A review of the occurrence, analyses, toxicity, and biodegradation of naphthenic acids

Chemosphere

Volumn 60, Issue 5, 2005, Pages 585-600

  Clemente, Joyce S ^a   Fedorak, Phillip M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

HPLC; Mass spectrometry; Microtox; Oil sands; Petroleum

Indexed keywords

BIODEGRADATION; CARBON; COMPOSITION; CRUDE PETROLEUM; HYDROGEN; INDUSTRIAL APPLICATIONS; OIL SANDS; TOXICITY; WASTEWATER;

CARBON NUMBER; INDUSTRIAL USES; NAPHTHENIC ACIDS; TOXIC COMPONENTS;

CARBOXYLIC ACIDS;

ACTIVATED CARBON; ASPHALT; NAPHTHALENE DERIVATIVE; NAPHTHENIC ACID; OIL; UNCLASSIFIED DRUG;

BIODEGRADATION; NAPHTHALENE; TOXICITY; WASTEWATER; WATER QUALITY;

BIODEGRADATION; NAPHTHALENE; TOXICITY; WASTEWATER; WATER QUALITY;

ANALYTIC METHOD; BIODEGRADABILITY; CHELATION; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHEMICAL WASTE; CORROSION; ECOTOXICOLOGY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; LETHAL DOSE; LIVER INJURY; LIVER TOXICITY; LIVER WEIGHT; MASS SPECTROMETRY; NEGATIVE ION ELECTROSPRAY; OIL INDUSTRY; PETROCHEMICAL INDUSTRY; QUANTITATIVE ANALYSIS; REVIEW; STRUCTURE ANALYSIS; TOXICITY TESTING;

EID: 20444507210     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2005.02.065     Document Type: Review

References (68)

