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PubMed2004

An electrospray ionization-tandem mass spectrometry method for identifying chlorinated drinking water disinfection byproducts.

Identification of chlorinated drinking water disinfection byproducts (DBPs) was investigated by using electrospray ionization-mass spectrometry/mass spectrometry (ESI-MS/MS). Chlorine-containing compounds were found to form chloride ion fragments by MS/MS, which can be used as a 'fingerprint' for chlorinated DBPs. Instrumental parameters that affect the formation of chloride ions by ESI-MS/MS were examined, and appropriate conditions for use in finding specific structural information were evaluated. The results show that maximizing the formation of chloride ions by MS/MS required a relatively high collision energy and collision gas pressure; also, limiting the scan range to m/z 30-40 allowed improved sensitivity for detection; but obtaining structural information required the use of lower collision energies. The conditions obtained were demonstrated to be effective in identifying chlorinated DBPs in a standard sample with relatively low concentrations of each component and in a chlorinated humic substance sample. Sample pretreatment techniques including ultrafiltration and size exclusion chromatography appeared to be helpful for identifying highly polar or high molecular weight chlorine-containing DBPs by ESI-MS/MS.

Chlorine↗
PubMed1985

Disinfecting capabilities of oxychlorine compounds.

The bacterial virus f2 was inactivated by chlorine dioxide at acidic, neutral, and alkaline pH values. The rate of inactivation increased with increasing pH. Chlorine dioxide disproportionation products, chlorite and chlorate, were not active disinfectants. As chlorine dioxide solutions were degraded under alkaline conditions, they displayed reduced viricidal effectiveness, thereby confirming the chlorine dioxide free radical as the active disinfecting species.

Chlorates↗
PubMed2001

Formation and inhibition of chloroaromatic micropollutants formed in incineration processes.

The formation pathways for chlorinated aliphatic and chlorinated aromatic compounds in technical incineration processes are reviewed. It is shown that acetylene is converted to chloroaromatic compounds including PCDD/F in a special flow reactor by catalytic activity of CuCl2 in the temperature regime of a post-combustion zone of technical incinerators. Mechanistic pathways begin with chlorination of acetylene. Dichloroacetylene is further condensed to C-4 and C-6 units. Hexachlorobenzene is the dominant aromatic compound and a likely precursor to chlorinated phenols and PCDD/F. Two specific mechanisms of formation of chlorinated aromatic compounds including PCDD/F have been advanced. Both mechanisms begin with the formation of dichloroacetylene from flame pyrolysis products like acetylene. Condensation of dichloroacetylene is mediated by copper species via metallacyclic intermediates and/or a catalytic cycle involving copper stabilized trichlorovinyl radicals. The final pathways of conversion of chlorinated benzenes to PCDD/F via chlorophenols are under active investigation.

Acetylene↗
PubMed1993

Influence of alternative electron acceptors on the anaerobic biodegradability of chlorinated phenols and benzoic acids.

Nitrate, sulfate, and carbonate were used as electron acceptors to examine the anaerobic biodegradability of chlorinated aromatic compounds in estuarine and freshwater sediments. The respective denitrifying, sulfidogenic, and methanogenic enrichment cultures were established on each of the monochlorinated phenol and monochlorinated benzoic acid isomers, using sediment from the upper (freshwater) and lower (estuarine) Hudson River and the East River (estuarine) as source materials. Utilization of each chlorophenol and chlorobenzoate isomer was observed under at least one reducing condition; however, no single reducing condition permitted the metabolism of all six compounds tested. The anaerobic biodegradation of the chlorophenols and chlorobenzoates depended on the electron acceptor available and on the position of the chlorine substituent. In general, similar activities were observed under the different reducing conditions in both the freshwater and estuarine sediments. Under denitrifying conditions, degradation of 3- and 4-chlorobenzoate was accompanied by nitrate loss corresponding reasonably to the stoichiometric values expected for complete oxidation of the chlorobenzoate to CO2. Under sulfidogenic conditions, 3- and 4-chlorobenzoate, but not 2-chlorobenzoate, and all three monochlorophenol isomers were utilized, while under methanogenic conditions all compounds except 4-chlorobenzoate were metabolized. Given that the pattern of activity appears different for these chlorinated compounds under each reducing condition, their biodegradability appears to be more a function of the presence of competent microbial populations than one of inherent molecular structure.

