Controls on distributions of methylphenanthrenes in sedimentary rock extracts: Critical evaluation of existing geochemical data from molecular modelling

Organic Geochemistry

Volumn 41, Issue 12, 2010, Pages 1297-1311

  Szczerba, Marek ^a   Rospondek, Mariusz J ^b  

^a INSTITUTE OF GEOLOGICAL SCIENCES   (Poland)

^b JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; ALKYLATION; ANTHRACENE; BIODEGRADATION; CALCULATIONS; CATALYSIS; ENERGY BARRIERS; FREE RADICALS; ISOMERIZATION; KEROGEN; MATRIX ALGEBRA; METHYLATION; MOLECULAR MODELING; MOLECULES; PLANTS (BOTANY); QUANTUM CHEMISTRY; QUANTUM THEORY; REACTION RATES; SEDIMENTARY ROCKS; SOLUTIONS; THERMODYNAMIC STABILITY;

AB INITIO QUANTUM CHEMICAL CALCULATIONS; CATALYTIC EFFECTS; COMPLEX PROCESSES; CRITICAL EVALUATION; LOWER ENERGY BARRIERS; MATURITY PARAMETERS; METHYLPHENANTHRENE; REVERSE REACTIONS;

ISOMERS;

AQUEOUS SOLUTION; BIODEGRADATION; CATALYSIS; CATALYST; CONCENTRATION (COMPOSITION); ENERGY EFFICIENCY; GEOCHEMICAL METHOD; HETEROGENEITY; IDENTIFICATION METHOD; KEROGEN; MATRIX; MATURATION; MINERAL; MOLECULAR ANALYSIS; NUMERICAL MODEL; PERFORMANCE ASSESSMENT; REACTION KINETICS; SEDIMENT CHEMISTRY; SEDIMENTARY ROCK; THERMODYNAMIC PROPERTY;

EID: 84962433716     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orggeochem.2010.09.009     Document Type: Article

References (59)

