Identification of alkenylbenzenes in pyrolyzates using GC-MS and GC-FTIR techniques: Evidence for kerogen aromatic moieties with various binding sites

Organic Geochemistry

Volumn 30, Issue 7, 1999, Pages 651-665

  Ellis, Leroy ^a,b   Fisher, Steven J ^a   Singh, Raj K ^a   Alexander, Robert ^a   Kagi, Robert I ^a  

^a CURTIN UNIVERSITY   (Australia)

^b Baseline Resolution Inc   (United States)

Author keywords

Alkenylbenzcne; Alkylbenzene; GC FTIR; Kerogen aromatic moleties; Pyrolysis GC FTIR; Pyrolysis GC MS

Indexed keywords

ALKENYLBENZENES; ALKYLBENZENE; ELECTRON IMPACT MASS SPECTRA; KEROGEN AROMATIC MOIETIES; PYROLYZATES;

ELECTRONS; FATTY ACIDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GAS CHROMATOGRAPHY; HYDROGEN BONDS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PYROLYSIS; SHALE;

AROMATIC HYDROCARBONS;

ALIPHATIC HYDROCARBON; HYDROCARBON; KEROGEN; PYROLYSIS; SHALE;

EID: 0032791896     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(99)00013-3     Document Type: Article

References (46)

