Novel aryl polycyclic aromatic hydrocarbons: Phenylphenanthrene and phenylanthracene identification, occurrence and distribution in sedimentary rocks

Organic Geochemistry - Tập 40 - Trang 986-1004 - 2009
Mariusz J. Rospondek1, Leszek Marynowski2, Anna Chachaj3, Maciej Góra3
1Institute of Geological Sciences, Jagiellonian University, ul. Oleandry 2a, 30-063 Kraków, Poland
2Faculty of Earth Sciences, Silesian University, 41-200 Sosnowiec, ul. Będzińska 60, Poland
3Faculty of Chemistry, Jagiellonian University, 30-063 Kraków, ul. Ingardena 3, Poland

Tài liệu tham khảo

Aceves, 1992, Gas chromatographic screening of organic compounds in urban aerosols: selectivity effects in semi-polar columns, Journal of Chromatography A, 607, 261, 10.1016/0021-9673(92)87084-L Armstroff, 2007, 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, 38, 1692, 10.1016/j.orggeochem.2007.06.002 Bachmann, 1936, Phenanthrene derivatives. V. The Beckmann rearrangement of the oximes of acetylphenanthrenes and benzoylphenanthrenes, Journal of the American Chemical Society, 58, 2097, 10.1021/ja01302a005 Bachmann, 1936, Phenanthrene derivatives. VI. The preparation of 1-, 2- and 3-phenanthryl halides, Journal of the American Chemical Society, 58, 2194, 10.1021/ja01302a030 Bechtel, 2001, Variable alteration of organic matter in relation to metal zoning at Rote Fäule front (Lubin-Sieroszowice mining district, SW Poland), Organic Geochemistry, 32, 377, 10.1016/S0146-6380(01)00002-X Beckwith, 1961, Free radical phenylation of phenanthrene, Journal of the Chemical Society, Chemical Communications, 73, 73 Blanco, 1991, Capillary gas chromatographic and combined gas chromatography–mass spectrometric study of the volatile fraction of a coal tar pitch using OV-1701 stationary phase, Journal of Chromatography, 539, 157, 10.1016/S0021-9673(01)95369-5 Borwitzky, 1979, Separation and identification of polynuclear aromatic compounds in coal tar by using gas capillary chromatography including combined gas chromatography–mass spectrometry, Journal of Chromatography, 170, 99, 10.1016/S0021-9673(00)84242-9 Budzinski, 1995, Alkylated phenanthrene distributions as maturity and origin indicators in crude oils and rock extracts, Geochimica et Cosmochimica Acta, 59, 2043, 10.1016/0016-7037(95)00125-5 Cadogan, 1977, Acylarylnitrosamines. Part 12. Decomposition of N-nitrosoacetanilide and p-nitro-N-nitrosoacetanilide in bromotrichloromethane. An answer to the long-standing problem of the mechanism of anomalous dual halogen abstractions, Journal of the Chemical Society, Perkin Transactions I, 183, 5 Clark, 1981, The addition of simple aromatic hydrocarbons to condensed aromatic thiophenes promoted by aluminium chloride. Part II. Naphtho[1,2-b]thiophene, Canadian Journal of Chemistry, 59, 1297, 10.1139/v81-190 Clifford, 1998, 2,3,6-/3,4,5-Trimethyl substituted diaryl carotenoid derivatives (Chlorobiaceae) in petroleums of the Belarussian Pripyat River Basin, Organic Geochemistry, 29, 1253, 10.1016/S0146-6380(98)00086-2 Dartiguelongue, 2006, Thermal stability of dibenzothiophene in closed system pyrolysis: experimental study and kinetic modelling, Organic Geochemistry, 37, 98, 10.1016/j.orggeochem.2005.08.019 de Las Heras, 1991, Novel C-ring cleaved triterpenoid-derived aromatic hydrocarbons in Tertiary brown coals, Geochimica et Cosmochimica Acta, 55, 3379, 10.1016/0016-7037(91)90495-Q Dickerman, 1973, Homolytic aromatic substitution. VIII. Phenylation of polycyclic aromatic hydrocarbons, Journal of the American Chemical Society, 95, 4624, 10.1021/ja00795a027 Dieckmann, 2006, Deep basin gas: new insights from kinetic modelling and isotopic fractionation in deep-formed gas precursors, Marine and Petroleum Geology, 23, 183, 