The catalytic effects of minerals on the formation of diamondoids from kerogen macromolecules

Organic Geochemistry

Volumn 37, Issue 11, 2006, Pages 1421-1436

  Wei, Zhibin ^a   Michael Moldowan, J ^a   Dahl, Jeremy ^a   Goldstein, Theodore P ^b   Jarvie, Daniel M ^c  

^a STANFORD UNIVERSITY   (United States)

^b JOHNS HOPKINS UNIVERSITY   (United States)

^c Services Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMONDOIDS; KEROGEN MACROMOLECULES; MONTMORILLONITE;

CATALYSIS; DECOMPOSITION; MACROMOLECULES; PYROLYSIS; SULFUR COMPOUNDS; THERMAL STRESS;

MINERALS;

DECOMPOSITION; DIAMOND; EXPERIMENTAL STUDY; KAOLINITE; KEROGEN; PYROLYSIS;

EID: 33750717846     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orggeochem.2006.07.006     Document Type: Article

References (68)

1. Alexander R., Kagi R.I., and Larcher A.V. Clay catalysis of alkyl hydrogen exchange reactions-reaction mechanisms. Organic Geochemistry 6 (1984) 755-760
2. Arcoya A., Senoane X.L., and Soria J. Effect of iron on the deactivation of Ni/clinoptilolite catalysts by thiophene poisoning. Journal of Chemical Technology and Biotechnology 68 (1997) 171-176
3. Balakrishnan V.K., Monteil-Rivera F., Gautier M.A., and Hawari J. Sorption and stability of the polycyclic nitramine explosive CL-20 in soil. Journal of Environmental Quality 33 (2004) 1362-1368
4. Brown D.R., and Rhodes C.N. Brønsted and Lewis acid catalysis with ion-exchanged clays. Catalysis Letters 45 (1997) 35-40
5. Collins M.J., Bishop A.N., and Farrimond P. Sorption by mineral surfaces: rebirth of the classical condensation pathway for kerogen formation?. Geochimica et Cosmochimica Acta 59 (1995) 2387-2391
6. Cseri T., Bekassy S., Figueras F., and Rizner S. Benzylation of aromatics on ion-exchanged clays. Journal of Molecular Catalysis A: Chemical 98 (1995) 101-107
7. Dahl J.E., Moldowan J.M., Peters K., Claypool G., Rooney M., Michael G., Mello M., and Kohnen M. Diamondoid hydrocarbons as indicators of oil cracking. Nature 399 (1999) 54-56
8. Davis J.B., and Stanley J.P. Catalytic effect of smectite clays in hydrocarbon generation revealed by pyrolysis-gas chromatography. Journal of Analytical and Applied Pyrolysis 4 (1982) 227-240
9. Eglinton, T.I., Rowland, S.J., Curtis, C.D., Douglas, A.G., 1986. Kerogen-mineral reactions at raised temperatures in the presence of water. In: Leythaeuser, D., Rullkötter, J. (Eds.), Advances in Organic Geochemistry 1985. Organic Geochemistry 10, 1041-1052.
10. Eltantawy I.M., and Arnold P.W. Catalytic decomposition of organic molecules by clays. Nature 244 (1973) 139
11. Espitalié J., Senga Makadi K., and Trichet J. Role of the mineral matrix during kerogen pyrolysis. Organic Geochemistry 6 (1984) 365-382
12. Fort R.C., and Schleyer P.v.R. Adamantane: consequences of the diamondoid structure. Chemical Reviews 64 (1964) 277-300
13. Fripiat J.J., and Cruz-Cumplido M.I. Clays as catalysts for natural processes. Annual Review Earth Planetary Science 2 (1974) 239-256
14. Ganter, C., 1992. A new approach to adamantane rearrangements. In: Osawa, E., Yonemitsu, O. (Eds.), Carbocyclic Cage Compounds-Chemistry and Application. New York, pp. 293-318.
15. 2S. Geochemical Transformations of Sedimentary Sulfur. In: Vairavamurthy M.A., and Schoonen M.A.A. (Eds). ACS Symposium Series 612 (1995), American Chemical Society, Washington, DC 412-425
16. Goldstein T.P. Geocatalytic reactions in the formation and maturation of petroleum. American Association of Petroleum Geologists Bulletin 67 (1983) 152-159
17. Grasset L., and Amblés A. Structure of humin and humic acids from an acid soil as revealed by PTC-hydrolysis. Organic Geochemistry 29 (1998) 881-891
18. Gravil P.A., and Toulhoat H. Hydrogen, sulphur and chlorine coadsorption on Pd (1 1 1): a theoretical study of poisoning and promotion. Surface Science 430 (1999) 176-191
19. Guenin M., Breysse M., Frety R., Tifouti K., Marecot P., and Barbier J. Resistance of sulfur poisoning of metal catalysts. Dehydrogenation of cyclohexane on platinum/alumina catalysts. Journal of Catalysis 105 (1987) 144-154