1. Alexander R., Kagi R.I., Larcher A.V. Clay catalysis of aromatic hydrogen-exchange reactions. Geochimica et Cosmochimica Acta 1982, 46:219-222.
2. Alexander R., Strachan M.G., Kagi R.I., van Bronswijk W. Heating rate effects on aromatic maturity indicators. Organic Geochemistry 1986, 10:997-1003.
3. Alexander R., Bastow T.P., Fisher S.J., Kagi R.I. Geosynthesis of organic compounds: II. Methylation of phenanthrene and alkylphenanthrenes. Geochimica et Cosmochimica Acta 1995, 59:4259-4266.
4. Armstroff A., Wilkes H., Schwarzbauer J., Littke R., Horsfield B. Aromatic hydrocarbon biomarkers in terrestrial organic matter of Devonian to Permian age. Palaeogeography, Palaeoclimatology, Palaeoecology 2006, 240:253-274.
5. Armstroff A., Wilkes H., Schwarzbauer J., Littke R., Horsfield B. The potential role of redox reactions for the distribution of alkyl naphthalenes and their oxygenated analogues in terrestrial organic matter of Late Palaeozoic age. Organic Geochemistry 2007, 38:1692-1714.
6. Bastow T.P., Alexander R., Kagi R.I. Geosynthesis of organic compounds IV. Methylation of 1,2,7-trimethylnaphthalene. Polycyclic Aromatic Compounds 1996, 9:177-183.
7. Bastow T.P., Alexander R., Fisher S.J., Singh R.K., van Aarssen B.G.K., Kagi R.I. Geosynthesis of organic compounds. Part V - methylation of alkylnaphthalenes. Organic Geochemistry 2000, 31:523-534.
8. Bastow T.P., Singh R.K., van Aarssen B.G.K., Alexander R., Kagi R.I. 2-Methylretene in sedimentary material: a new higher plant biomarker. Organic Geochemistry 2001, 32:1211-1217.
9. Becke A.D. Density-functional thermochemistry. 3. The role of exact exchange. Journal of Chemical Physics 1993, 98:5648-5652.
10. Behar F., Budzinski H., Vandenbroucke M., Tang Y. Methane generation from oil cracking: kinetics of 9-MP cracking and comparison with other pure compounds and oil fractions. Energy and Fuels 1999, 13:471-481.
11. Boreham C.J., Crick I.H., Powell T.G. Alternative calibration of the MP Index against vitrinite reflectance: application to maturity measurements on oils and sediments. Organic Geochemistry 1988, 12:289-294.
12. Budzinski H., Garrigues P., Radke M., Connan J., Oudin J.-L. Thermodynamic calculations on alkylated phenanthrenes: geochemical applications to maturity and origin of hydrocarbons. Organic Geochemistry 1993, 20:917-926.
13. Budzinski H., Nadalig T., Raymond N., Matuzahroh N., Gilewicz M. Evidence of two metabolic pathways for degradation of 2-MP by Sphingomonas sp. strain (2MPII). Environmental Toxicology and Chemistry 2000, 19:2672-2677.
14. Cassani, F., Gallango, O., Talukdar, S., Vallejos, C., Ehrmann, U., 1988. Methylphenanthrene maturity index of marine source rock extracts and crude oils from the Maracaibo Basin. In: Mattawelli, L., Novelli, L. (Eds.), Advances in Organic Geochemistry 1987, Organic Geochemistry 13, 73-80.
15. Dieckmann V. Modelling petroleum formation from heterogeneous source rocks: the influence of frequency factors on activation energy distribution and geological prediction. Marine and Petroleum Geology 2005, 22:375-390.
16. Ewald M., Lamotte M., Garrigues P., Rima J., Veyres A., Lapouyade R. Determination of isomers of monomethyl phenanthrene extracted from petroleum by capillary gas chromatography coupled with mass spectrometry and by high resolution spectrofluorometry in alkane crystals at a temperature of 15K. Advances in Organic Geochemistry 1981 1983, 705-709. John Wiley and Sons Limited. M. Bjøroy (Ed.).
17. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery Jr., J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mannucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, F., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Frakas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cislowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., Pople, J.A., 2004. Gaussian-94, Revision C.3. Gaussian, Inc., Pittsburgh, PA.
18. Garrigues P., Ewald M. Natural occurrence of 4-methylphenanthrene in petroleum and recent marine sediments. Organic Geochemistry 1983, 5:53-56.
