Analysis of ‘ARN’ naphthenic acids by high temperature gas chromatography and high performance liquid chromatography

Smith, Ben; Sutton, Peter G.; Lewis, C.A.; Dunsmore, Braden; Fowler, G.D.; Krane, Jostein; Lutnæs, Bjart Frode; Brandal, Øystein; Sjöblom, Johan; Rowland, Steven J.

doi:10.1002/jssc.200600266

Cited by 47 publications

(58 citation statements)

References 7 publications

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“…Positive ion ESI mass spectra of the tetramethyl esters of the C 80 hexacyclic acid regioisomeric mixture obtained under conditions which produced sodiated molecules [M + Na] + have been published previously 1, 4. However, under the conditions used herein, positive ion ESI mass spectra of tetramethyl esters produced ammoniated molecules [M + NH 4 ] + (Fig.…”

Section: Resultsmentioning

confidence: 71%

“…2). Mass spectrometric analysis was conducted on the regioisomeric mixtures of each of the purified C 80 acids obtained from a North Sea oil pipeline deposit 4. Several previously unreported acids were also isolated by HPLC 4 in semi‐pure state and brief details of the spectra are also reported.…”

Section: Resultsmentioning

confidence: 99%

“…Up to hundreds of milligrams of regioisomeric mixtures of each of the purified C 80 tetracyclic to hexacyclic acids as tetramethyl esters were isolated from a deposit from a North Sea oilfield by repetitive preparative high ‐ performance liquid chromatography (HPLC) as reported previously 4. The free acids were prepared by saponification of the esters followed by acidification and extraction.…”

Section: Methodsmentioning

confidence: 99%

“…For stable isotope MS, aliquots of eight replicate samples of 0.4 to 1.3 mg of mixtures of the C 80:4,5,6 free acids prepared by saponification and extraction of the semi‐pure4 ‘straw‐coloured esters’ were weighed into tin capsules and analysed using a ThermoFinnigan Delta Plus XP mass spectrometer (Thermo Fisher, Bremen, Germany) connected to a ECS 4010 elemental analyser (Costech, Milan, Italy). These analyses were run as part of a 12 h analytical experiment with three in‐house lab standards analysed every ten samples to allow for correction of instrumental drift and linearity effects.…”

Section: Methodsmentioning

confidence: 99%

“…The identification by nuclear magnetic resonance spectroscopy and mass spectrometry1 of unusual C 80‐82 polycyclic tetracarboxylic acids (coined ‘ARN’ acids), probably originating from Archaea, in solid deposits in some oilfield pipelines and oil processing equipment has proved to be an important step forward in understanding the nature of the deposits 2–6. However, mass spectrometric methods are probably the most useful for routine analysis of oils and deposits containing the acids, which is necessary because of the commercial costs associated with operating oilfields where oil flow assurance is interrupted by deposit formation.…”

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confidence: 99%

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Mass spectrometry of polycyclic tetracarboxylic ('ARN') acids and tetramethyl esters

Sutton

Smith²,

Rowland

2010

Rapid Commun. Mass Spectrom.

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Polycyclic C(80) tetracarboxylic (so-called 'ARN') acids are found as calcium salts in deposits which form in certain oilfield pipelines and equipment. Characterisation of these acids is important for improving the prediction and hence avoidance or minimisation of oilfield deposition problems. Although several of the acids have been isolated and characterised (as regioisomeric mixtures) by nuclear magnetic resonance spectroscopy, mass spectrometric methods are likely to be much more useful for the routine analysis of oils and deposits containing the acids. A publication summarising the mass spectra of the purified acids and major derivatives might thus be a very useful source of reference for scientists and technologists studying these unusual compounds. We now report the characterisation of several of the purified acids and of the tetramethyl esters by electrospray ionisation mass spectrometry (ESI-MS) in both positive ion and negative ion modes, by multistage ESI-MS with a suggested rationalisation of the ions produced, by positive ion atmospheric solids analysis probe (ASAP) atmospheric pressure chemical ionisation (APCI), and by positive ion electron ionisation (EI)-MS. Tentative identifications of C(80) acyclic, mono-, bi- and tricylic tetraacids and the δ(13)C isotope values of a mixture of the semi-pure acids determined by MS are also reported for the first time.

