Photooxidation products of polycyclic aromatic compounds containing sulfur

Environmental Science and Technology

Volumn 43, Issue 21, 2009, Pages 8119-8125

  Bobinger, Stefan ^a   Andersson, Jan T ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC COMPOUNDS; ALKYL GROUPS; ALKYL SIDE CHAINS; ALKYL SUBSTITUENT; AQUEOUS PHASE; AROMATIC RINGS; ATOMIC EMISSION DETECTION; CRUDE OIL; LIFE FORM; METHYL GROUP; OCTYL GROUPS; PHOTOPRODUCTS; POLYCYCLIC AROMATIC COMPOUNDS; POLYCYCLIC AROMATIC SULFUR HETEROCYCLES; PRODUCT ANALYSIS;

ALDEHYDES; ALKYLATION; CARBOXYLIC ACIDS; CHROMATOGRAPHIC ANALYSIS; CRUDE PETROLEUM; GAS CHROMATOGRAPHY; HYDROCARBONS; LEAKAGE (FLUID); ORGANIC ACIDS; PHOTOOXIDATION; SULFUR; SURFACE ACTIVE AGENTS; THIOPHENE;

GROUP TECHNOLOGY;

2,6 DIMETHYLBENZOTHIOPHENE; 2,7 DIMETHYLBENZOTHIOPHENE; 3,5 DIMETHYLBENZOTHIOPHENE; 4,6 DIMETHYLBENZOTHIOPHENE; 4,7 DIMETHYLBENZOTHIOPHENE; 5 OCTYLBENZOTHIOPHENE; 6,7 DIMETHYLBENZOTHIOPHENE; 7 ETHYLBENZOTHIOPHENE; BENZOTHIOPHENE DERIVATIVE; SULFUR; UNCLASSIFIED DRUG;

CARBOXYLIC ACID; CRUDE OIL; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PAH; PHOTOOXIDATION; POLLUTANT REMOVAL; SULFUR;

ARTICLE; ATOMIC EMISSION SPECTROMETRY; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; PH MEASUREMENT; PHOTOOXIDATION; WATER POLLUTION;

ACIDS; CHROMATOGRAPHY, GAS; IRAQ; LIGHT; OXIDATION-REDUCTION; PETROLEUM; POLYCYCLIC COMPOUNDS; SULFUR;

EID: 70350747588     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es901859s     Document Type: Article

References (26)

