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Received April 14, 2003
Accepted July 23, 2003
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Reaction Pathways and Kinetic Modeling for Sonochemical Decomposition of Benzothiophene
Department of Environmental Engineering, Pukyong National University, Busan 608-737, Korea 1Department of Civil and Environmental Engineering, University of Delaware, Newark, DE 19716, USA
ikkim@pknu.ac.kr
Korean Journal of Chemical Engineering, November 2003, 20(6), 1045-1053(9), 10.1007/BF02706935
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Abstract
Benzothiophene (BT) decomposed rapidly following pseudo-first-order kinetics by ultrasonic irradiation in aqueous solution. The rate constant increased with increasing ultrasonic energy intensity. Hydroxybenzothiophenes, dihydroxy-benzothiophenes, and benzothiophene-dione were identified as reaction intermediates. It was proposed that benzothiophene was oxidized by OH radical to sequentially form hydroxybenzothiophenes, dihydroxybenzothiophenes, and benzothiophene-dione. Evolution of carbon dioxide and sulfite was also observed during ultrasonic reaction. Kinetic analysis suggested that approximately 77% of the benzothiophene decomposition occurred via OH radical addition. Pathways and a kinetic model for ultrasonic decomposition of benzothiophene in aqueous solution were proposed.
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References
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Beckett MA, Hua I, Environ. Sci. Technol., 34(18), 3944 (2000)
Berthou F, Gourmelun Y, Dreano Y, Friocourt MP, J. Chromatogr., 203, 279 (1981)
Bobinger S, Andersson JT, Chemosphere, 36(12), 2569 (1998)
Boehm PD, Fiest DL, Elskus A, "In Amoco Cadiz: Fates and Effects of the Oil Spill. Proceedings, International Symposium Centre Oceanologique de Bretagne. Brest; le Centre National Pour l'Exploration des Oceans: Paris, 159 (1981)
Colussi AJ, Hung HM, Hoffmann MR, J. Phys. Chem. A, 103(15), 2696 (1999)
Destaillats H, Hung HM, Hoffmann MR, Environ. Sci. Technol., 34(2), 311 (2000)
Dillon TM, Neff JM, Warner JS, Environ. Contam. Tox., 20(3), 320 (1978)
Eastmond DA, Booth GM, Lee ML, Environ. Contam. Toxicol., 13, 105 (1974)
Eaton RW, Nitterauer JD, J. Bacteriology, 176(13), 3992 (1994)
Eisenhauer H, J. Water Pollut. Control. Fed., 40(11), 1887 (1968)
Fedorak PM, Grbic-Galic D, Appl. Environ. Microbiol., 57, 932 (1991)
Fringuel F, Marino G, Taticchi A, Grandoli G, J. Chem. Soc.-Perkin Trans. 1, 4, 332 (1974)
Gondrexon N, Renaudin V, bernis A, Gonthier Y, Boldo P, Environ. Technol., 14, 587 (1993)
Hoffmann MR, Hua I, Hochemer R, Ultrason. Sonochem., 3(3), S163 (1996)
Hua I, Hoffmann MR, Environ. Sci. Technol., 30(3), 864 (1996)
Hua I, Hoffmann MR, Environ. Sci. Technol., 31(8), 2237 (1997)
Huang CK, Hao OJ, "Degradation of Monochlorophenols by Sonochemical Process," Proceedings, 25th Mid-Atlantic Industrial Waste Conference, Sup. vol. 61 (1994)
Jardim WF, Pasquini C, Guimaraes JR, Defaria LC, Water Res., 24(3), 351 (1990)
Kang JW, Hoffmann MR, Environ. Sci. Technol., 32(20), 3194 (1998)
Kang JW, Hung HM, Lin A, Hoffmann MR, Environ. Sci. Technol., 33(18), 3199 (1999)
Karcher W, Nelen A, Depans R, Van EJ, Glande P, Jacob J, "Polynuclear Hydrocarbons: Chemical Analysis and Biological Fate," Columbus, OH, 317 (1981)
Kim DW, Lee DK, Ihm SK, Korean J. Chem. Eng., 19(4), 587 (2002)
Kim KL, Choi KS, Korean J. Chem. Eng., 5(2), 177 (1988)
Kim MC, Kim KL, Korean J. Chem. Eng., 13(1), 1 (1996)
Kotronatou A, Mills G, Hoffmann HR, J. Phys. Chem., 95, 3630 (1991)
Mingfang L, Jianmin X, Zhongxuan G, Huizhou L, Jiayong C, Korean J. Chem. Eng., 20(4), 702 (2003)
Mason TJ, Lorimer JP, "Sonochemistry," Ellis Horwood Ltd., New York, NY, 252 (1998)
McFall T, Booth GM, Lee ML, Tominaga Y, Pratap R, Tedjamulia M, Castle RN, Mutat. Res., 135, 97 (1984)
Nagata Y, Hirai K, Bandow H, Maeda Y, Environ. Sci. Technol., 30(4), 1133 (1996)
Ogata M, Fujisawa K, Water Res., 19, 107 (1985)
Park HK, Kim DS, Kim KL, Korean J. Chem. Eng., 15(6), 625 (1998)
Petrasek AC, Kugelman IJ, Austern BM, Thomas AP, Winslow LA, Wise RH, J. WPCF, 55(10), 1286 (1983)
Petrier C, Jiang Y, Lamy MF, Environ. Sci. Technol., 32(9), 1316 (1998)
Petrier C, Micolle M, Merlin G, Luche JL, Reverdy G, Environ. Sci. Technol., 26(8), 1639 (1992)
Riesz P, Kondo T, Krisna CM, Ultrasonics, 28, 295 (1990)
Smith JH, Mabey WR, Bohonos N, Holt BR, Lee SS, Chou TW, Bomberger DC, Mill T, "Environmental Pathways of Selected Chemicals in Freshwater Systems," Part II, EPA-600/7-78-074 (1978)
Solomons TWG, "Organic Chemistry," 4th edn. Wiley, New York, NY, 137 (1998)
Suslick KS, VCR Publ., "Ultrasound, Its Chemical, Physical and Biological Effects," New York, NY, 138 (1986)
Teal JM, Burns K, Farrington J, Can. J. Fish. Res., 35, 510 (1978)
Vassilaros DL, Stoker PW, Booth GM, Lee ML, Anal. Chem., 54(1), 106 (1982)
Weavers LK, Ling FH, Hoffmann MR, Environ. Sci. Technol., 32(18), 2727 (1998)
Weavers LK, Malmstadt N, Hoffmann MR, Environ. Sci. Technol., 34(7), 1280 (2000)
Zhang G, Hua I, Environ. Sci. Technol., 34(8), 1529 (2000)
