780470166352.ch3.
[29]
Radi, S.; Toubi, Y.; Tighadouini, S.; Baquet, M. Solid-phase extraction of Hg(II), Zn(II) and Cd(II) from water using silica gel modified with bipyrazolic tripodal receptor. Ind. J. Chem. Tech. 2013, 20, 423–428.
[30]
Radi, S.; Basbas, N.; Tighadouini, S.; Bacquet, M.; Degoutin, S.; Cazier, F. New amine-modified silica: Synthesis, characterisation and its use in the Cu(II)-Removal from aqueous solutions. Prog. Nanotech. Nanomat. 2013, 2, 108–116, doi:10.5963/PNN0204002.
[31]
Radi, S.; Toubi, T.; Bacquet, M.; Degoutin, S.; Cazier, F. 1-(Pyridin-2-yl) Imine functionalized silica gel: Synthesis, Characterization and preliminary use in metal ion extraction. Sep. Sci. Tech. 2013, 48, 1349–1355, doi:10.1080/01496395.2012.726309.
[32]
Radi, S.; Toubi, Y.; Bacquet, M. Synthesis of pyridin-3-yl-functionalized silica as a chelating sorbent for solid-phase adsorption of Hg(II), Pb(II), Zn(II) and Cd(II) from water. Chem. Res. Intermed. 2013, 39, 3791–3802, doi:10.1007/s11164-012-0881-6.
[33]
Montoya, V.; Pons, J.; Garcia-Anton, J.; Solans, X.; Font-Bardia, M.; Ros, J. New (η3-Allyl) palladium complexes with pyridylpyrazole ligands: Synthesis, characterization, and study of the influence of N1 substituents on the apparent allyl rotation. Organometallics 2007, 26, 3183–3190, doi:10.1021/om070093u.
Qu, R.; Wang, M.; Sun, C.; Zhang, Y.; Ji, C.; Chen, H.; Meng, Y.; Yin, P. Chemical modification of silica-gel with hydroxyl- or amino-terminated polyamine for adsorption of Au(III). Appl. Surf. Sci. 2008, 255, 3361–3370.
[36]
Han, D.M.; Fang, G.Z.; Yan, X.P. Preparation and evaluation of a molecularly imprinted sol–gel material for on-line solid-phase extraction coupled with high performance liquid chromatography for the determination of trace pentachlorophenol in water samples. J. Chromatogr. A 2005, 110, 131–136.
[37]
Jiang, Y.J.; Gao, Q.M.; Yu, H.G.; Chen, Y.R.; Deng, F. Intensively competitive adsorption for heavy metal ions by PAMAM-SBA-15 and EDTA-PAMAM-SBA-15 inorganic-organic hybrid materials. Micropor. Mesopor. Mater. 2007, 103, 316–324, doi:10.1016/j.micromeso.2007.02.024.
[38]
Abou-El-Sherbini, K.; Kenawy, I.; Hamed, M.; Issa, R.; Elmorsi, R. Separation and preconcentration in a batch mode of Cd(II), Cr(III, VI), Cu(II), Mn(II, VII) and Pb(II) by solid-phase extraction by using of silica modified with N-propylsalicylaldimine. Talanta 2002, 58, 289–300, doi:10.1016/S0039-9140(02)00248-5.
[39]
Sales, J.A.A.; Airoldi, C. Calorimetric investigation of metal ion adsorption on 3-glycidoxypropyltrimethylsiloxane + propane-1,3-diamine immobilized on silica gel. Thermochim. Acta 2005, 427, 77–83, doi:10.1016/j.tca.2004.08.015.
[40]
Sales, J.A.A.; Faria, F.P.; Prado, A.G.S.; Airoldi, C. Attachment of 2-aminomethyl-pyridine molecule onto grafted silica gel surface and its ability in chelating cations. Polyhedron 2004, 23, 719–725, doi:10.1016/j.poly.2003.11.051.
[41]
Roumeliotis, P.; Kurganov, A.A.; Davankov, V.A. Effect of the hydrophobic spacer in bonded (Cu(l-hydroxyprolyl)alkyl)+ silicas on retention and enantioselectivity of α-amino acids in high-performance liquid chromatography. J. Chromatogr. A 1983, 266, 439–450, doi:10.1016/S0021-9673(01)90915-X.
[42]
Kudryavtsev, G.V.; Milchenko, D.V.; Bernadyuk, S.Z.; Vertinskaya, T.E.; Lisichkin, G.V. Synthesis and properties of phosphate cation-exchangers based on silica. Theor. Exp. Chem. USSR 1988, 23, 658–663, doi:10.1007/BF00534608.
[43]
Brunauer, S.; Emmett, P.H.; Teller, E. Adsorption of gases in multimolecular layers. J. Am. Chem. Soc. 1938, 60, 309–319, doi:10.1021/ja01269a023.
[44]
Banerjee, I.A.; Yu, L.; Matsui, H. Cu nanocrystal growth on peptide nanotubes by biomineralization: Size control of Cu nanocrystals by tuning peptide conformation. Proc. Natl. Acad. Sci. USA 2003, 100, 14678–14682, doi:10.1073/pnas.2433456100.
