Recyclable Capture and Destruction of Aqueous Micropollutants Using the Molecule-Specific Cavity of Cyclodextrin Polymer Coupled with KMnO4 Oxidation

Environmental Science and Technology

Volumn 49, Issue 15, 2015, Pages 9264-9272

  Cai, Xiyun ^a   Liu, Qingquan ^a   Xia, Chunlong ^a,b   Shan, Danna ^a   Du, Juan ^a   Chen, Jingwen ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b Fushun Branch of Liaoning Province Hydrology and Water Resources Investigation Bureau   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; CYCLODEXTRINS; INDUSTRIAL CHEMICALS; MANGANESE OXIDE; OXIDATION; POLLUTION;

ADSORPTION EFFICIENCY; ADSORPTION POTENTIAL; CYCLODEXTRIN POLYMER; LINEAR FUNCTIONS; MOLECULAR SPECIFICITY; ORDERS OF MAGNITUDE; SOLID-TO-LIQUID RATIO; TREATMENT TECHNOLOGIES;

WATER POLLUTION;

ANTIBIOTIC AGENT; BETA CYCLODEXTRIN; MANGANESE; METAL NANOPARTICLE; NANOPARTICLE; PERMANGANATE POTASSIUM; POLYMER; RIVER WATER; TETRABROMOBISPHENOL A; CELLULOSE; CYCLODEXTRIN; CYCLODEXTRIN POLYMER; POLYBROMINATED BIPHENYL; WATER POLLUTANT;

ADSORPTION; AQUEOUS SOLUTION; BIODEGRADATION; CATALYSIS; DISSOLVED ORGANIC CARBON; INORGANIC COMPOUND; MOLECULAR ANALYSIS; OXIDATION; POLLUTANT REMOVAL; POLYMER; POROUS MEDIUM; RECYCLING;

ADSORPTION; AQUEOUS SOLUTION; ARTICLE; DEGRADATION; MOLECULAR RECOGNITION; OXIDATION; RECYCLING; SURFACE PROPERTY; WASTE COMPONENT REMOVAL; WATER POLLUTANT; WATER POLLUTION; WATER POLLUTION CONTROL; WATER TREATMENT; ANALYSIS; CHEMISTRY; ENVIRONMENT; OXIDATION REDUCTION REACTION; TIME FACTOR;

ADSORPTION; CELLULOSE; CYCLODEXTRINS; ENVIRONMENT; OXIDATION-REDUCTION; POLYBROMINATED BIPHENYLS; POTASSIUM PERMANGANATE; RECYCLING; TIME FACTORS; WATER POLLUTANTS, CHEMICAL;

EID: 84938674753     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/acs.est.5b01734     Document Type: Article

References (71)

