Structural identification and mass spectral interpretation of C3n highly branched alkanes in sediment and aquatic extracts and evidence for their anthropogenic origin

Organic Geochemistry

Volumn 40, Issue 10, 2009, Pages 1055-1062

  Greenwood, Paul F ^a,b   Lengkeek, Nigel A ^a   Piggott, Matthew J ^a   Pierce, Kieran ^b  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b CURTIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHROPOGENIC ORIGIN; BRANCHED ALKANES; DIASTEREOISOMERS; END GROUPS; ENVIRONMENTAL OCCURRENCE; ISOTACTICS; MASS SPECTRA; MASS SPECTRAL; STRUCTURAL IDENTIFICATION; WATER EXTRACTS;

CHROMATOGRAPHIC ANALYSIS; GAS CHROMATOGRAPHY; MASS SPECTROMETERS; MASS SPECTROMETRY; OLIGOMERS; PARAFFINS; PLASTIC PRODUCTS; POLLUTION DETECTION; PUMPING PLANTS; SEDIMENTOLOGY; STANDARDS;

SOLVENT EXTRACTION;

ALKANE; ANTHROPOGENIC EFFECT; AQUATIC ECOSYSTEM; CORRELATION; ENVIRONMENTAL CONDITIONS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; SEDIMENT CHEMISTRY;

EID: 69949144686     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orggeochem.2009.07.009     Document Type: Article

References (33)