19. Garrigues, P., Oudin, J.-L., Parlanti, E., Monin, J.C., Robcis, S., Bellocq, J., 1990. Alkylated phenanthrene distribution in artificially matured kerogen from Kimmeridge clay and the Brent Formation (North Sea). In: Durand, B., Tissot, B.P. (Eds.), Advances in Organic Geochemistry 1989, Organic Geochemistry 16, 167-173.
20. Greiner A., Spyckerelle C., Albrecht P. Aromatic hydrocarbons from geologic sources I. New naturally occur ring phenanthrene and chrysene derivatives. Tetrahedron 1976, 32:257-260.
21. Jensen F. Introduction to Computational Chemistry 1999, John Wiley and Sons, Chichester.
22. Koopmans M.P., Köster J., van Kaam-Peters H.M.E., King F., Schouten S., Hartgers W.A., de Leeuw J.W., Sinninghe Damsté J.S. Diagenetic and catagenetic products of isorenieratene: molecular indicators for photic zone anoxia. Geochimica et Cosmochimica Acta 1996, 60:4467-4496.
23. Köster J., Kotarba M., Lafaruge E., Kosakowski P. Source rock habitat and hydrocarbon potential of Oligocene Menilite Formation (Flysch Carpathians of Southeast Poland): an organic geochemical and isotope approach. Organic Geochemistry 1998, 29:543-558.
24. 13C nuclear magnetic resonance studies. Journal of the American Chemical Society 1981, 103:4624-4632.
25. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B 1988, 37:785-789.
26. Marynowski L., Gawe{ogonek}da A., Poprawa P., Żywiecki M., Ke{ogonek}pińska B., Merta H. Origin of organic matter from tectonic zones in the Western Tatra Mountains Crystalline Basement, Poland: an example of bitumen-source rock correlation. Marine and Petroleum Geology 2006, 23:261-279.
27. Marynowski L., Zatoń M., Simoneit B.R.T., Otto A., Je{ogonek}drysek M.O., Grelowski C., Kurkiewicz S. Compositions, sources and depositional environments of organic matter from the Middle Jurassic clays of Poland. Applied Geochemistry 2007, 22:151-161.
28. Miertus S., Scrocco E., Tomasi J. Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chemical Physics 1981, 55:117-129.
29. Oldenburg T.B.P., Wilkes H., Horsfield B., van Duin A.C.T., Stoddart D. Xanthones - novel aromatic oxygen-containing compounds in crude oils. Organic Geochemistry 2002, 33:595-609.
30. Otto A., Simoneit B.R.T., Rember W.C. Conifer and angiosperm biomarkers in clay sediments and fossil plants from the Miocene Clarkia Formation, Idaho, USA. Organic Geochemistry 2005, 36:907-922.
31. Püttmann W., Merz C., Speczik S. The secondary oxidation of organic material and its influence on Kupferschiefer mineralization of southwest Poland. Applied Geochemistry 1989, 4:151-161.
32. Radke M. Organic geochemistry of aromatic hydrocarbons. Advances in Petroleum Geochemistry 1987, vol. 2:141-207. Academic Press.
33. Radke M., Welte D.H. The MP Index (MPI): a maturity parameter based on aromatic hydrocarbons. Advances in Organic Geochemistry 1981 1983, 504-512. John Wiley and Sons Limited. M. Bjøroy (Ed.).
34. Radke M., Welte D.H., Willsch H. Geochemical study on a well in the Western Canada Basin: relation of the aromatic distribution pattern to maturity of organic matter. Geochimica et Cosmochimica Acta 1982, 46:1-10.
35. Radke M., Willsch H., Leythaeuser D., Teichmüller M. Aromatic components of coal: relation of distribution pattern to rank. Geochimica et Cosmochimica Acta 1982, 46:1831-1848.
36. Radke, M., Welte, D.H., Willsch, H., 1986. Maturity parameters based on aromatic hydrocarbons: influence of the organic matter type. In: Leythaeuser, D., Rullkötter, J. (Eds.), Advances in Organic Geochemistry 1985, Organic Geochemistry 10, 51-63.
37. Radke M., Garrigues P., Willsch H. Methylated dicyclic and tricyclic aromatic hydrocarbons in crude oils from the Handil field, Indonesia. Organic Geochemistry 1990, 15:17-34.
38. Radke M., Vriend S.P., Ramanampisao L.R. Alkyldibenzofurans in terrestrial rocks: influence of organic facies and maturation. Geochimica et Cosmochimica Acta 2000, 64:275-286.
39. Rospondek M.J., Marynowski L., Góra M. Novel arylated polyaromatic thiophenes: phenylnaphtho[b]thiophenes and naphthylbenzo[b]thiophenes as markers of organic matter diagenesis buffered by oxidising solutions. Organic Geochemistry 2007, 38:1729-1756.