1. Schwarzenbach, R. P.; Escher, B. I.; Fenner, K.; Hofstetter, T. B.; Johnson, C. A.; von Gunten, U.; Wehrli, B. The challenge of micropollutants in aquatic systems Science 2006, 313, 1072-1077 10.1126/science.1127291
2. Shannon, M. A.; Bohn, P. W.; Elimelech, M.; Georgiadis, J. G.; Marinas, B. J.; Mayes, A. M. Science and technology for water purification in the coming decades Nature 2008, 452, 301-310 10.1038/nature06599
3. Daughton, C. G. Cradle-to-cradle stewardship of drugs for minimizing their environmental disposition while promoting human health. I. Rationale for and avenues toward a green pharmacy Environ. Health Perspect. 2002, 111, 757-774 10.1289/ehp.5947
4. Boxall, A. B. A.; Sinclair, C. J.; Fenner, K.; Kolpin, D.; Maund, S. J. When synthetic chemicals degrade in the environment Environ. Sci. Technol. 2004, 38, 368A-375A 10.1021/es040624v
5. Cui, N.; Zhang, X. X.; Xie, Q.; Wang, S.; Chen, J. W.; Huang, L. P.; Qiao, X. L.; Li, X. H.; Cai, X. Y. Toxicity profile of labile preservative bronopol in water: the role of more persistent and toxic transformation products Environ. Pollut. 2011, 159, 609-615 10.1016/j.envpol.2010.09.036
6. Fenner, K.; Canonica, S.; Wackett, L. P.; Elsner, M. Evaluating pesticide degradation in the environment: blind spots and emerging opportunities Science 2013, 341, 752-758 10.1126/science.1236281
7. Cai, X. Y.; Xiong, W. N.; Xia, T. T.; Chen, J. W. Probing the stereochemistry of successive sulfoxidation of the insecticide fenamiphos in soils Environ. Sci. Technol. 2014, 48, 11277-11285 10.1021/es502834v
8. Hayes, T. B.; Khoury, V.; Narayan, A.; Nazir, M.; Park, A.; Brown, T.; Adame, L.; Chan, E.; Buchholz, D.; Stueve, T.; Gallipeau, S. Atrazine induces complete feminization and chemical castration in male African clawed frogs (Xenopus laevis) Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 4612-4617 10.1073/pnas.0909519107
9. Matatov-Meytal, Y. I.; Sheintuch, M. Catalytic abatement of water pollutants Ind. Eng. Chem. Res. 1998, 37, 309-326 10.1021/ie9702439
10. Carballa, M.; Omil, F.; Lema, J. M.; Llompart, M.; Garcia-Jares, C.; Rodriguez, I.; Gomez, M.; Ternes, T. Behavior of pharmaceuticals, cosmetics and hormones in a sewage treatment plant Water Res. 2004, 38, 2918-2926 10.1016/j.watres.2004.03.029
11. Gogate, P. R.; Pandit, A. B. A review of imperative technologies for wastewater treatment II: hybrid methods Adv. Environ. Res. 2004, 8, 5553-5597 10.1016/S1093-0191(03)00031-5
12. Oller, I.; Malato, S.; Sanchez-Perez, J. A. Combination of advanced oxidation processes and biological treatments for wastewater decontamination-A review Sci. Total Environ. 2011, 409, 4141-4166 10.1016/j.scitotenv.2010.08.061
13. von Gunten, U. Ozonation of drinking water: Part I. Oxidation kinetics and product formation Water Res. 2003, 37, 1443-1467 10.1016/S0043-1354(02)00457-8
14. Richardson, S. D.; Plewa, M. J.; Wagner, E. D.; Schoeny, R.; DeMarini, D. M. Occurrence, genotoxicity, and carcinogenicity of regulated and emerging disinfection by-products in drinking water: A review and roadmap for research Mutat. Res., Rev. Mutat. Res. 2007, 636, 178-242 10.1016/j.mrrev.2007.09.001
15. Westerhoff, P.; Yoon, Y.; Snyder, S.; Wert, E. Fate of endocrine-disruptor, pharmaceutical, and personal care product chemicals during simulated drinking water treatment processes Environ. Sci. Technol. 2005, 39, 6649-6663 10.1021/es0484799
16. Lu, J.; Huang, Q. Removal of acetaminophen using enzymemediated oxidative coupling processes: II. Cross-coupling with natural organic matter Environ. Sci. Technol. 2009, 43, 7068-7073 10.1021/es9001295
17. Jiang, J.; Gao, Y.; Pang, S. Y.; Wang, Q.; Huangfu, X. L.; Liu, Y. Z.; Ma, J. Oxidation of bromophenols and formation of brominated polymeric products of concern during water treatment with potassium permanganate Environ. Sci. Technol. 2014, 48, 10850-10858 10.1021/es5008577
