Anion-exchange chromatography particle beam mass spectrometry for the characterization of aromatic sulfonic acids as the major organic pollutants in leachates from Stringfellow, California

Kim, In Suk; Sasinos, Fassil I.; Stephens, Robert D.; Brown, Mark A.

doi:10.1021/es00082a007

Cited by 37 publications

(19 citation statements)

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“…2) enter the environment in waste streams: chemical synthesis of sulfonates typically give yields of 80–90% with many sulfonates as by‐products [33], and many of these compounds can be detected in e.g. rivers [3]or seepage from waste dumps [34, 35]. In addition, it is clear that some sulfonates in the environment (e.g.…”

Section: Xenobiotic Sulfonates In the Environmentmentioning

confidence: 99%

Microbial desulfonation

Cook¹,

Laue²,

Junker³

1998

FEMS Microbiol Rev

149

106

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Organosulfonates are widespread compounds, be they natural products of low or high molecular weight, or xenobiotics. Many commonly found compounds are subject to desulfonation, even if it is not certain whether all the corresponding enzymes are widely expressed in nature. Sulfonates require transport systems to cross the cell membrane, but few physiological data and no biochemical data on this topic are available, though the sequences of some of the appropriate genes are known. Desulfonative enzymes in aerobic bacteria are generally regulated by induction, if the sulfonate is serving as a carbon and energy source, or by a global network for sulfur scavenging (sulfate-starvation-induced (SSI) stimulon) if the sulfonate is serving as a source of sulfur. It is unclear whether an SSI regulation is found in anaerobes. The anaerobic bacteria examined can express the degradative enzymes constitutively, if the sulfonate is being utilized as a carbon source, but enzyme induction has also been observed. At least three general mechanisms of desulfonation are recognisable or postulated in the aerobic catabolism of sulfonates: (1) activate the carbon neighboring the C-SO3- bond and release of sulfite assisted by a thiamine pyrophosphate cofactor; (2) destabilize the C-SO3- bond by addition of an oxygen atom to the same carbon, usually directly by oxygenation, and loss of the good leaving group, sulfite; (3) an unidentified, formally reductive reaction. Under SSIS control, different variants of mechanism (2) can be seen. Catabolism of sulfonates by anaerobes was discovered recently, and the degradation of taurine involves mechanism (1). When anaerobes assimilate sulfonate sulfur, there is one common, unknown mechanism to desulfonate the inert aromatic compounds and another to desulfonate inert aliphatic compounds; taurine seems to be desulfonated by mechanism (1).

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Section: Xenobiotic Sulfonates In the Environmentmentioning

confidence: 99%

Microbial desulfonation

Cook¹,

Laue²,

Junker³

1998

FEMS Microbiol Rev

149

106

View full text Add to dashboard Cite

show abstract

“…2) enter the environment in waste streams: chemical synthesis of sulfonates typically give yields of 809 0% with many sulfonates as by-products [33], and many of these compounds can be detected in e.g. rivers [3] or seepage from waste dumps [34,35]. In Fig.…”

Section: Xenobiotic Sulfonates In the Environmentmentioning

confidence: 99%

Microbial desulfonation

Cook

1998

FEMS Microbiology Reviews

View full text Add to dashboard Cite

Organosulfonates are widespread compounds, be they natural products of low or high molecular weight, or xenobiotics. Many commonly found compounds are subject to desulfonation, even if it is not certain whether all the corresponding enzymes are widely expressed in nature. Sulfonates require transport systems to cross the cell membrane, but few physiological data and no biochemical data on this topic are available, though the sequences of some of the appropriate genes are known. Desulfonative enzymes in aerobic bacteria are generally regulated by induction, if the sulfonate is serving as a carbon and energy source, or by a global network for sulfur scavenging (sulfate starvation induced (SSI) stimulon) if the sulfonate is serving as a source of sulfur. It is unclear whether an SSI regulation is found in anaerobes. The anaerobic bacteria examined can express the degradative enzymes constitutively, if the sulfonate is being utilized as a carbon source, but enzyme induction has also been observed. At least three general mechanisms of desulfonation are recognisable or postulated in the aerobic catabolism of sulfonates: (1) activate the carbon neighboring the C y Q bond and release of sulfite assisted by a thiamine pyrophosphate cofactor; (2) destabilize the C y Q bond by addition of an oxygen atom to the same carbon, usually directly by oxygenation, and loss of the good leaving group, sulfite; (3) an unidentified, formally reductive reaction. Under SSIS control, different variants of mechanism (2) can be seen. Catabolism of sulfonates by anaerobes was discovered recently, and the degradation of taurine involves mechanism (1). When anaerobes assimilate sulfonate sulfur, there is one common, unknown mechanism to desulfonate the inert aromatic compounds and another to desulfonate inert aliphatic compounds; taurine seems to be desulfonated by mechanism (1).