1. 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. 59:1995;4259-4266.
2. Allan J., Bjorøy M., Douglas A.G. A geochemical study of the exinite group maceral alginite, selected from three Permo-Carboniferous Torbanites. Douglas A.G., Maxwell J.R. Advances in Organic Geochemistry 1979. 1980;599-618 Pergamon Press, Oxford.
3. Baset Z.H., Pancirov R.J., Ashe T.R. Organic compounds in coal: structure and origin. Douglas A.G., J.R. Maxwell. Advances in Organic Geochemistry 1979. 1980;619-630 Pergamon Press, Oxford.
4. Britt P.F., Buchanan A.C. Thermolysis of surface-attached 1,4-diphenylbutane: the role of hydrogen-transfer reactions on the surface in determining the product distribution. Journal of Organic Chemistry. 56:1991;6132-6140.
5. Clifford D.J., Hatcher P.G. Structural transformations of polylabdanoid resinites during maturation. Organic Geochemistry. 23:1995;407-418.
6. Connan J., Bouroullec J., Dessort D., Albrecht P. The microbial input in carbonate-anhydrite facies of a sabkha palaeoenvironment from Guatemala: a molecular approach. Organic Geochemistry. 10:1986;29-50.
7. Corey E.J., Schmidt G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media. Tetrahedron Letters. 20:1979;399-402.
8. DeLong E.F., Yayanos A.A. Biochemical function and ecological significance of novel bacterial lipids in deep-sea prokaryotes. Applied Environmental Microbiology. 51:1986;730-737.
9. Derenne, S., Largeau, C., Casadevall, E., Sinninghe Damsté, J.S., Tegelaar, E.W., de Leeuw, J.W., 1990. Characterization of Estonian Kukersite by spectroscopy and pyrolysis: evidence for abundant alkyl phenolic moieties in an Ordovician, marine, type II/I kerogen. In: Durand, B., Behar, F. (Eds.), Advances in Organic Geochemistry 1989. Pergamon Press, Oxford. Organic Geochemistry 16, 873-888.
10. Derenne, S., Largeau, C., Casadevall, E., Sinninghe Damsté, J.S., Tegelaar, E.W., de Leeuw, J.W., 1990. Characterization of Estonian Kukersite by spectroscopy and pyrolysis: evidence for abundant alkyl phenolic moieties in an Ordovician, marine, type II/I kerogen. In: Durand, B., Behar, F. (Eds.), Advances in Organic Geochemistry 1989. Pergamon Press, Oxford. Organic Geochemistry 16, 873-888.
11. Douglas A.G., Sinninghe Damsté J.S., Fowler M.G., Eglinton T.I., de Leeuw J.W. Unique distributions of hydrocarbons and sulphur compounds released by flash pyrolysis from the fossilized alga Gloeocapsomorpha prisca, a major constituent in one of four Ordovician kerogens. Geochimica et Cosmochimica Acta. 55:1991;275-291.
12. Dowling N.J.E., Widdel F., White D.C. Phospholipid ester-linked fatty acid biomarkers of acetate-oxidizing sulphate-reducers and other sulphide-forming bacteria. Journal of General Microbiology. 132:1986;1815-1825.
13. Dubreuil C., Derenne S., Largeau C., Berkaloff C., Rousseau B. Mechanism of formation and chemical structure of Coorongite-I. Role of the resistant biopolymer and of the hydrocarbons of Botryococcus braunii. Ultrastructure of Coorongite and its relationship with Torbanite. Organic Geochemistry. 14:1989;543-553.
14. Ellis L., Kagi R.I., Alexander R. Separation of petroleum hydrocarbons using dealuminated mordenite molecular sieve. I. Monoaromatic hydrocarbons. Organic Geochemistry. 18:1992;587-593.
15. Ellis L., Singh R.K., Alexander R., Kagi R.I. Geosynthesis of organic compounds. III. Formation of alkyltoluenes and alkylxylenes in sediments. Geochimica et Cosmochimica Acta. 24:1995;5133-5140.
16. Ellis L., Singh R.K., Alexander R., Kagi R.I. Formation of long-chain alkylnaphthalenes in sediments via alkylstyrene precursors. Grimalt J.O., Dorronsoro C. Organic geochemistry, Poster Sessions from the 17th International Meeting on Organic Geochemistry, Donostia-San Sebastian 1995. 1995;483-487 Graphycems.
17. Fisher S.J., Alexander R., Ellis L., Kagi R.I. The analysis of dimethylphenanthrenes by direct deposition gas chromatography-fourier transform infrared spectroscopy (GC-FTIR). Polycyclic Aromatic Compounds. 9:1996;257-264.
18. Frolov E.B., Smirnov M.B. Unsaturated hydrocarbons in crude oils. Organic Geochemistry. 21:1994;189-208.
19. Furniss B.S., Hannaford A.J., Smith P.W.G., Tatchell A.R. Vogel's Textbook of Practical Organic Chemistry. 5th ed. 1989;538 Longman Group UK Limited, UK.
20. Gelin F., de Leeuw J.W., Sinninghe Damsté J.S., Derenne S., Largeau C., Metzger P. The similarity of chemical structures of soluble aliphatic polyaldehyde and insoluble algaenan in the green microalga Botryococcus braunii race A as revealed by analytical pyrolysis. Organic Geochemistry. 21:1994;423-435.
21. Gerrard A.F., Djerassi C. Mass spectrometry in structural and stereochemical problems. CLXXIX. The electron impact induced rearrangements of 1-phenylheptenes. Further evidence for double bond lability. Journal of the American Chemical Society. 91:1969;6808-6814.
22. Gontcharov I. Long-chain alkylnaphthalenes in crude oils and rock extracts. Øygard K. Organic Geochemistry, Poster Sessions from the 16th International Meeting on Organic Geochemistry, Stavanger 1993. 1993;375-377 Falch Hurtigtrykk.
