Synthesis and application of a highly efficient polyvinylcalix[4]arene tetraacetic acid resin for adsorptive removal of lead from aqueous solutions

Chemical Engineering Journal

Volumn 172, Issue 1, 2011, Pages 341-353

  Adhikari, Birendra Babu ^a   Kanemitsu, Masaki ^a   Kawakita, Hidetaka ^a   Jumina, ^b   Ohto, Keisuke ^a  

^a SAGA UNIVERSITY   (Japan)

^b GADJAH MADA UNIVERSITY   (Indonesia)

Author keywords

Adsorption; Column separation; Lead ion; Polyvinylcalix 4 arene tetraacetic acid resin; Vinylic polymerization

Indexed keywords

ADSORPTION ABILITY; ADSORPTION BEHAVIOR; ADSORPTION OF PB; ADSORPTIVE REMOVAL; CALIX[4]ARENES; CALIXARENES; CARBOXYL GROUPS; CARBOXYLIC ACID GROUPS; CHEMICAL DAMAGES; COLUMN SEPARATION; DILUTE ACIDS; DIRECT POLYMERIZATION; EFFECT OF PH; GUEST SPECIES; LEAD ION; LEAD IONS; LOADING CAPACITIES; REACTIVE ADSORPTION; SEPARATION EFFICIENCY; TETRAACETIC ACID; TRACE AMOUNTS; UPTAKE CAPACITY; VINYLIC POLYMERIZATION; ZINC IONS; DILUTE ACID SOLUTIONS;

CARBOXYLIC ACIDS; HEAVY METALS; ION EXCHANGE; METAL IONS; PH EFFECTS; POLYMERIZATION; ZINC; ZINC COMPOUNDS; LEAD; PHENOLS; SEPARATION;

ADSORPTION;

EID: 79960973221     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2011.06.015     Document Type: Article

References (63)

