Distribution of naphthenic acids in tissues of laboratory-exposed fish and in wild fishes from near the Athabasca oil sands in Alberta, Canada

Young, Rozlyn F.; Michel, Lorelei Martínez; Fedorak, Phillip M.

doi:10.1016/j.ecoenv.2010.12.009

Cited by 27 publications

(13 citation statements)

References 27 publications

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“…In general, exposure solutions were prepared on a nominal basis using dilutions of a stock solution. In the few studies that reported measured concentrations of NAs in solution, relatively low analytical recoveries were reported (Peters et al, 2007;Young et al, 2011). Our studies show that exposure solutions prepared using the WAF technique produced consistent concentrations that were stable over time.…”

Section: Aquatic Toxicity Testssupporting

confidence: 54%

Aquatic hazard assessment of a commercial sample of naphthenic acids

Swigert¹,

Lee

Wong

et al. 2015

Chemosphere

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This paper presents chemical composition and aquatic toxicity characteristics of a commercial sample of naphthenic acids (NAs). Naphthenic acids are derived from the refining of petroleum middle distillates and can contribute to refinery effluent toxicity. NAs are also present in oil sands process-affected water (OSPW), but differences in the NAs compositions from these sources precludes using a common aquatic toxicity dataset to represent the aquatic hazards of NAs from both origins. Our chemical characterization of a commercial sample of NAs showed it to contain in order of abundance, 1-ring>2-ring>acyclic>3-ring acids (∼84%). Also present were monoaromatic acids (7%) and non-acids (9%, polyaromatic hydrocarbons and sulfur heterocyclic compounds). While the acyclic acids were only the third most abundant group, the five most abundant individual compounds were identified as C(10-14) n-acids (n-decanoic acid to n-tetradecanoic acid). Aquatic toxicity testing of fish (Pimephales promelas), invertebrate (Daphnia magna), algae (Pseudokirchneriella subcapitata), and bacteria (Vibrio fischeri) showed P. promelas to be the most sensitive species with 96-h LL50=9.0 mg L(-1) (LC50=5.6 mg L(-1)). Acute EL50 values for the other species ranged 24-46 mg L(-1) (EC50 values ranged 20-30 mg L(-1)). Biomimetic extraction via solid-phase-microextraction (BE-SPME) suggested a nonpolar narcosis mode of toxic action for D. magna, P. subcapitata, and V. fischeri. The BE analysis under-predicted fish toxicity, which indicates that a specific mode of action, besides narcosis, may be a factor for fishes.

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Section: Aquatic Toxicity Testssupporting

confidence: 54%

Aquatic hazard assessment of a commercial sample of naphthenic acids

Swigert¹,

Lee

Wong

et al. 2015

Chemosphere

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“…For GC analyses, the amenable NAFCs are generally derivatized to their methyl or tert‐butyldimethylsilyl analogs. Early research with GC‐MS (Headley et al, , ; Young, Coy, & Fedorak ; Young, Michel, & Fedorak ) paved the way for the extensive applications (Shepherd et al, ) of two‐dimensional GC‐MS, sometimes known as GCxGC MS or 2D‐GC‐MS, which had its first application to oil sands naphthenic acids in 2005 (Hao et al, ). Rowland et al have published a number of papers on the application of 2D‐GC‐MS to the characterization of NAFCs in OSPW (Rowland et al, 2011a–c; Jones et al, ).…”

Section: Advances In Methods For Analysis Of Nafcs With Mass Spectrommentioning

confidence: 99%

Advances in mass spectrometric characterization of naphthenic acids fraction compounds in oil sands environmental samples and crude oil—A review

