Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands

Bowman, David; Slater, G. F.; Warren, Lesley A.; McCarry, Brian E.

doi:10.1002/rcm.6996

Cited by 37 publications

(26 citation statements)

References 24 publications

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“…For comparison, (neutral) benzothiophene derivatives would appear at a DBE of 6 or higher (with a carbon number of 8 or higher) and (neutral) dibenzothiophene derivatives would appear at a DBE of 9 or higher (with a carbon number of 12 or higher). Both alkylbenzothiophenes and alkyldibenzothiophenes are soluble in water, as are alkylthiophenes, recently discovered in pore water near a tailings pond [52], highlighting their potential for migration. Figure9 shows the application of PCA to the positive-ion data.…”

Section: Percentage Of Total Intensitymentioning

confidence: 99%

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

Barrow

Peru

Fahlman

et al. 2015

J. Am. Soc. Mass Spectrom.

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There is a growing need for environmental screening of natural waters in the Athabasca region of Alberta, Canada, particularly in the differentiation between anthropogenic and naturally-derived organic compounds associated with weathered bitumen deposits. Previous research has focused primarily upon characterization of naphthenic acids in water samples by negative-ion electrospray ionization methods. Atmospheric pressure photoionization is a much less widely used ionization method, but one that affords the possibility of observing low polarity compounds that cannot be readily observed by electrospray ionization. This study describes the first usage of atmospheric pressure photoionization Fourier transform ion cyclotron resonance mass spectrometry (in both positive-ion and negative-ion modes) to characterize and compare extracts of oil sands process water, river water, and groundwater samples from areas associated with oil sands mining activities. When comparing mass spectra previously obtained by electrospray ionization and data acquired by atmospheric pressure photoionization, there can be a doubling of the number of components detected. In addition to polar compounds that have previously been observed, low-polarity, sulfur-containing compounds and hydrocarbons that do not incorporate a heteroatom were detected. These latter components, which are not amenable to electrospray ionization, have potential for screening efforts within monitoring programs of the oil sands.

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Section: Percentage Of Total Intensitymentioning

confidence: 99%

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

Barrow

Peru

Fahlman

et al. 2015

J. Am. Soc. Mass Spectrom.

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“…[26][27][28][29] This presented an opportunity to apply a proven approach to the challenges associated with the oil sands processing. use of the USEPA 16 PAHs for monitoring hydrocarbon contamination), but until recently this could not be applied to OSPW due to the unresolved nature of the constituents by GC, the unknown composition of individual components and associated lack of authentic reference compounds for comparison.…”

Section: Introductionmentioning

confidence: 99%

Use of the distributions of adamantane acids to profile short-term temporal and pond-scale spatial variations in the composition of oil sands process-affected waters

Lengger

Scarlett

West

et al. 2015

Environ. Sci.: Processes Impacts

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Oil industry produced waters, such as the oils sands process-affected waters (OSPW) of Alberta, Canada, represent a challenge in terms of risk assessment and reclamation due to their extreme complexity, particularly of the organic chemical constituents, including the naphthenic acids (NA). The identification of numerous NA in single samples has raised promise for the use of NA distributions for profiling OSPW. However, monitoring of the success of containment is still difficult, due to the lack of knowledge of the homogeneity (or otherwise) of OSPW composition within, and between, different industry containments. Here we used GC×GC-MS to compare the NA of five OSPW samples from each of two different industries. Short-term temporal and pond-scale spatial variations in the distributions of known adamantane acids and diacids and other unknown tricyclic acids were examined and a statistical appraisal of the replicate data made. The presence/absence of individual acids easily distinguished the OSPW NA of one industry from those of the other. The proportions of tricyclic acids with different carbon numbers also varied significantly between the OSPW of the two industries. The pond-scale spatial variation in NA in OSPW samples was higher than the short-term (2 weeks) temporal variations. An OSPW sample from an aged pond was exceptionally high in the proportion of C15,16,17 compounds, possibly due to increased biotransformation. Such techniques could possibly also help to distinguish different sources of NA in the environment.

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“…Attempts at quantification of the free acids by FTICRMS with a synthesised SO 3 keto acid by standard addition were unsuccessful, but environmental, corrosive or oil flow assurance effects should be easier to assess now that the partial structures are known. The origin of the hydroxy compounds is possibly via further biotransformation (hydroxylation) of the related S‐containing carboxylic acids, identified previously in a less polar fraction [29], cf. [42] …”

Section: Discussionmentioning

confidence: 99%

“…However, a remaining methanol eluate, probably containing more polar compounds, was not examined as these compounds were probably less amenable to GC‐based methods. As more knowledge has at last been obtained about some of the so‐called 'classical' naphthenic acids in OSPW and related samples, (e.g ).…”

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confidence: 99%

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Mass spectral characterisation of a polar, esterified fraction of an organic extract of an oil sands process water

Rowland

Pereira

Martin

et al. 2014

Rapid Comm Mass Spectrometry

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The results suggest the more polar acidic organic SO3 constituents of OSPW include C15-28 S-containing, alicyclic and aromatic hydroxy carboxylic acids. SO5 species are possibly sulphone analogues of these. The origin of such compounds is probably via further biotransformation (hydroxylation) of the related S-containing carboxylic acids identified previously in a less polar OSPW fraction. The environmental risks, corrosivity and oil flow assurance effects should be easier to assess, given that partial structures are now known, although further identification is still needed.

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Identification of individual thiophene-, indane-, tetralin-, cyclohexane-, and adamantane-type carboxylic acids in composite tailings pore water from Alberta oil sands

Abstract: This study underlines the complexity of naphthenic acid isomer distributions in composite tailings and provides a useful inventory of individual acids.

Cited by 37 publications

References 24 publications

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

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

Use of the distributions of adamantane acids to profile short-term temporal and pond-scale spatial variations in the composition of oil sands process-affected waters

Mass spectral characterisation of a polar, esterified fraction of an organic extract of an oil sands process water

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