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PubMed2002

Adsorption of phenolic compounds from aqueous solutions by a water-compatible hypercrosslinked polymeric adsorbent.

A water-compatible hypercrosslinked polymeric adsorbent (NJ-8) for adsorbing and removing phenolic compounds from their aqueous solutions was prepared. This product can be used directly without a wetting process. Its adsorption property toward four phenolic compounds, phenol, p-cresol, p-chlorophenol, and p-nitrophenol was tested using the commercial Amberlite XAD-4 as a reference. The capacities of equilibrium adsorption for all four phenolic compounds on the NJ-8 from their aqueous solutions are around two times as high as that of Amberlite XAD4 within the temperature range 283-323 K, which may contribute to their micropore structure and the partial polarity on the network. Freundlich isotherm equations, as well as relative adsorption capacities and isosteric adsorption enthalpies for the four phenolic compounds, indicate that the adsorption of phenolic compounds on the NJ-8 resin is a physical adsorption process. Mini-column adsorption studies for phenol on Amberlite XAD4 and NJ-8 resins show that the breakthrough adsorption capacities are 0.54 and 0.99 mmol/ml, and the total capacities are 0.62 and 1.37 mmol/ml, while no extra acetone was needed to remove the adsorbed phenol from NJ-8 as from Amberlite XAD4.

Adsorption↗
PubMed2002

Radical/radical vs radical/molecule reactions in the formation of PCDD/Fs from (chloro)phenols in incinerators.

Pathways from chlorinated phenols as precursors to PCDD/Fs are discussed with focus on the effect of (poly)chlorination on thermochemistry and rate in the displacement of chlorine from a chlorophenol molecule by a (chloro)phenoxy radical (reaction (A) as a key example). Through measurements on the respective methylethers (anisoles) the O-H bond of 2,4,6-TCP turns out to be 5 kcal/ mol, and that in PCP 4 kcal/mol, less strong than O-H in phenol itself. On this basis it is concluded that-in contrast with earlier proposals--displacements such as in reaction (A) are at least as slow as reaction (B) of phenoxy radical with chlorobenzene. PhO. + PhCl -->PhOPh + Cl. reaction B Compared with condensation of two (chloro)phenoxy radicals, such radical/molecule reactions are therefore an insignificant pathway to dioxins in incinerators.

Benzofurans↗
PubMed2002

Effect of reaction time on PCDD and PCDF formation by de novo synthetic reactions under oxygen deficient and rich atmosphere.

The effect of reaction time on formation of polychlorinated dibenzo-p-dioxins (PCDD) and dibenzofurans (PCDF) was studied under laboratory conditions in the system containing municipal waste incineration fly ash, activated carbon and copper chloride dihydrate at 300 degrees C in 99.999% N2 and N2 + 10% O2 atmosphere. The concentrations of tetra- to octa-chlorinated isomers as well as I-TEQ concentrations of toxic congeners are reported. The mechanism of PCDD and PCDF formation from chlorophenols and chlorinated biphenyls is discussed in the light of the time changes of PCDD/PCDF ratios.

Benzofurans↗
PubMed2003

Electrochemical degradation of p-substituted phenols of industrial interest on Pt electrodes. Attempt of a structure-reactivity relationship assessment.

The electrochemical oxidation of p-substituted phenols, with both electron donor (OH- and NH2-) and electron withdrawing groups (NO2-, COOH-, and halogens), on Pt anodes using sodium sulfate as support electrolyte has been studied. It was found that, except for p-halogen phenols, compounds with electron donor substituents are easier to remove and their initial rates of degradation are correlated to the octanol-water partitioning coefficient (log Poct) and the Hammett's constant. Degradation of all of our starting compounds produced the same intermediates, therefore, a general pathway of reaction is proposed. Additionally, the influence of pH, temperature, electrolyte concentration and current density on the initial and total degradation of p-chlorophenol was also investigated.

Chromatography, High Pressure Liquid↗
PubMed2003

Effects of sensitizers on the photodegradation of the systemic fungicide triadimenol.

