Dibenzothiophene in crude oils: Products from the photochemical degradation

被引:10
作者
Bobinger, S [1 ]
Traulsen, F [1 ]
Andersson, JT [1 ]
机构
[1] Univ Munster, Dept Analyt Chem, D-48149 Munster, Germany
关键词
PASH; dibenzothiophene; photochemistry; degradation; products; crude oil;
D O I
10.1080/10406639908019131
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The photochemical degradation of dibenzothiophene in aqueous solution was studied to elucidate the fate of crude oil components after an oil spill, The major reaction pathway is based on the oxidation of a benzo ring to form benzothiophene-2,3-dicarboxylic acid and ultimately, after opening of the thiophene ring, 5-sulfobenzoic acid as the stable photolysis product, Opening of both benzo rings also occurs in which case thiophenedi-, -tri- and -tetracarboxylic acids are formed. One minor reaction pathway leads to the sulfone by oxidation of the sulfur atom, The products were identified through gas chromatography-mass spectrometry and comparison with reference compounds.
引用
收藏
页码:253 / 263
页数:11
相关论文
共 14 条
[1]   POLYCYCLIC AROMATIC SULFUR HETEROCYCLES .1. USE OF HYDROGEN-PEROXIDE OXIDATION FOR THE GROUP SEPARATION OF POLYCYCLIC AROMATIC-HYDROCARBONS AND THEIR SULFUR ANALOGS [J].
ANDERSSON, JT .
INTERNATIONAL JOURNAL OF ENVIRONMENTAL ANALYTICAL CHEMISTRY, 1992, 48 (01) :1-15
[2]   POLYCYCLIC AROMATIC SULFUR HETEROCYCLES .2. PHOTOCHEMICAL OXIDATION OF BENZO[B]THIOPHENE IN AQUEOUS-SOLUTION [J].
ANDERSSON, JT ;
BOBINGER, S .
CHEMOSPHERE, 1992, 24 (04) :383-389
[3]   Polycyclic aromatic sulfur heterocycles .6. Photochemical degradation of crude oil components: 2-methyl-, 3-methyl- and 2,3-dimethylbenzothiophene [J].
Andersson, JT ;
Bobinger, S .
POLYCYCLIC AROMATIC COMPOUNDS, 1996, 11 (1-4) :145-151
[4]   THE OCCURRENCE OF HYDROCARBONS AND HISTOPATHOLOGICAL ABNORMALITIES IN OYSTERS FOR 7 YEARS FOLLOWING THE WRECK OF THE AMOCO-CADIZ IN BRITTANY (FRANCE) [J].
BERTHOU, F ;
BALOUET, G ;
BODENNEC, G ;
MARCHAND, M .
MARINE ENVIRONMENTAL RESEARCH, 1987, 23 (02) :103-133
[5]   ANALYSIS AND FATE OF DIBENZOTHIOPHENE DERIVATIVES IN THE MARINE-ENVIRONMENT [J].
BERTHOU, F ;
VIGNIER, V .
INTERNATIONAL JOURNAL OF ENVIRONMENTAL ANALYTICAL CHEMISTRY, 1986, 27 (1-2) :81-96
[6]  
BOBINGER S, IN PRESS CHEMOSPHERE
[7]   HYDROCARBONS AND RELATED PHOTOOXIDATION PRODUCTS IN SAUDI-ARABIAN GULF COASTAL WATERS AND HYDROCARBONS IN UNDERLYING SEDIMENTS AND BIOINDICATOR BIVALVES [J].
EHRHARDT, MG ;
BURNS, KA .
MARINE POLLUTION BULLETIN, 1993, 27 :187-197
[8]   CONVENIENT ROUTES TO 4,4''-FUNCTIONALIZED ORTHO-TERPHENYLS AND 2,2'-FUNCTIONALIZED BIPHENYLS [J].
HANSON, G ;
KEMP, DS .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (26) :5441-5443
[9]   PHOTOLYSIS OF POLYCYCLIC AROMATIC-HYDROCARBONS IN WATER [J].
MILL, T ;
MABEY, WR ;
LAN, BY ;
BARAZE, A .
CHEMOSPHERE, 1981, 10 (11-1) :1281-1290
[10]   PHOTOCHEMISTRY OF PETROLEUM IN WATER [J].
PAYNE, JR ;
PHILLIPS, CR .
ENVIRONMENTAL SCIENCE & TECHNOLOGY, 1985, 19 (07) :569-579