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PubMed2004

Evaluation of a polyclonal antiserum to pentachlorothiophenol-acetic acid-KLH immunogen: binding properties and use with heterologous PCP derivatives in ELISA for pentachlorophenol.

A polyclonal antiserum to pentachlorothiophenol-acetic acid-KLH was generated in sheep and assessed by solid phase ELISA. The assessment procedure included use of double checkerboard analysis in the absence and in the presence of analyte loads, estimation of cross reactivities of chlorophenol pesticides, assessment of the effect of pH, Tween 20, and Thames water matrix. The antiserum was highly specific for pentachlorophenol and enabled minimum detection limits of less than 0.2 ng mL(-1) in river water matrix. Particularly important was the significant improvement of assay performance in the absence of Tween 20 and at pH 4 and the very low cross reactivity (less than 0.01%) for other commonly used chlorophenols-2,4,5-trichlorophenol and 2,4,6-trichlorophenol, 2-methyl-4-chlorophenoxyacetic acid, and 2,4-dichlorophenoxy acetic acid. The study re-affirms the importance of the judicious choice of hapten derivatives in the synthesis of immunogens and assay reagents for pentachlorophenol analysis by competitive immunoassays.

Acetic Acid↗

PubMed2005

Simultaneous determination of phenolic compounds by means of an automated voltammetric "electronic tongue".

This contribution describes the simultaneous determination of three phenolic compounds, o-cresol, p-chlorophenol and 4-chloro-3-methylphenol, using direct oxidation and amperometric detection coupled by signal deconvolution, accomplished via chemometric methods. Direct oxidation of phenolic compounds is performed at the surface of an epoxy-graphite transducer, by linear scan voltammetry. Due to strong signal overlapping, artificial neural networks (ANNs) were used during data treatment, in a combination of chemometrics and electrochemical sensors known as an "electronic tongue". To calibrate this system properly, a total of 80 mixed samples were prepared automatically by employing a sequential injection analysis (SIA) system designed to automatically generate the information needed to train the network. The phenolic compound concentration varied from 1 to 70 microM for o-cresol, from 0.5 microM to 140 microM for p-chlorophenol and from 1 microM to 100 microM for 4-chloro-3-methylphenol. A good prediction capability was obtained, with correlation coefficients >0.964 when the obtained values were compared with those expected for a set of 24 external test samples not used for training. The results presented here indicate that this technique is a simple and robust analytical method of environmental interest.

Journal Article↗

PubMed2001

Internal exposure to polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans (PCDDs/PCDFs) of Bavarian chimney sweeps.

This study was carried out to evaluate the internal exposure to polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans (PCDDs/PCDFs) of chimney sweeps in Bavaria compared to a control group without occupational exposure. The PCDD/PCDF concentrations in the blood fat of 227 chimney sweeps were compared with the concentrations in samples from 60 controls. Using an internal standard containing 17 (13)C(12)-labeled PCDD/F congeners, the samples were cleaned up after fat elution using standard methods. The statistical analysis was adjusted to account for demographic differences, dietary habits, smoking status, and both occupational and nonoccupational contact with chlorinated hydrocarbons. Detailed information on the type of heating in the households swept, the length of time the chimney sweeps had carried out the profession (min 34, med 195, max 466 months) and the protective measures employed, were used to examine the influence of the working conditions specific to chimney sweeps on the internal PCDD/PCDF exposure. The correlation between blood-fat PCB concentrations as well as urinary chlorophenol concentrations and the exposure to PCDDs/PCDFs was evaluated. The sum of PCDD/PCDF components in chimney sweeps, expressed by International Toxic Equivalents (I-TEQ), was significantly increased compared to the control group (median: 26.36 versus 20.75 pg I-TEQ/g blood fat). For 37 chimney sweeps (16.3%) the sum of PCDDs/PCDFs exceeded the 95th percentile of the control group, i.e., 38.23 pg I-TEQ/g blood fat. Multiple regression analysis revealed that in addition to occupation, the variables age, district, and proximity to a waste incineration plant seem to have an effect on the internal PCDD/PCDF exposure. An additional influence on the internal exposure could not be determined for any of the special aspects of the work. We identified no high correlations between the concentrations of PCBs and chlorophenols and PCDDs/PCDFs. This study revealed significantly higher internal exposure to PCDDs/PCDFs in chimney sweeps than in the control group. The differences are small and within the range of the internal exposure to PCDDs/PCDFs in blood found in the general population in Germany since 1989. Further investigations in to PCDD/PCDF-related diseases in these study groups were not carried out.