The photochemical behaviour of triadimenol (1) under various conditions has been examined. Significant degradation is obtained only in the presence of electron-acceptor sensitizers as 9,10-dicyanoanthracene or 2,4,6-triphenylpyrylium tetrafluoroborate, and long irradiation times are required. 1H-1,2,4-Triazole (2), 4-chlorophenyl formate (3), 4-chlorophenol (4), 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one (5), 4-chlorophenyl 2,2-dimethylpropanoate (6) and 4-chlorobenzoic acid (7) were identified as photoproducts by NMR and GC-MS.

Fungicides, Industrial↗
PubMed2003

Linear free energy relationships for dechlorination of aromatic chlorides by Pd/Fe.

Reductive dechlorination rate constants for five chlorobenzenes in the presence of Pd/Fe as catalyst were determined experimentally. Linear free energy relationships (LFER) for the dechlorination rate constants of five chlorobenzenes and three chlorophenols were developed by partial least squares (PLS) regression based on quantum chemical parameters computed by PM3 Hamiltonian. The optimal LFER model obtained is logk=-1.63+1.46 x 10(-3)DeltaH(f)-7.69 x 10(-1)E(LUMO)where k stands for the dechlorination rate constants, DeltaH(f) is the standard heat of formation, and E(LUMO) is the energy of the lowest unoccupied molecular orbital. The Q(2)(cum) value of the model is 0.879, indicating good robustness and predictive power of the model.

Chlorides↗
PubMed2004

Photochemical transformations of tetrabromobisphenol A and related phenols in water.

A method was developed for studies of the phototransformation at UV irradiation of aqueous solutions of tetrabromobisphenol A (TBBPA), tribromobisphenol A (TriBBPA), tetrachlorobisphenol A (TCBPA), 2,4-dichlorophenol at various pHs as well as 2-chlorophenol, 2-bromophenol, 3,4-dichlorophenol and bisphenol A at pH 11. The absorbance spectra of the compounds and the emission spectra of the light-source were determined and used to calculate disappearance quantum yields of the photochemical reactions that were taking place. No major differences between the disappearance quantum yields of TBBPA and TCBPA were observed at pH 10, while the disappearance quantum yield of TriBBPA was approximately two times higher. The rate of decomposition of TBBPA was six times higher at pH 8 than at pH 6. Identification of the degradation products of TBBPA and TriBBPA, by GC-MS analysis and by comparison to synthesised reference compounds, indicated that TBBPA and TriBBPA decompose via different mechanisms. Three isopropylphenol derivatives; 4-isopropyl-2,6-dibromophenol, 4-isopropylene-2,6-dibromophenol and 4-(2-hydroxyisopropyl)-2,6-dibromophenol, were identified as major degradation products of TBBPA while the major degradation product of TriBBPA was tentatively identified as 2-(2,4-cyclopentadienyl)-2-(3,5-dibromo-4-hydroxyphenyl)propane.

Gas Chromatography-Mass Spectrometry↗
PubMed2004

Formation of chlorinated and brominated dioxins and other organohalogen compounds at the pilot incineration plant VERONA.

Experiments were conducted at the VERONA pilot plant, an incineration plant with stationary grate and separate post-combustion chamber, using wood and propane as basic combustible materials and with controlled dosage of various bromine-, chlorine- and copper-containing compounds. The behaviour of the following compounds was studied in the combustion chamber, after the post-combustion chamber and after the heat exchanger: polychlorinated phenols (PCPh), polybrominated phenols (PBrPh), polychlorinated benzenes (PCBz), polybrominated benzenes (PBrBz), polychlorinated dioxins and furans (PCDD/F) and polybrominated dioxins and furans (PBDD/F). The bromine co-incineration leaded to very high bromophenol concentrations after the post-combustion chamber. The formation of brominated and mixed-halogenated phenols and the further reaction to halogenated dioxins is apparently a relevant reaction mechanism for dioxin formation in processes involving bromine. This assumption is supported by the high formation rates of PBDD/F found in the heat exchanger, which were 4-20 times higher than those of PCDD/F. Moreover, the strong correlations found between the formation rates of PCPh, PCBz and PCDD/F in the heat exchanger indicate that in addition considerable new formation of dioxins takes place through de novo synthesis. Experiments involving the variation of primary operational parameters and fuel properties have shown that the quality of post-combustion plays a much greater role than the other parameters. Furthermore, it became apparent that the congeners of the chlorophenols and of the chlorobenzenes, measured in various incineration stages, do not correlate closely with the dioxin concentrations after the heat exchanger.