18. Crini, G. Review: a history of cyclodextrins Chem. Rev. 2014, 114, 10940-10975 10.1021/cr500081p
19. Sawicki, R.; Mercier, L. Evaluation of mesoporous cyclodextrin-silica nanocomposites for the removal of pesticides from aqueous media Environ. Sci. Technol. 2006, 40, 1978-1983 10.1021/es051441r
20. Liu, H. H.; Cai, X. Y.; Wang, Y.; Chen, J. W. Adsorption mechanism-based screening of cyclodextrin polymers for adsorption and separation of pesticides from water Water Res. 2011, 45, 3499-3511 10.1016/j.watres.2011.04.004
21. 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
22. Yoshizawa, M.; Tamura, M.; Fujita, M. Diels-Alder in aqueous molecular hosts: unusual regioselectivity and efficient catalysis Science 2006, 312, 251-254 10.1126/science.1124985
23. Lee, T. C.; Kalenius, E.; Lazar, A. I.; Assaf, K. I.; Kuhnert, N.; Grün, C. H.; Jänis, J.; Scherman, O. A.; Nau, W. M. Chemistry inside molecular containers in the gas phase Nat. Chem. 2013, 5, 376-382 10.1038/nchem.1618
24. Szejtli, J. Introduction and general overview of cyclodextrin chemistry Chem. Rev. 1998, 98, 1743-1753 10.1021/cr970022c
25. Liu, L.; Guo, Q. X. The driving forces in the inclusion complexation of cyclodextrins J. Inclusion Phenom. Mol. Recognit. Chem. 2002, 42, 1-14 10.1023/A:1014520830813
26. Liu, H. H.; Cai, X. Y.; Chen, J. W. Mathematical model for cyclodextrin alteration of bioavailability of organic pollutants Environ. Sci. Technol. 2013, 47, 5835-5842 10.1021/es303724b
27. Chen, L.; Dionysiou, D. D.; O'Shea, K. Complexation of microcystins and nodularin by cyclodextrins in aqueous solution, a potential removal strategy Environ. Sci. Technol. 2011, 45, 2293-2300 10.1021/es102865b
28. Crini, G. Studies on adsorption of dyes on β-cyclodextrin polymer Bioresour. Technol. 2003, 90, 193-198 10.1016/S0960-8524(03)00111-1
29. Nagy, Z. M.; Molnar, M.; Fekete-Kertesz, I.; Molnar-Perl, I.; Fenyvesi, E.; Gruiz, K. Removal of emerging micropollutants from water using cyclodextrin Sci. Total Environ. 2014, 485-486, 711-719 10.1016/j.scitotenv.2014.04.003
30. Zhang, Y.; Cai, X. Y.; Xiong, W. N.; Jiang, H.; Zhao, H. T.; Yang, X. H.; Li, C.; Fu, Z. Q.; Chen, J. W. Molecular insights into the pH-dependent adsorption and removal of ionizable antibiotic oxytetracycline by adsorbent cyclodextrin polymers PLoS One 2014, 9 (1) e86228 10.1371/journal.pone.0086228
31. Takahashi, K. Organic reaction mediated by cyclodextrins Chem. Rev. 1998, 98, 2013-2033 10.1021/cr9700235
32. Barr, L.; Dumanski, P. G.; Easton, C. J.; Harper, J. B.; Lee, K.; Lincoln, S. F.; Meyer, A. G.; Simpson, J. S. Cyclodextrin molecular reactors J. Inclusion Phenom. Mol. Recognit. Chem. 2004, 50, 19-24 10.1007/s10847-003-8833-9
33. Easton, C. J. Cyclodextrin-based catalysts and molecular reactors Pure Appl. Chem. 2005, 77, 1865-1871 10.1351/pac200577111865
34. Sletten, E. M.; Nakamura, H.; Jewett, J. C.; Bertozzi, C. R. Difluorobenzocyclooctyne: synthesis, reactivity, and stabilization by β-cyclodextrin J. Am. Chem. Soc. 2010, 132, 11799-11805 10.1021/ja105005t
35. Shen, H. M.; Ji, H. B.; Wu, H. K.; Shi, H. X. Recent advances in the immobilization of β-cyclodextrin and their application Youji Huaxue 2014, 34, 1549-1572 10.6023/cjoc201402024
36. Yan, Y. E.; Schwartz, F. W. Oxidative degradation and kinetics of chlorinated ethylenes by potassium permanganate J. Contam. Hydrol. 1999, 37, 343-365 10.1016/S0169-7722(98)00166-1
37. Waldemer, R. H.; Tratnyek, P. G. Kinetics of contaminant degradation by permanganate Environ. Sci. Technol. 2006, 40, 1055-1061 10.1021/es051330s