Adult↗

PubMed1999

Body residues and responses of the midge chironomus riparius to sediment-associated 2,4,5-trichlorophenol in subchronic and chronic exposures

Subchronic and chronic toxicity of sediment-associated 2,4, 5-trichlorophenol to the midge Chironomus riparius was determined by conducting a 10-day growth and a 50-day emergence tests with spiked lake sediment (nominal initial TCP concentrations were 25, 51, 101, 203, 304 and 405 &mgr;mol kg-1 dry weight in the growth test and 25, 76, 152 and 304 &mgr;mol kg-1 dry weight the emergence test). In addition, we measured the residue of chlorophenol in larval tissue and made an attempt to relate it with the observed adverse biological responses. The larvae were exposed individually to avoid density-dependent effects of mortality on food ration and growth of the surviving larvae. In the growth test, mortality was low at sediment concentrations </=193 &mgr;mol TCP kg-1, but it increased sharply at the higher concentrations being 37 and 94% at 334 and 441 &mgr;mol kg-1 DW, respectively. The effect of sediment TCP concentration on larval mortality was highly significant (10-day LC50 337 &mgr;mol TCP kg-1 dry sediment) in the growth test. In the emergence test, however, mortality was low (3-13%) at all concentrations. TCP did not affect larval growth at the concentrations used. The concentration of TCP in the whole larvae after the 10-day exposure was proportional to sediment concentration, being at highest 160 &mgr;mol kg-1 fresh weight. When the average body residues of TCP were below 80 &mgr;mol kg-1, mortality was low, but it increased when the body residue approached 100 &mgr;mol kg-1. After the 10-day exposure, the body residue, at which 50% of the larvae survived (CBR50) was 113 &mgr;mol g-1. TCP exposure accelerated larval development and the midges exposed to 171 and 324 &mgr;mol TCP kg-1 emerged earlier than those in the other concentrations or in the control sediment. In natural environments, sediment-associated chlorophenolics are probably not a major environmental problem to benthic fauna because concentrations similar to that which we observed to cause adverse effects to C. riparius (>60 mg kg-1 dry sediment) are rare.http://link.springer-ny. com/link/service/journals/00244/bibs/37n1p42.html

Journal Article↗

PubMed2006

Biosorption and biodegradation of pentachlorophenol (PCP) in an upflow anaerobic sludge blanket (UASB) reactor.

In order to understand the fate of PCP in upflow anaerobic sludge blanket reactor (UASB) more completely, the sorption and biodegradation of pentachlorophenol (PCP) by anaerobic sludge granules were investigated. The anaerobic granular sludge degrading PCP was formed in UASB reactor, which was seeded with anaerobic sludge acclimated by chlorophenols. At the hydraulic retention time (HRT) of 20-22 h, and PCP loading rate of 200-220 mg l(-1) d(-1), UASB reactor exhibited good performance in treating wastewater which containing 170-180 mg l(-1) PCP and the PCP removal rate of 99.5% was achieved. Sequential appearance of tetra-, tri-, di-, and mono-chlorophenol was observed in the reactor effluent after 20 mg l(-1) PCP introduction. Sorption and desorption of PCP on the anaerobic sludge granules were all fitted to the Freundlich isotherm equation. Sorption of PCP was partly irreversible. The Freundlich equation could describe the behavior of PCP amount sorbed by granular sludge in anaerobic reactor reasonably well. The results demonstrated that the main mechanism leading to removal of PCP on anaerobic granular sludge was biodegradation, not sorption or volatization.