Dioxins↗
PubMed1999

Microbial dechlorination of polychlorinated biphenyls in anaerobic sewage sludge.

The potential of a chlorophenol (CP)-adapted consortium to dechlorinate polychlorinated biphenyls (PCBs) in sewage sludge was investigated. Results show that dechlorination rates differed significantly depending on sludge source and PCB congener. Higher total solid concentrations in sewage sludge and higher concentrations of chlorine in PCB resulted in slower dechlorination rates. No significant difference was found for 2,3,4,5-CB dechlorination from pH 6.0 to pH 8.0; however, dechlorination did not occur at pH 9.0 during a 41-day incubation period. Results show that at concentrations of 1 to 10 mg/L, the higher the PCB concentration, the faster the dechlorination rate. In addition, dechlorination rates were in the following order: methanogenic conditions > sulfate-reducing conditions > denitrifying conditions. The addition of acetate, lactate, pyruvate, and ferric chloride decreased lag times and enhanced dechlorination; however, the addition of manganese dioxide had an inhibitory effect. Dechlorination rates were also enhanced by the addition of PCB congeners, including 2,3,4-CB, 2,3,4,5-CB and 2,3,4,5,6-CB in mixture. Overall results show that the CP-adapted consortium has the potential to enhance PCB dechlorination. The optimal dechlorination conditions presented in this paper may be used as a reference for feasibility studies of PCB removal from sludge.

Anaerobiosis↗
PubMed2000

Polychlorinated organic compounds in the Arctic cod liver: trends and profiles.

Polychlorinated organic compounds (POCs) have been measured in Arctic cod liver from Vestertana Fjord for a period of 1987-1998. Significant decrease was observed for DDD (p = 0.043), alpha-HCH (p = 0.001), and gamma-HCH (lindane; p = 0.001). Contents of DDE, 2,3,7,8-tetrachlorodibenzofuran, PCBs, chlordanes, chloronaphthalenes, hexachlorobenzene and polychlorodiphenyl ethers had no significant trend. Contents of three hexa- and two heptachlorodibenzofurans and octachlorodibenzofuran increased slightly from 1987 to 1994, but then at very high rate from 1994 to 1998. Trends of HCHs, profiles of PCBs and levels of chlordanes are in accordance with atmospheric long range transport. The hexa-, hepta- and octachlorodibenzofurans observed are major impurities in chlorophenol formulation Ky-5, which has been used as wood preservative and as fungicide/slimicide in industrial processes. Their profile in Vestertana cod was similar to that observed in Ky-5 contaminated fish.

Animals↗
PubMed2003

Effect of chlorine content in feeding wastes of incineration on the emission of polychlorinated dibenzo-p-dioxins/dibenzofurans.

This study attempts to clarify the effects of chlorine content in waste on the formation mechanisms of polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs) in full scale incinerators by proposing and using the principal component analysis (PCA) to compare the congener profiles of PCDD/Fs in the stack flue gases of 17 emission sources, including incinerators and vehicles. Four incinerators, among these 17 emission sources, were sampled and analyzed in this study, and the data for the other 13 emission sources were selected from previous studies. These 17 emission sources can be classified into four categories, including medical waste incinerators (MWIs, H1-H5), municipal solid waste incinerators (MSWIs, M1-M8), vehicle fuel combustion (unleaded gas-fueled vehicles, UGFV; diesel-fueled vehicles, DFV, n = 2) and polyvinylchloride (PVC) facility vent combustors (PVC1 and PVC2, n = 2). PCA was conducted for these emission sources with the fractions of 17 2,3,7,8-congeners in the stack flue gases as variables to clarify the effect of chlorine content in feeding wastes on the emission of PCDD/Fs. From the results of PCA, we extrapolated that the threshold value of the chlorine content was at 0.8-1.1%, and the formation mechanisms of PCDD/Fs are influenced first by whether the chlorine content in the feeding waste is over or below the threshold value then by other factors, which furnaces or APCDs represent. When the chlorine level in the waste is below the threshold value at 0.8-1.1%, the formation of PCDDs dominates, probably because the chlorine is used to chlorinate the non-substituted phenol to produce chlorophenols, which are important precursors for PCDDs. rather than chlorinate the dibenzofuran. While the chlorine level in the waste exceeds this threshold (0.8-1.1%), the rates of formation of PCDFs increase faster than those of PCDDs, probably because the chlorine content in the waste contributes to the deterioration of combustion conditions, and many products of incomplete combustion (PICs) like PAHs, will grow to a substantial level. When PCDD/Fs are formed from PAHs, the formation rates of PCDFs are higher than those of PCDDs.

