Geosynthesis of organic compounds: II. Methylation of phenanthrene and alkylphenanthrenes

Bastow, Trevor P.; Fisher, Shannon J.; Kagi, Robert I.

doi:10.1016/0016-7037(95)00285-8

Cited by 99 publications

(24 citation statements)

References 18 publications

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“…8c). Compared to Alexander et al (1995), the spectra of these compounds have the same molecular ion and mass fragments, but are different by the fragment intensities.…”

Section: Tricyclic Diterpenoidmentioning

confidence: 99%

Determination of the molecular signature of fossil conifers by experimental palaeochemotaxonomy – Part 1: The Araucariaceae family

Hautevelle

Michels

2013

Biogeosciences

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Twelve species of the conifer family Araucariaceae, including Araucaria (6 species), Agathis (3 species) and Wollemia (1 species) genera, were submitted to artificial maturation by confined pyrolysis. The aim of these experiments is to transform the biomolecules synthesized by these species into their homologous geomolecules in laboratory conditions. Determination of the diagenetic molecular signatures of Araucariaceae through experimentation on extant representatives allows us to complete our knowledge in botanical palaeochemotaxonomy. Such knowledge is relevant to palaeoenvironmental, environmental and archaeology purposes. All artificially diagenetic species of Araucariaceae are firstly characterized by a predominance of saturated tetracyclic diterpenoids including ent-beyerane, phyllocladanes and ent-kauranes. Moreover, Araucaria genus shows a high relative abundance of bicyclic sesquiterpenoids, particularly the cadalane-type compounds accompanied by those of eudesmane and bisabolane types as well as chamazulene and pentamethyl-dihydroindenes. Diterpenoids are of labdane, isopimarane and abietane types (essentially derived from abietanoic acids) as well as isohexyl alkylaromatic hydrocarbons. Compared to the tetracyclic diterpenoids, these compounds show a relatively lower abundance, reaching trace levels in the case of saturated abietanes. Distributions of sesquiterpenoids and diterpenoids of Agathis show some similarities to that of Araucaria, with the exception of one species, in which the tetracyclic compounds are absent and the abietane type (essentially derived from abietanoic acids) predominant. High similarities between the Wollemia and Araucaria genera are observed. Both are characterized by some high relative abundance of tetracyclic compounds with no predominance of other specific diterpenoids

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“…8c). Compared to Alexander et al (1995), the spectra of these compounds have the same molecular ion and mass fragments, but are different by the fragment intensities.…”

Section: Tricyclic Diterpenoidmentioning

confidence: 99%

Determination of the molecular signature of fossil conifers by experimental palaeochemotaxonomy – Part 1: The Araucariaceae family

Hautevelle

Michels

2013

Biogeosciences

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“…As the chemical structures of alkylcarbazoles are similar to those of the alkyl dibenzothiophenes, Clegg et al (1998b) suggested that alkylcarbazoles may be formed through alkylation of the parent compound and interconversion of isomers in similar ways to those proposed for dibenzothiophenes (Radke et al, 1982), phenanthrenes (Alexander et al, 1995) and phenols (Ioppolo-Armanios et al, 1994). This suggestion may be quite plausible if potential source rocks across a wide range of thermal maturity are concerned, e.g.…”

Section: Dmc/18dmc+1ecmentioning

confidence: 91%

Occurrence and Geochemical Significance of Carbazoles and Xanthones in Crude Oil from the Western Desert, Egypt