1. Azure Environmental. Retrieved June 22, 2003. Available from: < http://www.azurenv.com/mtox.htm.
2. D.A. Barnett, B. Ells, R. Guevrenomont, and R.W. Purves Separation of leucine and isoleucine by electrospray ionization high-field waveform ion mobility mass spectrometry-mass spectrometry J. Am. Soc. Mass Spectrom. 10 1999 1279 1284
3. M.P. Barrow, L.A. McDonnell, X. Feng, J. Walker, and P.J. Derrick Determination of the nature of naphthenic acids present in crude oils using nanospray Fourier transform ion cyclotron resonance mass spectrometry: the continued battle against corrosion Anal. Chem. 75 2003 860 866
4. E.R. Blakley The microbial degradation of cyclohexanecarboxylic acid: a pathway involving aromatization to form p-hydroxybenzoic acid Can. J. Microbiol. 20 1974 1297 1306
5. E.R. Blakley The microbial degradation of cyclohexanecarboxylic acid by a β-oxidation pathway with simultaneous induction to the utilization of benzoate Can. J. Microbiol. 24 1978 847 855
6. E.R. Blakley, and B. Papish The metabolism of cyclohexanecarboxylic acid and 3-cyclohexenecarboxylic acid by Pseudomonas putida Can. J. Microbiol. 28 1982 1324 1329
7. Brient, J.A., 1998. Commercial utility of naphthenic acids recovered from petroleum distillates. Abstract of papers of the Am. Chem. Soc. 215, April 2, Dallas, TX (U119 018-PETR Part 2).
8. J.A. Brient, P.J. Wessner, and M.N. Doly Naphthenic acids fourth ed. J.I. Kroschwitz Encyclopedia of chemical technology vol. 16 1995 John Wiley New York 1017 1029
9. Clemente, J.S., 2004. The Characterization, Analyses and Biodegradation of Naphthenic Acids. MSc Thesis. University of Alberta, Edmonton, Canada.
10. J.S. Clemente, and P.M. Fedorak Evaluation of the analyses of t-butyldimethylsilyl derivatives of naphthenic acids by gas chromatography- electron impact mass spectrometry J. Chromatogr. A 1047 2004 117 128
11. J.S. Clemente, T.-W. Yen, and P.M. Fedorak Development of a high performance liquid chromatography method to monitor the biodegradation of naphthenic acids J. Environ. Eng. Sci. 2 2003 177 186
12. J.S. Clemente, N.G.N. Prasad, M.D. MacKinnon, and P.M. Fedorak A statistical comparison of naphthenic acids characterized by gas chromatography-mass spectrometry Chemosphere 50 2003 1265 1274
13. J.S. Clemente, M.D. MacKinnon, and P.M. Fedorak Aerobic biodegradation of two commercial naphthenic acids preparations Environ. Sci. Technol. 38 2004 1009 1016
14. B.K. Dokholyan, and A.K. Magomedov Effect of sodium naphthenate on survival and some physiological-biochemical parameters of some fishes J. Ichthyol. 23 1984 125 132
15. P.B. Dorn Case histories-the petroleum industry Toxicity reduction: evaluation and control D.L. Ford Water quality management library vol. 3 1992 Technomic Publishing Company Lancaster, PA 183 223
16. A.W. Drews Manual on hydrocarbon analysis sixth ed. 1998 ASTM Manual Series Conshohocken, PA 159 165
17. I. Dzidic, A.C. Somerville, J.C. Raia, and H.V. Hart Determination of naphthenic acids in California crudes and refinery wastewaters by fluoride-ion chemical ionization mass-spectrometry Anal. Chem. 60 1988 1318 1323
18. B. Ells, K. Froese, S.E. Hrudey, R.W. Purves, R. Guevrenomont, and D.A. Barnett Detection of microcystins using electrospray ionization high-field waveform ion mobility mass spectrometry/mass spectrometry Rapid Commun. Mass Spectrom. 14 2000 1538 1542
19. T.-P. Fan Characterization of naphthenic acids in petroleum by fast atom bombardment mass spectrometry Energy Fuels 5 1991 371 375
20. W. Gabryelski, and K.L. Froese Characterization of naphthenic acids by electrospray ionization high-field asymmetric waveform ion mobility spectrometry mass spectrometry Anal. Chem. 75 2003 4612 4623
21. J.V. Headley, K.M. Peru, D.W. McMartin, and M. Winkler Determination of dissolved naphthenic acids in natural waters by using negative-ion electrospray mass spectrometry J. AOAC Int. 85 2002 182 187
22. D.C. Herman, P.M. Fedorak, M.D. MacKinnon, and J.W. Costerton Biodegradation of naphthenic acids by microbial populations indigenous to oil sands tailings Can. J. Microbiol. 40 1994 467 477