Air Pollutants↗
PubMed1997

A review of dioxin releases to land and water in the UK.

UK government policy is to identify and control the sources of some chlorinated organic compounds including polychlorinated dibenzo-p-dioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs), often known collectively as dioxins. This requires the gathering of information on the scale of releases of PCDD/PCDFs to all environmental media. While a number of recent studies have produced inventories of PCDD/PCDF emissions to air, this study, commissioned by Her Majesty's Inspectorate of Pollution (HMIP--now part of the Environment Agency), is the first attempt at producing a comprehensive UK inventory of emissions of dioxins to land and water from industrial and non-industrial processes. Release of PCDD/PCDFs in wastes taken to landfill are included under the definitions or releases to land used by the Environment Agency. Assembly of the inventory, particularly for releases to water, was severely hampered by lack of data from the UK or overseas; further work is required to remedy the data gaps and deficiencies revealed. The inventory puts total quantified releases to land at 1500-12,000 g toxic equivalent quantities (TEQ) per year--significantly more than releases to air or water. This is as expected, given the nature of the processes that form PCDD/PCDFs and their propensity to bind tightly to solid materials. The bulk of releases to land are to landfills rather than the open environment. From the data available, the open use of chemicals (including the disposal of wood treated with PCP), the manufacture of pesticides, the incineration of municipal solid waste (MSW) and accidental fires appear to be the largest contributors. The processes with greatest potential for releases to water appear to be the open use of chemicals, sewage treatment, disposal of waste oil, accidental fires, production of pesticides and chlorophenols and chemical waste incineration. In addition, the run-off from roads may be a significant source of releases as this is untreated. For the majority of processes studied, the trend is towards reduced releases to land and water, but improvements in the control of releases to air may lead to increased quantities of PCDD/PCDFs in some wastes and thus to increased releases to land. One exception may be from increasing quantities of sewage sludge disposed of to farm land. Changes in waste disposal practice--for example, use of wastes for soil improvement--may also inadvertently increase the probability of human exposure to PCDD/PCDF releases to land. The study did not attempt to assess the risks to humans and ecosystems from releases of PCDD/PCDFs to land and water: it recommends the development of an appropriate risk-assessment methodology.

Benzofurans↗
PubMed2000

Halorespiring bacteria-molecular characterization and detection.

Recently, a rapidly increasing number of bacteria has been isolated that is able to couple the reductive dehalogenation of various halogenated aromatic and aliphatic compounds like chlorophenols and tetrachloroethene to energy conservation by electron-transport-coupled phosphorylation. The potential of these halorespiring bacteria for innovative clean-up strategies of polluted anoxic environments has greatly stimulated efforts to unravel the molecular basis of the novel respiratory chains they possess. The thorough characterization of halorespiratory key components at the physiological, biochemical and molecular genetic level has revealed both structural and functional similarity of chloroaryl- and chloroalkyl-respiratory chains from different phylogenetically distinct microorganisms. The reductive dehalogenases from halorespiring bacteria were found to comprise a novel class of corrinoid-containing Fe/S-proteins. Sensitive molecular methods for monitoring both presence and fate of halorespiring bacteria have been developed, which will be instrumental for the design and maintenance of optimised in situ bioremediation processes.

Journal Article↗
PubMed2002

Expression of beta-galactosidase by recombinant respiratory syncytial viruses for microneutralization assay.