Headley

Peru

Barrow

2015

Mass Spectrometry Reviews

158

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There has been a recent surge in the development of mass spectrometric methods for detailed characterization of naphthenic acid fraction compounds (all C(c)H(h)N(n)O(o)S(s), species, including heteroatomic and aromatic components in the acid-extractable fraction) in environmental samples. This surge is driven by the increased activity in oil sands environmental monitoring programs in Canada, the exponential increase in research studies on the isolation and toxicity identification of components in oil sands process water (OSPW), and the analytical requirements for development of technologies for treatment of OSPW. There has been additional impetus due to the parallel studies to control corrosion from naphthenic acids during the mining and refining of heavy bitumen and crude oils. As a result, a range of new mass spectrometry tools have been introduced since our last major review of this topic in 2009. Of particular significance are the developments of combined mass spectrometric methods that incorporate technologies such as gas chromatography, liquid chromatography, and ion mobility. There has been additional progress with respect to improved visualization methods for petroleomics and oil sands environmental forensics. For comprehensive coverage and more reliable characterization of samples, an approach based on multiple-methods that employ two or more ionization modes is recommended. On-line or off-line fractionation of isolated extracts, with or without derivatization, might also be used prior to mass spectrometric analyses. Individual ionization methods have their associated strengths and weaknesses, including biases, and thus dependence upon a single ionization method is potentially misleading. There is also a growing trend to not rely solely on low-resolution mass spectrometric methods (<20,000 resolving power at m/z 200) for characterization of complex samples. Future research is anticipated to focus upon (i) structural elucidation of components to determine the correlation with toxicity or corrosion, (ii) verification of characterization studies based on authentic reference standards and reference materials, and (iii) integrated approaches based on multiple-methods and ionization methods for more-reliable oil sands environmental forensics.

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“…Most previous in vivo bioconcentration studies with OSPW have focused only on naphthenic acids, since these were previously assumed to be major contributors to toxicity of OSPW. , An effects-directed analysis study recently confirmed that naphthenic acids are a major cause of the acute toxicity, but that other polar neutral substances containing nitrogen and oxygen (NO + empirical formula class) and sulfur and oxygen (SO + empirical formula class) also contributed . Naphthenic acids have been detected in tissues of rainbow trout fingerlings exposed to OSPW, and also in tissues of wild fishes collected from rivers near oil sands deposits. , On the basis of muscle of rainbow trout ( Oncorhynchus mykiss ) that had been exposed to a commercial mixture of naphthenic acids, the BCF of one species of naphthenic acid with 13 carbons and 3 double bond equivalents (DBE) (C 13 H 22 O 2 ) was estimated to be approximately 2 at pH 8.2, and approximately 4 at pH 7.6. , However, the D OW for naphthenic acids increases with number of carbons and decreases with increasing DBE . Thus, data for a single naphthenic acid species is insufficiently informative, and a more detailed in vivo study of bioconcentration is needed to assess the accumulation potential for the wide range of organic chemical species in authentic OSPW.…”

Section: Introductionmentioning

confidence: 99%

Bioconcentration of Dissolved Organic Compounds from Oil Sands Process-Affected Water by Medaka (Oryzias latipes): Importance of Partitioning to Phospholipids

Zhang

Wiseman

Giesy

et al. 2016

Environ. Sci. Technol.

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The complex mixture of dissolved organics in oil sands process-affected water (OSPW) is acutely lethal to fish at environmentally relevant concentrations, but few bioconcentration factors (BCFs) have been measured for its many chemical species. Japanese medaka (Oryzias latipes) were exposed to 10% OSPW, and measured BCFs were evaluated against predicted BCFs from octanol-water distribution ratios (DOW) and phospholipid membrane-water distribution ratios (DMW). Two heteroatomic chemical classes detected in positive ion mode (SO(+), NO(+)) and one in negative mode (O2(-), also known as naphthenic acids) had the greatest DMW values, as high as 10 000. Estimates of DMW were similar to and correlated with DOW for O(+), O2(+), SO(+), and NO(+) chemical species, but for O2(-) and SO2(-) species the DMW values were much greater than the corresponding DOW, suggesting the importance of electrostatic interactions for these ionizable organic acids. Only SO(+), NO(+), and O2(-) species were detectable in medaka exposed to OSPW, and BCFs for SO(+) and NO(+) species ranged from 0.6 to 28 L/kg, lower than predicted (i.e., 1.4-1.7 × 10(3) L/kg), possibly because of biotransformation of these hydrophobic substances. BCFs of O2(-) species ranged from 0.7 to 53 L/kg, similar to predicted values and indicating that phospholipid partitioning was an important bioconcentration mechanism.

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Distribution of naphthenic acids in tissues of laboratory-exposed fish and in wild fishes from near the Athabasca oil sands in Alberta, Canada

Cited by 27 publications

References 27 publications

Aquatic hazard assessment of a commercial sample of naphthenic acids

Aquatic hazard assessment of a commercial sample of naphthenic acids

Advances in mass spectrometric characterization of naphthenic acids fraction compounds in oil sands environmental samples and crude oil—A review

Bioconcentration of Dissolved Organic Compounds from Oil Sands Process-Affected Water by Medaka (Oryzias latipes): Importance of Partitioning to Phospholipids

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