EDTA-Cross-Linked β-Cyclodextrin: An Environmentally Friendly Bifunctional Adsorbent for Simultaneous Adsorption of Metals and Cationic Dyes

Environmental Science and Technology

Volumn 49, Issue 17, 2015, Pages 10570-10580

  Zhao, Feiping ^a,b   Repo, Eveliina ^a   Yin, Dulin ^b   Meng, Yong ^b   Jafari, Shila ^a   Sillanpää, Mika ^a  

^a LAPPEENRANTA UNIVERSITY OF TECHNOLOGY   (Finland)

^b HUNAN NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; COMPLEXATION; CROSSLINKING; CYCLODEXTRINS; DYES; HEALTH RISKS; INDUSTRIAL WATER TREATMENT; METALS; POLLUTION; PUBLIC HEALTH; REUSABILITY; WASTEWATER TREATMENT;

ADSORPTION CAPACITIES; ADSORPTION MECHANISM; CYCLODEXTRIN CAVITIES; HAZARDOUS POLLUTANTS; INDUSTRIAL WASTEWATERS; POLYCONDENSATION REACTIONS; SORPTION PERFORMANCE; THERMODYNAMIC STUDIES;

ADSORPTION;

ADSORBENT; BETA CYCLODEXTRIN; COPPER; CRYSTAL VIOLET; DYE; EDETIC ACID; METHYLENE BLUE; SAFRANIN O; UNCLASSIFIED DRUG; BETA CYCLODEXTRIN DERIVATIVE; CATION; COLORING AGENT; CROSS LINKING REAGENT; METAL; WATER POLLUTANT;

ADSORPTION; DISCHARGE; DYE; EDTA; METAL; PERFORMANCE ASSESSMENT; POLLUTANT SOURCE; PUBLIC HEALTH; REACTION KINETICS; SORPTION; THERMODYNAMICS; TOXIC MATERIAL; WASTEWATER; WATER TREATMENT;

ADSORPTION; ADSORPTION KINETICS; ARTICLE; CROSS LINKING; DECOLORIZATION; DESORPTION; EFFLUENT; HEAVY METAL REMOVAL; INFRARED SPECTROSCOPY; METAL BINDING; PH; POLLUTANT; ROENTGEN SPECTROSCOPY; SCANNING ELECTRON MICROSCOPY; TEXTILE; THERMODYNAMICS; THERMOGRAVIMETRY; ZETA POTENTIAL; CHEMISTRY; GREEN CHEMISTRY; ISOLATION AND PURIFICATION; KINETICS; SEWAGE; TEMPERATURE; WATER POLLUTANT;

ADSORPTION; BETA-CYCLODEXTRINS; CATIONS; COLORING AGENTS; CROSS-LINKING REAGENTS; EDETIC ACID; GENTIAN VIOLET; GREEN CHEMISTRY TECHNOLOGY; HYDROGEN-ION CONCENTRATION; KINETICS; METALS; METHYLENE BLUE; TEMPERATURE; TEXTILES; WASTE DISPOSAL, FLUID; WATER POLLUTANTS, CHEMICAL;

EID: 84940981747     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/acs.est.5b02227     Document Type: Article

References (58)

1. 2 suspensions under visible-light illumination Environ. Sci. Technol. 2005, 39, 2376-82 10.1021/es0492788
2. Hernandez-Montoya, V.; Perez-Cruz, M. A.; Mendoza-Castillo, D. I.; Moreno-Virgen, M. R.; Bonilla-Petriciolet, A. Competitive adsorption of dyes and heavy metals on zeolitic structures J. Environ. Manage. 2013, 116, 213-21 10.1016/j.jenvman.2012.12.010
3. Ling, C.; Liu, F.-Q.; Long, C.; Chen, T.-P.; Wu, Q.-Y.; Li, A.-M. Synergic removal and sequential recovery of acid black 1 and copper (II) with hyper-crosslinked resin and inside mechanisms Chem. Eng. J. 2014, 236, 323-331 10.1016/j.cej.2013.09.058
4. Malachova, K.; Rybkova, Z.; Sezimova, H.; Cerven, J.; Novotny, C. Biodegradation and detoxification potential of rotating biological contactor (RBC) with Irpex lacteus for remediation of dye-containing wastewater Water Res. 2013, 47, 7143-8 10.1016/j.watres.2013.07.050
5. Bellas, J.; Vazquez, E.; Beiras, R. Toxicity of Hg, Cu, Cd, and Cr on early developmental stages of Ciona intestinalis (Chordata, Ascidiacea) with potential application in marine water quality assessment Water Res. 2001, 35, 2905-12 10.1016/S0043-1354(01)00004-5
6. Vinu, R.; Madras, G. Kinetics of sonophotocatalytic degradation of anionic dyes with Nano-TiO2 Environ. Sci. Technol. 2009, 43, 473-9 10.1021/es8025648
7. Salima, A.; Benaouda, B.; Noureddine, B.; Duclaux, L. Application of Ulva lactuca and Systoceira stricta algae-based activated carbons to hazardous cationic dyes removal from industrial effluents Water Res. 2013, 47, 3375-88 10.1016/j.watres.2013.03.038
8. Bailey, S. E.; Olin, T. J.; Bricka, R. M.; Adrian, D. D. A review of potentially low-cost sorbents for heavy metals Water Res. 1999, 33, 2469-2479 10.1016/S0043-1354(98)00475-8
9. Wang, H.; Ren, Z. J. Bioelectrochemical metal recovery from wastewater: a review Water Res. 2014, 66, 219-32 10.1016/j.watres.2014.08.013
10. Skold, M. E.; Thyne, G. D.; Drexler, J. W.; Macalady, D. L.; McCray, J. E. Enhanced solubilization of a metal-organic contaminant mixture (Pb, Sr, Zn, and perchloroethylene) by cyclodextrin Environ. Sci. Technol. 2008, 42, 8930-4 10.1021/es801835x
11. Deng, J.-H.; Zhang, X.-R.; Zeng, G.-M.; Gong, J.-L.; Niu, Q.-Y.; Liang, J. Simultaneous removal of Cd(II) and ionic dyes from aqueous solution using magnetic graphene oxide nanocomposite as an adsorbent Chem. Eng. J. 2013, 226, 189-200 10.1016/j.cej.2013.04.045
12. Brusseau, M. L.; Wang, X.; Wang, W.-Z. Simultaneous Elution of Heavy Metals and Organic Compounds from Soil by Cyclodextrin Environ. Sci. Technol. 1997, 31, 1087-1092 10.1021/es960612c
13. Oonnittan, A.; Shrestha, R. A.; Sillanpää, M. Effect of cyclodextrin on the remediation of hexachlorobenzene in soil by electrokinetic Fenton process Sep. Purif. Technol. 2009, 64, 314-320 10.1016/j.seppur.2008.10.021
14. Uekama, K.; Hirayama, F.; Irie, T. Cyclodextrin Drug Carrier Systems Chem. Rev. 1998, 98, 2045-2076 10.1021/cr970025p