1. Brady M.E. A theoretical analysis of the environmental effects of lead contamination over time on IQ, education and crime in America: a viewpoint. Int. J. Environ. Stud. 1993, 44:189-201.
2. Tong S., von Schirnding Y.E., Prapamonto T. Environmental lead exposure: a public health problem of global dimensions. Bull. World Health Organ. 2000, 78:1068-1077.
3. Volesky B. Detoxification of metal-bearing effluents: biosorption for the next century. Hydrometallurgy 2001, 59:203-216.
4. Jain V.K., Pandya R.A., Pillai S.G., Agrawal Y.K., Shrivastav P.S. Application of a chelate forming calix[4]arene-o-vanillinthiosemicarbazone resin to the separation, preconcentration and trace determination of Cu(II), Cd(II) and Pb(II) in natural water samples. Microchim. Acta 2004, 147:253-264.
5. Ghaedi M., Ahmadi F., Tavakoli Z., Montazerozohori M., Khanmohammadi A., Soylak M. Three modified activated carbons by different ligands for the solid phase extraction of copper and lead. J. Hazard. Mater. 2008, 152:1248-1255.
6. Li Z., Chang X., Hu Z., Huang X., Zou X., Wu Q., Nie R. Zincon-modified activated carbon for solid-phase extraction and preconcentration of trace lead and chromium from environmental samples. J. Hazard. Mater. 2009, 166:133-137.
7. Rao T.P., Metilda P., Gladis J.M. Preconcentration techniques for uranium(VI) and thorium(IV) prior to analytical determination - an overview. Talanta 2006, 68:1047-1064.
8. Draa M.T., Belaid T., Benamor M. Extraction of Pb(II) by XAD-7 impregnated resins with organophosphorous extractants (DEHPA, IONOQUEST 801, CYANEX 272). Sep. Purif. Technol. 2004, 40:77-86.
9. Wang L., Yang L., Li Y., Zhang Y., Ma X., Ye Z. Study on adsorption mechanism of Pb(II) and Cu(II) in aqueous solution using PS-EDTA resin. Chem. Eng. J. 2010, 163:364-372.
10. Yang L., Li Y., Jin X., Ye Z., Ma X., Wang L., Liu Y. Synthesis and characterization of a series of chelating resins containing amino/imino-carboxyl groups and their adsorption behavior for lead in aqueous phase. Chem. Eng. J. 2011, 168:115-124.
11. Xiong C., Yao C. Synthesis, characterization and application of triethylenetetramine modified polystyrene resin in removal of mercury, cadmium and lead from aqueous solutions. Chem. Eng. J. 2009, 155:844-850.
12. Zhu X., Cui Y., Chang X., Zou X., Li Z. Selective solid-phase extraction of lead(II) from biological and natural water samples using surface-grafted lead(II)-imprinted polymers. Microchim. Acta 2009, 164:125-132.
13. Cui Y., Chang X., Zhu X., Zou X. Selective solid phase extraction of trace cadmium(II) and lead(II) from biological and natural water samples by ofloxacin-modified-silica gel. Int. J. Environ. Anal. Chem. 2008, 88:857-868.
14. Akama Y., Yamada K., Itoh O. Solid phase extraction of lead by Chelest Fiber Iry (aminopolycarboxylic acid-type cellulose). Anal. Chim. Acta 2003, 485:19-24.
15. Xiang G., Huang Y., Luo Y. Solid phase extraction of trace cadmium and lead in food samples using modified peanut shell prior to determination by flame atomic absorption spectrometry. Microchim. Acta 2009, 165:237-242.
16. Li Y.-H., Di Z., Ding J., Wu D., Luan Z., Zhu Y. Adsorption thermodynamic, kinetic and desorption studies of Pb2+ on carbon nanotubes. Water Res. 2005, 39:605-609.
17. Wang S.-G, Gong W.-X., Liu X.-W., Yao Y.-W., Gao B.-Y., Yue Q.-Y. Removal of lead(II) from aqueous solution by adsorption onto manganese-oxide coated carbon nanotubes. Sep. Purif. Technol. 2010, 58:751-757.
18. Gerçel Ö., Gerçel H.F. Adsorption of lead(II) ions from aqueous solutions by activated carbon prepared from biomass plant material of Euphorbia rigida. Chem. Eng. J. 2007, 132:289-297.
19. Goel J., Kadirvelu K., Rajagopal C., Garg V.K. Removal of lead(II) by adsorption using treated granular activated carbon: batch and column studies. J. Hazard. Mater. 2005, 125:211-220.
