Xanthones - Novel aromatic oxygen-containing compounds in crude oils

Organic Geochemistry

Volumn 33, Issue 5, 2002, Pages 595-609

  Oldenburg, Thomas B P ^a,b   Wilkes, Heinz ^a,d   Horsfield, Brian ^a,d   Van Duin, Adri C T ^b   Stoddart, Daniel ^c   Wilhelms, Arnd ^c  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

^b Fossil Fuels/Environ Geochem (NRG)   (United Kingdom)

^c STATOIL   (Norway)

^d GFZ GERMAN RESEARCH CENTRE FOR GEOSCIENCES   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GEOSYNTHESIS;

BIODEGRADATION; CRUDE PETROLEUM; ISOMERS; OXIDATION;

AROMATIC COMPOUNDS;

METHYLXANTHONE; PETROLEUM; XANTHONE DERIVATIVE;

AROMATIC HYDROCARBON; BIODEGRADATION; CRUDE OIL; ORGANIC GEOCHEMISTRY;

CONCENTRATION (PARAMETERS); ELUTION; GEOGRAPHIC DISTRIBUTION; NORWAY; OFFSHORE OIL INDUSTRY;

NORTH SEA;

EID: 0036909013     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(02)00015-3     Document Type: Conference Paper

References (70)

1. Allen, M.P., Tildesley, D.J., 1987. Computer Simulation of Lipids. Clarendon Press, Oxford.
2. Anders, D.E., Doolittle, F.G., Robinson, W.E., 1975. Polar constituents isolated from Green River oil shale. Geochimica et Cosmochimica Acta 39, 1423-1430.
3. Andersen, H.C., 1983. RATTLE: A "velocity" version of the SHAKE algorithm for molecular dynamics calculations. Journal of Computational Physics 52, 24-34.
4. Azevedo, D.A., Aquino Neto, F.R., Simoneit, B.R.T., 1994. Extended saturated and monoaromatic tricyclic terpenoid carboxylic acids found in Tasmanian tasmanite. Organic Geochemistry 22, 991-1004.
5. Bailey, N.J.L., Burwood, R., Harriman, G.E., 1989. Application of pyrolysate carbon isotope and biomarker technology to organofacies definition and oil correlation problems in North Sea basins. Organic Geochemistry 16, 1157-1172.
6. Barakat, A.O., Rullkötter, J., 1995. Extractable and bound fatty acids in core sediments from the Nördlinger Ries, southern Germany. Fuel 74, 416-425.
7. Barnard, P.C., Cooper, B.S., 1981. Oils and source rocks of the North Sea area. In: Illing, L.V., Hobson, G.D. (Eds.), Petroleum Geology of the Continental Shelf of North-West Europe. Heyden & Son, London, pp. 169-175.
8. Bennett, B., Larter, S.R., 2000. The isolation, occurrence and origin of fluorenones in crude oils and rock extracts. Organic Geochemistry 31, 117-126.
9. Berendsen, H.J.C., Postma, J.P.M., van Gunsteren, W.F., DiNola, A., Haak, J.R., 1984. Molecular dynamics with coupling to an external bath. Journal of Chemistry and Physics 81, 3684-3690.
10. Berglund, L.T., Augustson, J., Færseth, R., Gjelberg, J., Ramberg-Moe, H., 1986. The evolution of the Hammerfest Basin. In: Spencer, A.M. (Ed.), Habitat of Hydrocarbons on the Norwegian Continental Shelf. Graham & Trotman, London, pp. 319-338.
11. Berti, G., Bottari, F., 1968. Constituents of ferns. In: Reinhold, L., Liwschitz, Y. (Eds.), Progress in Phytochemistry 1. John Wiley & Sons, New York, pp. 589-685.
12. Bester, K., Theobald, N., 2000. Results of non target screening of lipophilic organic pollutants in the German Bight V: Xanthen-9-one. Water Research 34, 2277-2282.
13. Bodzek, D., Janoszka, B., 1995. Determination of polycyclic aromatic hydrocarbons and their derivates in sewage sludges in Upper Silesia. Vom Wasser 84, 19-33.
14. Chexal, K.K., Holker, J.S.E., Simpon, T.J., Young, K., 1975. The biosynthesis of fungal metabolites, part V. Journal of the Chemical Society 1 543-548.
15. Cornford, C., Needham, C.E.J., De Walque, L., 1986. Geo-chemical habitat of North Sea oils and gases. In: Spencer, A.M. (Ed.), Habitat of Hydrocarbons on the Norwegian Continental Shelf. Graham & Trotman, London, pp. 39-54.
