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PubMed2001

Fast determination of phenols in contaminated soils.

An extraction method for the determination of phenols in contaminated soils, based on the application of solid-phase microextraction (SPME) coupled with GC-flame ionization detection analysis, was developed and tested. This method was developed using a natural soil spiked with phenol to a concentration level typical of an acute contamination event that can occur in an industrial site. The effects of the extraction parameters (pH, extraction time and salt concentration) on the extraction efficiency were studied and the method was then applied to determine the pollutant concentration at the beginning and during the biological treatment of a soil, contaminated with phenol and 3-chlorophenol, respectively. The SPME results were validated by comparison with those obtained with an US Environmental Protection Agency certified extraction method. The SPME method was also successfully applied to the determination of the adsorption behavior of 3-chlorophenol on a natural clay soil and was shown to be suitable for different matrices and phenolic compounds. Application of SPME technique results in a sharp reduction of the extraction times with negligible solvent consumption.

Chromatography, Gas↗
PubMed1983

Possibilities and limitations of tracing industrial effluents in the sea by means of capillary chromatography.

Certain organic constituents of waste water, such as halocarbons and chlorophenols, can be used to establish the distribution pattern of effluents discharged into the sea. The approach requires simple sampling techniques and highly sensitive and rapid analytical methods. The combination of glass capillary column gas chromatography and electron-capture-detection meets the analytical requirements. The selectivity of the detector, together with the high resolving power of the column, makes it possible to handle the complex sea-water matrix. Selective derivatization directly in the water sample is combined with simultaneous extraction to increase the number of suitable tracers. Halocarbons can be measured at pg/l levels. Chlorophenols are determined at ng/l concentration levels.

Chromatography, Gas↗
PubMed2002

Separation and determination of phenolic compounds by capillary electrophoresis with chemiluminescence detection.

Phenolic compounds were analyzed by means of capillary electrophoresis with chemiluminescence detection. Peroxyoxalate chemiluminescence reagent was used together with dansyl chloride as a labeling reagent. The reagent concentrations, the labeling procedures, and the performance of chemiluminescence detection cells were examined for sensitive detection of phenolic compounds. Six kinds of phenolic compounds (phenol, 2-chlorophenol, 4-chlorophenol, 2,4-dichlorophenol, 2,6-dichlorophenol, and 2,4,6-trichlorophenol) were determined over a range of three orders of magnitude with detection limits of the order of 10(-7) M; their detection limits were ca. 10 times as low as those obtained by an ordinary fluorescence detector. A running buffer solution containing sodium dodecylsulfate and acetonitrile provided satisfactory results in the separation of 15 kinds of phenolic compounds. The combination of capillary electrophoresis with chemiluminescence detection and column concentration procedure supported the possibility that the present system could be applied to real samples such as surface and reused waters.

Electrophoresis, Capillary↗
PubMed1999

Discrimination of structural isomers of chlorinated phenols in waters using gas chromatography-mass spectrometry in the negative chemical ionization mode.

The analysis and identification of structural isomers of mono-, di- and trichlorophenols is reported. The fragmentation of the phenols was examined by GC-MS in both electron impact (EI) and negative chemical ionization (NCI) modes, using methane as reagent gas. The ability of NCI to discriminate these isomeric compounds from differences in relative intensities for selected peaks is demonstrated. 3- and 4-chlorophenols have similar retention times; however, they can still be discriminated because their negative mass spectra and rather different. In dichlorophenols, the presence of one chlorine atom in the ortho position decreases their retention time and the relative intensity of the fragment ion at m/z 140. The NCI mass spectra for trichlorophenols are different from the rest, particularly for the m/z value corresponding to the chlorine atom. Tetra- and pentachlorophenols were also studied and sequential losses of Cl observed. An automatic solid-phase extraction system can optionally be used to preconcentrate chlorophenols in waters prior to determination at legally established toxic levels.

Gas Chromatography-Mass Spectrometry↗
PubMed1999

Synthesis and analytical properties of a novel columnar metallomesogenic polymer.

A metallomesogenic side-chain polymer with copper carboxylato discotic units in stacks prepared by covalent bonding of 14-pentadecenoic acid, stearic acid and poly(methylhydrosiloxane) is described. The physico-chemical and thermal properties of both monomeric and polymeric metallomesogens were determined by elemental analysis, IR, polarizing optical microscopy, thermal gravimetric analysis and differential scanning calorimetry. The polymeric states showed a discotic lamellar phase at 50-95 degrees C and an ordered discotic hexagonal phase at 95-200 degrees C. By dynamic coating, the metallomesogenic polymer was crosslinked to the capillary wall via benzoyl peroxide. The wall-coated capillary columns (15 m x 0.25 mm I.D.) were used for the separation of phenols. Factors affecting the retention and the sample selectivity were examined. Van 't Hoff plots as a function of temperature indicated that phase transitions were occurring. Thermodynamic properties of the analytes in this system were also studied. For the determination of a mixture of 3-aminophenol, 2-chlorophenol, 2-nitrophenol, 4-nitrophenol, o-methylphenol, m-methylphenol, p-methylphenol, 2,4-dichlorophenol, 2,4-dimethylphenol, 2,4-dinitrophenol, 2,4,6-trichlorophenol, 2,4,6-trimethylphenol, 4-bromophenol, 3-methyl-4-chlorophenol, pentachlorophenol, and unsubstituted phenol, the calibration graphs for most phenols were linear over the range of 10-1000 microg ml(-1) and the mass detection limits were in the ng range based on three times standard deviation of seven measurements of the lowest peak that could be detected.

Calorimetry, Differential Scanning↗
PubMed2003

Novel poly (vinyl chloride) matrix membrane electrodes for the determination of phenolic pollutants in waste water.

The construction and electrochemical response characteristics of poly (vinyl chloride) matrix membrane sensors for seven phenolic compounds (phenol, o-cresol, p-cresol, p-chlorophenol, o-nitrophenol, alpha-naphthol and beta-naphthol) are described. The membranes incorporate ion association complexes of these seven phenolic anions with phenanthroline-iron(II) as electroactive materials. These sensors show linear response for phenol, o-cresol, p-cresol, p-chlorophenol, o-nitrophenol, alpha-naphthol, and beta-naphthol over wide concentration ranges, with an average anionic slope 54.3 mV per concentration decade. The suggested sensors exhibit fast response time (1 min), low determination limits (1 x 10(-5)M), good stability (2-3 weeks), reasonable selectivity to phenolic compounds in the presence of other water pollutants. The average percentage recovery was 99.78+/-0.088 for individual phenolates and 99.61+/-0.198 for phenolates in mixtures. The investigated sensors were successfully used for direct potentiometric determination of traces of these phenolic compounds in wastewater samples. Results with mean accuracy of 99.74+/-0.29%, 99.82+/-0.36%, 99.65+/-0.47%, 99.73+/-0.37%, 99.77+/-0.30%, 99.86+/-0.31% and 99.91+/-0.22% was obtained for the seven sensors, respectively. These results were compared with data obtained using the British pharamacopial method (The British Pharmacopoeia, Her Majesty's Stationary Office, London, 1993) and others (Clarke's Isolation and Identification of Drugs in Pharmaceuticals Body Fluids and Post-mortem Materials, 2nd Edition, The Pharmaceutical Press, London, 1998).

Electrodes↗
PubMed2002

Acute toxicity of crude and dispersed oil to Octopus pallidus (Hoyle, 1885) hatchlings.

There is an increasing risk of a major oil spill in Australian waters over the next 20 years but there have been few studies on the impact of oil spills, and subsequent remedial action, on native Australian fauna. Octopus pallidus is a native Australian octopus species found in south-eastern Australia. The aim of the experiment was to investigate the effects of acute exposure to crude and dispersed crude oil and 4-chlorophenol (a reference toxicant) on recently hatched O. pallidus by calculating the 48-h LC50. Water-accommodated fraction (WAF) of Bass Strait crude oil was prepared using a ratio of one part crude oil to nine parts filtered seawater and mixing for 23 h. Dispersed-WAF was prepared using a ratio of one part Corexit 9527 to 50 parts crude oil and an oil to water ratio of one to nine and mixing for 23 h. Mean (SE) 48 h LC50 values were 0.39 (0.04), 1.83 (0.64) and 0.89 (0.08) ppm for WAF, dispersed-WAF and 4 chlorophenol, respectively. These results demonstrate that addition of the chemical dispersant Corexit 9527 to WAF does not increase the toxicity of WAF to O. pallidus hatchlings.

