Anaerobic degradation and carbon isotopic fractionation of alkylbenzenes in crude oil by sulphate-reducing bacteria

Organic Geochemistry

Volumn 31, Issue 1, 2000, Pages 101-115

  Wilkes, Heinz ^a   Boreham, Chris ^b   Harms, Gerda ^c   Zengler, Karsten ^c   Rabus, Ralf ^c  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

^b AUSTRALIAN GEOLOGICAL SURVEY ORGANISATION   (Australia)

^c MAX PLANCK INSTITUTE FOR MARINE MICROBIOLOGY   (Germany)

Author keywords

Alkylbenzenes; Anaerobic biodegradation; Benzoic acids; Carbon isotopic fractionation; Crude oils; Metabolite formation; Sulphate reducing bacteria

Indexed keywords

2 ETHYLTOLUENE; 2 XYLENE; 3 ETHYLTOLUENE; 3 XYLENE; ALKYLBENZENE; BACTERIAL GROWTH; BACTERIUM CULTURE; BENZOIC ACID; CARBON ISOTOPE; FRACTIONATION; FUMARIC ACID; METABOLITE; MICROBIAL DEGRADATION; OXIDATION; PETROLEUM;

BACTERIUM; BIODEGRADATION; CRUDE OIL; ISOTOPIC FRACTIONATION; MICROBIAL ACTIVITY;

BACTERIA; BENZENE; BIODEGRADATION; CARBOXYLIC ACIDS; CELL CULTURE; FRACTIONATION; METABOLITES; PETROLEUM CHEMISTRY; TOLUENE; TRACE ANALYSIS; XYLENE;

ALKYLBENZENE; ALKYLPHENYLSUCCINIC ACID; BENZOIC ACID; FUMARIC ACID;

CRUDE PETROLEUM;

EID: 0033622937     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(99)00147-3     Document Type: Article

References (72)