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“…In previous works, some of these compounds were found in Llobregat River water samples [4] (3‐nitro‐BS: 3.3 ng/ml; 1‐NS: 10.2 ng/ml; and 2‐NS: 49.9 ng/ml) and in treated sewage water samples from the Llobregat and Besos Rivers [17] (3‐nitro‐BS, 4‐methyl‐BS, 4‐chloro‐BS, 2‐NS, and 1‐hydroxy‐6‐amino‐3‐NS) at concentration levels from ng/ml to μg/ml. In addition, 3‐nitro‐BS, 4‐methyl‐BS, and 2‐NS have been found in untreated textile and tannery wastewaters and in effluents from wastewater treatment plants at high concentrations (2.7–100 ng/ml) [6].…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, their low pK ow values indicate a high mobility within the aquatic system [4]. In fact, some benzenesulfonates and naphthalenesulfonates have been found in waste and river waters [5][6][7][8][9][10][11][12][13][14][15][16]. In spite of several papers relating to the presence of many BS and NS compounds in natural, surface, landfill leachates, and wastewaters, a limited number of papers report the concentration of aromatic sulfonic acids in coastal waters [14,17].…”

Section: Introductionmentioning

confidence: 99%

Monitoring of aromatic monosulfonic acids in coastal waters by ion‐pair liquid chromatography followed by electrospray‐mass spectrometric detection

Alonso

Pocurull

Marcé

et al. 2002

Enviro Toxic and Chemistry

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Spain is one of the European countries that still discharges untreated wastewaters and sewage sludge into the sea. Aromatic monosulfonated compounds were detected in 36 seawater samples collected bimonthly on the Catalonian coast (Spain) over a period of 18 months. These compounds are of environmental concern because of their limited biodegradability and high mobility within the aquatic system. A method based on a sequential solid-phase extraction procedure (SSPE) followed by ion-pair liquid chromatography coupled to electrospray ionization-mass spectrometry (IPC-ESI-MS) in negative ionization mode was used to monitor aromatic monosulfonated compounds in the Catalonian coastal waters. Triethylamine (TEA) and acetic acid (HOAc) were used as volatile mobile-phase additives. A comparison of two polymeric solid-phase extraction (SPE) materials for the extraction of 15 aromatic monosulfonated compounds of environmental concern was performed. The investigated adsorbents were the polystyrene-divinylbenzene materials Lichrolut EN, from Merck, and Isolute ENV+, from International Sorbent Technology (IST). The influence of the matrix on the analysis of seawater samples was also studied. Applications of the developed analytical procedure to seawater samples gave limits of detection (n = 3) ranging from 0.6 to 45 pg on column for the target analytes. Barcelona and Tarragona locations were chosen along the Catalonian coast as sampling sites because of their large sewage discharges and intensive industrial activities. Samples were acquired from submarine outfalls of two rivers, Besos and Llobregat, located in the north and south of Barcelona city, respectively. Samples from petrochemical industry submarine outfalls located near the commercial port of Tarragona were also studied. Concentrations of benzenesulfonates (BS) and naphthalenesulfonates (NS) were of the order of ng/ml. Most of the collected samples were found to contain both isomers of mononaphthalenesulfonate. The study showed that these compounds can contaminate marine coastal waters.

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Anion-exchange chromatography particle beam mass spectrometry for the characterization of aromatic sulfonic acids as the major organic pollutants in leachates from Stringfellow, California

Cited by 37 publications

References 4 publications

Microbial desulfonation

Microbial desulfonation

Microbial desulfonation

Monitoring of aromatic monosulfonic acids in coastal waters by ion‐pair liquid chromatography followed by electrospray‐mass spectrometric detection

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