40. Rospondek M.J., Szczerba M., Małek K., Góra M., Marynowski L. Comparison of phenyldibenzothiophene distributions predicted by molecular modelling with relevant experimental and geological data. Organic Geochemistry 2008, 39:1800-1815.
41. Rospondek M.J., Marynowski L., Chachaj A., Góra M. Novel aryl polycyclic aromatic hydrocarbons: phenylphenanthrene and phenylanthracene identification, occurrence and distribution in sedimentary rocks. Organic Geochemistry 2009, 40:986-1004.
42. Rospondek, M.J., Lewandowska, A., Marynowski, L., 2009b. Fate of organic matter during contact metamorphism induced by Permian magmatic activity in the De{ogonek}bnik Anticline, Southern Poland. In: Lewandowska, A., Rospondek, M.J. (Eds.), Permo-Carboniferous volcanism of the Kraków region, Mineralogia, Special Papers 34, VENTS4 Kraków,
43. Sawłowicz Z., Gize A.P., Rospondek M. Organic matter from Zechstein copper deposits (Kupferschiefer) in Poland. Organic Matter and Mineralization 2000, 220-242. Kluwer Academic Publications, Dordrecht. M. Glikson, M. Mastalerz (Eds.).
44. Simoneit, B.R.T., Grimalt, J.O., Wang, T.-G., Cox, R.E., Hatcher, P.G., Nissenbaum, A., 1986. Cyclic terpenoids of contemporary resinous plant detritus and fossil wood, ambers and coals. In: Leythaeuser, D., Rullkötter, J. (Eds.), Advances in Organic Geochemistry 1985, Organic Geochemistry 10, 877-889.
45. Smith C.M., Savage P.E. Reactions of polycyclic alkylaromatics. 2. Hydrogenolysis mechanisms in 1-alkylpyrene pyrolysis. Energy and Fuels 1992, 6:195-202.
46. Smith, D.G., Zorn, C.E., Sneider, R.M., 1984. The paleogeography of the Lower Cretaceous of western Alberta and northeastern British Columbia in and adjacent to the Deep Basin of the Elmworth area. In: Masters, J.A. (Ed.), Elmworth - Case Study of a Deep Basin Gas Field. AAAPG Memoir 38, pp. 79-114.
47. Smith J.W., George S.C., Batts B.D. The geosynthesis of alkylaromatics. Organic Geochemistry 1995, 23:71-80.
48. Snowdon L.R. Errors in extrapolation of experimental kinetic parameters to organic geochemical systems. American Association of Petroleum Geologists Bulletin 1979, 63:1113-1128.
49. Strachan M.G., Alexander R., Kagi R.I. Trimethylnaphthalenes in crude oils and sediments: effects of source and maturity. Geochimica et Cosmochimica Acta 1988, 52:1255-1264.
50. Sreibl M., Herout V. Terpenoids - especially oxygenated mono-, sesqui-, di-, and triterpenes. Organic Geochemistry, Methods and Results 1969, 401-424. Springer, Berlin. G. Eglinton, M.T.J. Murphy (Eds.).
51. Sun Y.-Z. Influences of secondary oxidation and sulfide formation on several maturity parameters in Kupferschiefer. Organic Geochemistry 1998, 29:1419-1429.
52. Thomas B.R. Kauri resins - Modern and Fossil Organic Geochemistry. Methods and Results 1969, Springer-Verlag, Berlin, pp. 599-618.
53. van Aarssen B.G.K., Bastow T.P., Alexander R., Kagi R.I. Distributions of methylated naphthalenes in crude oils: indicators of maturity, biodegradation and mixing. Organic Geochemistry 1999, 30:1213-1227.
54. van Duin A.C.T., Baas J.M.A., de Graaf W., de Leeuw J.W., Bastow T.P., Alexander R. Comparison of calculated equilibrium mixtures of alkylnaphthalenes and alkylphenanthrenes with experimental data; the importance of entropy calculations. Organic Geochemistry 1997, 26:275-280.
55. Varma R. Clay and clay-supported reagents in organic synthesis. Tetrahedron 2002, 58:1235-1255.
56. Voigtmann M.F., Yang K., Batts B.D., Smith J.W. Evidence for synthetic generation of methylphenanthrene in sediments. Fuel 1994, 73:1899-1903.
57. Wei Z., Moldowan M.J., Dahl J., Goldstein T.P., Jarvie D.M. The catalytic effects of minerals on the formation of diamondoids from kerogen macromolecules. Organic Geochemistry 2006, 37:1421-1436.
58. Waples D.W. The kinetics of in-reservoir oil destruction and gas formation: constraints from experimental and empirical data, and from thermodynamics. Organic Geochemistry 2000, 31:553-575.
59. Willsch H., Radke M. Distribution of polycyclic aromatic compounds in coals of high rank. Polycyclic Aromatic Compounds 1995, 7:231-251.