23. F.M. Holowenko, M.D. MacKinnon, and P.M. Fedorak Methanogens and sulfate-reducing bacteria in oil sands fine tailings wastes Can. J. Microbiol. 46 2000 927 937
24. F.M. Holowenko, M.D. MacKinnon, and P.M. Fedorak Naphthenic acids and surrogate naphthenic acids in methanogenic microcosms Water Res. 35 2001 2595 2606
25. F.M. Holowenko, M.D. MacKinnon, and P.M. Fedorak Characterization of naphthenic acids in oil sands wastewaters by gas chromatography-mass spectrometry Water Res. 36 2002 2843 2855
26. C.S. Hsu, G.J. Dechert, W.K. Robbins, and E.K. Fukuda Naphthenic acids in crude oils characterized by mass spectrometry Energy Fuels 14 2000 217 223
27. M.N. Jivraj, M. MacKinnon, and B. Fung Naphthenic acid extraction and quantitative analysis with FT-IR spectroscopy Syncrude analytical manuals fourth ed. 1995 Research Department, Syncrude Canada Ltd. Edmonton, AB
28. D.M. Jones, J.S. Watson, W. Meredith, M. Chen, and B. Bennett Determination of naphthenic acids in crude oils using nonaqueous ion exchange solid-phase extraction Anal. Chem. 73 2001 703 707
29. K.L.E. Kaiser, and S.R. Esterby Regression and cluster analysis of the acute toxicity of 267 chemicals to six species of biota and the octanol/water partition coefficient Sci. Total Environ. 109/110 1991 499 514
30. M. Kamaluddin, and J.J. Zwiazek Naphthenic acids inhibit root water transport, gas exchange and leaf growth in aspen (Populus tremuloides) seedlings Tree Physiol. 22 2002 1265 1270
31. R.D. Kane, and M.S. Cayard Understanding critical factors that influence refinery crude corrosiveness Mater. Perform. 38 7 1999 48 54
32. a of fatty acid salt solutions Langmuir 16 2000 172 177
33. J.L. Lai, W.S. Pinto, E. Kiehlmann, L.I. Bendell-Young, and M.M. Moore Factors that affect the degradation of naphthenic acids in oil sands wastewater by indigenous microbial communities Environ. Toxicol. Chem. 15 1996 1482 1491
34. C.C. Lo, B.G. Brownlee, and N.J. Bunce Electrospray-mass spectrometric analysis of reference carboxylic acids and Athabasca oil sands naphthenic acids Anal. Chem. 75 2003 6394 6400
35. H.L. Lochte, and E.R. Litman The petroleum acids and bases 1955 Chemical Publishing Co. Inc. New York
36. M.D. MacKinnon Development of the tailings pond at Syncrude's oil sands plant: 1978-1987 AOSTRA J. Res. 5 1989 109 133
37. M.D. MacKinnon, and H. Boerger Description of two treatment methods for detoxifying oil sands tailings pond water Water. Pollut. Res. J. Can. 21 1986 496 512
38. R.E.A. Madill, M. Orzechowski, G. Chen, B.G. Brownlee, and N.J. Bunce Preliminary risk assessment of the wet landscape option for reclamation of oil sands mine tailings: bioassays with mature fine tailings pore water Environ. Toxicol. 16 2001 197 208
39. W. Meredith, S.-J. Kelland, and D.M. Jones Influence of biodegradation on crude oil acidity and carboxylic acid composition Org. Geochem. 31 2000 1059 1073
40. H. Miwa High performance liquid chromatographic determination of mono-, poly- and hydroxycarboxylic acids in foods and beverages as their 2-nitrophenylhydazides J. Chromatogr. A 881 2000 365 385
41. 22:6 fatty acids as their 2-nitrophenylhydrazides by reversed-phase high-performance liquid chromatography J. Chromatogr. 351 1986 275 282
42. H. Miwa, and M. Yamamoto High performance liquid chromatographic analysis of serum long chain fatty acids by direct derivatization method J. Chromatogr. 416 1987 237 245
43. H. Miwa, C. Hiyama, and M. Yamamoto High-performance liquid chromatography of short- and long-chain fatty acids as 2-nitrophenylhydrazides J. Chromatogr. 321 1985 165 174
44. L.R. Nascimento, L.M.C. Reboucas, L. Koike, F.D.M. Reis, L. Soldan, J.R. Cerqueira, and A.J. Marsaioli Acidic biomarkers from Albacora oils, Campos Basin, Brazil Org. Geochem. 30 1999 1175 1191
45. R.W. Purves, and R. Guevremont Electrospray ionization high-field asymmetric waveform ion mobility spectrometry-mass spectrometry Anal. Chem. 71 1999 2346 2357