Adsorption↗

PubMed1995

Comparison of PCDD and PCDF concentrations after aerobic and anaerobic digestion of sewage sludge.

The anaerobic stabilization of raw sludges of different origin was investigated. Precursors like chlorophenol and chlorobenzene isomers were added to some of the samples. The change of the PCDD/F concentrations as well as the change in the pattern of the isomers and congeners was independent of the type and amount of the added precursor. With respect to the change of the PCDD/F concentrations the digestion properties were typical in each digestion series but not applicable to other digestion processes. The quality of the digestion was characterized by measuring the change of pH, controlling the biogas flow rate and the determination of the mineralization degree. The added chlorobenzenes and chlorophenols were almost completely degraded. The aerobic digestion occurred in ventilated batch reactors leading to a significant degradation of all PCDD/F homologues. The degradation ratio depends on the origin of the sewage sludge. Independent of origin individual congeners were partially or completely degraded.

Aerobiosis↗

PubMed1975

[Polychlorodibenzo-p-dioxins (author's transl)].

Polychlorodibenzo-p-dioxins (chlorodioxins) appear most frequently by heating of chlorophenols in alkaline solution specially when producing organic derivatives. Consequently chlorodioxins may contaminate several industrial chemical products largely used, for instance, as pesticides. Occasionally, chlorodioxins are also synthesized from chlorophenols or their derivatives in situ during industrial processes. Chlorodioxins are the cause of chloracne and chick edema which killed thousands of broiler chickens in the U.S.A. Furthermore chlorodioxins seem to be foetotoxic possible even for man. The present paper is the first part of our work. It is a review of the chemical and toxicological properties of chlorodioxins. We hope to publish later a review of analytical methods and the results of our analyses.

2,4,5-Trichlorophenoxyacetic Acid↗

PubMed2005

Analysis of phenols in water by high-performance liquid chromatography using coumarin-6-sulfonyl chloride as a fluorogenic precolumn label.

A simple, sensitive and rapid reversed-phase high-performance liquid chromatography (RP-HPLC) method is proposed for the analysis of some environmentally important phenols in water. The use of coumarin-6-sulphonyl chloride (C6SCl) as a fluorescence-labeling reagent has been investigated. The compound reacts with phenols within 20 min under mild conditions (ambient temperature, pH 9.0) to give sulphonates that can be separated by RP-HPLC employing fluorescence detection at lambda(ex) = 360 and lambda(em) = 460 nm. The optimum conditions for fluorescence, derivatization and chromatographic separation have been established and detection limits in the range 0.1-0.9 microg l(-1) were obtained for the studied compounds. The calibration curves were linear for the range 6-200 microg l(-1) for phenol, 3-200 microg l(-1) for 2-chlorophenol, 4-chlorophenol and 2,3,5-trichlorophenol and for the range of 3-100 microg l(-1) for 2,3-dichlorophenol and 3,5-dichlorophenol. The practical applicability of the method to environmental samples was demonstrated by analyzing drinking and industrial water samples spiked with the phenolic compounds.

Chromatography, High Pressure Liquid↗

PubMed2006

Estimation of the critical effect level for pollution prevention based on oyster embryonic development toxicity test: the search for reliability.

