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PubMed2005

Dechlorination of chlorophenols found in pulp bleach plant E-1 effluents by advanced oxidation processes.

Studies were conducted on the response of 2,4,6-trichlorophenol (1), 2,3,4,5-tetrachloro-phenol (2) and 4,5-dichloroguaiacol (3) toward advanced oxidation processes, such as UV-, O2/UV-, H2O2/UV-, O3/UV- and O3-H2O2/UV-photolyses with irradiation of 254 nm photons. The compounds 1-3 are among the chlorophenols found in the Kraft-pulp bleach plant E-1 effluents. The studies were extended to treatment of these compounds with ozonation and O3-H2O2 oxidation systems in alkaline aqueous solution. Except for the O2/UV-photolysis of 1 and H2O2/UV-photolysis of 2, the dechlorination of 1-3 by O2/UV- and H2O2/UV-potolyses were less effective than the corresponding N2UV-potolysis of 1-3. Guaiacol-type chlorophenols were more readily able to undergo dechlorination than non-guaiacol type chlorophenols by N2/UV-, O2/UV- and H2O2/UV-potolyses. In addition, the efficiency for the dechlorination of 1-3 by N2/UV-, O2/UV- and H2O2/UV-potolyses appeared to be dependent upon the inductive and resonance effects of substituents as well as number and position of chlorine substituent in the aromatic ring of the compounds. The dechlorination of 2 by treatment with O3 alone is slightly more effective than the corresponding the O3/UV-photlysis, whereas the dechlorination of 2 by treatment with the combination of O3 and H2O2 was slightly less effective than the corresponding O3-H2O2/UV-photolysis. In contrast, the dechlorination of 3 on treatment with O3 alone was slightly less effective than the corresponding the O3/UV-photolysis, whereas the dechlorination of 3 on treatment with the combination of O3 and H2O2 was slightly more effective than the corresponding the O3-H2O2/UV-photolysis. In the dechlorination of 2 and 3, chemical species derived from ozone and hydrogen peroxide in alkaline solution were dominant reactions in the O3/UV- and O3-H2O2/UV-photolysis systems as in the O3 and O3-H2O2 oxidation systems. Possible dechlorination mechanisms involved were discussed on the basis of kinetic data.

Chlorophenols↗

PubMed2005

para-Chlorophenol inhibition on COD, nitrogen and phosphate removal from synthetic wastewater in a sequencing batch reactor.

COD, nitrogen, phosphate and para-chlorophenol (4-chlorophenol, 4-CP) removal from synthetic wastewater was investigated using a four-step sequencing batch reactor (SBR) at different sludge ages and initial para-chlorophenol (4-CP) concentrations. The nutrient removal process consisted of anaerobic, oxic, anoxic and oxic phases with hydraulic residence times (HRT) of 1/3/1/1 h and a settling phase of 0.75 h. A Box-Wilson statistical experiment design was used considering the sludge age (5-25 days) and 4-CP concentration (0-400 mg l(-1)) as independent variables. Variations of percent COD, NH4-N, PO4-P and 4-CP removals with sludge age and initial 4-CP concentration were investigated. Percent nutrient removals increased with increasing sludge age and decreasing 4-CP concentrations. Low nutrient removals were obtained at high initial 4-CP concentrations especially at low sludge ages. However, high sludge ages partially overcome the adverse effects of 4-CP and resulted in high nutrient removals. COD, NH4-N, PO4-P and 4-CP removals were 76%, 72%, 26% and 34% at a sludge age of 25 days and initial 4-CP concentration of 200 mg l(-1). Sludge volume index (SVI) also decreased with increasing sludge age and decreasing 4-CP concentrations. An SVI value of 104 ml g(-1) was obtained at a sludge age of 25 days and initial 4-CP of 200 mg l(-1).

Acinetobacter↗

PubMed2005

Toxicity of chlorophenols to Pseudokirchneriella subcapitata under air-tight test environment.

