Advertisement

Environmental Earth Sciences

, 76:828 | Cite as

Profiling of dissolved organic compounds in the oil sands region using complimentary liquid–liquid extraction and ultrahigh resolution Fourier transform mass spectrometry

  • Yi Yi
  • Jun Han
  • S. Jean Birks
  • Christoph H. Borchers
  • John J. Gibson
Original Article

Abstract

Understanding and characterizing organics in aquatic environments is a great challenge for environmental monitoring, especially for the oil sands industry due to the complexity and potential toxicity of dissolved organics in water. To date, significant efforts have been made in investigating the toxicity of naphthenic acids, although other compounds may also contribute to the toxicity of oil sands process-affected water (OSPW). Here, we present a case study showing a systematic approach for profiling the organic composition of OSPW and environmental water samples by concentrating and separating dissolved organics through complementary liquid–liquid extractions followed by positive- or negative-ion mode ultrahigh resolution mass detection. Our comparative investigation shows clear differences in the composition of dissolved organics (homologues particularly) not only between OSPW samples and environmental water samples, but also differences among oil sands operators. Sulfur-containing compounds (especially the SO n classes) appear to have great potential to be used for evaluating the impact of OSPW, while our understanding of oxygen-only containing compounds should not be limited to O2 (i.e., classic naphthenic acids), but rather can be broadened to include many other compound classes (for instance O n , n = 1–9). Systematic profiling of water samples should be more widely implemented for monitoring the origin and transport of organics in aquatic ecosystems of the oil sands development region, northeastern Alberta, Canada.

Keywords

Environmental forensics Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) Oil sands Alberta 

Notes

Acknowledgements

Research funding for sample collection and FTICR-MS measurements was provided by InnoTech Alberta (formerly Alberta Innovates Technology Futures), Alberta Environment and OSRIN (Oil Sands Research Information Network). The University of Victoria—Genome BC Proteomics Centre—is supported by Genome Canada, Genome British Columbia and Genome Alberta through grants for “Science & Technology Innovation Centre (S&TIC)” in proteomics and partially through “The Metabolomics Innovation Centre (TMIC)” in metabolomics. We especially thank Drs. Roger Foxall and Preston McEachern for championing the application of new methods for OSPW tracing, and Dr. Carol E. Parker for helpful comments on an earlier version of this manuscript.

Supplementary material

12665_2017_7161_MOESM1_ESM.docx (150 kb)
Supplementary material 1 (DOCX 150 kb)