1. 2 by a new type of sulfate-reducing bacterium. Archives of Microbiology. 156:1991;5-14.
2. Aeckersberg F., Rainey F.A., Widdel F. Growth, natural relationships, cellular fatty acids and metabolic adaptation of sulfate-reducing bacteria that utilize long-chain alkanes under anoxic conditions. Archives of Microbiology. 170:1998;361-369.
3. 2 - a multivariate approach. Organic Geochemistry. 25:1996;427-438.
4. Bastin E.S., Greer F.E., Merritt C.A., Moulton G. The presence of sulphate reducing bacteria in oil field waters. Science. 63:1926;21-24.
5. Beeder J., Nilsen R.K., Rosnes J.T., Torsvik T., Lien T. Archaeoglobus fulgidus isolated from hot North Sea oil field waters. Applied and Environmental Microbiology. 60:1994;1227-1231.
6. Beeder J., Nilsen R.K., Thorstenson T., Torsvik T. Penetration of sulfate reducers through a porous North Sea oil reservoir. Applied and Environmental Microbiology. 62:1996;3551-3553.
7. Beller H.R., Spormann A.M. Benzylsuccinate formation as a means of anaerobic toluene activation by sulfate-reducing strain PRTOL1. Applied and Environmental Microbiology. 63:1997;3729-3731.
8. Beller H.R., Spormann A.M. Anaerobic activation of toluene and o-xylene by addition to fumarate in denitrifying strain T. Journal of Bacteriology. 179:1997;670-676.
9. Beller H.R., Ding W.-H., Reinhard M. Byproducts of anaerobic alkylbenzene metabolism useful as indicators of in situ bioremediation. Environmental Science and Technology. 29:1995;2864-2870.
10. Beller H.R., Reinhard M., Grbic-Galic D. Metabolic by-products of anaerobic toluene degradation by sulfate-reducing enrichment cultures. Applied and Environmental Microbiology. 58:1992;3192-3195.
11. Beller H.R., Spormann A.M., Sharma P.K., Cole J.R., Reinhard M. Isolation and characterization of a novel toluene-degrading, sulfate-reducing bacterium. Applied and Environmental Microbiology. 62:1996;1188-1196.
12. Bernard, F.P., Connan, J., Magot, M., 1992. Indigenous microorganisms in connate water of many oil fields: a new tool in exploration and production techniques. In: Proc. 67th SPE a. tech. Conf. Exhibition, Vol. 2. SPE, Dallas, TX, pp. 467-476.
13. Biegert T., Fuchs G., Heider J. Evidence that anaerobic oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate. European Journal of Biochemistry. 238:1996;661-668.
14. Blanc P., Connan J. Crude oils in reservoirs. the factors influencing their composition Bordenave M.L. Applied Petroleum Geochemistry. 1993;151-174 Éditions Technip, Paris.
15. Bodrossy L., Murrell J.C., Dalton H., Kalman M., Puskas L.G., Kovacs K.L. Heat-tolerant methanotrophic bacteria from the hot water effluent of a natural gas field. Applied and Environmental Microbiology. 61:1995;3549-3555.
16. Borgund A.E., Barth T. Generation of short-chain organic acids from crude oils by hydrous pyrolysis. Organic Geochemistry. 21:1994;943-952.
17. Caldwell M.E., Garrett R.M., Prince R.C., Suflita J.M. Anaerobic biodegradation of long-chain n-alkanes under sulfate-reducing condition. Environmental Science and Technology. 32:1998;2191-2195.
18. Chee-Sanford J.C., Frost J.W., Fries M.R., Zhou J., Tiedje J.M. Evidence for acetyl coenzyme A and cinnamoyl coenzyme A in the anaerobic toluene mineralization pathway in Azoarcus tolulyticus Tol-4. Applied and Environmental Microbiology. 62:1996;964-973.
19. Coates J.D., Anderson R.T., Lovley D.R. Oxidation of polycyclic aromatic hydrocarbons under sulfate-reducing conditions. Applied and Environmental Microbiology. 62:1996;1099-1101.
20. Coates J.D., Anderson R.T., Woodward J.C., Phillips E.J.P., Lovley D.R. Anaerobic hydrocarbon degradation in petroleum-contaminated harbor sediments under sulfate-reducing and artificially, imposed iron-reducing conditions. Environmental Science and Technology. 30:1996;2784-2789.
21. Coates J.D., Woodward J., Allen J., Philp P., Lovley D. Anaerobic degradation of polycyclic aromatic hydrocarbons and alkanes in petroleum-contaminated harbor-sediments. Applied and Environmental Microbiology. 63:1997;3589-3593.
22. Connan J. Biodegradation of crude oils in reservoirs. Brooks J., Welte D.H. Advances in Petroleum Geochemistry. 1984;299-330 Academic Press, London.
23. Connan J., Lacrampe-Coulome G., Magot M. Origin of gases in reservoirs. Dolenc D. Proceedings of the 1995 International Gas Research Conference, Vol. 1. 1996;21-62 Government Institutes, Rockville.
24. Cord-Ruwisch R., Kleinitz W., Widdel F. Sulfatreduzierende Bakterien in einem Erdölfeld - Arten und Wachstumsbedingungen. Erdöl, Erdgas, Kohle. 102:1986;281-289.
25. Cozzarelli I., Baedecker M.J., Eganhouse R.P., Goerltz D.F. The geochemical evolution of low-molecular-weight organic acids derived from the degradation of petroleum contaminants in groundwater. Geochimica et Cosmochimica Acta. 58:1994;863-877.