A closed-system algal toxicity test with no headspace was applied to evaluate the toxicity of chlorophenols to Pseudokirchneriella subcapitata. The dissolved oxygen production and the growth rate based on cell density were the response endpoints. Phenol and seven chlorophenols were tested using the above test technique. Median effective concentrations (EC50) range from 0.004 to 25.93 mg/l (based on DO production) and 0.0134 to 20.90 mg/l (based on growth rate). No-observed-effect concentration (NOEC) is within the range of 0.001-8.19 mg/l. In general, growth rate is a more sensitive response endpoint than the oxygen production, except for the case of pentachlorophenol. However, the differences in sensitivity between the two parameters were marginal. Furthermore, quantitative structure-activity relationships (QSAR's) based on the n-octanol/water partition coefficient (log P) and the acid dissociation constant (pK(a)) values were established with R(2) ranged from 0.90 to 0.96. From literature data also based on P. subcapitata, the new test method is 1.65-108 times more sensitive than the conventional algal batch tests. A completely different relative-sensitivity relationship among various aquatic organisms was thus observed. The results of this study indicate that the toxicity data of volatile organic chemicals derived by conventional algal toxicity tests may severely underestimate the impact of these toxicants. Our results show that alga is very sensitive to chlorophenols compared to other aquatic organisms such as the luminescent bacteria (the Microtox test), Daphnia magna, and rainbow trout.

Chlorophenols↗

PubMed2005

Uptake and transformation of phenol and chlorophenols by hairy root cultures of Daucus carota, Ipomoea batatas and Solanum aviculare.

Hairy root cultures of Daucus carota L., Ipomoea batatas L. and Solanum aviculare Forst were investigated for their susceptibility to the highly toxic pollutants phenol and chlorophenols and for the involvement of inherent peroxidases in the removal of phenols from liquid media. Roots of D. carota grew normally in medium containing 1000 micromol l(-1) of phenol, whilst normal growth of roots of I. batatas and S. aviculare was only possible at levels up to 500 micromol l(-1). In the presence of chlorophenols, normal root growth was possible only in concentrations not exceeding 50 micromol l(-1), except for I. batatas which was severely affected at all concentrations. Despite the reduction in biomass, the growth of S. aviculare cultures was sustained in medium containing up to 2000 micromol l(-1) of phenol or 2-chlorophenol, and up to 500 micromol l(-1) of 2,6-dichlorophenol. The amounts of phenol removed by the roots within 72 h of treatment were 72.7%, 90.7% and 98.6% of the initial concentration for D. carota, I. batatas and S. aviculare, respectively. For the removal of 2,6-dichlorophenol the values were, respectively, 83.0%, 57.7% and 73.1%. Phenols labelled with 14C were absorbed by the root tissues and condensed with highly polar cellular substances as well as being incorporated into the cell walls or membranes. The results suggest that S. aviculare, an ornamental plant, would be best suited for remediation trials under field conditions.

Chlorophenols↗

PubMed2006

Quantitative structure activity relationship (QSAR) for toxicity of chlorophenols on L929 cells in vitro.

Quantitative structure activity relationship (QSAR) were developed to predict toxicity of chlorophenols by correlating LC50 values with five molecular descriptors, chosen to represent lipophilic, electronic and steric effects: the n-octanol/water partition coefficient (log K(ow)), the constant of Hammett (sigma sigma), the acid dissociation constant (pKa), the order valence molecular connectivity index (1chi(v)) and the perimeter of the efficacious section (sigma D(g)). The results of the regression analysis showed that log K(ow) and sigma D(g) are the dominant (canonical) predictive factors in determining toxicity of chlorophenols to the cells during 24 h exposures, while log K(ow) was the only dominant predictive factor contributing to toxicity during in 48 h exposures. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were applied to investigate predictive relationships of the cytotoxicity of chlorophenols and develop visual 3D-QSAR models. The CoMFA model, in which the contribution of the electrostatic field to the biological activity was greater than that of the steric field, exhibited both high consistency and predictability (r2 = 0.968, Q2 = 0.891 for 24 h exposure; but the relationship was poorer for the 48 h exposure: r2 = 0.727, Q2 = 0.394). The CoMSIA model used in this study contained three fields: electrostatic, hydrophobic and steric, of which the relative contribution to the biological activity was 0.767:0.225:0.008. In addition, according to the models for 24 h and 48 h. The time-dependent toxicity and potential mechanisms for inhibition of L929 cells was discussed.

Animals↗

PubMed2004

Optimization of a microwave-assisted derivatization-extraction procedure for the determination of chlorophenols in ash samples.

