Biodegradation of crude oil into nonvolatile organic acids in a contaminated aquifer near Bemidji, Minnesota

Organic Geochemistry

Volumn 29, Issue 4, 1998, Pages 909-931

  Thorn, K A ^a   Aiken, G R ^a  

^a DENVER FEDERAL CENTER   (United States)

Author keywords

Alkylaromatics; Asphalt enes; Bemidji; Crude oil biodegradation; Dibenzothiophenes; Groundwater humic substances; Minnesota; Naphthenoaromatics; NMR; Polar metabolites; Resins

Indexed keywords

HYDROPHILIC ACIDS; HYDROPHOBIC ACIDS; NONVOLATILE ORGANIC ACIDS; POLAR METABOLITES;

ASPHALTENE; BIODEGRADATION; CARBOXYLIC ACID; CHEMICAL ANALYSIS; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PETROLEUM; RESIN; SULFUR; UNITED STATES; WATER CONTAMINATION;

AQUIFERS; BIODEGRADATION; CONTAMINATION; CRUDE PETROLEUM; GROUNDWATER; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; ORGANIC ACIDS; OXIDATION; RESINS;

ANALYTICAL GEOCHEMISTRY;

AQUIFER POLLUTION; BIODEGRADATION; CRUDE OIL; ORGANIC ACID;

UNITED STATES;

EID: 0032434181     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(98)00167-3     Document Type: Article

References (40)