Bacteria, Anaerobic↗
PubMed2003

Biodegradation of bis(1-chloro-2-propyl) ether via initial ether scission and subsequent dehalogenation by Rhodococcus sp. strain DTB.

Rhodococcus sp. strain DTB (DSM 44534) grows on bis(1-chloro-2-propyl) ether (DDE) as sole source of carbon and energy. The non-chlorinated diisopropyl ether and bis(1-hydroxy-2-propyl) ether, however, did not serve as substrates. In ether degradation experiments with dense cell suspensions, 1-chloro-2-propanol and chloroacetone were formed, which indicated that scission of the ether bond is the first step while dehalogenation of the chlorinated C(3)-compounds occurs at a later stage of the degradation pathway. Inhibition of ether scission by methimazole suggested that the first step in degradation is catalyzed by a flavin-dependent enzyme activity. The non-chlorinated compounds 1,2-propanediol, hydroxyacetone, lactate, pyruvate, 1-propanol, propanal, and propionate also supported growth, which suggested that the intermediates 1,2-propanediol and hydroxyacetone are converted to pyruvate or to propionate, which can be channeled into the citric acid cycle by a number of routes. Total release of chloride and growth-yield experiments with DDE and non-chlorinated C(3)-compounds suggested complete biodegradation of the chlorinated ether.

Biodegradation, Environmental↗
PubMed2002

Transfer of polychlorinated biphenyls and chlorinated pesticides from mother to pup in relation to cytochrome P450 enzyme activities in harp seals (Phoca groenlandica) from the gulf of St. Lawrence, Canada.

Congener-specific transfer of polychlorinated biphenyls (PCBs) and chlorinated pesticides from female to pup was studied in harp seals from eastern Canada. Possible effects on hepatic cytochrome P450 enzymes (CYP450) due to contaminant mobilization from blubber lipids in females and ingestion of contaminated milk in pups were studied. Contaminant transfer from blubber to milk in females favored the more polar compounds (lower chlorinated PCBs, toxaphenes, hexachlorocyclohexanes, and hexachlorobenzene) relative to more lipophilic compounds (higher chlorinated PCBs, dichlorodiphenyltrichloroethane [DDT], chlordane). In spite of substantial contaminant mobilization from blubber in females and ingestion of contaminated milk by pups, CYP450 activities were low in all animals. Possibly, increased plasma estradiol concentrations, involved in breeding after lactation, suppressed CYP450 directly. Although the pups were exposed to contaminants in milk, CYP450 activities were low, resulting in low contaminant metabolism. This was confirmed by similar contaminant patterns in milk and pups. A strong positive relation between CYP1A-like activities and body weight in the pups suggested not yet fully developed CYP1A enzymes. A negative association between CYP3A and pesticides in females and pups was hypothesized to be a result of metabolic inactivation of CYP450. The CYP450 enzyme activities were considered unsuitable indicators for contaminant mobilization and transfer in harp seals.

Adipose Tissue↗
PubMed1992

Mutagenicity from ozonation of humic substances.

Eight structural components of humic substances were ozonated. Mutagenic activity was found using TA100 with and without S9 mix for all ozonated components. p-Hydroxybenzaldehyde was chosen as an important component and ozonation products were determined by gas chromatography-mass spectrometry (GC-MS). Aldehydes, ketones and carboxylic acids were identified as the ozonation products. Among these products, acetaldehyde, formaldehyde, glyoxal, methylglyoxal and glyoxylic acid were recognized to be mutagenic. Furthermore, p-hydroxybenzaldehyde was first ozonated and then chlorinated. A great variety of chlorinated organic compounds, many of which are known mutagens, have been identified by GC-MS in the ether extract. The same compounds have previously been reported as chlorination products of humic substances. Aldehydic products by ozonation were identified from ozonation followed by chlorination of humic substances and p-hydroxybenzaldehyde.

Animals↗
PubMed2000

Deriving ecological risk-based soil quality values in the Basque Country.

Most industrialised countries are currently drawing up their procedures to deal with contaminated land. In the Basque Country generic soil quality values applicable to different land uses have been drawn up for many common soil inorganic and organic pollutants, to assist in the site assessment process. In this paper we present those values aimed at protecting ecosystems as the main target at risk. Ecological risk was defined on the basis of effects on the structure of the soil invertebrate community. Ecotoxicological data from laboratory tests were used in combination with a theoretical extrapolation method. The following groups of compounds were assayed: heavy metals, cyanides, aromatic compounds, polycyclic aromatic hydrocarbons, HCH isomers, chlorinated organic compounds, and mineral oil. A specific toxicity database was created. The reliability of the values obtained as well as the limitations of the derivation process are discussed.

Animals↗
PubMed1971

2,5-Dichlorophenol (from ingested herbicide?) in defensive secretion of grasshopper.

The defensive froth emitted by the grasshopper Romalea microptera contains several odorous compounds (phenols, terpenes, benzoquinone), including a chlorinated aromatic compound, 2,5-dichlorophenol. This compound, which is repellent to ants and therefore defensively useful to the grasshopper, probably stems from herbicide or herbicide derivative ingested by the insect with its diet. Although there is precedent for the defensive employ by one species of chemical agents produced by another, no instance was known involving secondary utilization of a pesticide dispensed by man.

Animals↗
PubMed1982

Reaction products of chlorine dioxide.

Inspection of the available literature reveals that a detailed investigation of the aqueous organic chemistry of chlorine dioxide and systematic identification of products formed during water disinfection has not been considered. This must be done before an informed assessment can be made of the relative safety of using chlorine dioxide as a disinfectant alternative to chlorine. Although trihalomethanes are generally not formed by the action of chlorine dioxide, the products of chlorine dioxide treatment of organic materials are oxidized species, some of which also contain chlorine. The relative amounts of species types may depend on the amount of chlorine dioxide residual maintained and the concentration and nature of the organic material present in the source water. The trend toward lower concentrations of chlorinated by-products with increasing ClO2 concentration, which was observed with phenols, has not been observed with natural humic materials as measured by the organic halogen parameter. Organic halogen concentrations have been shown to increase with increasing chlorine dioxide dose, but are much lower than those observed when chlorine is applied. Aldehydes have been detected as apparent by-products of chlorine dioxide oxidation reactions in a surface water that is a drinking water source. Some other nonchlorinated products of chlorine dioxide treatment may be quinones and epoxides. The extent of formation of these moieties within the macromolecular humic structure is also still unknown.

Chemical Phenomena↗
PubMed2003

Reductive dechlorination of polychlorinated biphenyls in sediment from the Twelve Mile Creek arm of Lake Hartwell, South Carolina, USA.