1. Scheier, A.; Gominger, D. A preliminary study of the toxic effects of irradiated vs. non-irradiated water soluble fractions of #2 fuel oil. Bull. Environ. Contam. Toxicol. 1976, 16 (5), 595-603, DOI: 10.1007/BF01685370. (Pubitemid 8001509)
2. Maki, H.; Sasaki, T.; Harayama, S. Photo-oxidation of biode-graded crude oil and toxicity of the photo-oxidized products. Chemosphere 2001, 44 (5), 1145-1151, DOI: 10.1016/S0045- 6535(00)00292-297 (Pubitemid 32728994)
3. Farwell, A. J.; Nero, V.; Croft, M.; Rhodes, S.; Dixon, D. G. Phototoxicity of oil sands-derived polycyclic aromatic compounds to Japanese medaka (Oryzias latipes) embryos. Environ. Toxicol. Chem. 2006, 25 (12), 3266-3274, DOI 10.1897/05- 637R1.1.
4. Shiraishi, Y.; Hirai, T.; Komasawa, I. Identification of desulfurization products in the photochemical desulfurization process for benzothiophenes and dibenzothiophenes from light oil using an organic two-phase extraction system. Ind. Eng. Chem. Res. 1999, 38 (9), 3300-3309, DOI: 10.1021/ie990134p. (Pubitemid 29454750)
5. Andersson, J. T.; Bobinger, S. Photochemical degradation of crude oil components: 2-methyl-, 3-methyl-and 2,3-dimethylbenzothiophene. Polycycl. Aromat. Comp. 1996, 11 (1-4), 145-151, DOI: 10.1080/10406639608544660. (Pubitemid 126498846)
6. Traulsen, F.; Andersson, J. T.; Ehrhardt, M. G. Acidic and non-acidic products from the photo-oxidation of the crude oil component dibenzothiophene dissolved in seawater. Anal. Chim. Acta 1999, 392 (1), 19-28, DOI: 10.1016/S0003- 2670(99)00055-60
7. Bobinger, S.; Andersson, J. T. Degradation of the petroleum componentsmonomethylbenzothiophenesonexposure to light. Chemosphere 1998, 36 (12), 2569-2579, DOI: 10.1016/S0045- 6535(97)10219-10223
8. Bobinger, S.; Traulsen, F.; Andersson, J. T. Dibenzothiophene in crude oils: Products from the photochemical degradation. Polycycl. Aromat. Comp. 1999, 14 (1-4), 253-263, DOI: 10.1080/ 10406639908019131.
9. Andersson, J. T.; Bobinger, S. Polycyclic aromatic sulfur heterocycles. II. Photochemical oxidation of benzo[b]thiophene in aqueous solution. Chemosphere 1992, 24 (4), 383-389, DOI: 10.1016/0045-6535(92)90412-K.
10. Panda, S. K.; Schrader, W.; al-Hajji, A.; Andersson, J. T. Distribution of polycyclic aromatic sulfur heterocycles in three Saudi Arabian crude oils as determined by Fourier transform ion cyclotron resonance mass spectrometry. Energy Fuels 2007, 21 (2), 1071-1077, DOI: 10.1021/ef060511s.
11. Reineke, V.; Rullkötter, J.; Smith, E. L.; Rowland, S. J. Toxicity and compositional analysis of aromatic hydrocarbon fractions of two pairs of undegraded and biodegraded crude oils from the Santa Maria (California) and Vienna basins. Org. Geochem. 2006, 37 (12), 1885-1899, DOI: 10.1016/j. orggeochem. 2006.07.017. (Pubitemid 44855124)
12. Andersson, J. T. Polycyclic aromatic sulfur heterocycles. I. Use of hydrogen peroxide oxidation for the group separation of polycyclic aromatic hydrocarbons and their sulfur analogs. Intern. J. Environ. Anal. Chem. 1992, 48 (1), 1-15, DOI: 10.1080/ 03067319208027038.
13. Andersson, J. T.; Sielex, K. Dimethylbenzothiophenes and methyldibenzothiophenes in crude oils from different sources. J. High Resol. Chromatogr. 1996, 19 (1), 49-53, DOI: 10.1002/ jhrc.1240190109.
14. Arpino, P. J.; Ignatiadis, I.; de Rycke, G. Sulphur-containing polynuclear aromatic hydrocarbons from petroleum: Examination of their possible statistical formation in sediments. J. Chromatogr. A1987,390(2),329-348,DOI:10. 1016/S00219673(01)94385-94387
15. Hegazi, A. H.; Andersson, J. T.; Abu-Elgheit, M. A.; El-Gayar, M. Sh. Utilization of GC/AED for investigating the effect of maturity on the distribution of thiophenic compounds in Egyptian crude oils. Polycycl. Aromat. Comp. 2004, 24 (2), 123-134, DOI: 10.1080/ 10406630490432846.
16. Depauw, G. A.; Froment, G. F. Molecular analysis of the sulphur components in a light cycle oil of a catalytic cracking unit by gas chromatography with mass spectrometric and atomic emission detection. J. Chromatogr. A 1997, 761 (1-2), 231-247, DOI: 10.1016/S0021-9673(96)00819-9.
17. Garrett, R. M.; Pickering, I. J.; Haith, C. E.; Prince, R. C. Photooxidation of crude oils. Environ. Sci. Technol. 1998, 32 (23), 3719-3723, DOI: 10.1021/es980201r.
18. Charrié-Duhaut, A.; Lemoine, S.; Adam, P.; Connan, J.; Albrecht, P. Abiotic oxidation of petroleum bitumens under natural conditions. Org. Geochem. 2000, 31 (10), 977-1003, DOI: 10.1016/ S0146-6380(00)00109-111 (Pubitemid 32058191)
19. Saftic, S.; Fedorak, P. M.; Andersson, J. T. Diones, sulfoxides, and sulfones from the aerobic cometabolism of methylbenzothiophenes by Pseudomonas strain BT1. Environ. Sci. Technol. 1992, 26 (9), 1759-1764, DOI: 10.1021/es00033a007.
20. Kropp, K. G.; Saftic, S.; Andersson, J. T.; Fedorak, P. M. Transformations of six isomers of dimethylbenzothiophene by three Pseudomonas strains. Biodegradation 1996, 7 (3), 203-221, DOI: 10.1007/BF00058180.
21. Moza, P. N.; Hustert, K.; Leoff, S. Photochemical transformations of selected organic chemicals in two phase system. Toxicol. Environ. Chem. 1991, 31 (1), 103-106, DOI: 10.1080/ 02772249109357678.
22. Hansen, H. P. Photochemical degradation of petroleum hydrocarbon surface films on seawater. Mar. Chem. 1975, 3 (3), 183-195, DOI: 10.1016/0304-4203(75) 90001-8.
23. Lamathe, J. Formation of seawater-in-oil emulsions subsequent to an oil spill. C. r. hebd. Séanc. Acad. Sci., Paris, Série II,. 1982, 295, 301-304.
24. Gaur, J. P.; Singh, A. K. Regulatory influence of light and temperature on petroleum toxicity to Anabaena doliolum. Environ. Toxicol. Water Qual. 1991, 6 (3), 341-350, DOI: 10.1002/ tox.2530060306.
25. Dutta, T. K.; Harayama, S. Fate of crude oil by the combination of photooxidation and biodegradation. Environ. Sci. Technol. 2000, 34 (8), 1500-1505, DOI: 10.1021/es991063o. (Pubitemid 30217476)
26. Tanaka, T.; Yamada, K.; Iijima, T.; Iriguchi, T.; Kido, Y. Complete degradation of the endocrine-disrupting chemical phthalic acid by Flavobacterium sp. J. Health Sci. 2006, 52, 800-804, DOI: 10.1248/jhs.52.800. (Pubitemid 44903952)