Abstract:
Hydrocarbons are among the most abundant organic compound classes in the biogeosphere. They are formed directly by living organisms as biosynthetic products or through geological transformation of biomass in sedimentary systems. This article provides an introduction to the structural variability of hydrocarbons and their occurrence in natural environments. Besides saturated, unsaturated and aromatic hydrocarbons also selected types of functionalized organic compounds which play key roles in biogeochemical processes are discussed. For each compound type reactivity and important reaction types with a special focus on mechanisms relevant in biochemical transformations are presented. Bio- and geomacromolecules and their role in the formation of fossil fuels are briefly introduced. Important physico-chemical parameters are discussed in relation to the structural characteristics of the presented compound classes.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Allred AL (1961) Electronegativity values from thermochemical data. J Inorg Nucl Chem 17: 215–221.
Ballschmiter K, Schäfer W, Buchert H (1987) Isomer-specific identification of PCB congeners in technical mixtures and environmental samples by HRGC-ECD and HRGC-MSD. Fresenius Journal of Anal Chem 326: 253–257.
Ballschmiter K (2003) Pattern and sources of naturally produced organohalogens in the marine environment: biogenic formation of organohalogens. Chemosphere 52: 313–324.
Boll M, Fuchs G, Heider J (2002) Anaerobic oxidation of aromatic compounds and hydrocarbons. Curr Opin Chem Biol 6: 604–611.
Brown RJC, Brown RFC (2000) Melting point and molecular symmetry. J Chem Educ 77:
Buckel W, Golding BT (2006) Radical enzymes in anaerobes. Ann Rev Microbiol 60: 27–49.
Curiale JA, Frolov EB (1998) Occurrence and origin of olefins in crude oils. A critical review. Org Geochem 29: 397–408.
Dahl JE, Liu SG, Carlson RMK (2003a) Isolation and structure of higher diamondoids, nanometer-sized diamond molecules. Science 299: 96–99.
Dahl JEP, Moldowan JM, Peakman TM, Clardy JC, Lobovsky E, Olmstead MM, May PW, Davis TJ, Steeds JW, Peters KE, Pepper A, Ehkuan A, Carlson RMK (2003b) Isolation and structural proof of the large diamond molecule, cyclohexamantane (C26H30). Angew Chem 115: 2086–2090.
Dahl JE, Moldowan JM, Peters KE, Claypool GE, Rooney MA, Michael GE, Mello MR, Kohnen ML (1999) Diamondoid hydrocarbons as indicators of natural oil cracking. Nature 399: 54–57.
Boer J, de deBoer K, Boon JP (2000) Polybrominated biphenyls and diphenyl ethers. In The Handbook of Environmental Chemistry, vol 3 Anthropogenic compounds Part K. J. Paasivirta (ed.). Berlin: Springer. pp. 61–96.
Ficken KJ, Li B, Swain DL, Eglinton G (2000) An n-alkane proxy for the sedimentary input of submerged/floating freshwater aquatic macrophytes. Org Geochem 31: 745–749.
Fiedler H (1996) Sources of PCDD/PCDF and impact on the environment. Chemosphere 32: 55–64.
Fleming FF (1999) Nitrile-containing natural products. Nat Prod Reports 16: 597–606.
Francke W, Schulz S (1998) pheromones. In: Comprehensive Natural Products Chemistry, vol 8. K Mori (ed.). Oxford: Pergamon, pp. 197–261.
Gribble GW (1994) The natural production of chlorinated compounds. Environ Sci Technol 28: 310A–319A.
Gribble GW (2000) The natural production of organobromine compounds. Environ Sci Pollut Res Int 7: 37–49.
Grice K, Alexander R, Kagi RI (2000) Diamondoid hydrocarbon ratios as indicators of biodegradation in Australian crude oils. Org Geochem 31: 67–73.
Hall C, Tharakan P, Hallock J, Cleveland C, Jefferson M (2003) Hydrocarbons and the evolution of human culture. Nature 426: 318–322.
Hebting Y, Schaeffer P, Behrens A, Adam P, Schmitt G, Schneckenburger P, Bernasconi SM, Albrecht P (2006) Biomarker evidence for a major preservation pathway of sedimentary organic carbon. Science 312: 1627–1631.
Heider J (2007) Adding handles to unhandy substrates: anaerobic hydrocarbon activation mechanisms. Curr Opin Chem Biol 11: 188–194.