38. Guan, X. H.; He, D.; Ma, J.; Chen, G. H. Application of permanganate in the oxidation of micropollutants: a mini review Front. Environ. Sci. Eng. China 2010, 4, 405-413 10.1007/s11783-010-0252-8
39. Hu, L. H.; Martin, H. M.; Strathmann, T. J. Oxidation kinetics of antibiotics during water treatment with potassium permanganate Environ. Sci. Technol. 2010, 44, 6416-6422 10.1021/es101331j
40. Liu, R. P.; Liu, H. J.; Zhao, X.; Qu, J. H.; Zhang, R. Treatment of dye wastewater with permanganate oxidation and in situ formed manganese dioxides adsorption: cation blue as model pollutant J. Hazard. Mater. 2010, 176, 926-931 10.1016/j.jhazmat.2009.11.128
41. Hu, L. H.; Stemig, A. M.; Wammer, K. H.; Strathmann, T. J. Oxidation of antibiotics during water treatment with potassium permanganate: reaction pathways and deactivation Environ. Sci. Technol. 2011, 45, 3635-3642 10.1021/es104234m
42. Managaki, S.; Murata, A.; Takada, H.; Tuyen, B. C.; Chiem, N. H. Distribution of macrolides, sulfonamides, and trimethoprim in tropical waters: ubiquitous occurrence of veterinary antibiotics in the Mekong Delta Environ. Sci. Technol. 2007, 41, 8004-8010 10.1021/es0709021
43. Edwards, M.; Topp, E.; Metcalfe, C. D.; Li, H.; Gottschall, N.; Bolton, P.; Curnoe, W.; Payne, M.; Beck, A.; Kleywegt, S. Pharmaceutical and personal care products in tile drainage following surface spreading and injection of dewatered municipal biosolids to an agricultural field Sci. Total Environ. 2009, 407, 4220-4230 10.1016/j.scitotenv.2009.02.028
44. Luo, Y.; Xu, L.; Rysz, M.; Wang, Y. Q.; Zhang, H.; Alvarez, P. J. J. Occurrence and transport of tetracycline, sulfonamide, quinolone, and macrolide antibiotics in the Haihe River Basin, China Environ. Sci. Technol. 2011, 45, 1827-1833 10.1021/es104009s
45. Li, W. H.; Shi, Y. L.; Gao, L. H.; Liu, J. M.; Cai, Y. Q. Occurrence of antibiotics in water, sediments, aquatic plants, and animals from Baiyangdian Lake in North China Chemosphere 2012, 89, 1307-1315 10.1016/j.chemosphere.2012.05.079
46. Ladbury, J. W.; Cullis, C. H. Kinetics and mechanism of oxidation by permanganate Chem. Rev. 1958, 58, 403-438 10.1021/cr50020a005
47. Huang, K. C.; Hoag, G. E.; Chheda, P.; Woody, B. A.; Dobbs, G. M. Oxidation of chlorinated ethenes by potassium permanganate: a kinetics study J. Hazard. Mater. 2001, 87, 155-169 10.1016/S0304-3894(01)00241-2
48. Forsey, S. P.; Thomson, N. R.; Barker, J. F. Oxidation kinetics of polycyclic aromatic hydrocarbons by permanganate Chemosphere 2010, 79, 628-636 10.1016/j.chemosphere.2010.02.027
49. Jiang, J.; Pang, S. Y.; Ma, J.; Liu, H. L. Oxidation of phenolic endocrine disrupting chemicals by potassium permanganate in synthetic and real waters Environ. Sci. Technol. 2012, 46, 1774-1781 10.1021/es2035587
50. Barontini, F.; Cozzani, V.; Marsanich, K.; Raffa, V.; Petarca, L. An experimental investigation of tetrabromobisphenol A decomposition pathways J. Anal. Appl. Pyrolysis 2004, 72, 41-53 10.1016/j.jaap.2004.02.003
51. Brenner, A.; Mukmenev, I.; Abeliovich, A.; Kushmaro, A. Biodegradability of tetrabromo-bisphenol A and tribromophenol by activated sludge Ecotoxicology 2006, 15, 399-402 10.1007/s10646-006-0072-6
52. Lin, K. D.; Liu, W. P.; Gan, J. Reaction of tetrabromobisphenol A (TBBPA) with manganese dioxide: kinetics, products, and pathways Environ. Sci. Technol. 2009, 43, 4480-4486 10.1021/es803622t
53. Zhong, Y. H.; Liang, X. L.; Zhong, Y.; Zhu, J. X.; Zhu, S. Y.; Yuan, P.; He, H. P.; Zhang, J. Heterogeneous UV/Fenton degradation of TBBPA catalyzed by titanomagnetite: catalyst characterization, performance and degradation products Water Res. 2012, 46, 4633-4644 10.1016/j.watres.2012.06.025
54. Pang, S. Y.; Jiang, J.; Gao, Y.; Zhou, Y.; Huangfu, X. L.; Liu, Y. Z.; Ma, J. Oxidation of flame retardant tetrabromobisphenol A by aqueous permanganate: reaction kinetics, brominated products, and pathways Environ. Sci. Technol. 2014, 48, 615-623 10.1021/es4041094