16. Costa Neto, C., Maçaira, A.M.P., Pinto, R.C.P., Nakayama, H.T., Cardoso, J.N., 1980. New analytical approaches to organic geochemistry: Solid phase functional group extraction for bitumens and functional markers for kerogens. In: Douglas, A.G., Maxwell, J.R. (Eds.), Advances in Organic Geochemistry 1979. Pergamon Press, Oxford, pp. 249-263.
17. Cowley, E.G., Partington, J.R., 1936. Studies in dielectric polarisation. Part XV. The dipole moments of five-membered nitrogen ring compounds: Indole, skatole, carbazole, isatin, phthalimide, and succinimide. Journal of the Chemical Society 47, 47-50.
18. Culberson, C.F., 1969. Chemical and Botanical Guide to Lichen Products. University of North Carolina Press, Chapel Hill.
19. DeBolt, S.E., Kollman, P.A., 1995. Investigation of structure, dynamics, and solvation in 1-octanol and its water-saturated solution: Molecular dynamics and free-energy perturbation studies. Journal of the American Chemical Society 117, 5316-5340.
20. Devan, T.K., Scott, A.I., 1975. Handbook of Naturally Occurring Compounds. Academic Press, Inc, New York.
21. van Duin, A.C.T., Larter, S., 1997. Application of molecular dynamics calculations in the prediction of dynamical molecular properties. Organic Geochemistry 29, 1043-1050.
22. Falbe, J., Regitz, M., 1999. Römpp Chemie Lexikon. Thieme Verlag, Stuttgart.
23. Fernandez, P., Bayona, J.M., 1992. Use of off-line gel permeation chromatography-normal-phase liquid chromatography for the determination of polycyclic aromatic compounds in environmental samples and standard reference materials (air particulate matter and marine sediment). Journal of Chromatography 625, 141-149.
24. Field, J.D., 1985. Organic geochemistry in exploration of the Northern North Sea. In: Doré, A.G., Eggen, S.S., Home, P.C., Larsen, R.M., Thomas, B.M. (Eds.), Petroleum Geochemistry in Exploration of the Norwegian Shelf. Graham & Trotman, London, pp. 39-57.
25. Fjaeran, T., Spencer, A.M., 1991. Proven hydrocarbon plays, offshore Norway. In: Spencer, A.M. (Ed.), Generation, Accumulation, and Production of Europe's Hydrocarbons, 1, Special Publication of the European Association of Petroleum Geoscientists. Oxford University Press, Oxford, pp. 25-48.
26. Fortnagel, P., Wittich, R.-M., Harms, H., Schmidt, S., Franke, S., Sinnwell, V., Wilkes, H., Francke, W., 1989. New bacterial degradation of the biaryl ether structure. Regioselective dioxygenation prompts cleavage of ether bonds. Naturwissenschaften 76, 523-524.
27. Frenkel, D., Smit, B., 1996. Understanding Molecular Simulation. Academic Press, San Diego.
28. Gage, M.S., Doré A.G., 1986. A regional geological perspective of the Norwegian offshore exploration provinces. In: Spencer, A.M. (Ed.), Habitat of Hydrocarbons on the Norwegian Continental Shelf. Graham & Trotman, London, pp. 21-38.
29. George, S.C., Jardine, D.R., 1994. Ketones in a Proterozoic dolerite sill. Organic Geochemistry 21, 829-839.
30. Goff, J.C., 1983. Hydrocarbon generation and migration from Jurassic source-rocks in the East Shetland Basin and in Viking Graben of the Northern North Sea. Journal of the Geological Society of London 140, 445-474.
31. 28 triterpane content of a North Sea core and various North Sea crudes. In: Douglas, A.G., Maxwell, J.R. (Eds.), Advances in Organic Geochemistry 1979. Pergamon Press, Oxford, pp. 29-38.
32. Grimalt, J.O., Angulo, L., López-Galindo, A., Comas, M.C., Albaigés, J., 1990. Lipid and mineralogical composition of the Cretaceous black shale deposits of the Fardes Formation (southern Iberian Paleomargin, Betic Cordillera, south Spain). Chemical Geology 82, 341-363.
33. Hale, J.M., 1992. Molecular Dynamics Simulation. Wiley, New York.