References

  1. Altieri KE, Turpin BJ, Seitzinger SP (2009) Composition of dissolved organic nitrogen in continental precipitation investigated by ultra-high resolution FT-ICR mass spectrometry. Environ Sci Technol 43:6950–6955CrossRefGoogle Scholar
  2. Ávila BMF, Vaz BG, Pereira R, Gomes AO, Pereira RCL, Corilo YE, Simas RC, Nascimento HDL, Eberlin MN, Azevedo DA (2012) Comprehensive chemical composition of gas oil cuts using two-dimensional gas chromatography with time-of-flight mass spectrometry and electrospray ionization coupled to Fourier transform ion cyclotron resonance mass spectrometry. Energy Fuels 26:5069–5079CrossRefGoogle Scholar
  3. Barrow MP, Witt M, Headley JV, Peru KM (2010) Athabasca oil sands process water: characterization by atmospheric pressure photoionization and electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. Anal Chem 82:3727–3735CrossRefGoogle Scholar
  4. Barrow MP, Peru KM, Fahlman B, Hewitt LM, Frank RA, Headley JV (2015) Beyond naphthenic acids: environmental screening of water from natural sources and the Athabasca oil sands industry using atmospheric pressure photoionization fourier transform ion cyclotron resonance mass spectrometry. J Am Soc Mass Spectrom 26:1508–1521CrossRefGoogle Scholar
  5. Bataineh M, Scott AC, Fedorak PM, Martin JW (2006) Capillary HPLC/QTOF-MS for characterizing complex naphthenic acid mixtures and their microbial transformation. Anal Chem 78:8354–8361CrossRefGoogle Scholar
  6. Clark KA (1944) Hot-water separation of Alberta bituminous sand. Trans Can Inst Min Metall 47:18Google Scholar
  7. ERCB (2013) Alberta energy reserves 2012 and supply-demand outlook 2013–2022. ERCB, CalgaryGoogle Scholar
  8. Ferguson GP, Rudolph DL, Barker JF (2009) Hydrodynamics of a large oil sand tailings impoundment and related environmental implications. Can Geotech J 46:1446–1460CrossRefGoogle Scholar
  9. Frank RA, Roy JW, Bickerton G, Rowland SJ, Headley JV, Scarlett AG, West CE, Peru KM, Parrott JL, Conly FM, Hewitt LM (2014) Profiling oil sands mixtures from industrial developments and natural groundwaters for source identification. Environ Sci Technol 48:2660–2670CrossRefGoogle Scholar
  10. Gibson JJ, Birks SJ, Moncur M, Yi Y, Tattrie K, Jasechko S, Richardson K, Eby P (2011) Isotopic and geochemical tracers for fingerprinting process-affected waters in the oil sands industry: a pilot study. Oil Sands Research and Information Network, University of Alberta, EdmontonGoogle Scholar
  11. Gibson JJ, Fennell J, Birks J, Yi Y, Moncur MC, Hansen B, Jasechko S (2013) Evidence of discharging saline formation water to the Athabasca River in the oil sands mining region, northern Alberta. Can J Earth Sci 50:1244–1257CrossRefGoogle Scholar
  12. Giesy JP, Anderson JC, Wiseman SB (2010) Alberta oil sands development. P Natl Acad Sci USA 107:951–952CrossRefGoogle Scholar
  13. Gosselin P, Hrudey SE, Naeth MA, Plourde A, Therrien R, van der Karaak G, Xu Z (2010) Environmental and health impacts of Canada’s oil sands industry. Royal Society of Canada, OttawaGoogle Scholar
  14. Grewer DM, Young RF, Whittal RM, Fedorak PM (2010) Naphthenic acids and other acid-extractables in water samples from Alberta: what is being measured? Sci Total Environ 408:5997–6010CrossRefGoogle Scholar
  15. Han J, Danell RM, Patel JR, Gumerov DR, Scarlett CO, Speir JP, Parker CE, Rusyn I, Zeisel S, Borchers CH (2008) Towards high-throughput metabolomics using ultrahigh-field Fourier transform ion cyclotron resonance mass spectrometry. Metabolomics 4:128–140CrossRefGoogle Scholar
  16. Han XM, MacKinnon MD, Martin JW (2009) Estimating the in situ biodegradation of naphthenic acids in oil sands process waters by HPLC/HRMS. Chemosphere 76:63–70CrossRefGoogle Scholar
  17. Han J, Yi Y, Lin K, Birks J, Gibson J, Borchers CH (2016) Molecular profiling of naphthenic acids in technical mixtures and oil sands process water using a polar reversed-phase liquid chromatography-mass spectrometry. Electrophoresis 37(23–24):3089–3100CrossRefGoogle Scholar
