Detecting naphthenic acids in waters by gas chromatography–mass spectrometry

Merlin, Mireya; Guigard, Selma E.; Fedorak, Phillip M.

doi:10.1016/j.chroma.2006.11.089

Cited by 49 publications

(31 citation statements)

References 15 publications

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“…1 A) the remaining NAs were those with n from 9 to 21 and Z values from 0 (acyclic) to À12 (hexacyclic). Analyzing the distribution of NAs in raw OSPW, the most representative NAs were those with n from 12 to 19 and Z values from À4 (bicyclic) to À12 (hexacyclic), similar to other reports (Merlin et al, 2007).…”

Section: Naphthenic Acidsmentioning

confidence: 80%

The impact of various ozone pretreatment doses on the performance of endogenous microbial communities for the remediation of oil sands process-affected water

Dong

Zhang

Islam

et al. 2015

International Biodeterioration & Biodegradation

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Section: Naphthenic Acidsmentioning

confidence: 80%

The impact of various ozone pretreatment doses on the performance of endogenous microbial communities for the remediation of oil sands process-affected water

Dong

Zhang

Islam

et al. 2015

International Biodeterioration & Biodegradation

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“…The possibility that NAs or OSPW-OF may affect the immune system of vertebrates, as suggested by previous studies (Gentes et al, 2007b;van den Heuvel et al, 2000), prompted us to compare the effects of C-NAs and OSPW-OF on mammalian immunity. We compared the effects of a commercial NA preparation widely used in OSPW-related research (Merichem Chemicals and Refinery Services; Bataineh et al, 2006;Biryukova et al, 2007;Clemente et al, 2004;Edge et al, 2010;Grewer et al, 2010;Han et al, 2008;Merlin et al, 2007;Young et al, 2007: Clemente et al, 2003 to OSPW-OF administered to mice at the same NA concentrations. Looking specifically at proinflammatory immune mechanisms, we demonstrated that C-NAs and OSPW-OF have very different effects on both the proinflammatory gene expression in various organs and phagocytosis of peritoneal macrophages.…”

Section: Discussionmentioning

confidence: 99%

“…To evaluate whether C-NAs are an adequate model to study OSPW immuno-toxicity in complex organisms, we analyzed the effects of C-NAs and the extractable OSPW-OF on mice proinflammatory immune response. We compared the effects of a commercial NA preparation widely used in OSPW-related studies (Merichem Chemicals and Refinery Services; Bataineh et al, 2006;Biryukova et al, 2007;Clemente et al, 2003Clemente et al, , 2004Edge et al, 2010;Grewer et al, 2010;Han et al, 2008;Merlin et al, 2007;Young et al, 2007Young et al, , 2008 to OSPW-OF administered to mice at the same NA doses. We analyzed the expression of several pro-inflammatory genes in different organs, and phagocytosis by peritoneal macrophages.…”

Section: Introductionmentioning

confidence: 99%

Commercial naphthenic acids and the organic fraction of oil sands process water induce different effects on pro‐inflammatory gene expression and macrophage phagocytosis in mice

García‐García

Pun

Hodgkinson

et al. 2011

J of Applied Toxicology

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Naphthenic acids (NAs) are believed to be the major toxic component of oil sands process water (OSPW). Different OSPW preparations have distinct NA compositions, and additional organics, that differ from the commercial NAs (C-NAs) often used for toxicology studies. To evaluate whether C-NAs are an adequate model to study OSPW toxicity in complex organisms, we compared the effects of C-NAs and the extractable organic fraction of OSPW (OSPW-OF) on mice immune mechanisms. Mice were orally exposed to different C-NA doses, or OSPW-OF at the same NA dose, for up to 8 weeks, and the expression of pro-inflammatory genes in different organs was determined using quantitative PCR. C-NAs and OSPW-OF altered the expression of pro-inflammatory genes, inducing either expression down-regulation or up-regulation, depending on the organ examined and time after exposure. The time at which gene expression alterations occurred, and the specific sets of genes whose expression was altered, were very different between animals exposed to C-NAs or to OSPW-OF. We evaluated the ability of mouse peritoneal macrophages to phagocytose yeast cell wall, as a measure of the ability of mice to mount a central function of the innate immune response. Phagocytosis was significantly reduced in animals exposed to C-NAs, but enhanced in mice exposed to OSPW-OF. Our results indicate that studies using C-NAs may not necessarily reflect the possible effects induced in animals by process water from tailing ponds.

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“…However, interpretation of the electron impact mass spectra may still be the limiting factor in the structural characterisation of individual NA isomers by such methods. More recently, Merlin et al 22. reported a procedure that included liquid‐liquid extraction, cleanup, and derivatisation to form tert ‐butyldimethylsilyl esters prior to GC/MS using low‐ and high‐resolution MS to detect the ion C 15 H 27 O 2 Si + (nominal m/z = 267) as an indicator of naphthenic acids at concentrations ≥10 µg L −1 and Young et al 23.…”

mentioning

confidence: 99%

A derivatisation and liquid chromatography/electrospray ionisation multistage mass spectrometry method for the characterisation of naphthenic acids

Smith

Rowland

2008

Rapid Comm Mass Spectrometry

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Naphthenic acids (NAs) are partially uncharacterised complex mixtures of carboxylic acids, resulting from the microbial oxidation of petroleum hydrocarbons. They are associated with the fouling of pipelines and process equipment in oil production and with corrosion in oil refineries. As by-products of the rapidly expanding oil (tar) sands industries, NAs are also pollutants and have proved to be toxic to a range of organisms. They also have important beneficial uses as fungicides, tyre additives and, paradoxically, also in the manufacture of corrosion inhibitors. These features make the characterisation of NAs an important goal for analytical chemists. Here we describe the synthesis of amide derivatives of NAs for characterisation by liquid chromatography/electrospray ionisation multistage mass spectrometry (LC/ESI-MS(n)). The method was applied to commercially available carboxylic acids, novel synthetic NAs, commercial NAs refined from crude oils, crude oil NAs and Athabasca oil sands NAs. In addition to confirming the number of alicyclic rings and length of alkyl side chain substituents (confirming information from existing methods), the MS(n) results provided further structural information. Most important of these was the finding that bi- to polycyclic acids containing ethanoate side chains, in addition to alkyl substituents, were widespread amongst the oil and oil sands NAs. The latter NAs are known end members of the beta-oxidation of NAs with even carbon number alkanoate chains. Since such NA mixtures are toxic, they should be targets for bioremediation. Bioremediation of NAs can also be monitored better by application of the methods described herein.

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Detecting naphthenic acids in waters by gas chromatography–mass spectrometry

Cited by 49 publications

References 15 publications

The impact of various ozone pretreatment doses on the performance of endogenous microbial communities for the remediation of oil sands process-affected water

The impact of various ozone pretreatment doses on the performance of endogenous microbial communities for the remediation of oil sands process-affected water

Commercial naphthenic acids and the organic fraction of oil sands process water induce different effects on pro‐inflammatory gene expression and macrophage phagocytosis in mice

A derivatisation and liquid chromatography/electrospray ionisation multistage mass spectrometry method for the characterisation of naphthenic acids

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