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С21n‑alkylbenzene and 1‑n‑alklylnaphthalene in Oils: Isotope Effect during Cyclization/Aromatization?

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Abstract—Carbon isotope composition was analyzed in С21n‑alkylbenzene and n‑alklylnaphthalene from five Upper Devonian oils of the Timan–Pechora Basin. In spite of the variations in carbon isotope composition, the difference in δ13C between n‑alkylbenzene and n‑alklylnaphthalene is relatively constant and accounts for, on average, 2.7‰. It is generally accepted that these compounds were derived from a common source. Thus, the revealed carbon isotope fractionation is related to the cyclization and aromatization of aliphatic chain.

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REFERENCES

  1. M. Blumer, M. M. Mullin, and R. R. L. Guillard, “A polyunsaturated hydrocarbon (3,6,9,12,15,18‑heneicosahexaene) in the marine food web,” Mar. Biol. 6, 226–235 (1970).

    Article  Google Scholar 

  2. D. A. Bushnev and N. S. Burdel’naya, “Crude oils and organic matter of Late Devonian deposits of the Timan–Pechora Basin: comparison by molecular and isotopic data,” Petrol. Chemistry 55 (7), 522–529 (2015).

    Article  Google Scholar 

  3. D. A. Bushnev and O. V. Valyaeva, “Generation conditions and migration pathways of petroleums of the Upper Devonian complex from the northern portion of the Pechora Basin,” Petrol. Chemistry 40 (5), 299–308 (2000).

    Google Scholar 

  4. D. A. Bushnev and O. V. Valyaeva, “N‑alkylbenzene and 1‑n‑alkylnaphthalene in series of Late Devonian oils of the Timan–Pechora province,” Vestn. Inst. Geol. Komi Nauchn. Ts. Ur. Otd. Ross. Akad. Nauk 10, 17–20 (2015).

    Google Scholar 

  5. D. A. Bushnev, N. S. Burdel’naya, O. V. Valyaeva, and A. A. Drevesnikova, “Geochemistry of Late Devonian oils of the Timan–Pechora basin,” Russ. Geol. Geophys. 58 (3–4), 332–342 (2017).

    Article  Google Scholar 

  6. J. Connan, J. Bouroullec, D. Dessort, and P. Albrecht, “The microbial input in carbonate‑anhydrite facies of a sabkha palaeoenvironment from Guatemala: a molecular approach,” Advances in Organic Geochemistry 1985, Ed. by D. Leythaueser, and J. Rullkotter, Org. Geochem. 10, 29–50 (1986).

  7. K. H. Freeman, R. E. Boreham, R. E. Summons, and J. M. Hayes, “The effect of aromatization on the isotopic compositions of hydrocarbons during early diagenesis,” Org. Geochem. 21 (10–11), 1037–1049 (1994).

    Article  Google Scholar 

  8. E. M. Galimov, Carbon Isotopes in Petroleum Geology (Nedra, Moscow, 1973) [in Russian].

    Google Scholar 

  9. E. M. Galimov, “Isotope organic geochemistry,” Org. Geochem. 37, 1200–1262 (2006).

    Article  Google Scholar 

  10. I. K. Ivanova and V. A. Kashirtsev, “Distribution of monoalkylbenzene C12H18–C27H48 in Vendian–Cambrian oils of the Siberian Platform,” Russ. Geol. Geophys. 51 (11), 1199–1203 (2010).

    Article  Google Scholar 

  11. R. F. Lee, and A. R. Loeblich, “Distribution of 21:6 hydrocarbon and its relationship to 22 : 6 fatty acid in algae,” Phytochemistry 10, 593–602 (1971).

    Article  Google Scholar 

  12. R. F. Lee, J. C. Nevenzel, G.‑A. Paffenhöfer, A. A. Benson, S. Patton, and T. E. Kavanagh, “A unique hexaene hydrocarbon from a diatom (Skeletonema costatum),” Biochim. Biophys. Acta 202, 386–388 (1970).

    Article  Google Scholar 

  13. J. Liao, H. Lu, G. Sheng, P. Peng, and C. S. Hsu, “Monoaromatic, diaromatic, triaromatic, and tetraaromatic hopanes in kukersite shale and their stable carbon isotopic composition,” Energy Fuels 29, 3573−3583 (2015).

    Article  Google Scholar 

  14. P. Le Métayer, K. Grice, C. N. Chow, L. Caccetta, E. Maslen, D. Dawson, and L. Fusetti, “The effect of origin and genetic processes of low molecular weight aromatic hydrocarbons in petroleum on their stable carbon isotopic compositions,” Org. Geochem. 72, 23–33 (2014).

    Article  Google Scholar 

  15. S. B. Ostroukhov, “On question of origin of C21 n‑alkylbenzene in oils,” Petroleum Chemistry. Proc. 7th International Conference (Inst. Optiki Atmosfery SO RAN, Tomsk, 2009), pp. 189–190.

  16. J. S. Sinninghe Damste, S. Schouten, W. E. I. C. Rijpsra, E. C. Hopmans, H. Peletier, W. W. C. Gieskes, and J. A. J. Geenevasen, “Novel polyunsaturated n‑alkanes in the marine diatom Rhizosolenia setigera,” Eur. J. Biochem. 267, 5727–5732 (2000).

    Article  Google Scholar 

  17. J. A. Williams, D. L. Dolcater, B. E. Torkelson, and J. C. Winters, “Anomalous concentrations of specific alkylaromatic and alkylcycloparafin components in West Texas and Michigan crude oils,” Advances in Organic Geochemistry 1987, Ed. by L. Mattavelli and L. Novelli, Org. Geochem. 13, 47–59 (1988).

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This work was carried out using facilities of the Geonauka Center for Collective Use.

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Correspondence to D. A. Bushnev.

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Translated by M. Bogina

SUPPLEMENTARY

SUPPLEMENTARY

Chemical structures: (I) n‑henicosahexaene‑3,6,9,12,15,18; (II) n‑ henicosahexaene ‑1,3,5,7,9,12; (III) n‑pentadecylbenzene; (IV) 1‑n‑undecyl naphthalene; (V) 5‑n‑ undecyltetralin; (VI) 1‑n‑ undecyltetralin; (VII) 1‑n‑decyl‑5‑methyltetralin.

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Bushnev, D.A., Burdel’naya, N.S. & Valyaeva, O.V. С21n‑alkylbenzene and 1‑n‑alklylnaphthalene in Oils: Isotope Effect during Cyclization/Aromatization?. Geochem. Int. 58, 61–65 (2020). https://doi.org/10.1134/S0016702920010036

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