The beta-galactosidase gene (lacZ) was inserted into a recombinant respiratory syncytial virus (RSV) A2 strain of subgroup A RSV (designated as A-lacZ) and a chimeric RSV that had the G and F surface glycoproteins of A2 replaced by those of the subgroup B RSV 9320 strain (designated as B-lacZ). Both recombinant RSVs, A-lacZ and B-lacZ, grew well in tissue culture and expressed high levels of beta-galactosidase. Using these two beta-galactosidase-expressing recombinant RSVs, a novel microneutralization assay was developed to measure serum anti-RSV neutralizing antibody from subgroup A or subgroup B RSV infection. The assay was carried out in 96-well plates and the unneutralized virus was quantitated by spectrophotometric measurement of the beta-galactosidase enzymatic reaction following incubation of the infected cell lysate with the enzyme substrate, chlorophenol red beta-D-galactopyranoside (CPRG). Adult human sera positive for anti-RSV antibody as shown by Western blot analysis and subgroup A or subgroup B RSV infected monkey sera were examined for the levels of anti-RSV neutralizing antibodies by the microneutralization assay in comparison with the plaque reduction neutralization assay. A higher antibody titer was detected when the neutralization assay was performed with the homologous RSV than the heterologous RSV, indicating that neutralization assay could distinguish antigenic differences between the two RSV subgroups. The microneutralization assay is comparable to the plaque reduction neutralization assay in sensitivity, but it is rapid, less laborious and suitable for screening a large number of samples.

Adult↗
PubMed2002

Tolerance and metabolism of phenol and chloroderivatives by hairy root cultures of Daucus carota L.

Hairy root cultures are shown to be suitable experimental systems to screen higher plants for tolerance to various inorganic and organic pollutants, and for determining the role of the root matrix in the uptake and further metabolism of contaminants. A number of clones were obtained by infection of carrot tissues with Agrobacterium rhizogenes and two (the fastest and the slowest growing root clones) were chosen for further experimentation. Both clones showed a similar degree of tolerance towards phenol and its chlorinated derivatives, i.e. the growth of root biomass was maintained in concentrations of phenol equivalent to 1000 micromol/l, whilst the chlorophenols were tolerated only at concentrations 20 times lower (50 micromol/l). Transformed carrot roots were able to remove more than 90% of the exogenous phenolic compounds from the culture medium within 120 h after treatment. Metabolism of these compounds occurred in the root tissue and was accompanied by an increase in peroxidase activity.

Biological Assay↗
PubMed2003

Contaminant risks from biosolids land application: contemporary organic contaminant levels in digested sewage sludge from five treatment plants in Greater Vancouver, British Columbia.

This study examines the potential for environmental risks due to organic contaminants at sewage sludge application sites, and documents metals and various potential organic contaminants (volatile organics, chlorinated pesticides, PCBs, dioxins/furans, extractable petroleum hydrocarbons, PAHs, phenols, and others) in current production biosolids from five wastewater treatment plants (WWTPs) within the Greater Vancouver Regional District (GVRD). There has been greater focus in Europe, North America and elsewhere on metals accumulation in biosolids-amended soil than on organic substances, with the exception of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans. Another objective, therefore, was to evaluate the extent to which management of biosolids re-use based on metal/metalloid levels coincidentally minimizes environmental risks from organic contaminants. Historical-use contaminants such as chlorophenols, PCBs, and chlorinated pesticides were not detected at environmentally relevant concentrations in any of the 36 fresh biosolids samples, and appear to have virtually eliminated from sanitary collection system inputs. The few organic contaminants found in freshly produced biosolids samples that exhibited high concentrations relative to British Columbia and Canadian soil quality benchmarks included p-cresol, phenol, phenanthrene, pyrene, naphthalene, and heavy extractable petroleum hydrocarbons (HEPHs--nCl9-C34 effective carbon chain length). It was concluded that, with the exception of these petroleum hydrocarbon constituents or their microbial metabolites, the mixing of biosolids with uncontaminated soils during land application and based on the known metal concentrations in biosolids from the Greater Vancouver WWTPs investigated provides adequate protection against the environmental risks associated with organic substances such as dioxins and furans, phthalate esters, or volatile organics. Unlike many other organic contaminants, the concentrations of petroleum hydrocarbon derived substances in biosolids has not decreased within the last decade or more in the WWTPs studied, and--unlike persistent chlorinated compounds--the associated PAHs and other hydrocarbon constituents merit careful consideration, especially in the context of repeated land-application of biosolid.