26. Cozzarelli I.M., Eganhouse R.P., Baedecker M.J. Transformation of monoaromatic hydrocarbons to organic acids in anoxic groundwater environment. Environmental Geology and Water Science. 16:1990;135-141.
27. Cozzarelli I.M., Herman J.S., Baedecker M.J. Fate of microbial metabolites of hydrocarbons in a coastal plain aquifer. the role of electron acceptors Environmental Science and Technology. 29:1995;458-469.
28. Davis J.B., Yarbrough H.F. Anaerobic oxidation of hydrocarbons by Desulfovibrio desulfuricans. Chemical Geology. 1:1966;137-144.
29. Dempster H.S., Sherwood Lollar B., Feenstra S. Tracing organic contaminants in groundwater. a new methodology using compound-specific isotope analysis Environmental Science and Technology. 31:1997;3193-3197.
30. Edwards E.A., Grbic-Galic D. Complete mineralization of benzene by aquifer microorganisms under strictly anaerobic conditions. Applied and Environmental Microbiology. 58:1992;2663-2666.
31. Evans P.J., Ling W., Goldschmidt B., Ritter E.R., Young L.Y. Metabolites formed during anaerobic transformation of toluene and o-xylene and their proposed relationship to the initial steps of toluene mineralization. Applied and Environmental Microbiology. 58:1992;496-501.
32. Fisher, S.J., Alexander, R., Kagi, R.I., Oliver, G.A., 1998. Aromatic hydrocarbons as indicators of biodegradation in north Western Australian reservoirs. In: Purcell, P.G., Purcell, R.R. (Eds.), The Sedimentary Basins of Western Australia 2: Proceedings of Petroleum Exploration Society Symposium, Perth, WA, 1998, pp. 185-194.
33. Harms G., Zengler K., Rabus R., Aeckersberg F., Minz D., Rosselló-Mora R.et al. Anaerobic oxidation of o-xylene, m-xylene, and homologous alkylbenzenes by new types of sulfate-reducing bacteria. Applied and Environmental Microbiology. 65:1999;999-1004.
34. 4 alkylated benzenes in flash pyrolysates of kerogens, coals and asphaltenes. Journal of Chromatography. 606:1992;211-220.
35. Heider J., Fuchs G. Anaerobic metabolism of aromatic compounds. European Journal of Biochemistry. 243:1997;577-596.
36. Heider J., Fuchs G. Microbial anaerobic metabolism. Anaerobe. 3:1997;1-22.
37. Jobson A.M., Cook F.D., Westlake D.W.S. Interaction of aerobic and anaerobic bacteria in petroleum biodegradation. Chemical Geology. 24:1979;355-365.
38. Kazumi J., Caldwell M.E., Suflita J.M., Lovley D.R., Young L.Y. Anaerobic degradation of benzene in diverse anoxic environments. Environmental Science and Technology. 31:1997;813-818.
39. Lafargue E., le Thiez P. Effect of waterwashing on light ends compositional heterogeneity. Organic Geochemistry. 24:1996;1141-1150.
40. L'Haridon S., Reysenbach A.-L., Glénat P., Prieur D., Jeanthon C. Hot subterranean biosphere in a continental oil reservoir. Nature. 377:1995;223-224.
41. Lovley D.R., Coates J.D., Woodward J.C., Philipps E.J.P. Benzene oxidation coupled to sulfate reduction. Applied and Environmental Microbiology. 61:1995;953-958.
42. Mariotti A., Germon J.J., Hubert P., Kaiser P., Letolle R., Tardieux A., Tardieux P. Experimental determination of nitrogen kinetic isotope fractionation. illustration for the denitrification and nitrification processes Plant and Soil. 62:1981;413-430.
43. Means J.L., Hubbard N. Short-chain aliphatic acid anions in deep subsurface brines. a review of their origin, occurrence, properties, and importance and new data on their distribution and geochemical implications in the Palo Duro Basin, Texas Organic Geochemistry. 11:1987;177-191.
44. Migaud M.E., Chee-Sanford J.C., Frost J.W. Benzylfumaric, benzylmaleic, and Z- and E-phenylitaconic acids. synthesis, characterization, and correlation with a metabolite generated by Azoarcus tolulyticus Tol-4 during anaerobic toluene degaradation Applied and Environmental Microbiology. 62:1996;974-978.
45. Mueller R.F., Nielsen P.H. Characterization of thermophilic consortia from two souring oil reservoirs. Applied and Environmental Microbiology. 62:1996;3083-3087.
46. Nazina T.N., Rozanova E.P., Kuznetsov S.I. Microbial oil transformation processes accompanied by methane and hydrogen sulfide formation. Geomicrobiology Journal. 4:1985;103-130.
47. Nilsen R.K., Torsvik T. Methanococcus thermolithotrophicus isolated from North sea oil field reservoir water. Applied and Environmental Microbiology. 62:1996;728-731.
48. Nilsen R.K., Beeder J., Thorstensen T., Torsvik T. Distribution of thermophilic marine sulfate reducers in North Sea oil field waters and oil reservoirs. Applied and Environmental Microbiology. 62:1996;1793-1798.
49. Novelli G.D., ZoBell C.E. Assimilation of petroleum hydrocarbons by sulfate-reducing bacteria. Journal of Bacteriology. 47:1944;447-448.