10.1016/j.marpetgeo.2005.08.002 Fabbri, 2008, Levoglucosan and other cellulose markers in pyrolysates of Miocene lignites – geochemical and environmental implications, Environmental Science & Technology, 42, 2957, 10.1021/es7021472 Fabiańska, 2007 Grimalt, 1988, Molecular composition of ambers, 677 Grimmer, 1985, Determination of polycyclic aromatic hydrocarbons, azaarenes, and thiaarenes emitted from coal-fired residential furnaces by gas chromatography/mass spectrometry, Fresenius’ Journal of Analytical Chemistry, 322, 595, 10.1007/BF00464595 Hausmann, 1997, Scavenging of hydrocarbon radicals from flames with dimethyldisulfide. II. Hydrocarbon radicals in fuel-rich low-pressure flames of acetylene, ethylene, 1,3-butadiene and methane with oxygen, Berichte der Bunsen-Gesellschaft, 101, 651, 10.1002/bbpc.19971010403 Haworth, 1932, Syntheses of alkylphenanthrenes. Part I. 1-, 2-, 3-, and 4-methylphenanthrenes, Journal of the Chemical Society, 112, 5 Hayward, 1971, Photocyclization reactions of aryl polyenes – II. The photocyclization of 1-aryl-4-phenyl-1, 3-butadienes, Tetrahedron, 27, 2085, 10.1016/S0040-4020(01)91606-0 Heynderickx, 2002, A one-pot synthesis of hindered 2,3-diarylbenzo[b]thiophenes via the Suzuki reaction, Synthesis, 2, 213, 10.1055/s-2002-19808 Jiang, 1998, Polycyclic aromatic hydrocarbons in ancient sediments and their relationship to palaeoclimate, Organic Geochemistry, 29, 1721, 10.1016/S0146-6380(98)00083-7 Kagi, R.I., Alexander, R., Toh, E., 1990. Kinetics and mechanism of cyclization reaction of ortho-methylbiphenyls. In: Durand, B., Behar, F. (Eds.), Advances in Organic Geochemistry 1989 (Organic Geochemistry 16), pp. 161–166. Kanno, 2005, Chromium-mediated synthesis of polycyclic aromatic compounds from halobiaryls, Organic Letters, 7, 5453, 10.1021/ol052214x Kawka, 1990, Polycyclic aromatic hydrocarbons in hydrothermal petroleums from the Guaymas Basin spreading centre, vol. 5, 17 Killops, 1992, Polycyclic aromatic hydrocarbons of pyrolytic origin in ancient sediments: evidence for Jurassic vegetation fires, Organic Geochemistry, 18, 1, 10.1016/0146-6380(92)90137-M Kissin, 1998, Catagenesis of light aromatic compounds in petroleum, Organic Geochemistry, 29, 947, 10.1016/S0146-6380(98)00144-2 Köster, 1998, Biomarker geochemistry of a foreland basin: the Oligocene Menilite Formation in the Flysch Carpathians of southeast Poland, Organic Geochemistry, 29, 649, 10.1016/S0146-6380(98)00182-X Kotarba, 2006, Organic geochemistry, depositional history and hydrocarbon generation modelling of the Upper Permian Kupferschiefer and Zechstein Limestone strata in south-west Poland, Marine and Petroleum Geology, 23, 371, 10.1016/j.marpetgeo.2005.10.003 Kováts, 1958, Gas chromatographische charakteriserung organischer verbindungen. I. Retentions indices aliphatischer halogenide, alkohole, aldehyde und ketone, Helvetica Chimica Acta, 61, 1915, 10.1002/hlca.19580410703 Kruge, 1994, Fossil charcoal in Cretaceous – Tertiary boundary strata: evidence for catastrophic firestorm and megawave, Geochimica et Cosmochimica Acta, 58, 1393, 10.1016/0016-7037(94)90394-8 Lauer, 1988, Improved characterization of coal tar distillation cuts (200–500°C). 