Selective biodegradation of extended hopanes to 25-norhopanes in petroleum reservoirs. Insights from molecular mechanics

Organic Geochemistry - Tập 24 - Trang 765-783 - 1996
Kenneth E. Peters1, J.Michael Moldowan2, Mark A. McCaffrey3, Frederick J. Fago2
1Mobil Exploration and Producing Technical Center, P.O. Box 650232, Dallas, TX 75265, U.S.A.
2Stanford University, Department of Geological and Environmental Sciences, Stanford, CA 94305, U.S.A.
3Chevron Petroleum Technology Company, P.O. Box 446, La Habra, CA 90446, U.S.A.

Tài liệu tham khảo

Alexander, 1983, The geochemistry of some biodegraded Australian oils, Australian Petrol. Expl. Assoc. J., 23, 53 Armanios, 1995, Molecular sieving, analysis and geochemistry of some pentacyclic triterpanes in sedimentary organic matter, 188 Berkert, 1982, Molecular Mechanics, Amer. Chem. Soc. Monograph 177, 339 Blanc, 1992, Origin and occurrence of 25-norhopanes: A statistical study, Org. Geochem., 18, 813, 10.1016/0146-6380(92)90050-8 Bragg, 1992, Bioremediation for Shoreline Clean-up Following the 1989 Alaska Oil Spill, 94 Bragg, 1993, Bioremediation effectiveness following the Exxon Valdez spill, 435 Brooks, 1988, Biological marker and conventional organic geochemistry of oils sands/heavy oils, Western Canada Basin, Org. Geochem., 12, 519, 10.1016/0146-6380(88)90144-1 Chang, 1989, An internal coordinate Monte Carlo method for searching conformational space, J. Am. Chem. Soc., 111, 4379, 10.1021/ja00194a035 Chosson, 1992, In vitro biodegradation of steranes and terpanes: a clue to understanding geological situations, 320 Connan, 1975, Alteration of Petroleum in Reservoirs, 2, 171 van Duin, 1996, Biogeochemical applications of a newly developed carbocation force field, 271 van Duin, 1994, DMM, J. Chem. Soc. Faraday Trans., 90, 2881, 10.1039/ft9949002881 Goodwin, 1983, Crude oil biodegradation under simulated and natural conditions, 650 van Graas, 1982, Theoretical organic geochemistry. I. The thermodynamic stability of several cholestane isomers calculated by molecular mechanics, Geochim. Cosmochim. Acta, 46, 2399, 10.1016/0016-7037(82)90211-3 Hunt, 1996, Petroleum Geochemistry and Geology, 743 Kolaczkowska, 1990, Thermodynamic stability of various alkylated, dealkylated and rearranged 17α-and 17β-hopane isomers using molecular mechanics calculations, Org. Geochem., 4–6, 1033, 10.1016/0146-6380(90)90140-U de Lemos Scofield, 1990, Nouveau marqueurs biologiques de sediments et petroles riches en soufre: Identification et mode de formation, 193 Lii, 1989, Molecular mechanics, J. Am. Chem. Soc., 111, 8553 McCaffrey, 1996, Using biomarkers to improve heavy oil reservoir management: An example from the Cymric Field, Kern County, California, Am. Assoc. Pet. Geol., 80, 898 Moldowan, 1995, A novel microbial hydrocarbon degradation pathway revealed by homohopane demethylation in a petroleum reservoir, Geochim. Cosmochim. Acta, 59, 1891, 10.1016/0016-7037(95)00072-8 Moldowan, 1992, Source correlation and maturity assessment of select oils and rocks from the Central Adriatic Basin (Italy and Yugoslavia), 370 Moldowan, 1995, Application of biological marker technology to bioremediation of refinery by-products, Energy and Fuels, 9, 155, 10.1021/ef00049a023 Noble, 1985, The occurrence of bisnorhopane, trisnorhopane and 25-norhopanes as free hydrocarbons in some Australian shales, Org. Geochem., 8, 171, 10.1016/0146-6380(85)90035-X Peters, 1991, Effects of source, thermal maturity, and biodegradation on the distribution and isomerization of homohopanes in petroleum, Org. Geochem., 17, 47, 10.1016/0146-6380(91)90039-M Peters, 1993, The Biomarker Guide, 363 Peters, 1994, Multiple oil families in the West Siberian basin, Am. Assoc. Pet. Geol., 78, 893 Peters, 1994, Identification of petroleum systems adjacent to the San Andreas Fault, California, U.S.A., Vol. 60, 423 Philp, 1983, Correlation of crude oils from the San Jorges Basin, Argentina, Geochim. Cosmochim. Acta, 47, 267, 10.1016/0016-7037(83)90139-4 Reed, 1977, Molecular compositions of weathered petroleum and comparison with its possible source, Geochim. Cosmochim. Acta, 41, 237, 10.1016/0016-7037(77)90231-9 Requejo, 1989, An unusual homohopane biodegradation sequence in tar sands from the Pt. Arena (Monterey) Formation, Nature, 342, 670, 10.1038/342670a0 Rohmer, 1992, The hopanoids, prokaryotic triterpenoids and precursors of ubiquitous molecular fossils, 1 Rullkötter, 1982, Microbial alteration of 17α(H)-homohopane in Madagascar asphalts: removal of C-10 methyl group and ring opening, Geochim. Cosmochim. Acta, 46, 1543, 10.1016/0016-7037(82)90313-1 Seifert, 1979, The effect of biodegradation on steranes and terpanes in crude oils, Geochim. Cosmochim. Acta, 43, 111, 10.1016/0016-7037(79)90051-6 Seifert, 1986, Use of biological markers in petroleum exploration, Vol. 24, 261 Seifert, 1984, Source correlation of biodegraded oils, Org. Geochem., 6, 633, 10.1016/0146-6380(84)90085-8 Sinninghe Damsté, 1995, Early diagenesis of bacteriohopanepolyol derivatives: formation of fossil homohopanoids, Geochim. Cosmochim. Acta, 59, 5141, 10.1016/0016-7037(95)00338-X Smith, 1975, The crystal and molecular structure of 29-nor-17α(H)hopane, C29H50, Acta Cryst., B31, 526, 10.1107/S0567740875003160 Subroto, 1991, 30-Norhopanes: Their occurrence in sediments and crude oils, Chem. Geol., 93, 179, 10.1016/0009-2541(91)90071-X Tissot, 1984, Petroleum Formation and Occurrence, 699 Trendel, 1990, Identification of two C-10 demethylated C28, hopanes in biodegraded petroleum, J. Chem. Soc., Chem. Commun., 424, 10.1039/c39900000424 Volkman, 1983, Demethylated homohopanes in crude oils and their applications in petroleum geochemistry, Geochim. Cosmochim. Acta, 47, 785, 10.1016/0016-7037(83)90112-6 Whitehead, 1974, The structure of petroleum pentacyclanes, 225 Zumberge, 1987, Terpenoid biomarker distributions in low maturity crude oils, Org. Geochem., 11, 479, 10.1016/0146-6380(87)90004-0