46. K. Qian, W.K. Robbins, C.A. Hughey, H.J. Cooper, R.P. Rodgers, and A.G. Marshall Resolution and identification of elemental compositions for more than 3000 crude acids in heavy petroleum by negative-ion microelectrospray high-field Fourier transform ion cyclotron resonance mass spectrometry Energy Fuels 15 2001 1505 1511
47. E.M. Rho, and W.C. Evans The aerobic metabolism of cyclohexanecarboxylic acid by Acinetobacter anitratum Biochem. J. 148 1975 11 15
48. V.V. Rogers, K. Liber, and M.D. MacKinnon Isolation and characterization of naphthenic acids from Athabasca oil sands tailings pond water Chemosphere 48 2002 519 527
49. V.V. Rogers, M. Wickstrom, K. Liber, and M.D. MacKinnon Acute and subchronic mammalian toxicity of naphthenic acids from oil sands tailings Toxicol. Sci. 66 2002 347 355
50. D.E. Roques, E.B. Overton, and C.B. Henry Using gas chromatography/mass spectrometry fingerprint analyses to document process and progress of oil degradation J. Environ. Qual. 23 1994 851 855
51. W.E. Rudzinski, L. Oehlers, and Y. Zhang Tandem mass spectrometric characterization of commercial naphthenic acids and a Maya crude oil Energy Fuels 16 2002 1178 1185
52. L.L. Schramm, E.N. Stasiuk, and M. MacKinnon Surfactants in Athabasca oil sands slurry conditioning, flotation recovery, and tailings processes L.L. Schramm Surfactants: fundamentals and applications in the petroleum industry 2000 Cambridge University Press Cambridge 365 430
53. W.K. Seifert, and R.M. Teeter Preparative thin-layer chromatography and high resolution mass spectrometry of crude oil carboxylic acids Anal. Chem. 41 1969 786 795
54. W.K. Seifert, R.M. Teeter, W.G. Howells, and M.J.R. Cantow Analysis of crude oil carboxylic acids after conversion to their corresponding hydrocarbons Anal. Chem. 41 1969 1638 1647
55. R.M. Silverstein, and F. Webster Spectrometric identification of organic compounds sixth ed. 1998 John Wiley New York (Chapter 2)
56. E. Slavcheva, R. Shone, and A. Turnbull Review of naphthenic acid corrosion in oil refining Brit. Corrosion J. 34 1999 125 131
57. W.P. St. John, J. Righani, S.A. Green, and G.D. McGinnis Analysis and characterization of naphthenic acids by gas chromatography-electron impact mass spectrometry of tert.-butyldimethylsilyl derivatives J. Chromatogr. A 807 1998 241 251
58. O.P. Strausz, and E.M. Lown The chemistry of Alberta oil sands, bitumens and heavy oils 2003 Alberta Energy Research Institute Calgary
59. Syncrude Canada Ltd. P. Ashcroft Syncrude factbook 2000 Vision Design Communications Inc. Fort McMurray, AB
60. D.G. Taylor, and P.W. Trudgill Metabolism of cyclohexane carboxylic acid by Alcaligenes strain W1 J. Bacteriol. 134 1978 401 411
61. B.P. Tissot, and D.H. Welte Petroleum formation and occurrence 1978 Springer-Verlag New York
62. N.A. Tomczyk, R.E. Winans, J.H. Shinn, and R.C. Robinson On the nature and origin of acidic species in petroleum. 1. Detailed acid type distribution in a California crude oil Energy Fuels 15 2001 1498 1504
63. A. Turnbull, E. Slavcheva, and B. Shone Factors controlling naphthenic acid corrosion Corrosion 54 1998 922 930
64. J.S. Watson, D.M. Jones, R.P.J. Swannell, and A.C.T. van Duin Formation of carboxylic acids during aerobic biodegradation of crude oil and evidence of microbial oxidation of hopanes Org. Geochem. 33 2002 1153 1169
65. D.C.L. Wong, R. van Compernolle, J.G. Nowlin, D.L. O'Neal, and G.M. Johnson Use of supercritical fluid extraction and fast ion bombardment mass spectrometry to identify toxic chemicals from a refinery effluent adsorbed onto granular activated carbon Chemosphere 32 1996 1669 1679
66. D.J. Wort, and K.M. Patel Response of plants to naphthenic and cycloalkanecarboxylic acids Agron. J. 62 1970 644 646
67. D.J. Wort, J.G. Severson Jr., and D.R. Peirson Mechanism of plant growth stimulation by naphthenic acids Plant Physiol. 52 1973 162 165
68. T.-W. Yen, W.P. Marsh, M.D. MacKinnon, and P.M. Fedorak Measuring naphthenic acids concentrations in aqueous environmental samples by HPLC J. Chromatogr. A 1033 2004 81 88