1. Preparative separation into hydrocarbons and polar aromatics and characterization of polycyclic aromatic hydrocarbons by capillary GC–MS of anthracene oil, Fuel, 67, 1273, 10.1016/0016-2361(88)90051-8 Lee, 1979, Retention indices for programmed-temperature capillary-column gas chromatography of polycyclic aromatic hydrocarbons, Analytical Chemistry, 51, 768, 10.1021/ac50042a043 Lewandowska, 1991, Minerals of the zone of altered Devonian dolomites from Dubie near Kraków (Southern Poland), Mineralogia Polonica, 22, 29 Lewandowska, 2000, Contact metamorphism induced by late Palaeozoic igneous activity in the Dębnik anticline, Polskie Towarzystwo Mineralogiczne – Prace Specjalne, 17, 41 Lewandowska, 2005, Organic matter in the contact metamorphism processes of the Devonian dolomites from Dębnik Anticline, southern Poland, 142 Marynowski, 2007, Water column euxinia and wildfire evidence during deposition of the Upper Famennian Hangenberg event horizon from the Holy Cross Mountains (central Poland), Geological Magazine, 144, 569, 10.1017/S0016756807003317 Marynowski, 2000, Biomarkers as environmental indicators in a carbonate complex, examples from the Middle Devonian, Holy Cross Mountains, Poland, Sedimentary Geology, 137, 187, 10.1016/S0037-0738(00)00157-3 Marynowski, 2001, Phenylnaphthalenes and polyphenyls in Palaeozoic source rocks of the Holy Cross Mountains, Poland, Organic Geochemistry, 32, 69, 10.1016/S0146-6380(00)00150-9 Marynowski, 2002, Phenyldibenzofurans and phenyldibenzothiophenes in marine sedimentary rocks and hydrothermal petroleum, Organic Geochemistry, 33, 701, 10.1016/S0146-6380(02)00040-2 Marynowski, 2004, Composition and source of polyaromatic compounds in deposited dust from selected sites of the Upper Silesia, Poland, Geological Quarterly, 48, 169 Marynowski, 2007, Biomolecules preserved in 168 million year old fossil conifer wood, Naturwissenschaften, 94, 228, 10.1007/s00114-006-0179-x Marynowski, 2007, Compositions, sources and depositional environments of organic matter from the Middle Jurassic clays of Poland, Applied Geochemistry, 22, 2456, 10.1016/j.apgeochem.2007.06.015 McCollom, 2001, Reactivity of monocyclic aromatic compounds under hydrothermal conditions, Geochimica et Cosmochimica Acta, 65, 455, 10.1016/S0016-7037(00)00533-0 Meyer zu Reckendorf, 1997, Identification of phenyl-substituted polycyclic aromatic compounds in ring furnace gases using GC–MS and GC–AED, Chromatographia, 45, 173, 10.1007/BF02505557 Meyer zu Reckendorf, 2000, Phenyl-substituted polycyclic aromatic compounds as intermediate products during pyrolytic reactions involving coal tars, pitches and related materials, Chromatographia, 52, 67, 10.1007/BF02490795 Nawrocki, 2007, Isotope and paleomagnetic ages of the Zalas rhyodacites (S Poland), Przegląd Geologiczny, 55, 475 Newman, 1944, New syntheses of picene, The Journal of Organic Chemistry, 9, 518, 10.1021/jo01188a005 Nodiff, 1975, Antimalarial phenanthrene amino alcohols. 3. Halogen-containing 9-phenanthrenemethanols, Journal of Medicinal Chemistry, 18, 1011, 10.1021/jm00244a012 Oldenburg, 2002, Xanthones–novel aromatic oxygen-containing compounds in crude oils, Organic Geochemistry, 33, 595, 10.1016/S0146-6380(02)00015-3 Oszczepalski, 1989, Kupferschiefer in Southwestern Poland: sedimentary environments, metal zoning, and ore controls, 571 Otto, 1999, Chemosystematics and diagenesis of terpenoids in fossil conifer species and sediment from the Eocene Zeitz Formation, Saxony, Germany, Geochimica et Cosmochimica Acta, 65, 3505, 10.1016/S0016-7037(01)00693-7 Püttmann, 1990, The Permian Kupferschiefer of southwest Poland: a geochemical trap for migrating, metal-bearing solutions, Applied Geochemistry, 5, 227, 10.1016/0883-2927(90)90050-F Püttmann, 1987, Occurrence and geochemical significance of 1, 2, 5, 6-tetramethylnaphthalene, Geochimica et Cosmochimica Acta, 51, 3023, 10.1016/0016-7037(87)90375-9 Püttmann, 1989, The secondary oxidation of organic material and its influence on Kupferschiefer mineralization of southwest Poland, Applied Geochemistry, 4, 151, 10.1016/0883-2927(89)90046-2 Püttmann, W., Heppenheimer, H., Diedel, R., 1990. Accumulation of copper in the Permian Kupferschiefer: a result of post-depositional redox reactions. In: Durand, B., Behar, F. (Eds.), Advances