1. Arouri K., Conaghan P.J., Walter M.R., Bischoff G.C.O., and Grey K. Reconnaissance sedimentology and hydrocarbon biomarkers of Ediacarian microbial mats and acritarchs, lower Ungoolya Group, Officer Basin. Precambrian Research 100 (2000) 235-280
2. Arouri K., Greenwood P.F., and Walter M. Biological affinities of neoproterozoic acritarchs from Australia: microscopic and chemical characterisation. Organic Geochemistry 31 (2000) 75-89
3. Brocks J.J., Grosjean E., and Logan G.A. Assessing biomarker syngeneity using branched alkanes with quaternary carbon (BAQC) and other plastic contaminants. Geochimica et Cosmochimica Acta 72 (2008) 871-888
4. Cesca S. The chemistry of unsaturated ethylene-propylene base terpolymers. Journal of Polymer Science, Macromolecular Reviews 10 (1975) 1-230
5. Davies-Coleman M.T., and Garson M.J. Marine polypropionates. Natural Product Reports 15 (1998) 477
6. Dembitsky V.M., Dor I., Shkrob I., and Aki M. Branched alkanes and other apolar compounds produced by the cyanobacterium Microcoleus vaginatus from the Negev Desert. Russian Journal of Bioorganic Chemistry 27 (2001) 110-119
7. Durkay, M.S., 2002. Use of Hydrocarbons in Winery Wastewater to Establish Hydraulic Connectivity in a Fractured Rock Aquifer, in a Clare Valley Winery, SA. BSc Honours Dissertation, University of Adelaide, SA.
8. Durkay, M.S., Arouri, K.R., McKirdy, D.M., 2003. Use of hydrocarbons in winery wastewater to establish hydraulic connectivity in a fractured rock aquifer: a pilot study in the Clare Valley, South Australia. In: 21st International Meeting on Organic Geochemistry, Krakow, Poland, pp. 365-366 (Book of Abstracts Part II).
9. Galeyeva Y., Morr M., Laschat S., Baro A., Nimtz M., and Sasse F. Ex chiral pool synthesis of (-)-siphonarienone from a methyl branched wax ester. Synthesis 17 (2005) 2875-2880
10. 3n alkanes detected in extant and ancient sediments with series of polypropylene oligomers. Organic Geochemistry 37 (2006) 755-771
11. 3n alkanes in diverse meso- and neoproterozoic sediments. Organic Geochemistry 35 (2004) 331-346
12. Greenwood, P.F., Logan, G.A., Boreham, C.J., Hope, J.M., Sandison, C.M., Summons, R.E., 2002. CSIA data of novel series of branched alkanes from Proterozoic and Cretaceous sediments. In: Proceedings 223 American Chemical Society, Division of Geochemistry, Orlando, Florida, April 7-11, 2002.
13. Greenwood, P.F., Logan, G.A., Summons, R.E., Arouri, K.R., 2001. Novel highly branched alkanes in Neoproterozoic rocks containing high microbial mat communities. In: 20th International Meeting on Organic Geochemistry, Nancy, France, pp. 132-133 (Book of Abstracts I).
14. Grosjean E., and Logan G.A. Incorporation of organic contaminants into geochemical samples and an assessment of potential sources: examples from Geoscience Australia marine survey S282. Organic Geochemistry 38 (2007) 853-869
15. Huang J., and Rempel G.L. Ziegler-Natta catalysts for olefin polymerization: mechanistic insights from metallocene systems. Progress in Polymer Science 20 (1995) 459-526
16. Jackson M., Stadthagen G., and Gicquel B. Long-chain multiple methyl-branched fatty acid-containing lipids of Mycobacterium tuberculosis: biosynthesis, transport, regulation and biological activities. Tuberculosis 87 (2007) 78-86
17. Kenig F., Simons D.-J.H., Crich D., Cowen J.P., Ventura G.T., Brown T.C., and Rehbein T. Alkanes with a quaternary carbon centre: a 2, 200 Myr record of sulfide oxidizing bacteria. Geochimica et Cosmochimica Acta 66 (2002) A393 (abstr)
18. Kenig F., Simons D.-J.H., Crich D., Cowen J.P., Ventura G.T., Rehbein-Khalily T., Brown T.C., and Anderson K.B. Branched aliphatic alkanes with quaternary substituted carbon atoms in modern and ancient geologic samples. Proceedings of the National Academy of Sciences USA 100 (2003) 12554-12558
19. Kenig F., Simons D.-J.H., Crich D., Cowen J.P., Ventura G.T., and Rehbein T. Structure and distribution of branched aliphatic alkanes with quaternary carbon atoms in Cenomanian and Turonian block shales of Pasquia Hills (Saskatchewan, Canada). Organic Geochemistry 36 (2005) 117-138
20. Kenig F., Sinninghe-Damsté J.S., Kock-van Dalen A.C., Rijpstra W.I.C., Huc A.Y., and de Leeuw J.W. Occurrence and origin of mono-, di-, and trimethylalkanes in modern and Holocene cyanobacterial mats from Abu Dhabi, United Arab Emirates. Geochimica et Cosmochimica Acta 59 (1995) 2999-3015
21. Köster J., Volkman J.K., Rullkötter J., Scholz-Böttcher B.M., Reithmeier J., and Fischer U. Mono-, di- and trimethyl-branched alkanes in cultures of the filamentous cyanobacterium Calothrix scopulorum. Organic Geochemistry 30 (1999) 1367-1379
22. Kvenholden K.A., Peterson E., and Pollock G.E. Optical configuration of amino-acids in pre-Cambrian Fig Tree chert. Nature 221 (1969) 141-143
23. McCarthy E.D., Han J., and Calvin M. Hydrogen atom transfer in mass spectrometric fragmentation patterns of saturated aliphatic hydrocarbons. Analytical Chemistry 40 (1968) 1475-1480
24. McKirdy, D.M., Webster, L.J., Arouri, K.R., Gostin, V.A., 2003. Contrasting sterane signatures in Neoproterozoic marine sediments of the Centralian Superbasin before and after the Acraman bolide impact. In: 21st International Meeting on Organic Geochemistry, Krakow, Poland, pp. 132-133 (Book of Abstracts I).
25. Morr M., Proppe C., and Wray V. Synthesis of asymmetrical methyl-branched chiral ketones from the corresponding homologous wax esters. A new synthesis of the insect pheromone lardolure and of 9-norlardolure. Liebigs Annalen der Chemie 11 (1995) 2001-2004
26. Morr M., Wray V., Fortkamp J., and Schmidt R.D. 2, 4, 6, 8-Tetramethyldecanoic and-undecanoic acid from the preen-gland wax of the domestic goose. Anser a.f. domesticus: isolation and synthesis of derivatives and of rac-2, 4, 6, 8-tetramethyldecanoic acid. Liebigs Annalen der Chemie 8 (1992) 433-439
27. Pino P., Cioni P., and Wei J. Asymmetric hydrooligomerisation of polypropylene. Journal of the American Chemical Society 109 (1987) 6189-6191
28. Rafidinarivo E., Savagnac A., Lacave C., and Prome J.-C. Branched fatty acids from mycobacterium Aurum. Biochimica et Biophysica Acta 711 (1982) 266-271
29. Shiea J., Brassell S.C., and Ward D.M. Mid-chain branched mono- and dimethyl alkanes in hot spring cyanobacterial mats: a direct biogenic source for branched alkanes in ancient sediments?. Organic Geochemistry 15 (1990) 223-231
30. Stevens M.P. Polymer Chemistry: An Introduction (1999), Oxford University Press, New York
31. Sugimura Y., Nagaya T., Tsuge S., Murata T., and Takeda T. Microstructural characterization of polypropylenes by high-resolution pyrolysis-hydrogenation glass capillary gas chromatography. Macromolecules 13 (1980) 928-932
32. Summons R.E. Branched alkanes from ancient and modern sediments: isomer discrimination by GC/MS with multiple reaction monitoring. Organic Geochemistry 11 (1987) 281-289
33. 3n alkanes and the Acraman impact event in Ediacarian deep marine shales of the Eastern Officer Basin, South Australia. In: Proceedings of the Origin and Fate of Naturally Occurring Organic Matter. Combined National Conference of the Australian Organic Geochemists and the Natural Organic Matter Interest Group 12-15 February 2006, Rottnest Island, Perth, W, Australia, pp. 69-70.