A procedure for the determination of 17 chlorophenolic compounds in ash samples obtained from the incineration of waste materials is described. Analytes were simultaneously derivatized with acetic anhydride in presence of triethylamine (TEA), and extracted from the sample in a mixture of n-hexane acetone using a microwave system equipped with closed extraction vessels. Influence of five experimental parameters (volume of TEA and acetic anhydride, extraction time and temperature, as well as the volume of n-hexane acetone) on the yield of the derivatization-extraction procedure was systematically studied using a uniform experimental design at four levels, followed by a conventional factorial design at two levels. Under optimal extraction conditions, recoveries from 72 to 94% were obtained for a spiked ash sample with a carbon content of 8.7%. Quantification limits of the proposed procedure ranged from 2 to 5 ng/g using GC-MS as detection technique. The proposed method was applied to the determination of chlorophenols in three ash samples obtained from different incineration plants. Total chlorophenol contents of 423 and 135 ng/g were found in two of these samples.

Chlorophenols↗

PubMed2006

Evaluation of solid-phase microextraction conditions for the determination of chlorophenols in honey samples using gas chromatography.

A rapid and solvent-free method for the determination of nine chlorophenol (CP) compounds in honey samples using headspace solid-phase microextraction (HS-SPME) and gas chromatography with atomic emission detection (GC-AED) is developed. The different factors affecting the efficiency of the extraction and derivatization steps were carefully optimized. The polydimethylsiloxane-divinylbenzene (PDMS/DVB) fiber was the most suitable for preconcentrating the analytes from the headspace of an aqueous solution containing the dissolved honey samples where the chlorophenols had been submitted to acetylation. When the matrix effect was evaluated for different samples, it was concluded that standard addition calibration was required for quantification purposes. Detection limits roughly ranged from 0.1 to 2.4 ng g(-1), depending on the compound and the honey sample analyzed, with a fiber time exposure of only 15 min at 75 degrees C. The optimized method was successfully applied to different samples, some of the studied chlorophenols being detected in some of the analyzed honeys at concentration levels 0.6-9.4 ng g(-1).

Chlorophenols↗

PubMed2006

Direct determination of chlorophenols in environmental water samples by hollow fiber supported ionic liquid membrane extraction coupled with high-performance liquid chromatography.

The 1-octyl-3-methylimidazolium hexafluorophosphate ([C8MIM][PF6]) ionic liquid was immobilized in the pores of a polypropylene hollow fiber for hollow fiber-protected liquid-phase microextraction. Analytes including 4-chlorophenol (4-CP), 3-chorophenol (3-CP), 2,4-dichlorophenol (2,4-DCP) and 2,4,6-trichlorophenol (2,4,6-TCP) were extracted into this ionic liquid membrane, and back extracted into 10microL sodium hydroxide acceptor solution in the lumen of the hollow fiber. Then, the acceptor solution was withdrawn into the high-performance liquid chromatography (HPLC) microsyringe connected to the hollow fiber, and directly injected into the HPLC system for analysis. Some parameters that might affect the extraction efficiency were optimized, and low detection limits (0.5microgL(-1) for 4-CP, 3-CP, DCP and 1.0microgL(-1) for TCP) were obtained. Good repeatability was achieved because of the stability of the hollow fiber-supported ionic liquid membrane. The proposed procedure was applied for direct determination of the four chlorophenols in some real water samples including groundwater, river water, wastewater and tap water. All of the four chlorophenols in these water samples were under the limits of determination, and the recoveries were in the range of 70.0-95.7% at 5microgL(-1) spiked level.

Chlorophenols↗

PubMed2004

Sorption of phenol and 4-chlorophenol onto pumice treated with cationic surfactant.

In this study the sorption of phenol and 4-chlorophenol on pumice modified with the cationic surfactants hexadecyltrimethyl ammonium bromide (HDTMA) and benzyldimethyl tetradecylammonium chloride (BDTDA) was investigated. Experimental studies indicate that HDTMA-pumice and BDTDA-pumice have the capability to remove phenol and 4-chlorophenol from aqueous solution. The influence of initial concentration and adsorbent dosage was studied. The adsorption of phenol and 4-chlorophenol increased with increasing initial concentration and decreased with increasing amount of adsorbent used. The Freundlich adsorption isotherm was found to describe well the equilibrium adsorption data. The parameters of the Freundlich model have been determined using the adsorption data.

Adsorption↗

PubMed2005

Toxicity measurements in aqueous solution during ozonation of mono-chlorophenols.