In spite of the consideration that toxicity testing is a reduced approach to measure the effects of pollutants on ecosystems, the early-life-stage (ELS) tests have evident ecological relevance because they reflect the possible reproductive impairment of the natural populations. The procedure and validation of Crassostrea rhizophorae embryonic development test have shown that it meets the same precision as other U.S. EPA tests, where EC(50) is generally used as a toxicological endpoint. However, the recognition that EC(50) is not the best endpoint to assess contaminant effects led U.S. EPA to recently suggest EC(25) as an alternative to estimate xenobiotic effects for pollution prevention. To provide reliability to the toxicological test results on C. rhizophorae embryos, the present work aimed to establish the critical effect level for this test organism, based on its reaction to reference toxicants, by using the statistical method proposed by Norberg-King (Inhibition Concentration, version 2.0). Oyster embryos were exposed to graded series of reference toxicants (ZnSO(4) x 7H(2)O; AgNO(3); KCl; CdCl(2)H(2)O; phenol, 4-chlorophenol and dodecyl sodium sulphate). Based on the obtained results, the critical value for C. rhizophorae embryonic development test was estimated as EC(15). The present research enhances the emerging consensus that ELS tests data would be adequate for estimating the chronic safe concentrations of pollutants in the receiving waters. Based on recommended criteria and on the results of the present research, zinc sulphate and 4-chlorophenol have been pointed out, among the inorganic and organic compounds tested, as the best reference toxicants for C. rhizophorae ELS-test.

Animals↗

PubMed2004

Characterization and determination of the thermodynamic and kinetic properties of p-CP adsorption onto organophilic bentonite from aqueous solution.

The characterization of tetraethylammonium bentonite and the adsorption of p-chlorophenol (p-CP) onto organophilic bentonite (tetraethylammonium bentonite) was studied as a function of the solution concentration and temperature. The observed adsorption rates were found to fit first-order kinetics. The rate constants were calculated for temperatures ranging between 15.0 and 35.0 degrees C at constant concentration. The adsorption energy E and adsorption capacity q(m) for the phenolic compound adsorbing on organophilic bentonite were estimated using the Dubinin-Radushkevic equation. Thermodynamic parameters (Deltag(a), Deltah(a), Deltas(a)) were calculated by a new approximation from the isotherms of p-CP adsorption on organophilic bentonite. These isotherms were modeled according to Freundlich and Dubinin-Radushkevic adsorption isotherms. The amount of adsorption of p-chlorophenol on organophilic bentonite was found to be dependent on the relative energies of adsorbent-adsorbate, adsorbate-solvent, and adsorbate-adsorbate interactions.

Journal Article↗

PubMed2006

Characteristics of phenol and chlorinated phenols sorption onto surfactant-modified bentonite.

Surfactant-modified bentonite was synthesized by replacing adsorbed Na+ with long-chain alkyl quaternary ammonium cation, hexadecyltrimethylammonium bromide (HDTMAB). The sorption isotherms of phenol, p-chlorophenol, and 2,4-dichlorophenol were modeled according to the Langmuir and Freundlich equations. The Langmuir isotherm was found to describe the equilibrium adsorption data well. The mechanisms and characteristics of sorption of these ionizable organic contaminants onto surfactant-modified bentonite from water were investigated systematically and described quantitatively. The sorption properties are affected by the treatment conditions, such as amount of organobentonite, and the properties of organic compounds. Results indicated that adsorption of phenols from water was in proportion to their hydrophobicities, which increased with chlorine addition (phenol<p-chlorophenol<2,4-dichlorophenol). Sorption isotherms of these phenols were typically nonlinear. Both adsorption and partition contribute to the sorption of investigated phenols to organobentonite. The separate contributions of adsorption and partition to the total sorption of these compounds to organobentonite is analyzed mathematically. Results indicate that the partition effect is weak and linear with contaminant concentration, whereas the adsorption effect is more powerful and nonlinear with contaminant concentration. The sorption of phenols onto organobentonite was dominated by adsorption at low concentrations and partition started to dominate at high concentrations, making the organobentonites powerful sorbents for organic contaminants over a wide range of concentrations.

Journal Article↗

PubMed2006

Chlorination of aromatic compounds in micellar media: regioselectivity.

Chlorination of phenol and ortho-chlorophenol was studied in micellar media in order to observe the effect on regioselectivity. Hydrogen peroxide/hydrochloric acid-aqueous system, which is environmentally a safer route was employed for chlorination. Selectivity ratio was found to be dependent on the nature and concentration of the surfactant. Ortho/para selectivity ratio up to 12 was realized for the chlorination of phenol. 2,6-/2,4-dichlorophenol ratio up to 1.01 was realized for the chlorination of ortho-chlorophenol.

