Oxidative degradation of chlorophenol derivatives promoted by microwaves or power ultrasound: A mechanism investigation

Environmental Science and Pollution Research

Volumn 17, Issue 3, 2010, Pages 674-687

  Cravotto, Giancarlo ^a   Binello, Arianna ^a   Di Carlo, Stefano ^a   Orio, Laura ^a   Wu, Zhi Lin ^b   Ondruschka, Bernd ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

2,4 Dichlorophenoxyacetic acid; Fenton reagent; Microwaves; Oxidative degradation; Ultrasound

Indexed keywords

2,4 DICHLOROPHENOXYACETIC ACID; CHLOROPHENOL; FENTON'S REAGENT; FREE RADICAL; HERBICIDE; HYDROGEN PEROXIDE; IRON;

COAL PROCESSING; DEGRADATION; GAS CHROMATOGRAPHY; HERBICIDE; INDUSTRIAL WASTE; MASS SPECTROMETRY; MICROWAVE RADIATION; MONITORING; PHENOL; REFINING INDUSTRY; RESIN; WASTEWATER;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; ECOSYSTEM RESTORATION; KINETICS; METHODOLOGY; MICROWAVE RADIATION; OXIDATION REDUCTION REACTION; ULTRASOUND; WATER POLLUTANT;

2,4-DICHLOROPHENOXYACETIC ACID; CHLOROPHENOLS; ENVIRONMENTAL REMEDIATION; FREE RADICALS; HERBICIDES; HYDROGEN PEROXIDE; IRON; KINETICS; MICROWAVES; MODELS, CHEMICAL; OXIDATION-REDUCTION; ULTRASONICS; WATER POLLUTANTS, CHEMICAL;

EID: 77949287820     PISSN: 09441344     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11356-009-0253-y     Document Type: Article

References (55)

