Fractionation of oil sands-process affected water using pH-dependent extractions: A study of dissociation constants for naphthenic acids species

Chemosphere

Volumn 127, Issue , 2015, Pages 291-296

  Huang, Rongfu ^a   Sun, Nian ^a   Chelme Ayala, Pamela ^a   McPhedran, Kerry N ^a   Changalov, Mohamed ^a   Gamal El Din, Mohamed ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Dissociation constant; Naphthenic acids; Oil sands process affected water; PH fractionation; Ultra performance liquid chromatography time of flight mass spectrometry

Indexed keywords

DISSOCIATION; ESTIMATION; LIQUID CHROMATOGRAPHY; LIQUIDS; MASS SPECTROMETRY; NAPHTHAS; OIL SANDS; ORGANIC ACIDS;

DISSOCIATION CONSTANT; ELECTRON WITHDRAWING GROUP; LIQUID-LIQUID EXTRACTION PROCESS; NAPHTHENIC ACID; OIL SANDS PROCESS-AFFECTED WATERS; PHYSICOCHEMICAL PARAMETERS; RELATIVE QUANTIFICATION; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

EXTRACTION;

ACID; NAPHTHENIC ACID; ORGANIC MATTER; OXYGEN; OZONE; UNCLASSIFIED DRUG; WATER; CARBOXYLIC ACID; WASTE WATER; WATER POLLUTANT;

ESTIMATION METHOD; FRACTIONATION; NAPHTHALENE; NUMERICAL MODEL; OIL SAND; PH; PHASE EQUILIBRIUM; PHYSICOCHEMICAL PROPERTY; WATER TREATMENT;

ACID DISSOCIATION CONSTANT; ARTICLE; ELECTRON TRANSPORT; FRACTIONATION; LIQUID LIQUID EXTRACTION; MATHEMATICAL MODEL; OXIDATION; PH; PHYSICAL CHEMISTRY; PKA; QUANTITATIVE ANALYSIS; TAR SAND; TIME OF FLIGHT MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ANALYSIS; CANADA; CHEMISTRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OIL AND GAS FIELD; PROCEDURES; WASTE WATER; WATER MANAGEMENT; WATER POLLUTANT;

CANADA; CARBOXYLIC ACIDS; CHEMICAL FRACTIONATION; CHROMATOGRAPHY, LIQUID; HYDROGEN-ION CONCENTRATION; LIQUID-LIQUID EXTRACTION; MASS SPECTROMETRY; OIL AND GAS FIELDS; WASTE WATER; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

EID: 84924763656     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2014.11.041     Document Type: Article

References (25)