34. Heum, O.R., Dalland, A., Meisingset, K.K., 1986. Habitat of hydrocarbons at Haltenbanken (PVT-modelling as a predictive tool in hydrocarbon exploration). In: Spencer, A.M. (Ed.), Habitat of Hydrocarbons on the Norwegian Continental Shelf. Graham & Trotman, London, pp. 259-274.
35. Horstad, I., Larter, S.R., Mills, N., 1991. A quantitative model of biological petroleum degradation within the Brent Group reservoir in the Gullfaks Field, Norwegian North Sea. Organic Geochemistry 19, 107-117.
36. Horstad, I., Larter, S.R., Mills, N., 1995. Migration of hydrocarbons in the Tampen Spur area, Norwegian North Sea: A reservoir geochemical evaluation. In: Cubitt, J.M., England, W.A. (Eds.), The Geochemistry of Reservoirs. The Geological Society, London, pp. 159-183.
37. Huc, A.Y., Irwin, H., Schoell, M., 1985. Organic matter quality changes in an Upper Jurassic shale sequence from the Viking Graben. In: Doré, A.G., Eggen, SS., Home, P.C., Larsen, R.M., Thomas, B.M. (Eds.), Petroleum Geochemistry in Exploration of the Norwegian Shelf. Graham & Trotman, London, pp. 179-183.
38. Jaffé, R., Gallardo, M.T., 1993. Application of carboxylic acid biomarkers as indicators of biodegradation and migration of crude oils from the Maracaibo Basin, Western Venezuela. Organic Geochemistry 20, 973-984.
39. Jaffé, R., Gardinali, P.R., 1990. Generation and maturation of carboxylic acids in ancient sediments from the Maracaibo Basin, Venezuela. Organic Geochemistry 16, 211-218.
40. Jorgensen, W.L., Chandrasekhar, J., Madura, J.D., 1983. Comparison of simple potential functions for simulating liquid water. Journal of Chemistry and Physics 79, 926-935.
41. Jorgensen, W.L., Nguyen, T.B., 1993. Monte Carlo simulations of the hydration of substituted benzenes with OPLS potential functions. Journal of Computational Chemistry 14, 195-205.
42. Karlsen, D.A., Nyland, B., Flood, B., Ohm, S.E., Brekke, T., Olsen, S., Bakker-Owe, K., 1995. Petroleum geochemistry of Haltenbanken, Norwegian continental shelf. In: Cubittt, J.M., England, W.A. (Eds.), The Geochemistry of Reservoirs. The Geological Society, London, pp. 203-256.
43. Karlsson, W., 1986. The Snorre, Statfjord and Gullfaks oil-fields and the habitat of hydrocarbons on the Tampen Spur, offshore Norway. In: Spencer, A.M. (Ed.), Habitat of Hydrocarbons on the Norwegian Continental Shelf. Graham & Trotman, London, pp. 181-197.
44. Latham, D.R., Ferrin, C.R., Ball, J.S., 1962. Identification of fluorenones in Wilmington petroleum by gas-liquid chromatography and spectrometry. Analytical Chemistry 34, 311-313.
45. Le Fèvre, C.G., Le Fèvre, R.J.W., 1937. The structure of xanrhone and the orientation of its α- and β-dinitro-derivatives. Journal of the Chemical Society 196-202.
46. Leif, R.N., Simoneit, B.R.T., 1995. Ketones in hydrothermal petroleums and sediment extracts from Guaymas Basin, Gulf of California. Organic Geochemistry 23, 889-904.
47. Mojelsky, T.W., Strausz, O.P., 1986. Detection of methyl fluorenones in Athabasca oil sand bitumens. Organic Geochemistry 9, 31-37.
48. Moriske, H.-J., Rüden, H., 1988. Polar organic components in emission and immission samples from urban suspended particulates and their mutagenicity in the Ames-bioassay. Chemosphere 17, 1167-1181.
49. Peres, V., Nagem, T.J., 1997. Trioxygenated naturally occurring xanthones. Phytochemistry 44, 191-214.
50. Peters, K.E., Moldowan, J.M., 1993. The Biomarker Guide. Prentice Hall, Englewood Cliffs.
51. 13C NMR chemical shifts. Archives of Pharmaceutical and Medicinal Chemistry 331, 177-192.
52. Radke, M., Willsch, H., Welte, D.H., 1980. Preparative hydrocarbon group type determination by automated medium pressure liquid chromatography. Analalytical Chemistry 52, 406-411.
53. Santamaria-Orozco, D., Horsfield, B., di Primio, R., Welte, D.H., 1998. Influence of maturity on distributions of benzo- and dibenzothiophenes in Tithonian source rocks and crude oils, Sonda de Campeche, Mexico. Organic Geochemistry 28, 423-439.
54. Schou, L., Eggen, S., Schoell, M., 1985. Oil-oil and oil-source rock correlation, Northern North Sea. In: Doré, A.G., Eggen, S.S., Home, P.C., Larsen, R.M., Thomas, B.M. (Eds.), Petroleum Geochemistry in Exploration of the Norwegian Shelf. Graham & Trotman, London, pp. 101-117.
55. Scotchman, I.C., 1991. Kerogen facies and maturity of the Kimmeridge Clay Formation in the southern and eastern England. Marine and Petroleum Geology 8, 278-295.
56. Seifert, K., 1975. Carboxylic acids in petroleum and sediments. Fortschritte der Chemie Organischer Naturstoffe 32, 1-49.
57. Sinninghe Damsté, J.S., Keely, B.J., Betts, S.E., Baas, M., Maxwell, J.R., de Leeuw, J.W., 1993. Variations in abundances and distributions of isoprenoid chromans and longchain alkylbenzenes in sediments of the Mulhouse Basin: A molecular sedimentary record of palaeosalinity. Organic Geochemistry 20, 1201-1215.
58. Sinninghe Damsté, J.S., Kock-van Dalen, A.S., de Leeuw, J.W., Schenck, P.A., Guoying, S., Brassell, S.C., 1987. The identification of mono-, di- and trimethyl 2-methyl-2-(4,8,12-trimethyldecyl)chromans and their occurrence in the geosphere. Geochimica et Cosmochimica Acta 51, 2393-2400.
59. Snyder, L.R., Buell, B.E., Howard, H.E., 1968. Nitrogen and oxygen compound types in petroleum. Analytical Chemistry 40, 1303-1317.
60. Strandell, M., Zakrisson, S., Alsberg, T., Weaserholm, R.T., Winquist, L., Rannug, U., 1994. Chemical analysis and biological testing of a polar fraction of ambient air, diesel engine and gasoline particulate extracts. Environmental Health Perspectives 102, 85-92.
61. Tomasek, P.H., Crawford, R.L., 1986. Initial reactions od xanthone biodegradation by an Arthrobacter sp. Journal of Bacteriology 167, 818-827.
62. de Vos Burchart, E., 1992. Studies on Zeolites: Molecular Mechanics, Framework Stability, and Crystal Growth. PhD thesis, Delft University of Technology, The Netherlands.
63. Wang, S., Rullkötter, J., 1997. Neutral polar lipids in freshwater and alkaline lacustrine sediments of the Green River Formation, Wyoming, U.S.A. In: Abstracts of the 18th International Meeting on Organic Geochemistry, Maastricht, The Netherlands, pp. 255-256.
64. Wilkes, H. 1993. Untersuchungen zur Aufklärung von Stoffwechselwegen beim Mikrobilellen Abbau von Diarylethern. PhD thesis, Universität Hamburg, Germany.
65. Wilkes, H., Clegg, H., Disko, U., Willsch, H., Horsfield, B., 1998a. Fluoren-9-ones and carbazoles in the Posidonia Shale, Hils Syncline, northwest Germany. Fuel 77, 657-668.
66. Wilkes, H., Disko, U., Horsfield, B., 1998b. Aromatic aldehydes and ketones in rock extracts from the Posidonia Shale, Hils Syncline, Germany. Organic Geochemistry 29, 107-117.
67. Willsch, H., Clegg, H., Horsfield, B., Radke, M., Wilkes, H., 1997. Liquid chromatographic separation of sediment, rock, and coal extracts and crude oil into compound classes. Analytical Chemistry 69, 4203-4209.
68. Wittich, R.-M., Wilkes, H., Sinnwell, V., Francke, W., Fortnagel, P., 1992. Metabolism of dibenzo-p-dioxin by Sghingomonas sp. Strain RW1. Applied and Environmental Microbiology 58, 1005-1010.
69. Wu, Q.L., Wang, S.-P., Du, L.-J., Yang, J.-S., Xiao, P.-G., 1998. Xanthones from Hypericum Japonicum and H. Henryi. Phytochemistry 49, 1395-1402.
70. Ziegler, W.H., Doery, R., Scott, J., 1986. Tectonic habitat of Norwegian oil and gas. In: Spencer, A.M. (Ed.), Habitat of Hydrocarbons on the Norwegian Continental Shelf. Graham & Trotman, London, pp. 3-19.