Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Letter
  • Published:

Occurrence and geochemical significance of long-chain dialkylthiacyclopentanes

Abstract

Small sulphur-containing molecules were first detected in petroleums and sediments many years ago1–3, but only recently have complex sulphur components related to biological markers been identified4–14. These discoveries have provided interesting information on the distribution of sulphur-containing compounds in geological samples, but the formation mechanisms of such molecules remain to be clarified. Recently, Connan et al.15 recognized the occurrence of series of long-chain sulphur-containing components in heavy sulphur-rich crude oils from carbonate basins and tentatively identified them as alkylthiacyclopentanes and alkylthiacyclohexanes on the basis of selective detection and gas chromatography/mass spectrometry studies. Here we report the conclusive identification and geochemical significance of long-chain 2,5-dialkylthiacyclopentanes of type 1 (see Fig. 4), occurring as major components in some of these petroleums, as shown for an immature carbonate crude oil from Maruejols (Oligocene Alès basin, France), containing 6.5% sulphur16. In addition to providing new information about the 'aromatic' fractions of these crude oils (which are in fact largely non-aromatic), these results give useful indications of some of the mechanisms of incorporation of sulphur into organic matter in the sub-surface environment. Furthermore, as confirmed by thermal simulation experiments, these dialkylthiacyclopentanes are thermally labile, which seems to restrict their occurrence to immature crude oils. They could therefore serve as useful maturation parameters for the early stages of petroleum formation in carbonate basins.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

  1. Aksenov, V. S. & Kamyanov, V. F. in Organic Sulfur Chemistry (eds Freidlina, R. Kh. & Skorova, A. E.) 1–13 (Pergamon, Oxford, 1981).

    Google Scholar 

  2. Thompson, C. J. in Organic Sulfur Chemistry (eds Freidlina, R. Kh. & Skorova, A. E.) 189–208 (Pergamon, Oxford, 1981).

    Google Scholar 

  3. Whelan, J. K., Hunt, J. M. & Berman, J. Geochim. cosmochim. Acta 44, 1767–1785 (1985).

    Article  ADS  Google Scholar 

  4. Rullkotter, J., Von der Dick, H. & Welte, D. H. in Init. Rep. DSDP Vol. 63 (eds Haq, B. et al.) 819–836 (US Government Printing Office, Washington DC, 1981).

    Google Scholar 

  5. Payzant, J. D., Montgomery, D. S. & Strausz, O. P. Tetrahedron Lett. 24, 651–654 (1983).

    Article  CAS  Google Scholar 

  6. Valisolalao, J., Perakis, N., Chappe B. & Albrecht, P. Tetrahedron Lett. 25, 1183–1186 (1984).

    Article  CAS  Google Scholar 

  7. Payzant, J. D., Cyr, T. D., Montgomery, D. S. & Strausz, O. P. Tetrahedron Lett. 26, 4175–4178 (1985).

    Article  CAS  Google Scholar 

  8. Cyr, T. D., Payzant, J. D., Montgomery, D. S. & Strausz, O. P. Org. Geochem. 9, 139–143 (1986).

    Article  CAS  Google Scholar 

  9. Payzant, J. D., Montgomery, D. S. & Strausz, O. P. Org. Geochem. 9, 357–369 (1986).

    Article  CAS  Google Scholar 

  10. Brassel, S. C., Lewis, C. A., de Leeuw, J. W., de Lange F. & Sinninghe Damste, J. S. Nature 320, 160–162 (1986).

    Article  ADS  Google Scholar 

  11. Sinninghe Damste, J. S., ten Haven, H. L., de Leeuw, J. W. & Schenck, P. A. in Advances in Organic Geochemistry 1985 (eds Leythaeuser, D. & Rullkotter, J.) Org. Geochem. 10, 791–805 (1986).

    Google Scholar 

  12. Schmid, J. C. thesis, Univ. Louis Pasteur, Strasbourg (1986).

  13. Sinninghe Damste, J. S. & de Leeuw, J. W. Int. J. Environ. anal. Chetn. (in the press).

  14. Sinninghe Damste, J. S., Kock-van Dalen, A. C., de Leeuw, J. W. & Schenck, P. A. Tetrahedron Lett. (in the press).

  15. Connan, J., Grondin, J. L., Colin, J. P., Hussler, G. & Albrecht, P. Communication at 11th Int. Meet. Org. Geochem. (The Hague, September, 1983).

  16. Ocampo, R. et al. Communication at 12th Int. Meet. Org. Geochem. Jülich, September 1985.

  17. Budzikiewicz, H., Djerassi, C. & Williams, D. H. Interpretation of Mass Spectra of Organic Compounds 284–286 (Holden-Day, San Francisco 1964).

    Google Scholar 

  18. Kursanov, D. N., Parnes, Z. N. & Loim, N. M. Synthesis, 633–650 (1974).

  19. Sinninghe Damste, J. S. et al. Geochim. cosmochim. Acta. (in the press).

  20. Perakis, N. thesis, Univ. Louis Pasteur, Strasbourg (1986).

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Schmid, J., Connan, J. & Albrecht, P. Occurrence and geochemical significance of long-chain dialkylthiacyclopentanes. Nature 329, 54–56 (1987). https://doi.org/10.1038/329054a0

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1038/329054a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing