Reactions of organic pollutants. 1. Ozonation of acenaphthylene and acenaphthene

Chen, Paul N.; Junk, Gregor A.; Svec, Harry J.

doi:10.1021/es60152a016

Cited by 21 publications

(8 citation statements)

References 9 publications

(21 reference statements)

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“…The compound eluting from the column at 42 min gave a mass spectrum (mle 168 [M+], 140 [M-CO]+) and UV spectrum in ethanol (95% [vol/vol]; Amax, 216, 251, 316, and 338 nm) identical to those given by synthetic 1-acenaphthenone. These results are consistent with values reported in the literature (5,28). In addition, the HPLC retention time of the metabolite and synthetic 1-acenaphthenone were identical.…”

Section: Hplc Resultssupporting

confidence: 92%

“…It has been suggested several times by other workers that 1,2-dihydroxyacenaphthylene and its keto tautomer, 1-hydroxy-2-ketoacenaphthene, are in equilibrium with 1,8naphthalic dialdehyde (1,14). Synthesis of the dialdehyde by published procedures gave a product whose UV and mass spectra were consistent with reported literature values (5,11). However, when analyzed by TLC and HPLC, the product appeared to have polymerized.…”

Section: Hplc Resultssupporting

confidence: 78%

“…Reaction products were isolated from a reaction mixture that contained: K2HPO4 buffer, pH 7.5, 300 ,umol; NAD', 50 ,umol; 1-acenaphthenol (dissolved in 50 [LI of methanol), 5 ,umol; and cell extract (prepared from cells grown with or without acenaphthene, 16 to 20 mg of protein). The reaction was allowed to proceed for 1 h at room temperature.…”

Section: Methodsmentioning

confidence: 99%

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Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene

Schocken¹,

Gibson²

1984

Appl Environ Microbiol

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A Beijerinckia sp. and a mutant strain, Beijerinckia sp. strain B8/36, were shown to cooxidize the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Both organisms oxidized acenaphthene to the same spectrum of metabolites, which included 1-acenaphthenol, 1-acenaphthenone, 1,2-acenaphthenediol, acenaphthenequinone, and a compound that was tentatively identified as 1,2-dihydroxyacenaphthylene. In contrast, acenaphthylene was oxidized to acenaphthenequinone and the compound tentatively identified as 1,2dihydroxyacenaphthylene by the wild-type strain of Beijerinckia. Both of these products were also formed when the organism was incubated with synthetic cis-1,2-acenaphthenediol. A metabolite identified as cis-1,2acenaphthenediol was formed from acenaphthylene by the mutant Beijerinckia sp. strain B8/36. Cell extracts prepared from the wild-type Beijerinckia strain contain a constitutive pyridine nucleotide-dependent dehydrogenase which can oxidize l-acenaphthenol and 9-fluorenol. The results indicate that although acenaphthene and acenaphthylene are both oxidized to acenaphthenequinone, the pathways leading to the formation of this end product are different.

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Section: Hplc Resultssupporting

confidence: 92%

Section: Hplc Resultssupporting

confidence: 78%

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Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene

Schocken¹,

Gibson²

1984

Appl Environ Microbiol

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“…Chlorination of coal-tar leachate is also expected to result in formation of PAHs with polar acidic functional groups. I t is interesting to note that such compounds are reported as products of ozonation of parent PAHs in water (23).…”

Section: R E S U L T S a N D Discussion Typical Chromatogrammentioning

confidence: 99%

Gas chromatographic-mass spectrometric analysis of chlorination effects on commercial coal-tar leachate

Alben¹

1980

Anal. Chem.