1. Babic S., Horvat A.J.M., Pavlovic D.M., Kastelan-Macan M. Determination of pK(a) values of active pharmaceutical ingredients. Trac. - Trend Anal. Chem. 2007, 26:1043-1061.
2. Bruice P.Y. Organic Chemistry 2004, Prentice Hall, Upper Saddle River, NJ. fourth ed.
3. Faust S.D., Aly O.M. Chemistry of Water Treatment 1998, CRC, Boca Raton, FL. second ed.
4. Gamal El-Din M., Fu H., Wang N., Chelme-Ayala P., Perez-Estrada L., Drzewicz P., Martin J.W., Zubot W., Smith D.W. Wastewater treatment: naphthenic acids speciation and removal during petroleum-coke adsorption and ozonation of oil sands process wastewater. Sci. Total Environ. 2011, 409:5119-5125.
5. Grbovic L., Pavlovic K., Prekodravac B., Kuhajda K., Kevresan S., Popsavin M., Milic J., Cirin-Novta V. Fractionation of complex mixtures of naphthenic acids, their characterization and biological activity. J. Serb. Chem. Soc. 2012, 77:147-157.
6. Grewer D.M., Young R.F., Whittal R.M., Fedorak P.M. Naphthenic acids and other acid-extractables in water samples from Alberta: What is being measured?. Sci. Total Environ. 2010, 408:5997-6010.
7. Hagen M.O., Garcia-Garcia E., Oladiran A., Karpman M., Mitchell S., El-Din M.G., Martin J.W., Belosevic M. The acute and sub-chronic exposures of goldfish to naphthenic acids induce different host defense responses. Aquat. Toxicol. 2012, 109:143-149.
8. Havre T.E., Sjoeblom J., Vindstad J.E. Oil/water-partitioning and interfacial behavior of naphthenic acids. J. Disper. Sci. Technol. 2003, 24:789-801.
9. He Y., Patterson S., Wang N., Hecker M., Martin J.W., El-Din M.G., Giesy J.P., Wiseman S.B. Toxicity of untreated and ozone-treated oil sands process-affected water (OSPW) to early life stages of the fathead minnow (Pimephales promelas). Water Res. 2012, 46:6359-6368.
10. Headley J.V., Peru K.M., McMartin D.W., Winkler M. Determination of dissolved naphthenic acids in natural waters by using negative-ion electrospray mass spectrometry. J. AOAC Int. 2002, 85:182-187.
11. Headley J.V., Peru K.M., Barrow M.P. Mass spectrometric characterization of naphthenic acids in environmental samples: a review. Mass Spectrom. Rev. 2009, 28:121-134.
12. Hoigne J., Bader H. Rate constants of reactions of ozone with organic and inorganic-compounds in water: dissociating organic-compounds. Water Res. 1983, 17:185-194.
13. Hwang G., Dong T., Islam M.S., Sheng Z., Perez-Estrada L.A., Liu Y., Gamal El-Din M. The impacts of ozonation on oil sands process-affected water biodegradability and biofilm formation characteristics in bioreactors. Biores. Technol. 2013, 130:269-277.
14. Kelly E.N., Short J.W., Schindler D.W., Hodson P.V., Ma M., Kwan A.K., Fortin B.L. Oil sands development contributes polycyclic aromatic compounds to the Athabasca River and its tributaries. Proc. Natl. Acad. Sci. 2009, 106:22346-22351.
15. Kim E.-S., Liu Y., Gamal El-Din M. Evaluation of membrane fouling for in-line filtration of oil sands process-affected water: the effects of pretreatment conditions. Environ. Sci. Technol. 2012, 46:2877-2884.
16. Kojima Y., Fukuta T., Yamada T., Onyango M.S., Bernardo E.C., Matsuda H., Yagishita K. Catalytic wet oxidation of o-chlorophenol at mild temperatures under alkaline conditions. Water Res. 2005, 39:29-36.
17. Lengger S.K., Scarlett A.G., West C.E., Rowland S.J. Diamondoid diacids ('O4' species) in oil sands process-affected water. Rapid Comm. Mass Spec. 2013, 27:2648-2654.
18. Mitra S. Sample Preparation Techniques in Analytical Chemistry 2003, Wiley-Interscience, Hoboken, NJ.
19. Pereira A.S., Bhattacharjee S., Martin J.W. Characterization of oil sands process-affected waters by liquid chromatography orbitrap mass spectrometry. Environ. Sci. Technol. 2013, 47:5504-5513.
20. Rowland S.J., West C.E., Jones D., Scarlett A.G., Frank R.A., Hewitt L.M. Steroidal aromatic 'naphthenic acids' in oil sands process-affected water: structural comparisons with environmental estrogens. Environ. Sci. Technol. 2011, 45:9806-9815.
21. Scarlett A.G., Reinardy H.C., Henry T.B., West C.E., Frank R.A., Hewitt L.M., Rowland S.J. Acute toxicity of aromatic and non-aromatic fractions of naphthenic acids extracted from oil sands process-affected water to larval zebrafish. Chemosphere 2013, 93:415-420.
22. Skoog D.A., West D.M., Holler F.J., Crouch S.R. Fundamentals of Analytical Chemistry 2013, Brooks/Cole, Belmont. ninth ed.
23. Wang B., Wan Y., Gao Y., Yang M., Hu J. Determination and characterization of oxy-naphthenic acids in oilfield wastewater. Environ. Sci. Technol. 2013, 47:9545-9554.
24. Wang N., Chelme-Ayala P., Perez-Estrada L., Garcia-Garcia E., Pun J., Martin J.W., Belosevic M., Gamal El-Din M. Impact of ozonation on naphthenic acids speciation and toxicity of oil sands process-affected water to Vibrio fischeri and mammalian immune system. Environ. Sci. Technol. 2013, 47:6518-6526.
25. West C.E., Scarlett A.G., Tonkin A., O'Carroll-Fitzpatrick D., Pureveen J., Tegelaar E., Gieleciak R., Hager D., Petersen K., Tollefsen K.E., Rowland S.J. Diaromatic sulphur-containing 'naphthenic' acids in process waters. Water Res. 2014, 51:206-215.