[45]
Xue, X.; Li, F. Removal of Cu (II) from aqueous solution by adsorption onto functionalized SBA-16 mesoporous silica. Micropor. Mesopor. Mater. 2008, 116, 116–122, doi:10.1016/j.micromeso.2008.03.023.
[46]
Pearson, R.G. Hard and soft acids and bases. J. Am. Chem. Soc. 1963, 85, 3533–3539, doi:10.1021/ja00905a001.
[47]
Myers, R.T. Thermodynamics of chelation. Inorg. Chem. 1978, 17, 952–958.
[48]
Mahmoud, R.E. Silica gel-immobilized Eriochrome blach-T as a potential solid phase extractor for zinc (II) and magnesium (II) from calcium (II). Talanta 1997, 45, 309–315, doi:10.1016/S0039-9140(97)00132-X.
[49]
Maquieira, A.; Elmahadi, H.A.M.; Puchades, R. Immobilized cyanobacteria for online trace metal enrichment by flow injection atomic absorption spectrometry. Anal. Chem. 1994, 66, 3632–3638, doi:10.1021/ac00093a016.
[50]
Lehn, J.M.; Sauvage, J.P. (2)-Cryptates: Stability and selectivity of alkali and alkaline-earth macrobicyclic complexes. J. Am. Chem. Soc. 1975, 97, 6700–6707, doi:10.1021/ja00856a018.
[51]
Radi, S.; Yahyi, A.; Ramdani, A.; Zidane, I.; Hacht, B. A new tetrapyrazolic macrocycle. Synthesis and its use in extraction and transport of Na+, Li+, and K+. Tetrahedron 2006, 62, 9153–9155.
[52]
Radi, S.; Ramdani, A.; Lekchiri, Y.; Morcellet, M.; Crini, G.; Morcellet, J.; Janus, L. New tetrapyrazolic macrocycle. Synthesis and cation binding properties. J. Chem. Res. 2003, 11, 712–714.
[53]
Radi, S.; Ramdani, A.; Lekchiri, Y.; Morcellet., M.; Crini, G.; Morcellet, J.; Janus, L. New tetrapyrazolic macrocycle. Synthesis and preliminary use in metal ion extraction. Tetrahedron 2004, 60, 939–942, doi:10.1016/j.tet.2003.11.029.
[54]
Xie, F.; Lin, X.; Wu, W.; Xie, Z. Solid phase extraction of lead (II), copper (II), cadmium (II), and nickel (II) using gallic acid modified silica gel prior to determination by flame atomic adsorption spectrometry. Talanta 2008, 74, 836–843, doi:10.1016/j.talanta.2007.07.018.
[55]
Chiron, N.; Guilet, R. Adsorption of Cu(II) and Pb(II) onto a grafted silica: Isotherms and kinrtic models. Water Res. 2003, 37, 3079–3086, doi:10.1016/S0043-1354(03)00156-8.
[56]
Radi, S.; Ramdani, A.; Lekchiri, Y.; Morcellet, M.; Crini, G.; Janus, L.; Bacquet, M. Immobilization of pyrazole compounds on silica gels and their preliminary use in metal ion extraction. New J. Chem. 2003, 27, 1224–1227, doi:10.1039/b301111a.
[57]
Radi, S.; Attayibat, A. Functionalized SiO2 with S-donor thiophene. Synthesis, Characterisation and its heavy metals adsorption. Phos. Sul. Sil. Relat. Elem. 2010, 185, 2003–2013.
[58]
Kocjan, R. Retention of some metal ions and their separation on silica gel modified with Acid Red 88. Mikrochim. Acta 1999, 131, 153–158, doi:10.1007/s006040050021.
[59]
Zaporozhets, O.; Petruniock, N.; Sukhan, V. Determination of Ag(I), Hg(II) and Pb(II) by using silica gel loeded with dithizone and zinc dithizonate. Talanta 1999, 50, 865–873, doi:10.1016/S0039-9140(99)00172-1.
[60]
Huang, X.; Chang, X.; He, Q.; Cui, Y.; Zhai, Y.; Jiang, N. Tris(2-aminoethyl) amine functionalized silica gel for solid-phase extraction and preconcentration of Cr(II), Cd(II), and Pb(II) from waters. J. Haz. Mater. 2008, 157, 154–160, doi:10.1016/j.jhazmat.2007.12.113.
[61]
Shahbazi, A.; Younesi, H.; Badiei, A. Functionalized SBA-15 mesoporous silica by melamine-based dendrimer amines for adsorptive characteristics of Pb(II), Cu(II) and Cd(II) heavy metal ions in batch and fixed bed column. Chem. Eng. J. 2011, 168, 505–518, doi:10.1016/j.cej.2010.11.053.
[62]
Fifani, J.; Ramdani, A.; Tarrago, G. 1,6,11,16-Tetraazaporphyrinogen, Synthesis and behavior. New J. Chem. 1977, 1, 521–528.
[63]
Tarrago, G.; Ramdani, A.; Elguero, J.; Espada, M. Orientation de la réaction d'alkylation des pyrazoles dans des conditions neutres et en catalyse par transfert de phase. J. Heterocycl. Chem. 1980, 17, 137–142, doi:10.1002/jhet.5570170128.