in Organic Geochemistry 1989 (Organic Geochemistry 16), pp. 1145–1156. Radke, 1983, The Methylphenanthrene Index (MPI): a maturity parameter based on aromatic hydrocarbons, 504 Radke, 1991, Occurrence and thermal evolution of methylated benzo- and dibenzothiophenes in petroleum source rocks of western Germany, 480 Radke, 1994, Extractable alkyldibenzothiophenes in Posidonia Shale (Toarcian) source rocks: relationship of yields to petroleum formation and expulsion, Geochimica et Cosmochimica Acta, 58, 5223, 10.1016/0016-7037(94)90307-7 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), pp. 51–63. Radke, 2000, Alkyldibenzofurans in terrestrial rocks: influence of organic facies and maturation, Geochimica et Cosmochimica Acta, 64, 275, 10.1016/S0016-7037(99)00287-2 Rao, 1991, Cycloaromatization of α-oxoketene dithioacetals and β-oxodithiacetals with benzyl-, 1-(naphthylmethyl) and 2-(naphthylmethyl)magnesium halides: synthesis of condensed polynuclear aromatic hydrocarbons, Tetrahedron, 47, 3499, 10.1016/S0040-4020(01)86411-5 Ré-Poppi, 2005, Polycyclic aromatic hydrocarbons and other selected organic compounds in ambient air of Campo Grande City, Brazil, Atmospheric Environment, 39, 2839, 10.1016/j.atmosenv.2004.10.006 Ricking, 2003, Molecular markers of anthropogenic activity in sediments of the Havel and Spree Rivers (Germany), Water Research, 37, 2607, 10.1016/S0043-1354(03)00078-2 Rospondek, M.J., 1998. Organiczne związki siarki, pochodne tiofenu, w cechsztyńskim łupku miedzionośnym z monokliny przedsudeckiej (Organic Sulfur Compounds, Thiophene Derivatives, in Zechstein Copper-bearing Shales (Kupferschiefer) from the Fore Sudetic Monocline). PhD thesis, Jagiellonian University, Kraków (in Polish). Rospondek, 2004, Phenyl-polyaromatic compounds and terphenyls in the Polish Carpathian sedimentary rocks, Polskie Towarzystwo Mineralogiczne, Prace Specjalne, 24, 341 Rospondek, 1993, The origin of organic matter in Lower Silesian copper-bearing shales, Rocznik Polskiego Towarzystwa Geologicznego, 63, 85 Rospondek, 1994, The role of organically bound sulfur in stratiform ore sulphide deposits, Organic Geochemistry, 21, 1181, 10.1016/0146-6380(94)90162-7 Rospondek, 1997, Novel C26 highly branched isoprenoid thiophenes and alkane from the Menilite Formation, Outer Carpathians, SE Poland, Organic Geochemistry, 26, 295, 10.1016/S0146-6380(97)00021-1 Rospondek, 1998, Origin of reduced sulfur in sediment-hosted stratiform sulphide deposits, Fore-Sudetic Monocline, Poland, 399 Rospondek, 2007, Novel arylated polyaromatic thiophenes: phenylnaphtho[b]thiophenes and naphthylbenzo[b]thiophenes as markers of organic matter diagenesis buffered by oxidising solutions, Organic Geochemistry, 38, 1729, 10.1016/j.orggeochem.2007.05.008 Rospondek, 2008, Comparison of phenyldibenzothiophene distributions predicted by molecular modelling with relevant experimental and geological data, Organic Geochemistry, 39, 1, 10.1016/j.orggeochem.2008.06.012 Rospondek, M.J., Lewandowska, A., Marynowski, L., 2009. Fate of organic matter during contact metamorphism induced by Permian magmatic activity in the Dębnik Anticline, southern Poland. In: Lewandowska, A., Rospondek, M.J. (Eds.), Mineralogia – Special Paper 34, pp. 22–23. Sawłowicz, 1993, Organic matter and its significance for the genesis of the copper-bearing shales (Kupferschiefer) from the Fore-Sudetic Monocline (Poland), 431 Sawłowicz, 2000, Organic matter from Zechstein copper deposits (Kupferschiefer) in Poland, 220 Schenk, 1998, Using natural maturation series to evaluate the utility of parallel reaction kinetics models: an investigation of Toarcian shales and carboniferous coals, Germany, Organic Geochemistry, 29, 137, 10.1016/S0146-6380(98)00139-9 