20. Bekta N., Kara S. Removal of lead from aqueous solutions by natural clinoptilolites: equilibrium and kinetic studies. Sep. Purif. Technol. 2004, 39:189-200.
21. Turan M., Mart U., Yüksel B., Celik M.S. Lead removal in fixed-bed columns by zeolite and sepiolite. Chemosphere 2005, 60:1487-1492.
22. Erdem M., Özverdi A. Lead adsorption from aqueous solution onto siderite. Sep. Purif. Technol. 2005, 42:259-264.
23. Kaludjerovic-Radoicic T., Raicevic S. Aqueous Pb sorption by synthetic and natural apatite: kinetics, equilibrium and thermodynamic studies. Chem. Eng. J. 2010, 160:503-510.
24. Wang X.-j., Xia S.-q., Chen L., Zhao J.-f., Chovelon J.-m., Nicole J.-r. Biosorption of cadmium(II) and lead(II) ions from aqueous solutions onto dried activated sludge. J. Environ. Sci. 2006, 5:840-844.
25. Naiya T.K., Chowdhury P., Bhattacharya A.K., Das S.K. Sawdust and neem bark as low-cost natural bioadsorbents for adsorptive removal of Zn(II) and Cd(II) ions from aqueous solutions. Chem. Eng. J. 2009, 148:68-79.
26. Reddy D.H.K., Harinath Y., Seshaiah K., Reddy A.V.R. Biosorption of Pb(II) from aqueous solutions using chemically modified Moringa oleifera tree leaves. Chem. Eng. J. 2010, 162:626-634.
27. Blázquez G., Martín-Lara M.A., Tenorio G., Calero M. Batch adsorption of lead (II) from aqueous solutions by olive tree pruning waste: equilibrium, kinetics and thermodynamic study. Chem. Eng. J. 2011, 168:170-177.
28. Gutsche C.D. Calixarenes 1989, Royal Society of Chemistry, Cambridge.
29. Gutsche C.D. Calixarenes Revisited 1998, Royal Society of Chemistry, Cambridge.
30. Vicens J., Böhmer V. Calixarenes: A Versatile Class of Macrocyclic Compounds 1992, Kluwer Academic Publishers, Netherlands.
31. Asfari Z., Böhmer V., Harrowfield J., Vicens J. Calixarenes 2001, Kluwer Academic Publishers, Netherlands.
32. Ohto K., Fujimoto Y., Inoue K. Stepwise extraction of two lead ions with a single molecule of calix[4]arene tetracarboxylic acid. Anal. Chim. Acta 1999, 387:61-69.
33. Ohto K., Yokomoto T., Higuchi H., Oshima T., Inoue K., Jumina Extraction mechanism of lead ion with p-allylcalix[4]arene tetracarboxylic acid. Ars Separatoria Acta 2004, 3:62-71.
34. Dung N.T.K., Ludwig R. Solvent extraction of heavy metals with macrocyclic ligands based on calix[4]arenes. New J. Chem. 1999, 23:603-607.
35. Toumi N., Kajo F., Fournier D., Vocanson F., Lamartine R., Dumazet-Bonnamour I. A useful approach towards solid-liquid extraction of metal cations with unsupported calixarenes. Mater. Sci. Eng. C 2008, 28:645-652.
36. Tu C., Surowiec K., Bartsch R.A. Efficient divalent metal cation extractions with di-ionizable calix[4]arene-1,2-crown-4 compounds. Tetrahedron 2007, 63:4184-4189.
37. Tu C., Surowiec K., Gega J., Purkiss D.W., Bartsch R.A. Di-ionizable calix[4]arene-1,2-crown-5 and crown-6 ethers in cone conformations: synthesis and divalent metal ion extraction. Tetrahedron 2008, 64:1187-1196.
38. Shimojo K., Goto M. Synergistic extraction of nucleobases by the combination of calixarene and D2EHPA. Sep. Purif. Technol. 2005, 44:175-180.
39. Thurman E.M., Mills M.S. Solid-phase Extraction: Principle and Practice 1998, John Wiley and Sons, New York.
40. Camel V. Solid phase extraction of trace elements. Spectrochim. Acta B 2003, 58:1177-1233.
41. Ohto K., Tanaka Y., Inoue K. Adsorptive separation of lead and zinc ions by novel type of calix[4]arene carboxylate resin immobilized with polyallylamine. Chem. Lett. 1997, 647-648.
42. Ohto K., Tanaka Y., Yano M., Shinohara T., Murakami E., Inoue K. Selective adsorption of lead ion on calix[4]arene carboxylate resin supported by polyallylamine. Solv. Extr. Ion Exch. 2001, 19:725-741.
43. Alexandrots S.D., Natesan S. Synthesis and ion-binding affinities of calix[4]arenes immobilized on cross-linked polystyrene. Macromolecules 2001, 34:206-210.