Animals↗
PubMed2002

Electrochemical removal of p-nonylphenol from dilute solutions using a carbon fiber anode.

p-Nonylphenol, which is widely used as raw material in industrial activities has been regarded as an environmental endocrine disrupter. In an effort to develop a new treatment method for p-nonylphenol, we initially investigated the electrochemical behavior of p-nonylphenol by voltammetric techniques. The electrochemical oxidation of p-nonylphenol led to the formation of electropolymerized film on the glassy carbon electrode surface. The fouling on the electrode surface by the electropolymerized film was evaluated by monitoring the electrode response of ferrocyanide ions as the redox marker. The electrochemical removal of p-nonylphenol based on the formation of the electropolymerized film on an anode surface was performed using a carbon fiber (CF) with a very large surface area. The high removal efficiency for p-nonylphenol was obtained by applying a potential at 0.7 V. The maximum surface coverage of electropolymerized p-nonylphenol on the CF was about 5 x 10(-9) mol/cm2. The presence of humic acid hardly inhibited the removal of p-nonylphenol. Furthermore, the application to the removal of phenol, o-chlorophenol, p-chlorophenol, 2,4-dichlorophenol, and 2,4,5-trichlorophenol was attempted by using this method.

Carbon↗
PubMed2002

Detoxification of phenolic solutions with horseradish peroxidase and hydrogen peroxide.

Phenolic solutions were treated with hydrogen peroxide and horseradish peroxidase (HRP) resulting in more than 95% removal of phenols within 3 h. Toxic compounds were formed during the treatment of aqueous solutions of phenol, 2-chlorophenol, 4-chlorophenol, 2,4-dichlorophenol and 2-methylphenol. However, the toxicities of HRP-treated solutions decreased within 21 h after the completion of the enzymatic reaction, except in the case of 2-methylphenol. The process of detoxification was significantly accelerated upon the addition of hydrogen peroxide to the dephenolized solutions. Solutions that were treated in the presence of chitosan exhibited lower toxicities than solutions treated in its absence if they were allowed to incubate for an extended period of time. Treatment in the presence of polyethylene glycol resulted in significantly higher toxicities. The toxicity of treated solutions was dependent on the addition mode of HRP and hydrogen peroxide. Treated solutions were also completely detoxified following illumination with UV light.

Animals↗
PubMedDate not supplied

An experimental and numerical study of the thermal oxidation of chlorobenzene.

A combustion-driven flow reactor was used to examine the formation of chlorinated and non-chlorinated species from the thermal oxidation of chlorobenzene under post-flame conditions. Temperature varied from 725 to 1000 K, while the equivalence ratio was held constant at 0.5. Significant quantities of chlorinated intermediates, vinyl chloride and chlorophenol, were measured. A dominant C-Cl scission destruction pathway seen in pyrolytic studies was not observed. Instead, hydrogen-abstraction reactions prevailed, leading to high concentrations of chlorinated byproducts. The thermal oxidation of benzene was also investigated for comparison. Chemical kinetic modeling of benzene and chlorobenzene was used to explore reaction pathways. Two chlorobenzene models were developed to test the hypothesis that chlorobenzene oxidation follows a CO-expulsion breakdown pathway similar to that of benzene. For the temperatures and equivalence ratio studied, hydrogen abstraction by hydroxyl radicals dominates the initial destruction of both benzene and chlorobenzene. Chlorinated byproducts (i.e., chlorophenol and vinyl chloride) were formed from chlorobenzene oxidation in similar quantities and at similar temperatures to their respective analogue formed during benzene oxidation (i.e., phenol and ethylene).

Journal Article↗
PubMed2002

Modeling the formation of PCDD/F in solid waste incinerators.

Polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/F) appear in unacceptable amounts in the gaseous emissions during the incineration of wastes containing significant quantities of chlorine and metals, such as MSW and medical waste. They are formed both in the gas phase at temperatures above 600 degrees C and on the surface of the solid phase (flyash) in the temperature range 400-225 degrees C. Both the precursor (from existing smaller chlorinated molecules) and de novo (from elemental carbon) routes are involved. An empirically derived global model for their de novo formation on flyash in MSW and medical waste incinerators has now been extended to include the precursor mechanism, and a gas phase formation component, with separate rate expressions for PCDD and PCDF. Homogeneous PCDD formation is governed by the concentration of chlorophenols and PCDF by that of chlorophenols and chlorobenzenes. The result is more complete system which distinguishes between the gas and solid phase contributions to the I-TEQ. An additional step for the adsorption of gaseous PCDD/F back onto the solid phase during cooling suggests this should be minimal in the gas ducts of an incinerator. The extended model has been tested against experimental data collected from a well-controlled pilot incinerator and commercial incinerators, and found to adequately describe the measured outputs. With the model it should be possible to predict the PCDD/F emissions from commercial incinerators, provided that the ash properties and the overall temperature-time profiles are known.

Adsorption↗
PubMed1999

Tolerance to trichlorophenols in microorganisms from a polluted and a pristine site of a river

The effect of 2,4,5- and 2,4,6-trichlorophenol on the microbiota from a polluted and a pristine site of a river was studied. Bacterial metabolic activity measurements by epifluorescence microscopy showed that the polluted site contained more metabolically active cells than the pristine site. Total culturable bacterial counts and tolerant bacterial counts from both sites were not affected by incubation (for up to 5 days) with 200 ppm of chlorophenols. However, the incubation with 500 ppm of 2,4,5-trichlorophenol prevented detection of total and tolerant bacterial counts in the pristine site, and inhibited tolerants in the polluted site. None of 250 bacterial colonies directly isolated from these samples was able to grow on chlorophenols. However, bacteria able to grow on 2,4,6-trichlorophenol, were obtained by enrichment of water and sediments samples.

Journal Article↗
PubMed2003

A new variant activator involved in the degradation of phenolic compounds from a strain of Pseudomonas putida.

A new variant type of regulatory activator and relevant promoters (designated capR, Pr and Po) involved in the metabolism of phenolic compounds were cloned from Pseudomonas putida KCTC1452 by using PCR. The deduced amino acid sequence of CapR revealed a difference in nine amino acids from the effector binding domain of DmpR. To measure effector specificity, plasmids were constructed in such a way that the expression of luc gene for firefly luciferase or lacZ for beta-galactosidase as a reporter was under the control of capR. When Escherichia coli transformed with the plasmids was exposed to phenol, dramatic increases in the activity of luciferase or beta-galactosidase were observed in a range of 0.01-1 mM. Among various phenolic compounds tested, other effective compounds included catechol, 2-methylphenol, 3-methylphenol, 4-methylphenol, 2-chlorophenol, 4-chlorophenol, 2-nitrophenol, resorcinol, and 2, 5-dimethylphenol. The results indicate that CapR has effector specificity different from other related activators, CatR and DmpR. Waste water and soil potentially containing phenolic compounds were also tested by this system and the results were compared with chemical and GC data. The present results indicate that the biosensor consisting of capR and the promoters may be utilized for the development of a phenolic compounds-specific biosensor in monitoring the environmental pollutant.

Bacterial Proteins↗
PubMed2000

Biomarkers for monitoring efficacy of bioremediation by microbial inoculants.

Bioaugmentation of contaminated sites with microbes that are adapted or genetically engineered for degradation of specific toxic compounds is an area that is currently being explored as a clean-up option. Biomarkers have been developed to track the survival and efficacy of specific bacteria that are used as inocula for bioremediation of contaminated soil. Examples of biomarkers include the luc gene, encoding firefly luciferase and the gfp gene, encoding the green fluorescent protein (GFP). The luc gene was used to tag different bacteria used for bioremediation of gasoline or chlorophenols. The bacteria were monitored on the basis of luciferase activity in cell extracts from soil. The gfp gene was also used to monitor bacteria during degradation of chlorophenol in soil, based on fluorescence of the GFP protein. Other biomarkers can also be used for monitoring of microbial inocula used for bioaugmentation of contaminated sites. The choice of biomarker and monitoring system depends on the particular site, bacterial strain and sensitivity and specificity of detection required.