Bakr¹

2009

ear

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Abstract. This paper describes an approach that involves the evaluation of the occurrence and distributions of nitrogen-and oxygen-containing aromatic compounds in Egyptian crude oils and source rocks. Carbazoles and xanthones represent nitrogen-and oxygen-containing aromatic compounds, respectively.Alkylcarbazoles and benzocarbazoles were quantitatively studied in crude oils taken from the Abu Gharadig and Shushan basins in north Western Desert of Egypt in order to investigate their occurrence, concentrations and distributions. The abundances of carbazole, methylcarbazoles and dimethylcarbazoles in the marine Abu Gharadig oils are much higher than that of the terrestrial Shushan oils. The results presented here indicate that thermal maturation can be ruled out as a major factor in controlling the changes in the carbazole ratios in the crude oils. Most likely, source characteristics of the studied samples play a significant role in controlling the distribution of carbazole compounds in reservoired oils. The alkylcarbazoles 1MC/1MC+1EC, 3MC/4MC and 18DMC/18DMC+1EC when correlated with specific biomarker signatures provide background information discriminating between two main types of depositional setting: 1) Terrestrial dominated source deposited in oxidizing conditions for the Shushan oils and, 2) marine shale dominated sourced oils deposited in suboxic environments for the Abu Gharadig samples. Similarly, benzocarbazole distributions were found to be independent of maturity, but influenced by organic facies and depositional environments. Therefore, in this study, alkylcarbazole and benzocarbazoles compounds are well suited for the differentiation of Abu Gharadig and Shushan crude oils with respect to origin and variations of facies and depositional environment. M.M.Y. Bakr 128Using various kinds of Egyptian crude oils derived from marine carbonates, marine clastics and terrestrial sources, the current study indicates that xanthones and its alkylated homologues are abundant only in source extracts and crude oils that have terrestrial organic matter input. This is the second description of xanthones in crude oils, and the first in Egyptian petroleum systems. Overall, based on the data of this study, xanthones signatures show great promise as terrestrial source markers in a given petroleum system.

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“…Two other experimental studies of MP isomerization using mineral catalysts are those of Alexander et al (1995) and McCollom et al (1999) but neither of these studies reported the relative abundances of the isomers of MP. Alexander et al (1995) reacted P in the presence of Ca-montmorillonite at 100…”

Section: Comparison With Field-derived and Experimental Values Of Mprmentioning

confidence: 99%

“…Geosynthetic pathways of methylation and isomerization of phenanthrene depend to varying extents on mineral catalysts and the energetics of the different isomerization reactions (Smith et al, 1995); in most cases the starting material is likely to be an α-methylated isomer (1-MP or 9-MP). 9-MP is an initial product of some geosynthetic pathways (Alexander et al, 1995). Application of the free valence number technique of Burkitt et al (1951) shows that alkylation at position 1 is highly kinetically favored over 2 and 3 (Karr et al, 1967).…”

Section: Introductionmentioning

confidence: 99%

“…Application of the free valence number technique of Burkitt et al (1951) shows that alkylation at position 1 is highly kinetically favored over 2 and 3 (Karr et al, 1967). 2-MP and 3-MP follow either by rearrangement (methyl shift) or are more susceptible to being formed by methylation at higher temperatures (Alexander et al, 1995;Smith et al, 1995).…”

Section: Introductionmentioning

confidence: 99%

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Estimation and application of the thermodynamic properties of aqueous phenanthrene and isomers of methylphenanthrene at high temperature

Dick

Evans

Holman

et al. 2013

Geochimica et Cosmochimica Acta

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Estimates of standard molal Gibbs energy (∆G • f ) and enthalpy (∆H indicative of more reducing conditions at a given temperature than those inferred from data reported for two sets of samples exposed to contact or regional metamorphism. These results are limiting-case scenarios for the modeled systems that do not account for effects of non-ideal mixing or kinetics, or external sources or transport of the organic matter. Nevertheless, quantifying the temperature dependence of equilibrium constants of organic reactions enables the utilization of organic maturity parameters as relative geothermometers at temperatures higher than the nominal limits of the oil window.

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Geosynthesis of organic compounds: II. Methylation of phenanthrene and alkylphenanthrenes

Cited by 99 publications

References 18 publications

Determination of the molecular signature of fossil conifers by experimental palaeochemotaxonomy – Part 1: The Araucariaceae family

Determination of the molecular signature of fossil conifers by experimental palaeochemotaxonomy – Part 1: The Araucariaceae family

Occurrence and Geochemical Significance of Carbazoles and Xanthones in Crude Oil from the Western Desert, Egypt

Estimation and application of the thermodynamic properties of aqueous phenanthrene and isomers of methylphenanthrene at high temperature

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