The Microtox toxicity and Oxygen Uptake Rate (OUR) inhibition tests were conducted to monitor the variation of toxicity during ozonation of 2-chlorophenol (2-CP), 3-chlorophenol (3-CP) and 4-chlorophenol (4-CP) under neutral conditions. The results revealed that the oxidized 2-CP solution exhibited new toxicity to pure bacteria and mixed microorganisms in the early stage of ozonation. The largest inhibition of OUR appeared at one mol of applied ozone dosage per mol of initial 2-CP, and the percentage of inhibition was 63.8%. In addition, ozonated 3-CP and 4-CP also significantly induced new aqueous toxicity, if these toxic intermediates were not further ozonated. Comparing the variation of toxicity and the hydroxylated/chlorinated intermediates formed, 3-chloro-catechol, 2-chloro-2, 4-hexadienedioic acid and the dimmer compounds may be related to the sources of toxicity during the ozonation of 2-CP.

Chlorophenols↗

PubMed2006

Para-chlorophenol containing synthetic wastewater treatment in an activated sludge unit: effects of hydraulic residence time.

Due to the toxic nature of chlorophenol compounds present in some chemical industry effluents, biological treatment of such wastewaters is usually realized with low treatment efficiencies. Para-chlorophenol (4-chlorophenol, 4-CP) containing synthetic wastewater was treated in an activated sludge unit at different hydraulic residence times (HRT) varying between 5 and 30 h while the feed COD (2500 mg l(-1)), 4-CP (500 mg l(-1)) and sludge age (SRT, 10 days) were constant. Effects of HRT variations on COD, 4-CP, toxicity removals and on settling characteristics of the sludge were investigated. Percent COD removals increased and the effluent COD concentrations decreased when HRT increased from 5 to 15 h and remained almost constant for larger HRT levels. Nearly, 91% COD and 99% 4-CP removals were obtained at HRT levels above 15 h. Because of the highly concentrated microbial population at HRT levels of above 15 h, low effluent (reactor) 4-CP concentrations and almost complete toxicity removals were obtained. High biomass concentrations obtained at HRT levels above 15 h were due to low 4-CP contents in the aeration tank yielding negligible inhibition effects and low maintenance requirements. The sludge volume index (SVI) decreased with increasing HRT up to 15 h due to high biomass concentrations at high HRT levels resulting in well settling sludge with low SVI values. Hydraulic residence times above 15 h resulted in more than 90% COD and complete 4-CP and toxicity removals along with well settling sludge.

Bacteria↗

PubMed2005

Chlorophenols in leachates originating from different landfills and aerobic composting plants.

Both type and concentration of organic contaminants in landfill leachates show great variation depending on many factors, such as type of wastes, rate of water application, moisture content, landfill design and operation age. In this paper, highly toxic chlorophenol derivatives, poorly biodegradable, carcinogenic existence and recalcitrant properties are determined by solid phase microextraction (SPME)-GC/FID in different leachates from landfill and composting plant in Istanbul. Leachates originated from acidogenic, methanogenic phases of Odayeri sanitary landfill (OSL) and from an aerobic composting plant are considered for different chlorophenol types. It is observed that acidogenic leachate from Odayeri landfill includes 2,4-dichlorophenol, 2,6-dichlorophenol, 2,3,4-trichlorophenol, 2,3,4,5-tetrachlorophenol and 2,3,4,6-tetrachlorophenol at concentration ranges, 15-130, 18-65, 8-40, 5-20 and 10-25 microg/l, respectively. Whereas, only 2,4-dichlorophenol at a concentration range 8-40 microg/l is determined in the methanogenic leachate of the landfill, which can be considered as an indication of reductive dechlorination. There is no chlorophenol derivative in aerobic composting leachate. It is determined that acidogenic leachate from Odayeri landfill includes more species of chlorinated phenols at higher concentration.

Aerobiosis↗

PubMed2005

Photo-degradation of chlorophenols in the aqueous solution.

The review presents the chlorophenols photo-degradation kinetics and mechanism in the aquatic environment under UV-vis in the presence of hydroxyl radicals and singlet oxygen. The influence of experimental parameters e.g. pH, dissociation degree, presence of oxidants in solution, number and position of Cl atoms on the quantum yield and reaction rate constant of chlorophenols are discussed. Mechanisms of photolysis, reaction with hydroxyl radicals, singlet oxygen and secondary reactions for mono-, di-, tri-, tetra- and pentachlorophenol are proposed. The pathways for intermediate reactions e.g. dechlorination, oxidation, dimerization for chlorophenols are also presented.

Chlorophenols↗

PubMed2006

Removal of phenol and 4-chlorophenol by surfactant-modified natural zeolite.