Simoneit, 1993, Hydrothermal activity and its effects on sedimentary organic matter, 81 Simoneit, 2002, Biomass burning – a review of organic tracers for smoke from incomplete combustion, Applied Geochemistry, 17, 129, 10.1016/S0883-2927(01)00061-0 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), pp. 877–889. Smith, 1995, The geosynthesis of alkylaromatics, Organic Geochemistry, 23, 71, 10.1016/0146-6380(94)00101-6 Spagnolo, 1972, The reactivity of Thieno[3,2-b]thiophene and thieno[2,3-b]thiophene with phenyl radicals, Journal of the Chemical Society, Perkin Transactions I, 9, 3 Stock, 1997, Oxidation and decarboxylation. A reaction sequence for the study of aromatic structural elements in Pocahontas No. 3 Coal, Energy and Fuels, 11, 987, 10.1021/ef960229t Strachan, 1988, Trimethylnaphthalenes in crude oils and sediments: effects of source and maturity, Geochimica et Cosmochimica Acta, 52, 1255, 10.1016/0016-7037(88)90279-7 Sun, 1998, Influences of secondary oxidation and sulfide formation on several maturity parameters in Kupferschiefer, Organic Geochemistry, 29, 1419, 10.1016/S0146-6380(98)00128-4 Sun, 1995, Differences in the depositional environment of basal Zechstein in southwest Poland: implications for base metal mineralization, Organic Geochemistry, 23, 819, 10.1016/0146-6380(95)80003-A Środoń, 2006, Diagenetic history of the Podhale-Orava Basin and the underlying Tatra sedimentary structural units (Western Carpathians): evidence from XRD and K–Ar of illite–smectite, Clay Minerals, 41, 751, 10.1180/0009855064130217 Tegelaar, 1989, A reappraisal of kerogen formation, Geochimica et Cosmochimica Acta, 53, 3103, 10.1016/0016-7037(89)90191-9 Tinnemans, 1976, Photocyclisations of 1, 4-diarylbut-1-en-3-ynes. Part III. Scope and limitations of the reaction, Journal of the Chemical Society, Perkin Transactions, 2, 1115, 10.1039/p29760001115 Tong, 1984, Quantification of polycyclic aromatic hydrocarbons in diesel exhaust particulate matter by high-performance liquid chromatography fraction and high-resolution gas chromatography, Analytical Chemistry, 56, 2129, 10.1021/ac00276a034 van Aarssen, 1999, Distributions of methylated naphthalenes in crude oils: indicators of maturity, biodegradation and mixing, Organic Geochemistry, 30, 1213, 10.1016/S0146-6380(99)00097-2 van den Dool, 1963, A generalization of retention index system including linear temperature programmed gas–liquid partition chromatography, Journal of Chromatography A, 11, 463, 10.1016/S0021-9673(01)80947-X Vassilaros, 1982, Linear retention index system for polycyclic aromatic compounds. Critical evaluation and additional indices, Journal of Chromatography, 252, 1, 10.1016/S0021-9673(01)88394-1 Venkatesan, 1989, Organic geochemical evidence for global fires at the Cretaceous/Tertiary boundary, Nature, 338, 57, 10.1038/338057a0 Wang, 2007, Identification, characterization and quantitation of pyrogenic polycyclic aromatic hydrocarbons and other organic compounds in tire fire products, Journal of Chromatography A, 1139, 14, 10.1016/j.chroma.2006.10.085 Wei, 2006, The catalytic effects of minerals on the formation of diamondoids from kerogen macromolecules, Organic Geochemistry, 37, 1421, 10.1016/j.orggeochem.2006.07.006 Wilkes, 1998, Aromatic aldehydes and ketones in the Posidonia Shale, Germany, Organic Geochemistry, 29, 107, 10.1016/S0146-6380(98)00138-7 Yunker, 1999, Natural and anthropogenic inputs of hydrocarbons to the Strait of Georgia, The Science of the Total Environment, 225, 181, 10.1016/S0048-9697(98)00362-3 Yunker, 2002, PAHs in the Fraser River basin: a critical appraisal of PAH ratios as indicators of PAH source and composition, Organic Geochemistry, 33, 489, 10.1016/S0146-6380(02)00002-5