1. Abramovitch RA, Michael C (2003) Remediation of waters contaminated with pentachlorophenol. Chemosphere 50: 955-957.
2. Agarry SE, Durojaiye AO, Solomon BO (2008) Microbial degradation of phenols: a review. Int J Environ Pollut 32: 12-28.
3. Ai ZH, Yang P, Lu XH (2005) Degradation of 4-chlorophenol by microwave irradiation enhanced advanced oxidation processes. Chemosphere 60: 824-827.
4. Aly OM, Faust SD (1964) Herbicides in surface waters, studies on fate of 2, 4-D and ester derivatives in natural surface waters. J Agric Food Chem 12: 541-546.
5. Antunes CS, Bietti M, Ercolani G, Lanzalunga O, Salamone M (2005) The effect of ring substitution on the O-neophyl rearrangement of 1, 1-diarylalkoxyl radicals. A product and time-resolved kinetic study. J Org Chem 70: 3884-3891.
6. Australian Government, Department of the Environment, Water, Heritage and the Arts, The National Pollutant Inventory (NPI) (2008). Available at http://www.npi.gov.au/database/substanceinfo/profiles/70.html.
7. Barrault J, Abdellaoui M, Bouchoule C, Majesté A, Tatiboüet JM, Laulodi A, Papayannakos N, Gangas NH (2000) Mechanism of the oxidation of aqueous phenol with dissolved oxygen. Appl Catal B Environ 27: 225-230.
8. Berlan J, Trabelsi F, Delmas H, Wilhelm AM, Petrignan JF (1994) Pulsed sonolysis of surfactants in aqueous solutions. Ultrason Sonochem 1: S97-S102.
9. Bhargava SK, Tardio J, Prasad J, Foger K, Akolekar DB, Grocott SC (2006) Wet oxidation and catalytic wet oxidation. Ind Eng Chem Res 45: 1221-1258.
10. Bremner D, Di Carlo S, Chakinala AG, Cravotto G (2008) Mineralisation of 2, 4-dichlorophenoxyacetic acid by acoustic or hydrodynamic cavitation in conjunction with the advanced Fenton process. Ultrasonics Sonochemistry 15: 416-419.
11. Busca G, Berardinelli S, Resini C, Arrighi L (2008) Technologies for the removal of phenol from fluid streams: a short review of recent developments. J Hazard Mater 160: 265-288.
12. Buxton G, Greenstock C, Helman WP, Ross AB (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (•OH/•O-) in aqueous solution. J Phys Chem Ref Data 17: 513-886.
13. Cravotto G, Di Carlo S, Tumiatti V, Roggero C, Bremner D (2005) Degradation of persistent organic pollutants by Fenton's reagent facilitated by microwave or high-intensity ultrasound. Environ Technol 26: 721-724.
14. Cravotto G, Di Carlo S, Curini M, Tumiatti V, Roggero C (2007a) A new flow reactor for the treatment of polluted water with microwave and ultrasound. J Chem Tech Biotech 82: 205-208.
15. Cravotto G, Ondruschka B, Di Carlo S, Roggero C, Tumiatti V (2007b) Decontamination of soil containing POPs by the combined action of solid Fenton-like reagents and microwaves. Chemosphere 69: 1326-1329.
16. Cravotto G, Di Carlo S, Mantegna S, Binello A, Girlanda M, Lazzari A (2008) Integrated sonochemical and microbial treatment for decontamination of nonylphenol-polluted water. Water Air Soil Pollut 187: 353-359.
17. Destaillats H, Colussi AJ, Joseph JM, Hoffmann MR (2000) Synergistic effects of sonolysis combined with ozonolysis for the oxidation of azobenzene and methyl orange. J Phys Chem A 104: 8930-8935.
18. Devlin HR, Harris IJ (1984) Mechanism of the oxidation of aqueous phenol with dissolved oxygen. Ind Eng Chem Fundam 23: 387-392.
19. Du Y, Zhou M, Lei L (2007) Kinetic model of 4-CP degradation by Fenton/O2 system. Water Res 41: 1121-1133.
20. Falvey DE, Khambatta BS, Schuster G (1990) Neophyl-like rearrangement of alkoxy radicals direct detection of a bridged intermediate by time-resolved absorption-spectroscopy. J Phys Chem 94: 1056-1059.
21. Gimeno O, Carbajo M, Beltran FJ, Rivas FJ (2005) Phenol and substituted phenols AOPs remediation. J Hazard Mater 119: 99-108.
22. Gogate PR, Pandit BA (2004) Review of imperative technologies for wastewater treatment I: oxidation technologies at ambient conditions. Adv Environ Res 8: 501-551.
23. Gopalan S, Savage PE (1994) Reaction mechanism for phenol oxidation in supercritical water. J Phys Chem 98: 12646-12652.
24. Goskonda S, Catallo WJ, Junk T (2002) Sonochemical degradation of aromatic organic pollutants. Waste Management 22: 351-356.
25. Hao H, Chen Y, Wu M, Wang H, Yin Y, Lü Z (2004) Sonochemistry of degrading p-chlorophenol in water by high frequency ultrasound. Ultrason Sonochem 11: 43-46.
26. Higashimura H, Fujisawa K, Kubota M, Kobayashi S (2005) "Radical-controlled" oxidative polymerization of phenol: comparison with that of 4-phenoxyphenol. J Polym Sci Part A Polym Chem 43: 1955-1962.
27. Jiang Y, Waite TD (2003) Degradation of trace contaminants using coupled sonochemistry and Fenton's reagent. Water Sci Technol 47: 85-92.
