Is Biodegradation of Bitumen a Source of Recalcitrant Naphthenic Acid Mixtures in Oil Sands Tailing Pond Waters?

REFERENCES

• Lai , J. W.S. , Pinto , L. J. and Kiehlmann , E. 1996 . Factors that affect the degradation of naphthenic acids in oil sands wastewater by indigenous microbial communities . Environ. Toxicol. Chem. , 15 : 1482 – 1491 . [CSA]
   Web of Science ®Google Scholar
• Headley , J. V. 2004 . D.W . McMartin. A review of the occurrence and fate of naphthenic acids in aquatic environments. J. Environ. Sci. Heal. A. , 39 : 1989 – 2010 . [CSA]
   Google Scholar
• Quagraine , E. K. , Peterson , H. G. and Headley , J. V. 2005 . In situ-bioremediation of naphthenic acids contaminated tailing pond waters in the Athabasca oil sands region: Demonstrated field studies and some other plausible options—Review . J. Environ. Sci. Heal. A , 40 : 685 – 722 .
   Web of Science ®Google Scholar
• Mackenzie , A. S. , Wolff , G. A. and Maxwell , J. R. 1981 . “ Fatty acids in some biodegraded petroleums: Possible origins and significance ” . In Advances in Organic Geochemistry , Edited by: Bjorøy , M. 637 – 649 . Chichester : Wiley .
   Google Scholar
• Watson , J. S. , Jones , D. M. , Swannell , R. P.J. and van Duin , A. C.T. 2002 . Formation of carboxylic acids during aerobic biodegradation of crude oil and evidence of microbial oxidation of hopanes . Org. Geochem. , 33 : 1153 – 1169 . [CROSSREF]
   Web of Science ®Google Scholar
• Potter , T. L. and Duval , B. 2001 . Cerro negro bitumen degradation by a consortium of marine benthic microorganisms . Environ. Sci. Technol. , 35 : 76 – 83 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMedGoogle Scholar
• American Petroleum Institute . 2003 . “ Petroleum High Productive Volume (HPV) Testing Group, Test Plan Crude Oil Category, HPV Chemical Challenge Program, Consortium Registration 201-14858A, November 21 ” .
   Google Scholar
• Dusseault , M. B. 2001 . Comparing Venezuelan and Canadian heavy oil and tar sands . Canadian International Petroleum Conference organized by Canadian Institute of Mining, Metallurgy and Petroleum Calgary . June 12–14 2001 , AB.
   Google Scholar
• Selucky , M. L. , Chu , Y. , Ruo , T. and Strauz , O. P. 1977 . Chemical composition of Athabasca bitumen . Fuel , 56 : 369 – 381 . [CROSSREF]
   Web of Science ®Google Scholar
• Wyndham , R. C. and Costerton , J. W. 1981 . Heterotrophic potentials and hydrocarbon biodegradation potentials of sediment microorganisms within the Athabasca oil sands deposit . Appl. Environ. Microbiol. , 41 : 783 – 790 . [CSA]
   PubMed Web of Science ®Google Scholar
• Venosa , A. D. and Zhu , X. 2003 . Biodegradation of crude oil contaminating marine shorelines and freshwater wetlands . Spill Sci. Techno. B. , 8 : 163 – 178 . [CROSSREF] [CSA]
   Google Scholar
• Watkinson , R. J. and Morgan , P. 1990 . Physiology of aliphatic hydrocarbon-degrading microorganisms . Biodegradation , 1 : 79 – 92 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Kanaly , R. A. and Harayama , S. 2000 . Biodegradation of high-molecular-weight polycyclic aromatic hydrocarbons by bacteria . J. Bacteriol. , 182 : 2059 – 2067 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Gibson , D. T. and Subramanian , V. 1984 . “ Microbial degradation of the aromatic hydrocarbons ” . In Microbial Degradation of Organic Compounds , Edited by: Gibson , D. T. 181 – 252 . New York : Marcel Dekker .
   Google Scholar
• Cheng , Q. , Thomas , S. M. and Rouvière , P. 2002 . Biological conversion of cyclic alkanes and cyclic alcohols into dicarboxylic acids: Biochemical and molecular basis . Appl. Microbiol. Biotechnol. , 58 : 704 – 711 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMedGoogle Scholar
• Trudgill , P. W. 1984 . “ Microbial degradation of the alicyclic ring ” . In Microbial Degradation of Organic Compounds , Edited by: Gibson , D. T. 131 – 180 . New York : Marcel Dekker .