20. Hart M.P., and Brown D.R. Surface acidities and catalytic activities of acid-activated clays. Journal of Molecular Catalysis A: Chemical 212 (2004) 315-321
21. Heller-Kallai L., Goldstein T.P., and Navrotsky A. Active components in clay condensates and extracts as potential geocatalysts. Clay and Clay Minerals 44 (1996) 393-397
22. Hoering T.C. Olefinic hydrocarbons from Bradford, Pennsylvania, crude oil. Chemical Geology 20 (1977) 1-8
23. Hoering T.C. Thermal reactions of kerogen with added water, heavy water and pure organic substrates. Organic Geochemistry 5 (1984) 267-278
24. Höld I.M., Brussee N.J., Schouten S., and Sinninghe Damsté J.S. Changes in the molecular structure of a Type II-S kerogen (Monterey Formation, U.S.A.) during sequential chemical degradation. Organic Geochemistry 29 (1998) 1403-1417
25. Horsfield B., and Douglas A.G. The influence of minerals on the pyrolysis of kerogens. Geochimica et Cosmochimica Acta 44 (1980) 1119-1131
26. Huizinga B.J., Tannenbaum E., and Kaplan I.R. The role of minerals in the thermal alteration of organic matter-III. Generation of bitumen in laboratory experiments. Organic Geochemistry 11 (1987) 591-604
27. 3 catalysts for aromatic hydrogenation. Journal of Catalysis 202 (2001) 220-228
28. Johns W.D. Clay mineral catalysis and petroleum generation. Annual Review Earth Planetary Science 7 (1979) 183-198
29. Johns W.D., and McKallip T.E. Burial diagenesis and specific catalytic activity of illite-smectite clays from Vienna Basin, Austria. American Association of Petroleum Geologists Bulletin 73 (1989) 472-482
30. Johns W.D., and Ulkus R. Clay mineral activators and hydrocarbon generation during experimental kerogen pyrolysis. Geologica Carpathica-Clays 1 (1993) 3-10
31. Kennedy M.J., Pevear D., and Hill R.J. Minerals surface control of organic carbon in black shales. Science 295 (2002) 657-660
32. Khaddor M., Ziyad M., Joffre J., and Amblés A. Pyrolysis and characterization of the kerogen from the Moroccan Youssoufia rock phosphate. Chemical Geology 186 (2002) 17-30
33. Kochubei D.I., Erenburg S.B., Komichev V.V., Volkov A.I., Plakhutin B.N., Ione K.G., Mazalov L.N., and Zamaraev K.I. X-ray-spectral and other physical methods for studying the mechanism of poisoning of Y zeolites by thiophene during the hydrogenation of n-hexene. Zhurnal Strukturnoi Khimii 23 (1982) 54-62 in Russian
34. Kumar P., Jasra R.V., and Bhat T.S.G. Evolution of porosity and surface acidity in montmorillonite clay on acid activation. Industrial and Engineering Chemical Research 34 (1995) 1440-1448
35. Landa S. Adamantane and its derivatives. Ropa a Uhlie 1 (1959) 5-7
36. Landa S., Kamycek Z., and Kamyckova J. Adamantane formation in crude oils. Ropa a Uhlie 3 (1961) 261-262
37. Landa S., and Machacek V. Adamantane, a new hydrocarbon extracted from petroleum. Collection Czechoslovkian Chemical Communication 5 (1933) 1-5
38. Lao Y., Korth J., Ellis J., and Crisp P.T. Heterogeneous reactions of 1-pristene catalyzed by clays under simulated geological conditions. Organic Geochemistry 14 (1989) 375-379
39. Larter S.R., and Horsfield B. Determination of structural components of kerogen by the use of analytical pyrolysis methods. In: Engel M.E., and Macko S.A. (Eds). Organic Geochemistry - Principles and Applications (1993), Plenum, New York 271-287
40. Lewan, M.D., 1994. Assessing natural oil expulsion from source rocks by laboratory pyrolysis. In: Magoon, L.B., Dow, W.G. (Eds.), The Petroleum System - from Source to Trap. American Association of Petroleum Geologists Memoir, vol. 60, pp. 201-210.
41. Lewan M.D. Experiments on the role of water in petroleum formation. Geochimica et Cosmochimica Acta 61 (1997) 3691-3723
42. Lewan M.D. Sulphur-radical control on petroleum formation rates. Nature 391 (1998) 164-166
43. Li S., Guo S., and Tan X. Characteristics and kinetics of catalytic degradation of immature kerogen in the presence of mineral and salt. Organic Geochemistry 29 (1998) 1431-1439
44. 2 alkylation catalysts. Catalysis Letters 35 (1995) 335-343