Journal Article↗

PubMed2005

Removal of organic compounds by alginate gel beads with entrapped activated carbon.

The adsorption of alginate gel (AG) beads and AG with activated carbon entrapped (AG-AC) beads prepared using different types of metal ions were investigated by measuring the removal of several organic compounds with different charges and size. AG-AC beads prepared in a CaCl2 solution adsorbed strongly positively charged compounds as well as electrically neutral and low molecular weight compounds such as p-chlorophenol. However, a high molecular weight humic acid was not adsorbed by AG-AC. The AG-AC selectively adsorbed p-chlorophenol from a humic acid solution. The adsorption capacity obtained from the adsorption isotherm of AC entrapped in AG was compared with that of AC. The AG-AC beads prepared in a solution of FeCl3 were able to specifically adsorb negatively charged gallic acid. Thus, entrapping AC into AG resulted in the selective adsorption.

Adsorption↗

PubMed2004

Monitoring of organic pollutants in coastal waters of the Gulf of Gdańsk, Southern Baltic.

This paper presents an overview of changes in organic pollution of coastal waters of the Gulf of Gdańsk (Baltic Sea). Toxic pollutants including volatile organic compounds (VOC), volatile organohalogen compounds (VOX), chlorophenols, phenoxyacids, polychlorinated biphenyls (PCBs) and polycyclic aromatic hydrocarbons (PAHs) were determined in seawater from the Gulf of Gdańsk coastal waters in the period 1996-2001. In the case of the Gulf of Gdańsk, non-conservative behaviour of VOC was observed due to random temporal and spatial of inputs along the Vistula estuary and to the dilution of VOC-enriched river water with seawater. The concentrations of VOX in seawater decreased throughout the period and the concentrations of VOX were in the range of few ng dm(-3) up to 250 ng dm(-3), similar to estuaries elsewhere. The average concentrations of chlorophenols and phenoxyacids were between 0.1 and 6.0 and 0.05 and 2.2 microg dm(-3), respectively. However, remarkably high concentrations of 2,4-dichlorophenol (6 microg dm(-3)) were obtained in samples collected from the Vistula River. Generally concentrations of PCBs did not exceed few ng dm(-3) with the exception of 1999, when all samples exhibited elevated concentrations of PCBs. In addition, higher concentrations of PCBs in the open sea compared to river waters suggested localised inputs. Due to the ability of most organic pollutants to bioaccumulate and biomagnify, especially the persistent organic pollutants, continued monitoring is of crucial importance for the health of marine life in the Gulf of Gdańsk.

Animals↗

PubMed2006

Oxygen-induced concurrent ultrasonic degradation of volatile and non-volatile aromatic compounds.

Acoustic cavitation, induced by ultrasound, can be used to eliminate organic pollutants from water. This type of ultrasonic treatment of polluted water can be grouped with those generally referred to as advanced oxidative processes since it involves hydroxyl radicals. In this case these highly active species are generated from the dissociation of water and oxygen dissociation caused by cavitation bubble collapse. The cavitation induced degradation rates of organic compounds in water are mainly linked to their vapor pressure and solubility and here we will further explore these links by examining the degradation of a mixture of two materials with different physical properties, chlorobenzene and 4-chlorophenol. The results obtained when a dilute solution of a mixture of these compounds saturated with argon is subjected to sonication at 300 kHz, parallels previous observations achieved in an aerated aqueous medium at 500 kHz. The two compounds exhibit sequential degradation with the more volatile chlorobenzene entering the cavitation bubble and being destroyed first. The 4-chlorophenol degradation occurs subsequently only when the chlorobenzene has been completely destroyed. The two compounds exhibit different behavior when sonicated in water saturated with oxygen. Under these conditions the two compounds are degraded simultaneously, a remarkable result for which two explanations can be proposed, both of which are based on the formation of additional OH radical species: The ability to produce conditions for the simultaneous elimination of two organic compounds by the use of oxygen is of great importance in the developing field of ultrasonic water treatment.