In this study the adsorption characteristics of phenol and 4-chlorophenol by surfactant-modified zeolite was investigated. Batch studies were performed to evaluate the effects of various experimental parameters such as contact time, adsorbent dose, initial concentration, and temperature on the removal of phenol and 4-chlorophenol. The sorption kinetics was tested for intraparticle diffusion, Elovich, and pseudo-second order reaction and rate constants of kinetic models were calculated. Equilibrium isotherms for the adsorption of phenol were analyzed by Freundlich, Langmuir, and Tempkin isotherm models. Freundlich isotherm was found to best represent the data for phenol and 4-chlorophenol adsorption.

Adsorption↗

PubMed2004

A combination of ultrasound and a bio-catalyst: removal of 2-chlorophenol from aqueous solution.

Phenolic compounds have become a cause for worldwide concern due to their persistence, toxicity and health risks. This paper reports a three-step approach to remove 2-chlorophenol from dilute aqueous solution and compares each technique. The first step utilizes Horse Radish Peroxidase (HRP) in presence of hydrogen peroxide to oxidize this organic pollutant (enzyme treatment). For a more efficient removal of 2-chlorophenol, it is necessary to add the enzyme solution gradually to the contents of the reactor instead of rapid addition. The second step, involving ultrasonic waves eliminated 2-chlorophenol through hydroxyl radical generated by the cavitation process (sono-degradation). In the third step, a combination of ultrasonic waves and enzyme was used (sono-enzyme degradation). It should be mentioned that, the enzyme can be active in the presence of ultrasonic waves under the proper sonication. The degradation has been studied at different temperatures, intensities of irradiation, and concentrations of enzyme. The rate of degradation exhibited pseudo-first order behavior and the combination method was more effective than sonolysis and enzyme treatment individually.

Catalysis↗

PubMed2000

Capillary electrophoresis-electrospray ion-trap mass spectrometry for the separation of chlorophenols.

Eighteen positional isomers of chlorophenols were separated by capillary electrophoresis (CE) and detected on-line by electrospray ionization ion-trap mass spectrometry (MS). Conditions for the coupling of CE to MS, e.g., the concentration of carrier electrolyte, the sheath liquid composition and the sheath gas flow-rate were optimized. Diethylmalonic acid (5 mM) at pH 7.25 and isopropanol-250 mM dimethylamine (80:20) as sheath liquid were used. The activation parameters for ion-trap mass spectrometric analysis of chlorophenols were optimized. The mass spectra, obtained for all the analytes, revealed that the [M-H]- ion was the base peak for all chlorophenols. Moreover, conditions for CE-MS-MS detection were established and [M-H-HCl]- ions were detected.

Chlorophenols↗

PubMed2002

Direct determination of chlorophenols in landfill leachates by solid-phase micro-extraction-gas chromatography-mass spectrometry.

Landfill leachates represent a serious environmental concern with regard to trace priority pollutants introduced into the aquatic environment. From the analytical point of view, they constitute complex matrices because of their high organic matter content and competition with the trace analytes in the extraction procedure. Although the use of SPME to extract chlorophenols in leachates has already been described in several publications, the limited number of chlorophenols restricts this analysis field of application. This paper presents a new analytical methodology to determine 13 chlorophenols and phenol by SPME-GC-MS in landfill leachates. The overall analysis was performed in 90 min and the detection limits range from 0.005 microg/l (pentachlorophenol) to 2.5 microg/l (phenol). Reproducibility, expressed by the coefficient of variation of repeated extractions at different concentration levels of the analytes, was on average inferior to 10%. Recovery, evaluated by standard addition to leachates, was 86.2% on average. Pentachlorophenol, 2,3,4,5-tetrachlorophenol and 2,3,4,6-tetrachlorophenol were the sole analytes detected at nanogram level in the landfill leachates analysed.

Chlorophenols↗

PubMed2001

Catalytic dechlorination of chlorophenols in water by palladium/iron.

Three isomer chlorophenols, o-, m-, p-chlorophenol, were dechlorinated by palladium/iron powder in water through catalytic reduction. The dechlorinated reaction is believed to take place on the surface site of the catalyst in a pseudo-first-order reaction. The reduction product for all the three isomers is phenol. The dechlorination rate increases with increase of bulk loading of palladium due to the increase of both the surface loading of palladium and the total surface area. The molecular structure also has an effect on the dechlorination rate. For conditions with 0.048% Pd/Fe, the rate constants are 0.0215, 0.0155 and 0.0112 min-1 for o-, m-, p-chlorophenol, respectively. Almost complete dechlorination is achieved within 5 h.

Catalysis↗