45. 4n + 12 diamondoid cage hydrocarbons with sodium borhydride/triflic acid. Journal of Organic Chemistry 54 (1989) 1450-1451
46. O'Loughlin E.J., Traina S.J., and Sims G.K. Effects of sorption on the biodegradation of 2-methylpyridine in aqueous suspensions of reference clay minerals. Environmental Toxicology and Chemistry 19 (2000) 2168-2174
47. Orr, W.L., 1986. Kerogen/asphaltene/sulfur relationships in sulfur-rich Monterey oils. In: Leythaeuser, D., Rullkötter, J. (Eds.), Advances in Organic Geochemistry 1985. Organic Geochemistry, vol. 10, pp. 499-516.
48. Petrov, A., Arefjev, D.A., Yakubson, Z.V., 1974. Hydrocarbons of adamantane series as indices of petroleum catagenesis process. In: Tissot, B., Bienner, F. (Eds.), Advances in Organic Geochemistry. Paris, pp. 517-522.
49. Putschew A., Schaeffer-Reiss C., Schaeffer P., Koopmans M.P., De Leeuw J.W., Lewan M.D., Sinninghe Damsté J.S., and Maxwell J.S. Release of sulfur- and oxygen-bound components from a sulfur-rich kerogen during simulated maturation by hydrous pyrolysis. Organic Geochemistry 29 (1998) 1875-1890
50. 1-3 alcohols in some alumina-pillared smectite clays. Applied Catalysis A: General 171 (1998) 85-97
51. Rhodes C.N., and Brown D.R. Catalytic activity of acid-treated montmorillonite in polar and non-polar reaction media. Catalysis Letters 24 (1994) 285-291
52. Rhodes C.N., and Brown D.R. Brønsted and Lewis acid catalysis with ion-exchanged clays. Catalysis Letters 45 (1997) 35-40
53. Rose H.R., Smith D.R., Hanna J.V., Palmissno J., and Wilson M.A. Comparison of the effect of minerals on aromatization reactions during kerogen pyrolysis. Fuel 71 (1992) 355-360
54. Rupert J.P., Granquist W.T., and Pinnavaia T.J. Catalytic properties of clay minerals. In: Newman A.C.D. (Ed). Chemistry of Clay and Clay Minerals (1987), John Wiley and Sons, New York 275-318
55. Schleyer P.v.R., Grubmuller P., Maier W.F., Vostrowsky O., Skattebol L., and Holm K.H. An adamantane rearrangement. A new pathway. Tetrahedron Letters 21 (1980) 921-924
56. Schneider A., Warren R.W., and Janoski E.J. Formation of perhydrophenalenes and polyalkyladamantanes by isomerization of tricyclic perhydroaromatics. Journal of Organic Chemistry 31 (1966) 1617-1625
57. Seewald J.S. Organic-inorganic interactions in petroleum-producing sedimentary basins. Nature 426 (2003) 327-333
58. Sieskind O., Jolly G., and Albrecht P. Simulation of the geochemical transformations of sterols: superacid effect of clay minerals. Geochimica et Cosmochimica Acta 43 (1979) 1675-1679
59. Siskin M., and Katritzky A.R. Reactivity of organic compounds in superheated water: general background. Chemical Reviews 101 (2001) 825-835
60. Solomon D.H., Swift J.D., and Murphy A.J. The acidity of clay minerals in polymerizations and related reactions. Journal of Macromolecular Science and Chemistry A5 (1971) 587-601
61. Sorensen T.S., and Whitworth S.M. The superacid route to 1-adamantyl cation. In: Olah G.A. (Ed). Cage Hydrocarbons (1990), Wiley, New York 65-102
62. Tamele M.W. Chemistry of the surface and the acidity of silica-alumina cracking catalyst. Discussions of the Faraday Society 8 (1950) 270-279
63. Tannenbaum E., Ruth E., and Kaplan I.R. Steranes and triterpanes generated from kerogen pyrolysis in the absence and presence of minerals. Geochimica et Cosmochimica Acta 50 (1986) 805-812
64. Taulbee D.N., and Seibert E.D. Comparison of the hydrocarbon pyrolysis products from a Devonian type II kerogen to those from kerogen/mineral blends. Energy & Fuels 1 (1987) 514-519
65. Tissot B.P., and Welte D.H. Petroleum Formation and Occurrence. second ed. (1984), Springer-Verlag, New York pp.160-198
66. 13C NMR spectroscopy. Energy and Fuels 19 (2005) 240-250
67. Wei Z., Moldowan J.M., and Paytan A. Diamondoids and molecular biomarkers generated from modern sediments in the absence and presence of minerals during hydrous pyrolysis. Organic Geochemistry 37 (2006) 891-911
68. Williams V.Z., Schleyer P.v.R., Gleicher G.J., and Rodewald L.B. Triamantane. Journal of American Chemical Society 88 (1966) 3862-3863