Origins of alkylphenols in crude oils: Hydroxylation of alkylbenzenes

被引:14
作者
Bastow, TP
van Aarssen, BGK
Alexander, R
Kagi, RI
机构
[1] Curtin Univ Technol, Ctr Appl Organ Geochem, Perth, WA 6845, Australia
[2] CSIRO Land & Water, Perth, WA 6913, Australia
关键词
D O I
10.1016/j.orggeochem.2005.03.007
中图分类号
P3 [地球物理学]; P59 [地球化学];
学科分类号
0708 [地球物理学]; 070902 [地球化学];
摘要
Laboratory experiments involving Lewis-acid catalysed hydroxylation of prepared alkylbenzene mixtures of similar composition as found in crude oils, yield alkylphenols in distributions very much like those found in the crude oils. Crude oils with different alkylbenzene distributions have associated differences in their alkylphenol distributions. These can be fully explained through a reaction mechanism involving electrophilic aromatic substitution. The results strongly suggest that acid catalysed hydroxylation of alkylbenzenes is a likely formation mechanism for alkylphenols present in crude oils. The mechanism may also account for the formation of other hydroxylated compounds found in crude oils. The hydroxylation reactions are suggested to take place in the source rock during petroleum formation. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:991 / 1001
页数:11
相关论文
共 28 条
[1]
GEOSYNTHESIS OF ORGANIC-COMPOUNDS .2. METHYLATION OF PHENANTHRENE AND ALKYLPHENANTHRENES [J].
ALEXANDER, R ;
BASTOW, TP ;
FISHER, SJ ;
KAGI, RI .
GEOCHIMICA ET COSMOCHIMICA ACTA, 1995, 59 (20) :4259-4266
[2]
Alexander R., 1984, Organic Geochemistry, V6, P755, DOI [10.1016/0146-6380, DOI 10.1016/0146-6380, 10.1016/0146-6380(84)90096-2, DOI 10.1016/0146-6380(84)90096-2]
[3]
Small-scale and rapid quantitative analysis of phenols and carbazoles in sedimentary matter [J].
Bastow, TP ;
van Aarssen, BGK ;
Chidlow, GE ;
Alexander, R ;
Kagi, RI .
ORGANIC GEOCHEMISTRY, 2003, 34 (08) :1113-1127
[4]
The effect of oxidation on the distribution of alkylphenols in crude oils [J].
Bastow, TP ;
van Aarssen, BGK ;
Herman, R ;
Alexander, R ;
Kagi, RI .
ORGANIC GEOCHEMISTRY, 2003, 34 (08) :1103-1111
[5]
Geosynthesis of organic compounds. Part V - methylation of alkylnaphthalenes [J].
Bastow, TP ;
Alexander, R ;
Fisher, SJ ;
Singh, RK ;
van Aarssen, BGK ;
Kagi, RI .
ORGANIC GEOCHEMISTRY, 2000, 31 (06) :523-534
[6]
BASTOW TP, 1997, J POLYCYCLIC AROMATI, V9, P177
[7]
Partition behaviour of alkylphenols in crude oil brine systems under subsurface conditions [J].
Bennett, B ;
Larter, SR .
GEOCHIMICA ET COSMOCHIMICA ACTA, 1997, 61 (20) :4393-4402
[8]
A mechanism for the production of hydroxyl radical at surface defect sites on pyrite [J].
Borda, MJ ;
Elsetinow, AR ;
Strongin, DR ;
Schoonen, MA .
GEOCHIMICA ET COSMOCHIMICA ACTA, 2003, 67 (05) :935-939
[9]
CADMAN SJ, 1993, 9 BUR RES
[10]
DALE JD, 1995, ORGANIC GEOCHEMISTRY, P396