   Google Scholar
• Perry , J. J. 1984 . “ Microbial metabolism of cyclic alkanes ” . In Petroleum Microbiology , Edited by: Atlas , R. M. 61 – 97 . New York : Macmillan Publishing Co. .
   Google Scholar
• Atlas , R. M. 1981 . Microbial degradation of petroleum hydrocarbons: An environmental perspective . Microbiol. Rev. , 45 : 180 – 209 . [PUBMED] [INFOTRIEVE]
   PubMedGoogle Scholar
• Beam , H. W. and Perry , J. J. 1974 . Microbial degradation of cycloparaffinic hydrocarbons via co-metabolism and commensalism . J. Gen. Microbiol. , 82 : 163 – 169 .
   Google Scholar
• Hou , C. T. 1982 . “ Microbial transformation of important industrial hydrocarbons ” . In Microbial Transformations of Bioactive Compounds , Edited by: Rosazza , J. P. Vol. 1 , 81 – 107 . Boca Raton, FL : CRC Press .
   Google Scholar
• Stirling , L. A. , Watkinson , R. J. and Higgins , I. J. 1977 . Microbial metabolism of alicyclic hydrocarbons: Isolation and properties of a cyclohexane-degrading bacterium . J. Gen. Microbiol. , 99 : 119 – 125 . [CSA]
   Google Scholar
• Anderson , M. S. , Hall , R. A. and Griffin , M. 1980 . Microbial metabolism of alicyclic hydrocarbons: Cyclohexane catabolism by a pure strain of Pseudomonas sp . J. Gen. Microbiol. , 120 : 89 – 94 .
   Google Scholar
• Johnson , F. H. , Goodale , W. T. and Turkevich , J. 1942 . The bacterial oxidation of hydrocarbons . J. Cell Comp. Physiol. , 19 : 163 – 172 .
   Google Scholar
• Huesemann , M. H. , Hausmann , T. S. and Fortman , T. J. 2003 . Biodegradation of hopane prevents use as a conservative biomarker during bioremediation of PAHs in petroleum contaminated soils . Bioremed. J. , 7 : 111 – 117 . [CSA]
   Google Scholar
• Rios-Hernandez , L. A. , Gieg , L. M. and Suflita , J. M. 2003 . Biodegradation of an alicyclic hydrocarbon by a sulfate-reducing enrichment from a gas-condensate-contaminated aquifer . Appl. Environ. Microbiol. , 69 : 434 – 443 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMed Web of Science ®Google Scholar
• Wyndham , R. C. and Costerton , J. W. 1981 . In vitro microbial degradation of bituminous hydrocarbons and in situ colonization of bitumen surfaces within the Athabasca oil sands deposit . Appl. Environ. Microbiol. , 41 : 791 – 800 . [CSA]
   PubMed Web of Science ®Google Scholar
• Gilbert , P. D. and Higgens , I. J. 1978 . The microbial degradation of crude mineral oils at sea . J. Gen. Microbiol. , 108 : 63 – 70 .
   Google Scholar
• Ait-Langomazino , N. , Sellier , R. , Jouquet , G. and Trescinski , M. 1991 . Microbial degradation of bitumen . Experentia , 47 : 533 – 539 .
   Google Scholar
• Liber , M. F. , Sellier , R. , Jouquet , G. , Trescinki , M. and Spor , H. Effects of microorganism growth on the long-term stability of cement and bitumen . Materials Research Society Symposium Proceedings . 1993 . pp. 267 – 272 . 294 (Scientific Basis for Nuclear Waste Management XVI)
   Google Scholar
• Lin , L. H. , Micheal , G. E. , Kovachev , G. , Zhu , H. , Philp , R. P. and Lewis , C. A. 1989 . Biodegradation of tar-sand bitumens from Ardmore and Anadarko Basins, Carter County, Oklahoma . Org. Geochem. , 14 : 511 – 523 . [CROSSREF]
   Google Scholar
• Cyr , T. D. and Strausz , O. P. 1983 . The structure of tricyclic terpenoid carboxylic acids and their parent alkanes in the Alberta oil sands . J. Chem. Soc. Chem. Commun. , : 1028 – 1030 . [CROSSREF]
   Google Scholar
• Koike , L. , Rebouças , L. M.C. , Reis , F. D.A. , Marsaioli , A. J. , Richnow , H. H. and Michaelis , W. 1992 . Naphthenic acids from crude oils of Campus Basin . Org. Geochem. , 18 : 851 – 860 . [CROSSREF] [CSA]
   Web of Science ®Google Scholar
• Cyr , T. D. and Strausz , O. P. 1984 . Bound carboxylic acids in the Alberta Oil Sands . Org. Geochem. , 7 : 127 – 140 . [CROSSREF]
   Google Scholar
• Meridith , W. , Kellend , S. J. and Jones , D. M. 2000 . Influence of biodegradation on crude oil acidity and carboxylic acid composition . Org. Geochem. , 31 : 1059 – 1073 . [CROSSREF] [CSA]
   Google Scholar
• Alexander , M. 1999 . Biodegradation and Bioremediation, , 2nd Ed , 453 pp San Diego : Academic Press .