  18. Headley JV, McMartin DW (2004) A review of the occurrence and fate of naphthenic acids in aquatic environments. J Environ Sci Health A 39:1989–2010CrossRefGoogle Scholar
  19. Headley JV, Peru KM, Barrow MP, Derrick PJ (2007) Characterization of naphthenic acids from Athabasca oil sands using electrospray ionization: the significant influence of solvents. Anal Chem 79:6222–6229CrossRefGoogle Scholar
  20. Headley JV, Peru KM, Barrow MP (2009) Mass spectrometric characterization of naphthenic acids in environmental samples: a review. Mass Spectrom Rev 28:121–134CrossRefGoogle Scholar
  21. Headley JV, Barrow MP, Peru KM, Fahlman B, Frank RA, Bickerton G, McMaster ME, Parrott J, Hewitt LM (2011) Preliminary fingerprinting of Athabasca oil sands polar organics in environmental samples using electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. Rapid Commun Mass Spectrom 25:1899–1909CrossRefGoogle Scholar
  22. Headley JV, Peru KM, Mohamed MH, Frank RA, Martin JW, Hazewinkel RRO, Humphries D, Gurprasad NP, Hewitt LM, Muir DCG, Lindeman D, Strub R, Young RF, Grewer DM, Whittal RM, Fedorak PM, Birkholz DA, Hindle R, Reisdorph R, Wang X, Kasperski KL, Hamilton C, Woudneh M, Wang G, Loescher B, Farwell A, Dixon DG, Ross M, Pereira ADS, King E, Barrow MP, Fahlman B, Bailey J, McMartin DW, Borchers CH, Ryan CH, Toor NS, Gillis HM, Zuin L, Bickerton G, McMaster M, Sverko E, Shang D, Wilson LD, Wrona FJ (2013a) Chemical fingerprinting of naphthenic acids and oil sands process waters—a review of analytical methods for environmental samples. J Environ Sci Health A 48:1145–1163CrossRefGoogle Scholar
  23. Headley JV, Peru KM, Fahlman B, Colodey A, McMartin DW (2013b) Selective solvent extraction and characterization of the acid extractable fraction of Athabasca oils sands process water by Orbitrap mass spectrometry. Int J Mass Spectrom 345–347:104–108CrossRefGoogle Scholar
  24. Herman DC, Fedorak PM, Mackinnon MD, Costerton JW (1994) Biodegradation of naphthenic acids by microbial-populations indigenous to oil sands tailings. Can J Microbiol 40:467–477CrossRefGoogle Scholar
  25. Holowenko FM, MacKinnon MD, Fedorak PM (2002) Characterization of naphthenic acids in oil sands wastewaters by gas chromatography-mass spectrometry. Water Res 36:2843–2855CrossRefGoogle Scholar
  26. Huang RF, McPhedran KN, Sun N, Chelme-Ayala P, Gamla El-Din M (2016) Investigation of the impact of organic solvent type and solution pH on the extraction efficiency of naphthenic acids from oil sands process-affected water. Chemosphere 146:472–477CrossRefGoogle Scholar
  27. Hughey CA, Hendrickson CL, Rodgers RP, Marshall AG, Qian KN (2001) Kendrick mass defect spectrum: a compact visual analysis for ultrahigh-resolution broadband mass spectra. Anal Chem 73:4676–4681CrossRefGoogle Scholar
  28. Hughey CA, Galasso SA, Zumberge JE (2007) Detailed compositional comparison of acidic NSO compounds in biodegraded reservoir and surface crude oils by negative ion electrospray Fourier transform ion cyclotron resonance mass spectrometry. Fuel 86:758–768CrossRefGoogle Scholar
  29. Kannel PR, Gan TY (2012) Naphthenic acids degradation and toxicity mitigation in tailings wastewater systems and aquatic environments: a review. J Environ Sci Health A 47:1–21CrossRefGoogle Scholar
  30. Kendrick E (1963) A, mass scale based on Ch2 = 14.0000 for high resolution mass spectrometry of organic compounds. Anal Chem 35:2146–2154CrossRefGoogle Scholar
  31. Kind T, Fiehn O (2007) Seven Golden Rules for heuristic filtering of molecular formulas obtained by accurate mass spectrometry. BMC Bioinform 8:105CrossRefGoogle Scholar
  32. Koch BP, Dittmar T, Witt M, Kattner G (2007) Fundamentals of molecular formula assignment to ultrahigh resolution mass data of natural organic matter. Anal Chem 79:1758–1763CrossRefGoogle Scholar
  33. Lee DD (1940) Thermosetting resin reaction product of furtural with an oxy-naphthenic acid. In: Office USP (ed) Standard Oil Co, p 4Google Scholar
  34. Marshall AG, Rodgers RP (2004) Petroleomics: the next grand challenge for chemical analysis. Acc Chem Res 37:53–59CrossRefGoogle Scholar