Hinrichs K-U, Hayes JM, Bach W, Spivack AJ, Hmelo LR, Holm NG, Johnson CG, Sylva SP (2006) Biological formation of ethane and propane in the deep marine subsurface. Proc Natl Acad Sci USA 103: 14684–14689.
Huc AY (1980) Origin and formation of organic matter in recent sediments and its relation to kerogen. In: Kerogen, Insoluble Organic Matter from Sedimentary Rocks. B Durand (ed.). Paris: Editions Technip, pp. 445–474.
Leeuw JW, de Largeau C (1993) A review of macromolecular organic compounds that comprise living organisms and their role in kerogen, coal and petroleum formation. In: Organic Geochemistry – Principles and Applications. MH Engel, SA Macko (eds.). New York: Plenum Press, pp. 23–72.
Lide DR (2002) CRC Handbook of Chemistry and Physics, 83rd edn. 2002–2003. Boca Raton, FL: CRC Press.
Mango FD (2000) The origin of light hydrocarbons. Geochim Cosmochim Acta 64: 1265–1277.
Marynowski L, Czechowski F, Simoneit BRT (2001) Phenylnaphthalenes and polyphenyls in Palaeozoic source rocks of the Holy Cross Mountains, Poland. Org Geochem 32: 69–85.
McMillen DF, Golden DM (1982) Hydrocarbon bond dissociation energies. Annu Rev Phys Chem 33: 493–532.
Peters KE, Walters CC, Moldowan JM (2005) The Biomarker Guide. Cambridge: Cambridge University Press.
Portella G, Poater J, Solà M (2005) Assessment of Clar’s aromatic pi-sextet rule by means of PDI, NICS and HOMA indicators of local aromaticity. J Phys Org Chem 18: 785–791.
Rabus R, Wilkes H, Behrends A, Armstroff A, Fischer T, Pierik AJ, Widdel F (2001) Anaerobic initial reaction of n-alkanes in a denitrifying bacterium: Evidence for (1-methylpentyl)succinate as initial product and for involvement of an organic radical in n-hexane metabolism. J Bacteriol 183: 1707–1715.
Randic M (2003) Aromaticity of polycyclic conjugated hydrocarbons. Chem Rev 103: 3449–3606.
Schenk HJ, Horsfield B, Krooss B, Schaefer RG, Schwochau K (1997) Kinetics of petroleum formation and cracking. In Petroleum and Basin Evolution. DH Welte, B Horsfield, DR Baker (eds.). Berlin: Springer, pp. 231–269.
Schneider-Belhaddad F, Kolattukudy P (2000) Solubilization, partial purification, and characterization of a fatty aldehyde decarbonylase from a higher plant, Pisum sativum. Arch Biochem Biophys 377: 341–349.
Schoell M (1980) The hydrogen and carbon isotopic composition of methane from natural gases of various origins. Geochim Cosmochim Acta 44: 649–661.
Sinninghe Damsté JS, Strous M, Rijpstra WIC, Hopmans EC, Geenevasen JAJ, Duin ACT, van Niftrik LA, van Jetten MSM (2002) Linearly concatenated cyclobutane lipids form a dense bacterial membrane. Nature 419: 708–712.
Taylor P, Larter S, Jones M, Dale J, Horstad I (1997) The effect of oil-water-rock partitioning on the occurrence of alkylphenols in petroleum systems. Geochim Cosmochim Acta 61: 1899–1910.
Vandenbroucke M, Largeau C (2007) Kerogen origin, evolution and structure. Org Geochem 38: 719–833.
Yunker MB, MacDonald RW, Vingarzan R, Mitchell RH, Goyette D, Sylvestre S (2002) pahs in the Fraser River basin: a critical appraisal of PAH ratios as indicators of PAH source and composition. Org Geochem 33: 489–515.
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer-Verlag Berlin Heidelberg
About this entry
Cite this entry
Wilkes, H., Schwarzbauer, J. (2010). Hydrocarbons: An Introduction to Structure, Physico-Chemical Properties and Natural Occurrence. In: Timmis, K.N. (eds) Handbook of Hydrocarbon and Lipid Microbiology. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-77587-4_1
Download citation
DOI: https://doi.org/10.1007/978-3-540-77587-4_1
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-77584-3
Online ISBN: 978-3-540-77587-4
eBook Packages: Biomedical and Life SciencesReference Module Biomedical and Life Sciences