Computer Simulation↗

PubMed2006

Removal of phenol and substituted phenols by newly developed emulsion liquid membrane process.

Emulsion liquid membrane (ELM) stabilized by non-Newtonian conversion of the liquid membrane phase and dispersed in a Taylor-Couette flow was applied to treat model industrial wastewaters containing phenols and selected substituted phenols (hydroquinone, three chlorophenols and two nitrophenols) at relatively high concentrations. Under optimized operating conditions, all the compounds except hydroquinone were extracted with the maximum extraction efficiency of over 96% and the time to reach maximum extraction ranged from 2 to 30 min. For 2-chlorophenol, 2,4-dichlorophenol, and 2-nitrophenol, maximum extraction efficiency of over 99% was reached in less than 2 min of contact time. Extraction of these compounds from the mixture was also highly efficient. Factors that affected the overall extraction efficiency such as acid-base speciation of the target compounds and the affinity between the target compounds and the membrane phase were determined. This study suggested that the newly developed ELM process might provide a promising alternative technology to treat industrial wastewaters containing high concentrations of phenolic compounds.

Emulsifying Agents↗

PubMed1987

In vitro cytotoxicity of organic pollutants to bluegill sunfish (BF-2) cells.

BF-2 cells, an established cell line derived from bluegill sunfish, (Lepomis macrochirus), were exposed to 18 organic toxicants, with cytotoxicity being assayed by the neutral red (NR) technique. Based on the concentration of toxicant that reduced lysosomal uptake of neutral red by 50% (NR50), the rank order of cytotoxicity was methyl mercury greater than pentachlorophenol greater than 2,3,5,6-tetrachlorophenol greater than 2,3,5-trichlorophenol greater than 2,3-dinitrotoluene greater than 2,4,6-trichlorophenol greater than 2,4-dichlorophenol greater than 2,4-dichlorotoluene greater than 6-chloro-3-hydroxytoluene greater than o-chlorotoluene greater than 4-chlorophenol greater than 2-chlorophenol, 2,4-dimethylphenol greater than 2,4-dinitrophenol greater than 4-nitrophenol greater than 3-methylphenol greater than phenol greater than toluene. Published in vivo LC50 values were identified for 11 of the 18 test agents and, with the exception of 2,4-dinitrophenol, there was a good correlation between the in vitro cytotoxicity of the test agents and their in vivo waterborne acute toxocity. The potencies of the substituted phenolics and chlorinated toluenes as determined by the in vitro cytotoxicity assay correlated strongly with their log octanol/water partition coefficients (log P). However, the toxicity of 2,3-dinitrotoluene in vitro, and apparently also in vivo, was not a function of its log P value.

Animals↗

PubMed2000

Continuous microwave-assisted extraction, solvent changeover and preconcentration of monophenols in agricultural soils.

An automatic extraction, preconcentration and clean-up module for the extraction of phenolic compounds from soils was developed; the separation and quantitation of each phenol is accomplished by GC-MS. The sorption-desorption of thirteen phenols on soils containing variable amounts of organic carbon (0.05-3.4%) and clay minerals (2-43%) at pH 5.7-8.6 was investigated. For this purpose, uncontaminated soils were spiked with 5 or 20 microg of each phenol per g of soil; the soils were then stored at 4 degrees C for at least 3 months prior to analysis in order to simulate analyte-matrix interactions other than material losses and environmental degradation in actual contaminated soils. The organic carbon content in acid and alkaline soils affects the sorption of chlorophenols but not that of alkylphenols. On the other hand, alkylphenols are preferentially sorbed by neutral soils, the process being influenced by the clay mineral content. Based on the results, alkylphenols interact more strongly with agricultural soils than do chlorophenols; also, both types of compound are less strongly sorbed by loamy sand soils owing to their increased sand contents.

Agriculture↗