Lake Hartwell is a U.S. Army Corps of Engineers reservoir system located on the state line between South Carolina and Georgia, USA. The lake was contaminated with an estimated 200 metric tons of polychlorinated biphenyls ([PCBs]; mainly Aroclor 1016 and 1254), and the entire Twelve Mile Creek watershed and the Seneca River arm of Lake Hartwell were placed on the National Priorities List. Monitored natural attenuation was chosen as a remedy for the contaminated sediment. The relatively warm temperature of Lake Hartwell and lack of significant cocontaminants along with the PCBs distinguish this site from others that have been studied for microbially mediated reductive dechlorination. Microcosm studies were conducted with sediment from two locations in the Twelve Mile Creek arm and confirmed the presence of indigenous microorganisms capable of reductively dechlorinating Aroclor 1254, which contains predominantly tetra-, penta-, and hexachlorobiphenyl. The average number of total chlorines per biphenyl decreased from 4.8 to 4.9 to 2.9 to 3.0, following 250 to 260 d of incubation. The maximum observed dechlorination rates were 0.29 to 0.87 microg-atoms Cl- per gram sediment dry weight per week. The onset of dechlorination activity correlated strongly with maximum methanogenesis, which occurred without a lag in samples from the site that showed signs of in situ fermentation activity. Dechlorination occurred primarily at the meta and para positions (58-63% removal), with no apparent decrease in ortho chlorines. This most closely resembles pattern M, characterized by preferential removal of unflanked and flanked meta chlorines. The microcosm results are consistent with sediment cores analyzed from the same locations, which indicate accumulation with depth of the same ortho- and para-substituted congeners. It therefore appears that the success of monitored natural attenuation for Lake Hartwell will hinge on covering the recalcitrant PCBs with a sufficient amount of uncontaminated sediment to isolate them from the food chain.

Aroclors↗
PubMed2001

Dependence of GC-RRTs on the electrical charge at substituents of chlorinated dioxins and related compounds.

The correlation between gas chromatograph relative retention times (GC-RRTs) of polychlorinated dioxins and related compounds (PCBs, PCDDs, PCDFs, and PCNs) and descriptors calculated from the electrical charges at substituents, such as the sums of the charges at hydrogen atoms (QH), and chlorine atoms (QCl), and the sum of QH and QCl (Qall), was analyzed for their congeners and isomers. The dependence of GC-RRTs on these descriptors varied dramatically. For the congeners, there was an approximately linear relationship between GC-RRTs and all the descriptors. For the isomers, although there was little significant relationships, by classifying GC-RRTs based on Nad-Cl or Nad-H defined from the number of adjacent chlorine and hydrogen substituents, a linear relationship between GC-RRTs and QH was found for CBs, CDDs, and CDFs, and GC-RRTs for CNs could be classified. From an analysis of the electrical charges at hydrogen substitutents bonded to adjacent and non-adjacent positions, the average-charge of such substituents bonded to adjacent positions decreased with an increase in Nad-H, and this tendency was similar to that for bonding to ortho-, meta-, para-, alpha-, and beta-positions.

Benzofurans↗
PubMed2001

In vitro dehalogenation of tetrachloroethylene (PCE) by cell-free extracts of Clostridium bifermentans DPH-1.

Cell-free extracts of Clostridium bifermentans DPH-1 catalyzed tetrachloroethylene (PCE) dechlorination. PCE degradation was stimulated by addition of a variety of electron donors. Ethanol (0.61 mM) was the most effective electron donor for PCE dechlorination. Maximum activity was recorded at 30 degrees C and pH 7.5. Addition of NADH as a cofactor stimulated enzymatic activity but the activity was not stimulated by addition of metal ions. When the cell-free enzyme extract was incubated in the presence of titanium citrate as a reducing agent, the dehalogenase was rapidly inactivated by propyl iodide (0.5 mM). The activity of propyliodide-reacted enzyme was restored by illumination with a 250 W lamp. The dehalogenase activity was also inhibited by cyanide. The substrate spectrum of activity included trichloroethylene (TCE), cis-1,2-dichloroethylene (cDCE), trans-dichloroethylene, 1,1-dichloroethylene, 1,2-dichloroethane, and 1,1,2-trichloroethane. The highest rate of degradation of the chlorinated aliphatic compounds was achieved with PCE, and PCE was principally degraded via TCE to cDCE. Results indicate that the dehalogenase could play a vital role in the breakdown of PCE as well as a variety of other chlorinated aliphatic compounds.

Biodegradation, Environmental↗