Canada↗
PubMed2000

Reproductive success and chlorinated hydrocarbon contamination in tree swallows (Tachycineta bicolor) nesting along rivers receiving pulp and paper mill effluent discharges.

The insectivorous tree swallow was chosen as an indicator species to investigate the uptake of pulp mill-related chlorinated hydrocarbons from emergent aquatic insects. Nest box populations were monitored for reproductive success at locations upstream and downstream of pulp mills on two river systems in British Columbia, Canada. Also, 16-day-old nestlings were collected and analysed for polychlorinated biphenyls (PCBs), polychlorinated dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs), pesticides, chlorophenols and chloroguaiacols. Most reproductive parameters were not different between populations at upstream and downstream locations, and were equivalent to or greater than those recorded for other tree swallow populations. Chlorinated hydrocarbon contamination of nestlings was low at all sites. The highest tissue concentrations were detected downstream of pulp mills on the Fraser River, where PCDD and PCDF patterns along with the presence of pentachlorophenol (PCP) suggested that the primary source of contaminants was past use of PCP for timber preservation. Although the absolute tissue concentration of contaminants was less, the toxic concentration (as estimated with I-TEQs) was greatest in nestlings downstream of a pulp mill on the Thompson River. The proportionately larger contributions from 2,3,7,8-TCDF and PCB-77 elevated these TEQs in comparison to other populations. Nest success was the one reproductive measure that showed substantial reductions in downstream populations on both rivers; however, there was little indication that nest failures were the direct result of contamination. Failures were largely due to parental abandonment, and, while poor parental attentiveness and nest abandonment have been associated with chlorinated hydrocarbon tissue concentrations in other studies, our 1-year assessment was insufficient to establish any link with pulp mill effluent exposure. Nestling growth models showed some subtle differences in growth patterns between nest box populations on the two rivers, but an association with pulp mill effects on aquatic insect prey availability was not established.

Journal Article↗
PubMed2000

Activation of the hsp70 promoter by environmental inorganic and organic chemicals: relationships with cytotoxicity and lipophilicity.

Stress proteins (heat shock proteins, HSPs) have been proposed as general markers of cellular aggression and their use for environmental monitoring is often suggested. The aim of this work was to study the potency of various environmentally relevant organic and inorganic chemicals to induce the expression of the HSP70 marker. For this purpose, we used an established HeLa cell line containing the chloramphenicol acetyl transferase (CAT) gene under the control of the hsp70 promoter. The screening of three metallic and 15 organic chemicals revealed differences in their capacities to induce the hsp70 promoter. The three metals tested (cadmium, zinc and mercury) were able to induce a stress response. Some organochlorine compounds (chlorophenol derivatives, tetrachlorohydroquinone, 3, 4-dichloroaniline, ethyl parathion and 1-chloro-2,4-dinitrobenzene) induced a response, whereas other common halogenated pesticides or aromatic hydrocarbons (e.g. benzo(a)pyrene, 2, 4-dichlorophenoxyacetic acid, endosulfan, diuron, 4-nonylphenol) did not. The potency to induce hsp70 was significantly correlated to the octanol-water partition coefficient (log K(ow)) of the inducing chemicals, except for 1-chloro-2,4-dinitrobenzene and ethyl parathion. Cytotoxicity assays run in parallel to the induction measurements revealed that the three metals were effective at non cytotoxic doses whereas all organic compounds, except tetrachlorohydroquinone and 1-chloro-2,4-dinitrobenzene, induced the promoter at cytotoxic doses. These results suggest that hsp70 is induced by different mechanisms of toxicity. We propose that this model can be used in mechanistic studies for the detection of toxic effects of certain pollutants.

Cadmium↗