28. Jones CW (1999) Applications of hydrogen peroxide and derivatives. Royal Society of Chemistry, Cambridge p 264. doi: 10. 1021/op000003w.
29. Joseph JM, Destaillats H, Hung HM, Hoffmann MR (2000) The sonochemical degradation of azobenzene and related azo dyes: rate enhancements via Fenton's reactions. J Phys Chem A 104: 301-307.
30. Kaioumova D, Kaioumov F, Opelz G, Susal C (2001) Toxic effects of the herbicide 2, 4-dichlorophenoxyacetic acid on lymphoid organs of the rat. Chemosphere 43: 801-805.
31. 2, frequency, and power density. Environ Sci Technol 33: 3199-3205.
32. Kidak R, Ince NH (2006) Ultrasonic destruction of phenol and substituted phenols: a review of current research. Ultrason Sonochem 13: 195-199.
33. Lesko T, Colussi AJ, Hoffmann MR (2006) Sonochemical decomposition of phenol: evidence for a synergistic effect of ozone and ultrasound for the elimination of total organic carbon from water. Environ Sci Technol 40: 6818-6823.
34. Li X, Cubbage JW, Jenks WS (1999) Photocatalytic degradation of 4-chlorophenol. 2. The 4-chlorocatechol pathway. J Org Chem 64: 8525-8536.
35. Liang J, Komarov S, Hayashi N, Kasai E (2007) Improvement in sonochemical degradation of 4-chlorophenol by combined use of Fenton-like reagents. Ultrason Sonochem 12: 201-207.
36. Liotta LF, Gruttadauria M, Di Carlo G, Perrini G, Librando V (2009) Heterogeneous catalytic degradation of phenolic substrates: catalysts activity. J Haz Mat 162: 588-606.
37. Mason TJ (1992) Industrial sonochemistry: potential and practicality. Ultrasonics 30: 192-196.
38. Matos J, Laine J, Hermann JM (2001) Effect of the type of activated carbons on the photocatalytic degradation of aqueous organic pollutants by UV-irradiated titania. J Catal 200: 10-20.
39. Menéndez JA, Inguanzo M, Pis JJ (2002) Microwave-induced pyrolysis of sewage sludge. Water Res 36: 3261-3264.
40. Papadaki M, Emery RJ, Abu-Hassan MA, Díaz-Bustos A, Metcalfe IS, Mantzavinos D (2004) Sonocatalytic oxidation processes for the removal of contaminants containing aromatic rings from aqueous effluents. Sep Purific Technol 34: 35-42.
41. Peller J, Wiest O, Kamat PV (2001) Sonolysis of 2, 4-dichlorophenoxyacetic acid in aqueous solutions. Evidence for •OH-radical-mediated degradation. J Phys Chem A 105: 3176-3181.
42. Petrier C, Jiang Y, Lamy MF (1998) Ultrasound and environment: sonochemical destruction of chloroaromatic derivative. Environ Sci Technol 32: 1316-1318.
43. Polaert I, Estel L, Ledoux A (2005) Microwave assisted remediation of phenol wastewater on activated charcoal. Chem Engin Sci 60: 6354-6359.
44. Riesz P, Kondo T (1992) Free radical formation induced by ultrasound and its biological implications. Free Radic Biol Med 13: 247-270.
45. Stavarache C, Yim B, Vinatoru M, Maeda Y (2002) Sonolysis of chlorobenzene in Fenton-type aqueous systems. Ultrason Sonochem 9: 291-296.
46. Song Q, Niu T, Wang H (2008) Theoretical study of the reaction of 2, 4-dichlorophenol with 1O2. J Mol Struct (Theochem) 861: 27-32.
47. Tauber A, Schuchmann HP, Von Sonntag C (2000) Sonolysis of aqueous 4-nitrophenol at low and high pH. Ultrason Sonochem 7: 45-52.
48. Uyama H, Maruichi N, Tonami H, Kobayashi S (2002) Peroxidase-catalyzed oxidative polymerization of bisphenols. Biomacromolecules 3: 187-193.
49. Weavers LK, Ling FK, Hoffmann MR (1998) Aromatic compound degradation in water using a combination of sonolysis and ozonolysis. Environ Sci Technol 32: 2727-2733.
50. Wu ZL, Ondruschka B, Cravotto G (2008) Degradation of phenol under combined irradiation of microwaves and ultrasound. Environ Sci Technol 42: 8083-8087.
51. Yasman Y, Bulatov V, Gridin V, Agur S, Galil N, Armon R, Schechter I (2004) A new sono-electrochemical method for enhanced detoxification of hydrophilic chloroorganic pollutants in water. Ultrason Sonochem 11: 365-372.
52. Yu J, Taylor KE, Zou H, Biswas N, Bewtra JK (1994) Phenol conversion and dimeric intermediates in horseradish peroxidase-catalyzed phenol removal from water. Environ Sci Technol 28: 2154-2160.
53. Yu Y, Ma J, Hou YJ (2006) Degradation of 2, 4-dichlorophenoxyacetic acid in water by ozone-hydrogen peroxide process. J Environ Sci 18: 1043-1049.
54. Zazo JA, Casas JA, Mohedano AF, Gilarranz MA, Rodríguez JJ (2005) Chemical pathway and kinetics of phenol oxidation by Fenton's reagent. Environ Sci Technol 39: 9295-9302.
55. Zhihui A, Peng Y, Xiaohua L (2005) Degradation of 4-chlorophenol by microwave irradiation enhanced advanced oxidation processes. Chemosphere 60: 824-882.