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Samples of leachate from a commercial coal tar have been analyzed for polycyclic aromatic hydrocarbons (PAHs) by capillary gas chromatography-mass spectrometry, using electronimpact and chemical ionization. Basneutral extracts Contained predominantly the parent PAHs and alkyl-and nitrogen-substituted PAHs. These compounds were considerably less abundant in samples of chlorinated leachate, which Contained, instead, a number of oxygenated and halogenated PAHs.In public water supply systems, storage tanks and pipes are often coated to prevent corrosion. Coal tar is one of the materials commony used (1-3). The potential for contamination of potable water by the coating material is of concern t o human health and can be assessed by analysis of leachate from the commercial product. Elevated concentrations of parent polycyclic aromatic hydrocarbons (PAHs) were found in the effluent of a storage tank coated with coal tar ( 4 ) . Evidence has also been reported that at least one parent PAH, fluoranthene, can be leached from bituminous linings of distribution pipes (5). Without identifying the possible sources of contamination, other investigators have also found low levels (ng/L) of PAHs in potable water systems (6-8). Recent mutagenicity studies indicate that concentrated extracts of water samples collected in distribution systems are more mutagenic than samples collected a t the corresponding treatment plants (9). However, the chemical basis for these observations is still not understood.In order to obtain background for more extensive field investigations, we investigated the effects of chlorination on the composition of the coal-tar leachate. A major advantage of the commercial coal tar for study is that it contains many compounds whose standards are not readily available. Its leachate thus simulates under controlled conditions the complexity of actual environmental samples. In addition, it can be coated in uniform layers on a well-defined surface area.T h e polarity of water biased by pH is expected to favor leaching of PAHs with polar functional groups. Water supplies typically range from pH 6 to 9 after treatment. Chlorination, as practiced for disinfection, should further modify the composition of PAHs in coal-tar leachate. Potable water is generally chlorinated to leave a residual of about 0.5 mg free chlorine/L. The water mains and storage tanks, after installation and maintenance, are disinfected at concentrations of 50,100, or 200 mg free chlorine/L, depending on the mode of application (10). Harrison et al. have shown that the parent PAHs are significantly degraded by free chlorine at 10 mg/ L (11,12). Aqueous chlorination products of standard PAHs include anthraquinone, fluoranthene chlorohydrin, and monochloro derivatives of fluorene, phenanthrene, methylnaphthalene, and methylphenanthrene (13).This paper deals primarily with identification of baseneutral compounds in the coal-tar leachate, since mutagenicity studies of coal-derived products have generally found activity highest in basic and neutral fractio...

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“…Ozone also produces the same epoxy compounds from cholesterol and abietic acid (15,16), and from acenaphthylene as well (33).…”

Section: Reactions Of Oxidants/disinfectants With Organic Aromatic Anmentioning

confidence: 99%

Occurrence of by-products of strong oxidants reacting with drinking water contaminants--scope of the problem.

Rice¹,

Gomez-Taylor²

1986

Environ Health Perspect

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This paper describes results of a detailed literature review of the organic and inorganic by-products that have been identified as being formed in aqueous solution with four of the strong oxidizing/disinfecting agents commonly employed in drinking water treatment. These agents are: chlorine, chlorine dioxide, chloramine, and ozone. Significant findings include the production of similar nonchlorinated organic oxidation products from chlorine, chlorine dioxide, and ozone. In addition, all three chlorinous oxidants/disinfectants can produce chlorinated by-products under certain conditions. The presence of chloronitrile compounds in drinking waters is indicated to arise from reactions of chlorine or chloramine to amine/amide functions in amino acids or proteinaceous materials, followed by dehydrohalogenation. These nitriles could hydrolyze to produce the corresponding chloroacetic acids. It is concluded that to minimize the presence of oxidation by-products in drinking waters, the concentrations of oxidizable organic/inorganic impurities should be lowered before any oxidizing agent is added.

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Reactions of organic pollutants. 1. Ozonation of acenaphthylene and acenaphthene

Cited by 21 publications

References 9 publications

Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene

Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene

Gas chromatographic-mass spectrometric analysis of chlorination effects on commercial coal-tar leachate

Occurrence of by-products of strong oxidants reacting with drinking water contaminants--scope of the problem.

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