1. Aiken G. R., Malcolm R. L. Molecular weight of aquatic fulvic acids by vapor pressure osmometry. Geochimica Cosmochimica Acta. 51:1987;2177-2184.
2. Aiken G. R., McKnight D. M., Thorn K. A., Thurman E. M. Isolation of hydrophilic organic acids from water using nonionic macroporous resins. Organic Geochemistry. 18:1992;567-573.
3. Altgelt, K. H. and Boduszynski, M. M. (1994) Composition and Analysis of Heavy Petroleum Fractions. Marcel Dekker.
4. Baedecker M. J., Cozzarelli I. M., Siegel D. I., Bennett P. C., Eganhouse R. P. Crude oil in a shallow sand and gravel aquifer. III. Biogeochemical reactions and mass balance modeling in anoxic groundwater. Applied Geochemistry. 8:1993;569-586.
5. Bax A., Morris G. A. An improved method for heteronuclear chemical shift correlation by two-dimensional NMR. Journal of Magnetic Resonance. 42:1981;501-505.
6. Bennett P. C., Seigel D. I., Baedecker M. J., Cozzarelli I. M., Hult M. F. Crude oil in a shallow sand and gravel aquifer. Applied Geochemistry. 8:1993;529-549.
7. Bossert, I. and Bartha, R. (1984) The fate of petroleum in soil ecosystems. In Petroleum Microbiology, ed. R. M. Atlas, Chap. 10. Macmillan, pp. 435-473.
8. Cerniglia, C. E. (1984) Microbial transformation of aromatic hydrocarbons. In Petroleum Microbiology, ed. R. M. Atlas, Chap. 3. Macmillan, pp. 99-128.
9. Connan, J. (1984) Biodegradation of Crude Oils in Reservoirs. In Advances in Petroleum Geochemistry, eds J. Brooks and D. Welte. Academic Press, pp. 299-335.
10. 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.
11. Cozzarelli I. M., Baedecker M. J., Eganhouse R. B., Goerlitz D. F. The geochemical evolution of low molecular-weight organic acids derived from the degradation of petroleum contaminants in groundwater. Geochimica Cosmochimica Acta. 58:1994;863-877.
12. DeCanio S. J., Nero V. P., DeTar M. M., Storm D. A. Determination of the molecular weights of the ratawi vacuum residue fractions: a comparison of mass spectrometric and vapour phase osmometry techniques. Fuel. 69:1990;1233-1236.
13. Dennis, L. and Pabst, R. E. (1987) Polarization transfer and 2-D experiments in nmr of solutions of humic materials and fossil fuel liquids. In NMR of Humic Substances and Coal, Techniques, Problems and Solutions, eds R. L. Wershaw and M. A. Mikita, Chap. 6. Lewis, pp. 99-128.
14. Dunnivant F. M., Schwarzenbach R. P., Macalady D. L. Reduction of substituted nitrobenzenes in aqueous solutions containing natural organic matter. Environmental Science and Technology. 26:1992;2133-2141.
15. Eganhouse R. P., Baedecker M. J., Cozzarelli I. M., Aiken G. R., Thorn K. A., Dorsey T. F. Crude oil in a shallow sand and gravel aquifer. II. Organic geochemistry. Applied Geochemistry. 8:1993;551-567.
16. Fedorak, P. M. (1990) Microbial metabolism of organosulfur compounds in petroleum. In Geochemistry of Sulfur in Fossil Fuels, eds. W. L. Orr and C. M. White, ACS Symposium Series 429. American Chemical Society, Washington, D.C., pp. 93-112.
17. Furlong, E., Koleis, J. C. and Aiken, G. R. (1997) Transport and degradation of semivolatile hydrocarbons in a petroleum-contaminated aquifer, Bemidji, Minnesota. In Molecular Markers in Environmental Geochemistry, ed. R. P. Eganhouse, ACS Symposium Series 671. American Chemical Society, Washington, D.C., pp. 398-412.
18. Jaffe R., Gallardo M. T. Application of carboxylic acid biomarkers as indicators of biodegradation and migration of crude oils from the Maracaibo Basin, Western Venezuela. Organic Geochemistry. 20:1993;973-984.
19. Kropp K. G., Andersson I. T., Fedorak P. M. Biotransformations of three dimethyldibenzothiophenes by pure and mixed bacterial cultures. Environmental Science and Technology. 31:1997;1547-1554.
20. Kutyrev A. A. Nucleophilic reactions of quinones. Tetrahedron. 47:1991;8043-8065.
21. Landon, M. K. (1993) Investigation of mass loss based on evolution of composition and physical properties of spilled crude oil contaminating a shallow outwash aquifer. Thesis, University of Minnesota.
22. Landon, M. K. and Hult, M. F. (1997) Source mass balance calculated from changes in composition of spilled crude oil in the subsurface near Bemidji, Minnesota. In U. S. Geological Survey Toxic Substances Hydrology Program: Proceedings of the Technical Meeting, Colorado Springs, Colorado, Sept. 20-24, 1993, eds. D. W. Morganwalp and D. A. Aronson. U.S. Geological Survey WRI Report 94-4015. pp. 631-641.
23. Patt S. L., Shoolery J. N. Attached proton test for carbon-13 NMR. Journal of Magnetic Resonance. 46:1982;535-539.
24. Perry, J. J. (1984) Microbial metabolism of cyclic alkanes. In Petroleum Microbiology, ed. R. M. Atlas, Chap. 2. Macmillan, pp. 61-97.
25. Peters, K. E. and Moldowan, J. M. (1993) The Biomarker Guide. Prentice Hall.
26. Petrakis, L. and Allen, D. (1987) NMR for Liquid Fossil Fuels. Elsevier.
27. Prince, R. C., Drake, E. N., Rothenburger, S. J., Stokley, K. E. and Douglas, G. S. (1996) Biodegradation of polynuclear aromatic hydrocarbons in the environment. In Division of Environmental Chemistry Preprints of Extended Abstracts, Vol. 36(1). American Chemistry Society, Washington, D.C., pp. 191-193.
28. Richnow H. H., Seifert R., Hefter J., Link M., Francke W., Schaefer G., Michaelis W. Organic pollutants associated with macromolecular soil organic matter: Mode of binding. Organic Geochemistry. 26:1997;745-758.
29. Rontani J. F., Bosser-Joulak F., Rambeloarison E., Bertrand J. C., Giusti G., Faure R. Analytical study of asthart crude oil asphaltenes biodegradation. Chemosphere. 14:1985;1413-1422.
30. Singer, M. E. and Finnerty, W. R. (1984) Microbial metabolism of straight-chain and branched alkanes. In Petroleum Microbiology, ed. R. M. Atlas, Chap. 1. Macmillan, pp. 1-59.
31. Sorensen O. W., Donstrup S., Bildsoe H., Jakobsen H. J. Suppression of J cross-talk in subspectral editing. The SEMUT GL pulse sequence. Journal of Magnetic Resonance. 55:1983;347-354.
32. Speight, J. G. (1990) Fuel Science and Technology Handbook. Marcel Dekker.
33. Speight, J. G. (1991) The Chemistry and Technology of Petroleum, 2nd edn. Marcel Dekker.
34. Storm D. A., Decanio S. J., DeTar M. M., Nero V. P. Upper bound on number average molecular weight of asphaltenes. Fuel. 69:1990;735-738.
35. 13C NMR investigation of hydroxylamine-derivatized humic substances Environmental Science and Technology. 26:1992;107-116.
36. Thorn K. A., Pettigrew P. J., Goldenberg W. S., Weber E. J. Covalent binding of aniline to humic substances, II. Nitrogen-15 NMR studies of nucleophilic addition reactions. Environmental Science and Technology. 30:1996;2764-2775.
37. Tissot, B. P. and Welte, D. H. (1984) Petroleum Formation and Occurrence. Springer-Verlag.
38. Waldo G. S., Carlson R. M. K., Moldowan J. M., Peters K. E., Penner-Hahn J. E. Sulfur speciation in heavy petroleums: information from X-ray absorption near-edge structure. Geochimica Cosmochimica Acta. 55:1991;801-814.
39. Wilson, M. A. (1987) NMR Techniques and applications in Geochemistry and Soil Chemistry. Pergamon.
40. Yen, T. F. and Chilingarian, G. V. (1994) Asphaltenes and Asphalt. Elsevier.