  35. Marshall AG, Rodgers RP (2008) Petroleomics: chemistry of the underworld. P Natl Acad Sci USA 105:18090–18095CrossRefGoogle Scholar
  36. Martin JW, Han XM, Peru KM, Headley JV (2008) Comparison of high- and low-resolution electrospray ionization mass spectrometry for the analysis of naphthenic acid mixtures in oil sands process water. Rapid Commun Mass Spectrom 22:1919–1924CrossRefGoogle Scholar
  37. Masliyah J, Zhou ZJ, Xu ZH, Czarnecki J, Hamza H (2004) Understanding water-based bitumen extraction from Athabasca oil sands. Can J Chem Eng 82:628–654CrossRefGoogle Scholar
  38. Mazzoleni LR, Ehrmann BM, Shen XH, Marshall AG, Collett JL (2010) Water-soluble atmospheric organic matter in fog: exact masses and chemical formula identification by ultrahigh-resolution Fourier transform ion cyclotron resonance mass spectrometry. Environ Sci Technol 44:3690–3697CrossRefGoogle Scholar
  39. Nyakas A, Han J, Peru KM, Headley JV, Borchers CH (2013) Comprehensive analysis of oil sands processed water by direct-infusion fourier-transform ion cyclotron resonance mass spectrometry with and without offline UHPLC sample prefractionation. Environ Sci Technol 47:4471–4479CrossRefGoogle Scholar
  40. Pereira AS, Bhattacharjee S, Martin JW (2013) Characterization of oil sands process-affected waters by liquid-Chromatography Orbitrap mass spectrometry. Environ Sci Technol 47:5504–5513CrossRefGoogle Scholar
  41. Quagraine EK, Peterson HG, Headley JV (2005) In situ bioremediation of naphthenic acids contaminated tailing pond waters in the Athabasca oil sands region-demonstrated field studies and plausible options: a review. J Environ Sci Health A 40:685–722CrossRefGoogle Scholar
  42. Reinardy HC, Scarlett AG, Henry TB, West CE, Hewitt LM, Frank RA, Rowland SJ (2013) Aromatic naphthenic acids in oil sands process-affected water, resolved by GCxGC-MS, only weakly induce the gene for vitellogenin production in zebrafish (Danio rerio) larvae. Environ Sci Technol 47:6614–6620CrossRefGoogle Scholar
  43. Ross MS, Pereira AS, Fonnell J, Davies M, Johnson J, Sliva L, Martin JW (2012) Quantitative and qualitative analysis of naphthenic acids in natural waters surrounding the Canadian oil sands industry. Environ Sci Technol 46:12796–12805CrossRefGoogle Scholar
  44. Rowland SJ, Scarlett AG, Jones D, West CE, Frank RA (2011) Diamonds in the rough: identification of individual naphthenic acids in oil sands process water. Environ Sci Technol 45:3154–3159CrossRefGoogle Scholar
  45. West CE, Scarlett AG, Tonkin A, O’Carroll-Fitzpatrick D, Pureveen J, Tegelaar E, Gieleciak R, Hager D, Petersen K, Tollefsen KE, Rowland SJ (2014) Diaromatic sulphur-containing ‘naphthenic’ acids in process waters. Water Res 51:206–215CrossRefGoogle Scholar
  46. Woynilowicz D, Severson-Baker C, Raynolds M (2005) Oil sands fever. The environmental implications of Canada’s oil sands rush. The Pembina Institute, CalgaryGoogle Scholar
  47. Yi Y, Gibson JJ, Birks S, Han J, Borchers CH (2014) Comments on “Profiling oil sands mixtures from industrial developments and natural groundwaters for source identification”. Environ Sci Technol 48:11013–11014.  https://doi.org/10.1021/es503498p CrossRefGoogle Scholar
  48. Yi Y, Birks SJ, Cho S, Gibson JJ (2015) Characterization of organic composition in snow and surface waters in the Athabasca Oil Sands Region, using ultrahigh resolution Fourier transform mass spectrometry. Sci Total Environ 518–518:148–158CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2017

Authors and Affiliations

  1. 1.InnoTech AlbertaVancouver Island Technology ParkVictoriaCanada
  2. 2.Department of GeographyUniversity of VictoriaVictoriaCanada
  3. 3.University of Victoria - Genome BC Proteomics CentreVancouver Island Technology ParkVictoriaCanada
  4. 4.InnoTech AlbertaCalgaryCanada
  5. 5.Department of Biochemistry and MicrobiologyUniversity of VictoriaVictoriaCanada
  6. 6.Environmental Monitoring and Science DivisionAlberta Environment and ParksEdmontonCanada

Personalised recommendations