44. Jain V.K., Handa A., Pandya R., Shrivastav P., Agrawal Y.K. Polymer supported calix[4]arene-semicarbazone derivative for separation and preconcentration of La(III), Ce(III), T(IV) and U(VI). React. Funct. Polym. 2002, 51:101-110.
45. Seyhan S., Colak M., Merdivan M., Demirel N. Solid phase extractive preconcentration of trace metals using p-tert-butylcalix[4]arene-1,2-crown-4-anchored chloromethylated polymeric resin beads. Anal. Chim. Acta 2007, 584:462-468.
46. Solangi I.B., Memon S., Bhanger M.I. Synthesis and application of a highly efficient tetraester calix[4]arene based resin for the removal of Pb2+ from aqueous environment. Anal. Chim. Acta 2009, 638:146-153.
47. Ohto K., Senba Y., Eguchi N., Shinohara T., Inoue K. Solid phase extraction of metal ions on resins impregnated with carboxylates of phenolic oligomers. Solv. Extr. Res. Dev. Jpn. 1999, 6:101-112.
48. Ohto K., Inoue S., Eguchi N., Shinohara T., Inoue K. Adsorption behavior of lead ion on calix[4]arene tetracarboxylic acid impregnated resin. Sep. Sci. Technol. 2002, 37:1943-1958.
49. Matsumiya H., Yasuno S., Iki N., Miyano S. Sulfinylcalix[4]arene-impregnated amberlite XAD-7 resin for the separation of niobium(V) from tantalum(V). J. Chromatogr. A 2005, 1090:197-200.
50. Oshima T., Saisho R., Ohe K., Baba Y., Ohto K. Adsorption of amino acid derivatives on calixarene carboxylic acid impregnated resins. React. Funct. Polym. 2009, 69:105-110.
51. Yang F., Guo H., Cai X., Chen X. Syntheses and adsorption properties of novel calixarene polymers; calix[6]-1,4-crown-4-based netty polymers. React. Funct. Polym. 2005, 64:63-168.
52. Yilmaz A., Memon S., Yilmaz M. Synthesis and binding properties of calix[4]arene telomers. J. Polym. Sci. A 1999, 37:4351-4355.
53. Blanda M.T., Adou E. Syntheses and characterizations of three vinyl copolymers containing pendant calix[4]arenes. Polymer 1998, 39:3821-3826.
54. Haris S.J., Barrett G., McKervey M.A. Polymeric calixarenes. Synthesis, polymerization and Na+ complexation of a calix[4]arene methacrylate. J. Chem. Soc., Chem. Commun. 1991, 1224-1225.
55. Mendes A.R., Gregório C.C., Barata P.D., Costa A.I., Prata J.V. Linear and crosslinked copolymers of p-tert-butylcalix[4]arene derivatives and styrene: new synthetic approaches to polymer-bound calix[4]arenes. React. Funct. Polym. 2005, 65:9-21.
56. Miloshev S., Petrova P. Preparation of copolymers of p-isopropenylcalix[8]arene and styrene. Polym. Bull. 2006, 56:485-494.
57. Usyal G., Memon S., Yilmaz M. Synthesis and binding properties of polymeric calix[4]arene nitriles. React. Funct. Polym. 2001, 50:77-84.
58. Macrocycle Synthesis: A Practical Approach 1996, Oxford University Press. D. Parker (Ed.).
59. Kim S.I., Shin T.J., Ree M., Hwang G.T., Kim B.H., Han H., Seo J. Synthesis and characterization of new polyimides containing calix[4]arenes in the polymer backbone. J. Polym. Sci. A 1999, 37:2013-2026.
60. Shinkai S., Nagasaki T., Iwamoto K., Ikeda A., He G.X., Matsuda T., Iwamoto M. New syntheses and physical properties of p-alkylcalix[n]arenes. Bull. Chem. Soc. Jpn. 1991, 64:381-386.
61. Mishra G.S. Introductory Polymer Chemistry 1993, New Age International Publishers, New Delhi.
62. Yang F.-F., Huang Z.-S., Zhang X.-Y., Guo H.-Y. Thiacalix[4]amido-based netty polymers; novel sorbents for heavy metal cations and derivatives of aniline. Iran. Polym. J. 2010, 19:309-318.
63. Portanova R., Lajunen L.H.J., Tolazzi M., Piispanen J. Critical evaluation of stability constants for alpha-hydroxycarboxylic acid complexes with protons and metal ions and the accompanying enthalpy changes. Part II. Aliphatic 2-hydroxycarboxylic acids. Pure Appl. Chem. 2003, 75:495. Stability constants supplement no. 1, Special publication 25, The Chemical Society London SBN: 851860192, pp. 114-116.