Sonochemical decomposition of dibenzothiophene in aqueous solution.

Dibenzothiophene is decomposed rapidly by sonication in aqueous solution. Decomposition of dibenzothiophene follows a first-order reaction kinetics. The rate constant was found to increase with increasing ultrasonic energy intensity, temperature, and pH and decrease with increasing initial dibenzothiophene concentration. The activation energy was 12.6 kJ mol in the temperature range of 15-50 degrees C, suggesting a diffusion-controlled reaction. Hydroxydibenzothiophenes and dihydroxydibenzothiophenes were identified as reaction intermediates. It is proposed that dibenzothiophene is oxidized by OH radical to hydroxy-dibenzothiophenes and then to dihydroxy-dibenzothiophenes. Kinetic analysis suggests that approximately 72% of the dibcnzothiophene decomposition occurred via OH radical addition. A pathway and a kinetic model for the sonochemical decomposition of dibenzothiophene in aqueous solution are proposed.

[1]  I. J. Kugelman,et al.  Fate of toxic organic compounds in wastewater treatment plants , 1983 .

[2]  I. Hua,et al.  Kinetics and Mechanism of the Sonolytic Degradation of CCl4: Intermediates and Byproducts , 1996 .

[3]  M. Ogata,et al.  Organic sulfur compounds and polycyclic hydrocarbons transferred to oyster and mussel from petroleum suspension: Identification by gas chromatography and capillary mass chromatography , 1985 .

[4]  C. Pétrier,et al.  Ultrasound and Environment: Sonochemical Destruction of Chloroaromatic Derivatives , 1998 .

[5]  J. Andersson,et al.  Degradation of the petroleum components monomethylbenzothiophenes on exposure to light , 1998 .

[6]  M. Lee,et al.  Microbial mutagenicity of 3- and 4-ring polycyclic aromatic sulfur heterocycles. , 1983, Mutation research.

[7]  T. Dillon,et al.  Toxicity and sublethal effects of no. 2 fuel oil on the supralittoral isopodLygia exotica , 1978, Bulletin of environmental contamination and toxicology.

[8]  Noah Malmstadt,et al.  Kinetics and Mechanism of Pentachlorophenol Degradation by Sonication, Ozonation, and Sonolytic Ozonation , 2000 .

[9]  J. Andersson,et al.  Polycyclic aromatic sulfur heterocycles. II. Photochemical oxidation of benzo[b]thiophene in aqueous solution , 1992 .

[10]  Linda K. Weavers,et al.  Aromatic Compound Degradation in Water Using a Combination of Sonolysis and Ozonolysis , 1998 .

[11]  D. Eastmond,et al.  Toxicity, accumulation, and elimination of polycyclic aromatic sulfur heterocycles inDaphnia magna , 1984 .

[12]  Inez Hua,et al.  Application of Ultrasonic Irradiation for the Degradation of Chemical Contaminants in Water , 1996 .

[13]  P. Boehm,et al.  A chemical investigation of the transport and fate of petroleum hydrocarbons in littoral and benthic environments: The TSESIS oil spill , 1982 .

[14]  N. Gondrexon,et al.  Etude de la cinetique de degradation du chlorophenol en solution aqueuse par les ultrasons , 1993 .

[15]  M. Hoffmann,et al.  Kinetics and Mechanism of the Sonolytic Destruction of Methyl tert-Butyl Ether by Ultrasonic Irradiation in the Presence of Ozone , 1998 .

[16]  P. Riesz,et al.  Sonochemistry of volatile and non-volatile solutes in aqueous solutions: e.p.r. and spin trapping studies. , 1990, Ultrasonics.

[17]  C. Livengood,et al.  Ultrasonic destruction of chlorinated compounds in aqueous solution , 1992 .

[18]  H. Destaillats,et al.  Degradation of Alkylphenol Ethoxylate Surfactants in Water with Ultrasonic Irradiation , 2000 .

[19]  F. Berthou,et al.  Application of gas chromatography on glass capillary columns to the analysis of hydrocarbon pollutants from the Amoco Cadiz oil spill , 1981 .

[20]  Kenneth S. Suslick,et al.  Ultrasound: Its Chemical, Physical, and Biological Effects , 1988 .

[21]  John W. Farrington,et al.  Analyses of Aromatic Hydrocarbons in Intertidal Sediments Resulting from Two Spills of No. 2 Fuel Oil in Buzzards Bay, Massachusetts , 1978 .

[22]  Y. Maeda,et al.  Decomposition of hydroxybenzoic and humic acids in water by ultrasonic irradiation , 1996 .

[23]  J. Andersson,et al.  Acidic and non-acidic products from the photo-oxidation of the crude oil component dibenzothiophene dissolved in seawater , 1999 .

[24]  I. Hua,et al.  Cavitation Chemistry of Polychlorinated Biphenyls: Decomposition Mechanisms and Rates , 2000 .

[25]  I. Hua,et al.  Optimization of Ultrasonic Irradiation as an Advanced Oxidation Technology , 1997 .

[26]  C. Pasquini,et al.  Short-term toxicity test using Escherichia coli: Monitoring CO2 production by flow injection analysis , 1990 .

[27]  Joon-Wun Kang,et al.  Sonolytic Destruction of Methyl tert-Butyl Ether by Ultrasonic Irradiation: The Role of O3, H2O2, Frequency, and Power Density , 1999 .

[28]  I. Hua,et al.  Elucidation of the 1,4-Dioxane Decomposition Pathway at Discrete Ultrasonic Frequencies , 2000 .

[29]  M. Hoffmann,et al.  Sonochemical Degradation Rates of Volatile Solutes , 1999 .

[30]  M. Lee,et al.  Mutagenic activity of methyl-substituted tri- and tetracyclic aromatic sulfur heterocycles. , 1984, Mutation research.

[31]  M. Lee,et al.  Capillary gas chromatographic determination of polycyclic aromatic compounds in vertebrate fish tissue. , 1982, Analytical chemistry.

[32]  Michael R. Hoffmann,et al.  Ultrasonic irradiation of p-nitrophenol in aqueous solution , 1991 .