55. Manhas, M. S.; Mohammed, F.; Khan, Z. A kinetic study of oxidation of β-cyclodextrin by permanganate in aqueous media Colloids Surf., A 2007, 295, 165-171 10.1016/j.colsurfa.2006.08.048
56. Ribeiro, A. R.; Nunes, O. C.; Pereira, M. F.; Silva, A. M. An overview on the advanced oxidation processes applied for the treatment of water pollutants defined in the recently launched Directive 2013/39/EU Environ. Int. 2015, 75, 33-51 10.1016/j.envint.2014.10.027
57. Chigane, M.; Ishikawa, M. Manganese oxide thin film preparation by potentiostatic electrolyses and electrochromism J. Electrochem. Soc. 2000, 147, 2246-2251 10.1149/1.1393515
58. Tan, B. J.; Klabunde, K. J.; Sherwood, P. M. A. XPS studies of solvated metal atom dispersed catalysts evidence for layered cobalt-manganese particles on alumina and silica J. Am. Chem. Soc. 1991, 113, 855-861 10.1021/ja00003a019
59. 2-disordered mesoporous carbon nanocomposites: synthesis and characterization as electrochemical pseudocapacitor electrodes J. Mater. Chem. 2010, 20, 390-398 10.1039/B915370E
60. Huq, R.; Mercier, L.; Kooyman, P. J. Incorporation of cyclodextrin into mesostructured silica Chem. Mater. 2001, 13, 4512-4519 10.1021/cm010171i
61. Liu, C. Q.; Lambert, J. B.; Fu, L. A novel family of ordered, mesoporous inorganic/organic hybrid polymers containing covalently and multiply bound microporous organic hosts J. Am. Chem. Soc. 2003, 125, 6452-6461 10.1021/ja0213930
62. Zhang, L. X.; Shi, J. L.; Yu, J.; Hua, Z. L.; Zhao, X. G.; Ruan, M. L. A new in-situ reduction route for the synthesis of pt nanoclusters in the channels of mesoporous silica SBA-15 Adv. Mater. 2002, 14, 1510-1513 10.1002/1521-4095(20021016)14:20<1510::AID-ADMA1510>3.0.CO;2-W
63. Li, L.; Shi, J. L.; Zhang, L. X.; Xiong, L. M.; Yan, J. N. A novel and simple in-situ reduction route for the synthesis of an ultra-thin metal nanocoating in the channels of mesoporous silica materials Adv. Mater. 2004, 16, 1079-1082 10.1002/adma.200306454
64. 2-Embedded-in- Mesoporous-Carbon-Wall structure for use as electrochemical capacitors J. Phys. Chem. B 2006, 110, 6015-6019 10.1021/jp056754n
65. Peters, O.; Ritter, H. Supramolecular Controlled Water Uptake of Macroscopic Materials by a Cyclodextrin-Induced Hydrophobic-to-Hydrophilic Transition Angew. Chem., Int. Ed. 2013, 52, 8961-8963 10.1002/anie.201301286
66. Zimmermann, S. G.; Wittenwiler, M.; Hollender, J.; Krauss, M.; Ort, C.; Siegrist, H.; von Gunten, U. Kinetic assessment and modeling of an ozenation step for full-scale municipal wastewater treatment: Micropollutant oxidation, by-product formation and disinfection Water Res. 2011, 45, 605-617 10.1016/j.watres.2010.07.080
67. Margot, J.; Kienle, C.; Magnet, A.; Weil, M.; Rossi, L.; de Alencastro, L. F.; Abegglen, C.; Thonney, D.; Chèvre, N.; Schärer, M.; Barry, D. A. Treatment of micropollutants in municipal wastewater: Ozone or powered activated carbon? Sci. Total Environ. 2013, 461-462, 480-498 10.1016/j.scitotenv.2013.05.034
68. Luo, Y. L.; Guo, W. S.; Ngo, H. H.; Nghiem, L. D.; Hai, F. I.; Zhang, J.; Liang, S.; Wang, X. C. A review on the occurrence of micropollutants in the aquatic environment and their fate and removal during wastewater treatment Sci. Total Environ. 2014, 473-474, 619-641 10.1016/j.scitotenv.2013.12.065
69. 2) in the pH range 4-8 Water Res. 2009, 43, 3417-3426 10.1016/j.watres.2009.05.018
70. 2 nanomaterials and their superior performance in catalytic phenol degradation Environ. Sci. Technol. 2013, 47, 5882-5887 10.1021/es400878c
71. 2) mediated degradation of organoarsenic feed additive p -arsanilic acid Environ. Sci. Technol. 2015, 49, 3473-3481 10.1021/es505358c