23. Goossens, H., Irene, W., Rijpstra, C., Düren, R.R., de Leeuw, J.W., Schenck, P.A., 1986. Bacterial contribution to sedimentary organic matter; a comparative study of lipid moieties in bacteria and recent sediments. In: Leythaeuser, D., Rullkotter, J. (Eds.), Advances in Organic Geochemistry 1985. Pergamon Press, Oxford. Organic Geochemistry 10, 683-696.
24. Goossens, H., Irene, W., Rijpstra, C., Düren, R.R., de Leeuw, J.W., Schenck, P.A., 1986. Bacterial contribution to sedimentary organic matter; a comparative study of lipid moieties in bacteria and recent sediments. In: Leythaeuser, D., Rullkotter, J. (Eds.), Advances in Organic Geochemistry 1985. Pergamon Press, Oxford. Organic Geochemistry 10, 683-696.
25. Guadalupe M.F.M., Castello Branco V.A., Schmid J.C. Isolation of sulfides in oils. Organic Geochemistry. 17:1991;355-361.
26. Hoffmann C.F., Foster C.B., Powell T.G., Summons R.E. Hydrocarbon biomarkers from Ordovician sediments and the fossil alga Gloeocapsomorpha prisca Zalessky 1917. Geochimica et Cosmochimica Acta. 51:1987;2681-2697.
27. Kawamura K., Ishiwatari R. Tightly bound aliphatic acids in Lake Biwa sediments: their origin and stability. Organic Geochemistry. 7:1984;121-126.
28. Kohnen M.E.L., Sinninghe Damsté J.S., Kock-Van Dalen A.C., de Leeuw J.W. Di- or polysulfide-bound biomarkers in sulfur-rich geomacromolecules as revealed by selective chemolysis. Geochimica et Cosmochimica Acta. 55:1991;1375-1394.
29. Largeau, C., Derenne, S., Casadevall, E., Kadouri, A., Sellier, N., 1986. Pyrolysis of immature Torbanite and of the resistant biopolymer (PRB A) isolated from extant alga Botryococcus braunii. Mechanism of formation and structure of Torbanite. In: Leythaeuser, D., Rullkötter, J. (Eds.), Advances in Organic Geochemistry 1985. Pergamon Press, Oxford. Organic Geochemistry 10, 1023-1032.
30. Largeau, C., Derenne, S., Casadevall, E., Kadouri, A., Sellier, N., 1986. Pyrolysis of immature Torbanite and of the resistant biopolymer (PRB A) isolated from extant alga Botryococcus braunii. Mechanism of formation and structure of Torbanite. In: Leythaeuser, D., Rullkötter, J. (Eds.), Advances in Organic Geochemistry 1985. Pergamon Press, Oxford. Organic Geochemistry 10, 1023-1032.
31. Larter S.R., Douglas A.G. Low molecular weight aromatic hydrocarbons in coal maceral pyrolysates as indicators of diagenesis and organic matter type. Krumbein W. Environmental Biogeochemistry and Geomicrobiology. vol. 1:1978;373-386 Ann Arbor Science Publishers, MI.
32. Larter S.R., Horsfield B. Determination of structural components of kerogens by the use of analytical pyrolysis methods. Engel M.H., Macko S.A. Organic Geochemistry: Principles and Applications. 1993;271-284 Plenum Press, New York.
33. March J. Advanced Organic Chemistry: Reactions, Mechanisms and Structure. 3rd ed :1985;348 John Wiley & Sons, New York.
34. Mendoza Y.A., Gülacar F.O., Hu Z.-L., Buchs A. Unsubstituted and hydroxy substituted fatty acids in a recent lacustrine sediment. International Journal of Environmental Analytical Chemistry. 31:1987;107-127.
35. Nakanishi K., Solomon P. Infrared Absorption Spectroscopy. 1977;14-18 Holden-Day, Oakland.
36. 30 n-alkylbenzenes in crude oils. Petroleum Chemistry USSR. 23:1983;1-12.
37. Petrov A.A. Petroleum Hydrocarbons. 1984;178-182 Springer-Verlag, Berlin.
38. Poutsma M.L., Dyer C.W. Thermolysis of model compounds for coal. 3. Radical chain decomposition of 1,3-diphenylpropane and 1,4-diphenylbutane. Journal of Organic Chemistry. 47:1982;4903-4914.
39. Rubinstein I., Strausz O.P. Geochemistry of the thiourea adduct fraction from an Alberta petroleum. Geochimica et Cosmochimica Acta. 43:1979;1387-1392.
40. Savage P.E., Klein M.T. Asphaltene reaction pathways. 2. Pyrolysis of n-pentadecylbenzene. Industrial Engineering and Chemical Research. 26:1987;488-494.
41. Shaw N. Lipid composition as a guide to the classification of bacteria. Advances in Applied Microbiology. 17:1974;63-108.
42. Sinninghe Damsté J.S., de Leeuw J.W. Analysis, structure and geochemical significance of organically-bound sulphur in the geosphere: state of the art and future research. Organic Geochemistry. 16:1990;1077-1101.
43. Sinninghe Damsté J.S., Kock-van Dalen A.C., Albrecht P.A., de Leeuw J.W. Identification of long-chain 1,2-di-n-alkylbenzenes in Amposta crude oil from the Tarragona Basin, Spanish Mediterranean: implications for the origin and fate of n-alkylbenzenes. Geochimica et Cosmochimica Acta. 55:1991;3677-3683.
44. Solli H., Larter S.R., Douglas A.G. Analysis of kerogens by pyrolysis-gas chromatography mass spectrometry using selective ion detection. Part III. Long chain alkylbenzenes. Douglas A.G., Maxwell J.R. Advances in Organic Geochemistry 1979. 1980;591-597 Pergamon Press, Oxford.
45. Sun M.-Y., Wakeham S.G., Lee C. Rates and mechanisms of fatty acid degradation in oxic and anoxic coastal marine sediments of Long Island Sound, NY, USA. Geochimica et Cosmochimica Acta. 61:1997;341-355.
46. Williams J.A., Dolcater D.L., Torkelson B.E., Winters J.C. Anomalous concentrations of specific alkylaromatic and alkylcycloparaffin components in West Texas and Michigan crude oils. Mattavelli L., Novelli L. Advances in Organic Geochemistry 1987. 1988;47-59 Pergamon Press, Oxford.