Is Acid Troubling You? Studies of the Synthesis, Characterisation, Biodegradation and Toxicity of Naphthenic Acids

Ben Smith1, S.J. Rowland1, C.A. Lewis1, V.V. Cheung1, H.M. Lappin-Scott2, M. Frenzel2 and C. Whitby2


Petroleum and Environmental Geochemistry Group, SEOES, University of Plymouth, Plymouth, U.K., PL4 8AA
2 Environmental Microbiology and Ecology Research Group, School of Biosciences, University of Exeter, Exeter, U.K., EX4 4PS

Presented at: 22nd International Meeting on Organic Geochemistry (IMOG), Seville, Spain, 12-16 September 2005.

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Brief Summary

Naphthenic acids (NAs) are a complex mix of aliphatic and cycloaliphatic carboxylic acids with the general formula CnH2n+zO2 where n indicates the carbon number and z specifies the degree of unsaturation. Major sources of NAs are Canadian Oil Sands and degraded petroleum from around the world. NAs cause problems at refineries as they are corrosive to steel alloys and they form naphthenate deposits which block pipe lines. Their toxicity is well documented, with studies showing toxic effects to zooplankton, bacteria, fish and rats. Biodegradation studies have used surrogate, commercial and natural NA mixtures as substrates. Some studies have shown that biodegradation can initially reduce the toxicity of NAs, while others have reported recalcitrant complex mixtures of NAs. Examples of analytical methods employed to characterise and quantify these compounds are FTIR, GC, GC-MS (EI, FAB, APCI, CI etc), HPLC-MS and ESI-MS. Our aim was (1) to synthesise an isomeric series of surrogate NAs, (2) to use these substrates to improve our understanding of NAs toxicity and biodegradation, and (3) to develop and optimise rigorous characterisation and quantification methods appropriate for complex NA mixtures.

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