Journal Article↗
PubMed1997

HPLC-fluorescence determination of chlorocresol and chloroxylenol in pharmaceuticals.

The use of 2-chloro-6,7-dimethoxy-3-quinolinecarboxaldehyde as a fluorogenic labelling reagent in pre-column derivatization for the HPLC separation of chlorophenols has been investigated. The compound reacts (50 min at 110 degrees C) with 2- and 4-chlorophenols to give fluorescent ethers that can be separated by reversed-phase HPLC and detected at lambda exc = 360 nm, lambda em = 500 nm. The experimental conditions for derivatization and chromatographic separation are discussed. Applications for the determination of chlorocresol (4-chloro-3-cresol) and chloroxylenol (4-chloro-3,5-xylenol) in pharmaceutical formulations (creams, ointments) are described.

Calibration↗
PubMed2001

A comparative adsorption/biosorption study of mono-chlorinated phenols onto various sorbents.

The potential use of dried activated sludge and fly ash as a substitute for granular activated carbon for removing mono-chlorinated phenols (o-chlorophenol and p-chlorophenol) was examined. The pollutant binding capacity of the adsorbent/biosorbent was shown to be a function of substituted group, initial pH and initial mono-chlorinated phenol concentration. The working sorption pH value was determined as 1.0 and the equilibrium uptake increased with increasing initial mono-chlorinated phenol concentration up to 500 mg dm(-3) for all the mono-chlorinated phenol-sorbent systems. The suitability of the Freundlich, Langmuir and Redlich-Peterson adsorption models to the equilibrium data were investigated for each mono-chlorinated phenol-sorbent system. The results showed that the equilibrium data for all the mono-chlorinated phenol-sorbent systems fitted the Redlich-Peterson model best within the concentration range studied.

Adsorption↗
PubMed1998

Sonochemistry of organic compounds in homogeneous aqueous oxidising systems.

The influence of ultrasound on the degradation of trichloroethylene, o-chlorophenol and 1,3-dichloro-2-propanol in some Fenton type aqueous systems was investigated. Kinetic analysis of the results revealed that the ultrasonic waves do not really enhance the reactivity of the system, but rather add their own degradation mechanism to the chemical degradation. This effect is comparable to the well known sonochemical switching effect. As a consequence, the degradation rate of the combined systems is the sum of the pure sonochemical degradation rate and the silent chemical degradation rate. The only exception to this rule is the degradation of o-chlorophenol in the presence of hydrogen peroxide, in the absence of catalysts. Care had to be taken in order to avoid artifacts that may arise, e.g., when neglecting temperature effects.

Journal Article↗
PubMed2000

Supersonic jet/multiphoton ionization/mass spectrometry of dioxins formed by the thermal reaction of phenols in the absence and presence of an FeCl3 catalyst.

Dioxins, which are thermally produced from several precursor molecules, were investigated by supersonic jet/multiphoton ionization/time-of-flight mass spectrometry (SSJ/MPI/TOF-MS). Dibenzofuran and dibenzo-p-dioxin were efficiently generated from o-chlorophenol and also from phenol after a chlorination reaction with FeCl3. The present technique was employed for the continuous monitoring of a specified isomer, e.g., m-chlorophenol, which is formed at relatively low temperatures by chlorination of phenol with FeCl3. A dimerization reaction that forms a dibenzo-p-dioxin, e.g., dichlorodibenzo-p-dioxin from 2,4-dichlorophenol, at relatively high temperatures was also investigated. The number of chlorine atoms in the dioxin molecule was largely correlated with the number of chlorine atoms in the precursor molecule. However, some unexpected compounds, which probably occur by dechlorination and rearrangement reactions, were also found. Thus, the SSJ/MPI/TOF-MS technique represents a sensitive, as well as selective, analytical method for monitoring thermally generated dioxins.

Catalysis↗