15. Kawano, S.; Kida, T.; Miyawaki, K.; Noguchi, Y.; Kato, E.; Nakano, T.; Akashi, M. Cyclodextrin polymers as highly effective adsorbents for removal and recovery of polychlorobiphenyl (PCB) contaminants in insulating oil Environ. Sci. Technol. 2014, 48, 8094-8100 10.1021/es501243v
16. Liu, H.; Cai, X.; Wang, Y.; Chen, J. Adsorption mechanism-based screening of cyclodextrin polymers for adsorption and separation of pesticides from water Water Res. 2011, 45, 3499-511 10.1016/j.watres.2011.04.004
17. Murai, S.; Imajo, S.; Takasu, Y.; Takahashi, K.; Hattori, K. Removal of Phthalic Acid Esters from Aqueous Solution by Inclusion and Adsorption on β-Cyclodextrin Environ. Sci. Technol. 1998, 32, 782-787 10.1021/es970463d
18. Sawicki, R.; Mercier, L. Evaluation of mesoporous cyclodextrin-silica nanocomposites for the removal of pesticides from aqueous media Environ. Sci. Technol. 2006, 40, 1978-83 10.1021/es051441r
19. Yu, O. Y.; Chung, J. W.; Kwak, S. Y. Reduced migration from flexible poly(vinyl chloride) of a plasticizer containing beta-cyclodextrin derivative Environ. Sci. Technol. 2008, 42, 7522-7 10.1021/es800895x
20. Fuhrer, R.; Herrmann, I. K.; Athanassiou, E. K.; Grass, R. N.; Stark, W. J. Immobilized beta-cyclodextrin on surface-modified carbon-coated cobalt nanomagnets: reversible organic contaminant adsorption and enrichment from water Langmuir 2011, 27, 1924-9 10.1021/la103873v
21. Sobocinski, J.; Laure, W.; Taha, M.; Courcot, E.; Chai, F.; Simon, N.; Addad, A.; Martel, B.; Haulon, S.; Woisel, P.; Blanchemain, N.; Lyskawa, J. Mussel inspired coating of a biocompatible cyclodextrin based polymer onto CoCr vascular stents ACS Appl. Mater. Interfaces 2014, 6, 3575-86 10.1021/am405774v
22. Schofield, W. C. E.; Bain, C. D.; Badyal, J. P. S. Cyclodextrin-Functionalized Hierarchical Porous Architectures for High-Throughput Capture and Release of Organic Pollutants from Wastewater Chem. Mater. 2012, 24, 1645-1653 10.1021/cm300552k
23. Crini, G. Studies on adsorption of dyes on beta-cyclodextrin polymer Bioresour. Technol. 2003, 90, 193-8 10.1016/S0960-8524(03)00111-1
24. Wilson, L. D.; Pratt, D. Y.; Kozinski, J. A. Preparation and sorption studies of beta-cyclodextrin-chitosan-glutaraldehyde terpolymers J. Colloid Interface Sci. 2013, 393, 271-7 10.1016/j.jcis.2012.10.046
25. Zeiger, E.; Gollapudi, B.; Spencer, P. Genetic toxicity and carcinogenicity studies of glutaraldehyde-a review Mutat. Res., Rev. Mutat. Res. 2005, 589, 136-151 10.1016/j.mrrev.2005.01.001
26. Hirakawa, B. Epichlorohydrin. In Encyclopedia of Toxicology, Third ed.; Wexler, P., Ed.; Academic Press: Oxford, U. K., 2014; pp 431-432.
27. Zhao, F.; Repo, E.; Sillanpää, M.; Meng, Y.; Yin, D.; Tang, W. Z. Green Synthesis of Magnetic EDTA- and/or DTPA-Cross-Linked Chitosan Adsorbents for Highly Efficient Removal of Metals Ind. Eng. Chem. Res. 2015, 54, 1271-1281 10.1021/ie503874x
28. Repo, E.; Warchol, J. K.; Kurniawan, T. A.; Sillanpää, M. E. T. Adsorption of Co(II) and Ni(II) by EDTA- and/or DTPA-modified chitosan: Kinetic and equilibrium modeling Chem. Eng. J. 2010, 161, 73-82 10.1016/j.cej.2010.04.030