   Google Scholar
• Herman , D. C. , Fedorak , P. M. and Costerton , J. W. 1993 . Biodegradation of cycloalkane carboxylic acids in oil sand tailings . Can. J. Microbiol. , 39 : 576 – 580 . [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Seifert , W. K. 1975 . “ Carboxylic acids in petroleum and sediments ” . In Progress in the Chemistry of Organic Natural Products , Vol. 32 , 1 – 49 . Berlin, , Germany : Springer-Verlag .
   Google Scholar
• Herman , D. C. , Fedorak , P. M. , Mackinnon , M. D. and Costerton , J. W. 1994 . Biodegradation of napthenic acids by microbial populations indigenous to oil sands tailings . Can. J. Microbiol. , 40 : 467 – 477 . [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Taylor , D. G. and Trudgill , P. W. 1978 . Metabolsim of cyclohexane carboxylic acid by Alcaligenes strain W1 . J. Bacteriol. , 134 : 410 – 411 .
   Web of Science ®Google Scholar
• Blakley , E. R. 1974 . The microbial degradation of cyclohexanecarboxylic acid: A pathway involving aromatization to form p-hydroxybenzoic acid . Can. J. Microbiol. , 20 : 1297 – 1306 .
   Web of Science ®Google Scholar
• Kaneda , T. 1974 . Enzymatic aromatization of 4-ketocycohexanecarboxylic acid to p-hydroxybenzoic acid . Biochem. Biophys. Res. Comm. , 58 : 140 – 144 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Smith , D. I. and Callely , A. G. 1975 . The microbial degradation of cyclohexane carboxylic acid . J. Gen. Microbial. , 91 : 210 – 212 .
   PubMedGoogle Scholar
• Dutta , T. K. and Harayama , S. 2001 . Biodegradation of n-alkylcycloalkanes and n-alkylbenzenes via new pathways in Alcanivorax sp . strain MBIC 4326. Appl. Environ. Microbiol. , 67 : 1970 – 1974 . [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Rontani , J.-F. and Bonin , P. 1992 . Utilization of n-alkyl-substituted cyclohexanes by a marine alcaligens . Chemosphere , 24 : 1441 – 1446 . [CROSSREF]
   Web of Science ®Google Scholar
• Beam , H. W. and Perry , J. J. 1974 . Microbial degradation and assimilation of n-alkyl-substituted cycloparaffins . J. Bacteriol. , 118 : 394 – 399 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Schumacher , J. D. and Fakoussa , R. M. 1999 . Degradation of alicyclic molecules by Rhodococcus ruber CD4 . Appl. Microbiol. Biotechnol. , 52 : 85 – 90 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMedGoogle Scholar
• Davis , J. B. and Raymond , R. L. 1961 . Oxidation of alkyl-substituted cyclic hydrocarbons by a Norcardia during growth on n-alkane . Appl. Microbiol. , 9 : 383 – 388 . [PUBMED] [INFOTRIEVE]
   PubMedGoogle Scholar
• Feinberg , E. I. , Ramage , P. I.N. and Trudgill , P. W. 1980 . The degradation of n-alkylcycloalkanes by a mixed bacterial culture . J. Gen. Microbiol. , 121 : 507 – 511 . [CSA]
   Google Scholar
• Marchal , R. , Penet , S. , Solano-Serena , F. and Vandecasteele , J. P. 2003 . Gasoline and diesel oil biodegradation . Oil Gas Sci. Technol. , 58 : 441 – 448 . [CSA]
   Web of Science ®Google Scholar