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Section: Resultsmentioning

confidence: 71%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Mass spectrometry of polycyclic tetracarboxylic ('ARN') acids and tetramethyl esters

Sutton

Smith²,

Rowland

2010

Rapid Commun. Mass Spectrom.

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Analysis of naphthenic acids in produced water samples by capillary electrophoresis‐mass spectrometry

Pinheiro

Sako

Rodrigues

et al. 2023

J of Separation Science

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A capillary electrophoresis‐mass spectrometry method was used to analyze naphthenic acids in produced water samples. It was possible to detect cyclopentanecarboxylic, benzoic, cyclohexanebutyric, 1‐naphthoic, decanoic, 3,5‐dimethyladamantane‐1‐carboxylic, 9‐anthracenecarboxylic, and pentadecanoic acids within ca. 13 min using a buffer composed of 40 mmol/L ammonium hydroxide, 32 mmol/L acetic acid and 20% v/v isopropyl alcohol, pH 8.6. The proposed method showed good repeatability, with relative standard deviation (RSD) values of 6.6% for the sum of the peak areas and less than 2% for the analysis time. In the interday analysis, the RSD values for the sum of the peak areas and migration time were 10.3% and 10%, respectively. The developed method demonstrated linear behavior in the concentration range between 5 and 50 mg/L for benzoic, decanoic, 3,5‐dimethyladamantane‐1‐carboxylic and 9‐anthracenecarboxylic acids, and between 10 and 50 mg/L for cyclopentanecarboxylic, cyclohexanebutyric, 1‐ naphthoic, and pentadecanoic acids. The detection limits values ranged from 0.31 to 1.64 mg/L. Six produced water samples were analyzed and it was possible to identify and quantify cyclopentanecarboxylic, benzoic, cyclohexanebutyric, and decanoic acids. The concentrations varied between 4.8 and 98.9 mg/L, proving effective in the application of complex samples.

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Mass spectrometric characterization of naphthenic acids in environmental samples: A review

Headley

Peru

Barrow

2008

Mass Spectrometry Reviews

151

124

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There is a growing need to develop mass spectrometric methods for the characterization of oil sands naphthenic acids (structural formulae described by C(n)H(2n+z)O(2) where n is the number of carbon atoms and "z" is referred to as the "hydrogen deficiency" and is equal to zero, or is a negative, even integer) present in environmental samples. This interest stems from the need to better understand their contribution to the total acid number of oil sands acids; along with assessing their toxicity in aquatic environments. Negative-ion electrospray ionization has emerged as the analytical technique of choice. For infusion samples, matrix effects are particularly evident for quantification in the presence of salts and co-elutants. However, such effects can be minimized for methods that employ chromatographic separation prior to mass spectrometry (MS) detection. There have been several advances for accurate identification of classes of naphthenic acid components that employ a range of MS hyphenated techniques. General trends measured for degradation of the NAs in the environment appear to be similar to those obtained with either low- or high-resolution MS. Future MS research will likely focus on (i) development of more reliable quantitative methods that use chromatography and internal standards, (ii) the utility of representative model naphthenic acids as surrogates for the complex NA mixtures, and (iii) development of congener-specific analysis of the principal toxic components.

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Analysis of ‘ARN’ naphthenic acids by high temperature gas chromatography and high performance liquid chromatography

Cited by 47 publications

References 7 publications

Mass spectrometry of polycyclic tetracarboxylic ('ARN') acids and tetramethyl esters

Mass spectrometry of polycyclic tetracarboxylic ('ARN') acids and tetramethyl esters

Analysis of naphthenic acids in produced water samples by capillary electrophoresis‐mass spectrometry

Mass spectrometric characterization of naphthenic acids in environmental samples: A review

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