29. Zhao, F.; Repo, E.; Yin, D.; Sillanpää, M. E. T. Adsorption of Cd(II) and Pb(II) by a novel EGTA-modified chitosan material: Kinetics and isotherms J. Colloid Interface Sci. 2013, 409, 174-182 10.1016/j.jcis.2013.07.062
30. Noradoun, C. E.; Cheng, I. F. EDTA degradation induced by oxygen activation in a zerovalent iron/air/water system Environ. Sci. Technol. 2005, 39, 7158-63 10.1021/es050137v
31. 2: toward environmental sustainability Environ. Sci. Technol. 2015, 49, 2541-8 10.1021/es504711e
32. Repo, E.; Warchoł, J. K.; Bhatnagar, A.; Mudhoo, A.; Sillanpää, M. Aminopolycarboxylic acid functionalized adsorbents for heavy metals removal from water Water Res. 2013, 47, 4812-4832 10.1016/j.watres.2013.06.020
33. Sillanpaa, M. E.; Ramo, J. H. Decomposition of beta-alaninediacetic acid and diethylenetriamine-pentaacetic acid by hydrogen peroxide in alkaline conditions Environ. Sci. Technol. 2001, 35, 1379-84 10.1021/es000167s
34. Kyzas, G. Z.; Siafaka, P. I.; Pavlidou, E. G.; Chrissafis, K. J.; Bikiaris, D. N. Synthesis and adsorption application of succinyl-grafted chitosan for the simultaneous removal of zinc and cationic dye from binary hazardous mixtures Chem. Eng. J. 2015, 259, 438-448 10.1016/j.cej.2014.08.019
35. Visa, M.; Bogatu, C.; Duta, A. Simultaneous adsorption of dyes and heavy metals from multicomponent solutions using fly ash Appl. Surf. Sci. 2010, 256, 5486-5491 10.1016/j.apsusc.2009.12.145
36. Lokhande, R. S.; Singare, P. U.; Pimple, D. S. Toxicity study of heavy metals pollutants in waste water effluent samples collected from Taloja Industrial Estate of Mumbai, India Res. Environ. 2011, 1, 13-19 10.5923/j.re.20110101.02
37. Zhao, D.; Zhao, L.; Zhu, C.; Tian, Z.; Shen, X. Synthesis and properties of water-insoluble β-cyclodextrin polymer crosslinked by citric acid with PEG-400 as modifier Carbohydr. Polym. 2009, 78, 125-130 10.1016/j.carbpol.2009.04.022
38. Morin-Crini, N.; Crini, G. Environmental applications of water-insoluble β-cyclodextrin-epichlorohydrin polymers Prog. Polym. Sci. 2013, 38, 344-368 10.1016/j.progpolymsci.2012.06.005
39. Gidwani, B.; Vyas, A. Synthesis, characterization and application of epichlorohydrin-beta-cyclodextrin polymer Colloids Surf., B 2014, 114, 130-7 10.1016/j.colsurfb.2013.09.035
40. OECD guideline for the testing of chemicals in the Hershberger assay; OECD: Paris, 2001.
41. Nilsson, I.; Möller, A.; Mattiasson, B.; Rubindamayugi, M. S. T.; Welander, U. Decolorization of synthetic and real textile wastewater by the use of white-rot fungi Enzyme Microb. Technol. 2006, 38, 94-100 10.1016/j.enzmictec.2005.04.020
42. Medronho, B.; Andrade, R.; Vivod, V.; Ostlund, A.; Miguel, M. G.; Lindman, B.; Voncina, B.; Valente, A. J. Cyclodextrin-grafted cellulose: physico-chemical characterization Carbohydr. Polym. 2013, 93, 324-30 10.1016/j.carbpol.2012.08.109
43. Badruddoza, A. Z.; Tay, A. S.; Tan, P. Y.; Hidajat, K.; Uddin, M. S. Carboxymethyl-beta-cyclodextrin conjugated magnetic nanoparticles as nano-adsorbents for removal of copper ions: synthesis and adsorption studies J. Hazard. Mater. 2011, 185, 1177-86 10.1016/j.jhazmat.2010.10.029
