Diamondoid diacids ('O<sub>4</sub>' species) in oil sands process‐affected water

Lengger, Sabine K.; Scarlett, Alan G.; West, Charles E.; Rowland, Steven J.

doi:10.1002/rcm.6729

Cited by 39 publications

(54 citation statements)

References 21 publications

(46 reference statements)

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“…S4(A) (Supporting Information). This spectrum is entirely compatible with that reported in Lengger et al . The closely similar RTs and EI mass spectra of analyte and authentic standard (see Supplementary Figs.…”

Section: Resultssupporting

confidence: 91%

“…Comprehensive two‐dimensional gas chromatography coupled to time‐of‐flight mass spectrometry (GC × GC/TOFMS) has been shown to be a promising tool for resolving individual naphthenic acids in tailings waters and identifying their structures . Previous analyses of OSPW have confirmed the structures of individual naphthenic acids such as diamondoid, tetra‐ and pentacyclic acids on the basis of a comparison with reference standards. In addition, steroidal and diaromatic thiophene acids have been tentatively identified on the basis of their EI mass spectra.…”

mentioning

confidence: 99%

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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

Bowman

Slater

Warren

et al. 2014

Rapid Commun. Mass Spectrom.

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Section: Resultssupporting

confidence: 91%

mentioning

confidence: 99%

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

Bowman

Slater

Warren

et al. 2014

Rapid Commun. Mass Spectrom.

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“…The compounds that were structurally identied by comparison with authentic standards are shown in Fig. 31 Also Xa was present in all samples, and Xb, Xc, Xd were present in all samples from industry B and in most samples from industry A. We identied adamantane acids in all OSPW samples by comparison of spectra and GCÂGC retention times with those of reference compounds 26,31 (Fig.…”

Section: Identied Compoundsmentioning

confidence: 94%

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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“…However, the presence of hydrophilic moieties on the hydrogel surface may enhance the uptake affinity with amphiphilic naphthenate species, according to the “law of matching water affinities” [18]. OSPW is reported to display toxicity [19,20,21,22,23,24] due to the water soluble organic fraction that contains the major persistent toxic constituent, referred to as the NAFCs. NAFCs exhibit chemical stability, surfactant-like properties, persistence in the environment, non-volatility and high viscosity, especially at pH values above the pK a of NAFCs.…”

Section: Introductionmentioning

confidence: 99%

Quaternized Cellulose Hydrogels as Sorbent Materials and Pickering Emulsion Stabilizing Agents

2016

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Quaternized (QC) and cross-linked/quaternized (CQC) cellulose hydrogels were prepared by cross-linking native cellulose with epichlorohydrin (ECH), with subsequent grafting of glycidyl trimethyl ammonium chloride (GTMAC). Materials characterization via carbon, hydrogen and nitrogen (CHN) analysis, thermogravimetric analysis (TGA), and Fourier transform infrared (FTIR)/13C solid state NMR spectroscopy provided supportive evidence of the hydrogel synthesis. Enhanced thermal stability of the hydrogels was observed relative to native cellulose. Colloidal stability of octanol and water mixtures revealed that QC induces greater stabilization over CQC, as evidenced by the formation of a hexane–water Pickering emulsion system. Equilibrium sorption studies with naphthenates from oil sands process water (OSPW) and 2-naphthoxy acetic acid (NAA) in aqueous solution revealed that CQC possess higher affinity relative to QC with the naphthenates. According to the Langmuir isotherm model, the sorption capacity of CQC for OSPW naphthenates was 33.0 mg/g and NAA was 69.5 mg/g. CQC displays similar affinity for the various OSPW naphthenate component species in aqueous solution. Kinetic uptake of NAA at variable temperature, pH and adsorbent dosage showed that increased temperature favoured the uptake process at 303 K, where Qm = 76.7 mg/g. Solution conditions at pH 3 or 9 had a minor effect on the sorption process, while equilibrium was achieved in a shorter time at lower dosage (ca. three-fold lower) of hydrogel (100 mg vs. 30 mg). The estimated activation parameters are based on temperature dependent rate constants, k1, which reveal contributions from enthalpy-driven electrostatic interactions. The kinetic results indicate an ion-based associative sorption mechanism. This study contributes to a greater understanding of the adsorption and physicochemical properties of cellulose-based hydrogels.

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Diamondoid diacids ('O₄' species) in oil sands process‐affected water

Cited by 39 publications

References 21 publications

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

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

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

Quaternized Cellulose Hydrogels as Sorbent Materials and Pickering Emulsion Stabilizing Agents

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Diamondoid diacids ('O4' species) in oil sands process‐affected water

Cited by 39 publications

References 21 publications

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

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

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

Quaternized Cellulose Hydrogels as Sorbent Materials and Pickering Emulsion Stabilizing Agents

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Resources

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Diamondoid diacids ('O₄' species) in oil sands process‐affected water