50. Palmer S.E. Effect of biodegradation and water washing on crude oil composition. Engel M.H., Macko S.A. Organic Geochemistry. 1993;511-533 Plenum Press, New York.
51. Peters K.E., Moldowan J.M. The Biomarker Guide. 1993;Prentice Hall, Englewood Cliffs.
52. Rabus R., Heider J. Initial reactions of anaerobic metabolism of alkylbenzenes in denitrifying and sulfate-reducing bacteria. Archives of Microbiology. 170:1998;377-384.
53. Rabus R., Widdel F. Conversion studies with substrate analogues of toluene in a sulfate-reducing bacterium, strain Tol2. Archives of Microbiology. 164:1995;448-451.
54. Rabus R., Widdel F. Utilization of alkylbenzenes during anaerobic growth of pure cultures of denitrifying bacteria on crude oil. Applied and Environmental Microbiology. 62:1996;1238-1241.
55. Rabus R., Nordhaus R., Ludwig W., Widdel F. Complete oxidation of toluene under strictly anoxic conditions by a new sulfate-reducing bacterium. Applied and Environmental Microbiology. 59:1993;1444-1451.
56. Rabus R., Fukui M., Wilkes H., Widdel F. Degradative capacities and 16S rRNA-targeted whole-cell hybridization of sulfate-reducing bacteria in an anaerobic enrichment culture utilizing alkylbenzenes from crude oil. Applied and Environmental Microbiology. 62:1996;3605-3613.
57. Radke M., Willsch H., Welte D.H. Preparative hydrocarbon group determination by automated medium pressure liquid chromatography. Analytical Chemistry. 52:1980;406-411.
58. Reinhard M., Shang S., Kitanidis P.K., Orwin E., Hopkins G.D., Lebron C.A. In situ BTEX biotransformation under enhanced nitrate- and sulfate-reducing conditions. Environmental Science and Technology. 31:1997;28-36.
59. Rosenfeld W.D. Anaerobic oxidation of hydrocarbons by sulfate-reducing bacteria. Journal of Bacteriology. 54:1947;664-665.
60. Rosnes J.T., Torsvik T., Lien T. Spore-forming thermophilic sulfate-reducing bacteria isolated from North Sea oil field waters. Applied and Environmental Microbiology. 57:1991;2302-2307.
61. Rozanova E.P., Galushko A.S., Ivanova A.E. Distribution of sulfate-reducing bacteria utilizing lactate and fatty acids in anaerobic ecotopes of flooded petroleum reservoirs. Microbiology. 60:1991;251-256.
62. Rueter P., Rabus R., Wilkes H., Aeckersberg F., Rainey F.A., Jannasch H.W.et al. Anaerobic oxidation of hydrocarbons in crude oil by new types of sulphate-reducing bacteria. Nature. 372:1994;455-458.
63. Schenk H.J., di Primio R., Horsfield B. The conversion of oil into gas in petroleum reservoirs. Part 1. comparative kinetic investigation of gas generation from crude oils of lacustrine, marine and fluviodeltaic origin by programmed-temperature closed-system pyrolysis Organic Geochemistry. 26:1997;467-481.
64. Schmitt R., Langguth H.-R., Püttmann W., Rohns H.P., Eckert P., Schubert J. Biodegradation of aromatic hydrocarbons under anoxic conditions in a shallow sand and gravel aquifer of the Lower Rhine Valley, Germany. Organic Geochemistry. 25:1996;41-50.
65. Scott, P.J.B., Davies, M., 1993. Souring of new Irian Jaya wells traced to indigenous bacteria. Oil & Gas Journal 92, 47-50.
66. Seyfried B., Glod G., Schocher R., Tschech A., Zeyer J. Initial reactions in the anaerobic oxidation of toluene and m-xylene by denitrifying bacteria. Applied and Environmental Microbiology. 60:1994;4047-4052.
67. Stetter K.O., Huber R., Blöchl E., Kurr M., Eden R.D., Fielder M., Cash H., Vance I. Hyperthermophilic archaea are thriving in deep North Sea and Alaskan oil reservoirs. Nature. 365:1993;743-745.
68. Thierrin J., Davis G.B., Barber C., Patterson B.M., Pribac F., Power T.R., Lambert M. Natural degradation rates of BTEX compounds and naphthalene in a sulfate-reducing ground water environment. Hydrological Sciences Journal. 38:1993;309-332.
69. Volkman J.K., Alexander R., Kagi R.I., Rowland S.J., Sheppard P.N. Biodegradation of aromatic hydrocarbons in crude oils from the Barrow Sub-basin of Western Australia. Organic Geochemistry. 6:1984;619-632.
70. Widdel, F., Bak, F., 1992. Gram-negative mesophilic sulfate-reducing bacteria. In: Balows, A., Trüper, H.G., Dworkin, M., Harder, W., Schleifer, K.H. (Eds.), The Prokaryotes, Vol. IV, 2nd Edition. Springer-Verlag, Berlin, pp. 3352-3378.
71. Wilkes H., Willsch H., Rabus R., Aeckersberg F., Rueter P., Widdel F. Compositional changes of crude oils upon anaerobic degradation by sulphate-reducing bacteria. Grimalt J.O., Dorronsoro C. Organic Geochemistry: Developments and Applications to Energy, Climate, Environment and Human History. 1995;321-323 AIGOA, Donostia - San Sebastian.
72. Zhang X., Young L.Y. Carboxylation as an initial reaction in the anaerobic metabolism of naphthalene and phenanthrene by sulfidogenic consortia. Applied and Environmental Microbiology. 63:1997;4759-4764.