44. Konkena, B.; Vasudevan, S. Covalently linked, water-dispersible, cyclodextrin: reduced-graphene oxide sheets Langmuir 2012, 28, 12432-7 10.1021/la3020783
45. Repo, E.; Kurniawan, T. A.; Warchol, J. K.; Sillanpää, M. E. T. Removal of Co(II) and Ni(II) ions from contaminated water using silica gel functionalized with EDTA and/or DTPA as chelating agents J. Hazard. Mater. 2009, 171, 1071-1080 10.1016/j.jhazmat.2009.06.111
46. Li, Y. F.; Ha, Y. M.; Guo, Q.; Li, Q. P. Synthesis of two beta-cyclodextrin derivatives containing a vinyl group Carbohydr. Res. 2015, 404, 55-62 10.1016/j.carres.2014.11.012
47. Zhao, F.; Tang, W. Z.; Zhao, D.; Meng, Y.; Yin, D.; Sillanpää, M. Adsorption kinetics, isotherms and mechanisms of Cd(II), Pb(II), Co(II) and Ni(II) by a modified magnetic polyacrylamide microcomposite adsorbent J. Water Process Eng. 2014, 4, 47-57 10.1016/j.jwpe.2014.09.003
48. Üçer, A.; Uyanik, A.; Aygün, Ş. F. Adsorption of Cu(II), Cd(II), Zn(II), Mn(II) and Fe(III) ions by tannic acid immobilised activated carbon Sep. Purif. Technol. 2006, 47, 113-118 10.1016/j.seppur.2005.06.012
49. Ghaedi, M.; Pakniat, M.; Mahmoudi, Z.; Hajati, S.; Sahraei, R.; Daneshfar, A. Synthesis of nickel sulfide nanoparticles loaded on activated carbon as a novel adsorbent for the competitive removal of Methylene blue and Safranin-O Spectrochim. Acta, Part A 2014, 123, 402-9 10.1016/j.saa.2013.12.083
50. El-Sayed, G. O. Removal of methylene blue and crystal violet from aqueous solutions by palm kernel fiber Desalination 2011, 272, 225-232 10.1016/j.desal.2011.01.025
51. 2-modified carbon J. Hazard. Mater. 2012, 199-200, 290-300 10.1016/j.jhazmat.2011.11.015
52. Luo, S.; Xu, X.; Zhou, G.; Liu, C.; Tang, Y.; Liu, Y. Amino siloxane oligomer-linked graphene oxide as an efficient adsorbent for removal of Pb(II) from wastewater J. Hazard. Mater. 2014, 274, 145-155 10.1016/j.jhazmat.2014.03.062
53. Saenger, W. Cyclodextrin Inclusion Compounds in Research and Industry Angew. Chem., Int. Ed. Engl. 1980, 19, 344-362 10.1002/anie.198003441
54. Hussein, K.; Turk, M.; Wahl, M. A. Comparative evaluation of ibuprofen/beta-cyclodextrin complexes obtained by supercritical carbon dioxide and other conventional methods Pharm. Res. 2007, 24, 585-92 10.1007/s11095-006-9177-0
55. Repo, E.; Warchoł, J. K.; Bhatnagar, A.; Sillanpää, M. Heavy metals adsorption by novel EDTA-modified chitosan-silica hybrid materials J. Colloid Interface Sci. 2011, 358, 261-267 10.1016/j.jcis.2011.02.059
56. Cosgrove, T.; Prestidge, C. A.; Vincent, B. Chemisorption of linear and cyclic polymethylsiloxanes on alumina studied by Fourier-transform infrared spectroscopy J. Chem. Soc., Faraday Trans. 1990, 86, 1377-1382 10.1039/ft9908601377
57. Murthy, C. N.; Geckeler, K. E. The water-soluble [small beta]-cyclodextrin-[60]fullerene complex Chem. Commun. 2001, 1194-1195 10.1039/b102142g
58. Fan, L.; Zhang, Y.; Luo, C.; Lu, F.; Qiu, H.; Sun, M. Synthesis and characterization of magnetic beta-cyclodextrin-chitosan nanoparticles as nano-adsorbents for removal of methyl blue Int. J. Biol. Macromol. 2012, 50, 444-50 10.1016/j.ijbiomac.2011.12.016