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PubMed1997

Selectivity optimization for the separation of chlorophenols in an irregularly shaped experimental region in capillary electrophoresis.

The separation of seventeen chlorophenol congeners and phenol was studied as a function of several variables. The pH and the concentration of sodium dodecylsulphate (SDS) were found to be important. During the implementation of a central composite design for the optimization of the separation it appeared that a part of the domain was not feasible as it resulted in very long migration times and extremely deformed peaks. Therefore, a D-optimal design was selected within the boundaries of the feasible region. The optimization of the selectivity did not result in selective regions for a simultaneous separation. It was, however, possible to find a region for the simultaneous separation of 15 compounds. Further optimization at these optimal conditions resulted in a separation where 17 peaks could be observed.

Chlorophenols↗
PubMed2002

Degradation of 4-chlorophenol by the white rot fungus Phanerochaete chrysosporium in free and immobilized cultures.

4-Chlorophenol (4-CP) degradation was investigated by suspended and immobilized Phanerochaete chrysosporium conducted in static and agitated cultures. The best results were achieved when experiment was carried out in a rotating biological contactor instead of an Erlenmeyer flask, for both batch degradation and repeated batch degradation. The relative contribution of lignin peroxidase (LiP) versus manganese peroxidase (MnP) to the 4-CP degradation by P. chrysosporium was investigated. 4-CP degradation slightly increased and a high level of MnP (38 nKat ml(-1)) was produced when P. chrysosporium was grown at high Mnll concentration. High LiP production in the medium had no significant effect on 4-CP degradation. 4-CP degradation occurred when P. chrysosporium was grown in a medium that repressed LiP and MnP production. This result indicates that LiP and MnP are not directly involved in 4-CP degradation by P. chrysosporium.

Chlorophenols↗
PubMed2003

Reductive dechlorination of 2-chlorophenol in a hydrogenotrophic, gas-permeable, silicone membrane bioreactor.

A gas-permeable silicone membrane bioreactor was used to cultivate the biofilm under hydrogenotrophic condition for reductive dechlorination of 2-chlorophenol (2-CP). The anaerobic sludge obtained from a swine wastewater treatment plant was immobilized by polyvinyl alcohol (PVA) so as to form a biofilm on the surface of the silicone tube. After acclimating for about 4 months, the bioreactor showed a high dechlorinating performance. Under the condition of continuous feeding with 2-CP at 25 mg/l and the hydraulic retention time of 15 h, the 2-CP removal efficiency reached 92.8% (2-CP decay rate: 0.67 g/m(2)d of surface area of silicone tube). H(2) was used as electron donor for dechlorinating 2-CP, and produced the dechlorinating intermediate, phenol. Both nitrate and sulfate played important roles in inhibiting 2-CP dechlorination through different biological mechanisms. Nitrate can be easily utilized as an electron acceptor by the biofilm, while sulfate cannot. Results of this study demonstrated that nitrate competed with 2-CP as the electron acceptor, while sulfate retarded the activity of hydrogen-dechlorinating bacteria and thus inhibited the 2-CP dechlorination.

Biofilms↗
PubMed2001

Sono-photocatalytic degradation of 2-chlorophenol in water: kinetic and energetic comparison with other techniques.

The degradation of 2-chlorophenol in water was kinetically investigated using the following different techniques, employed either separately or simultaneously, always with the same experimental set-up: light irradiation (315-400 nm), sonication, photocatalysis with different types of TiO2, photocatalysis with sonication. The influence of the reaction volume and of different gas mixtures, containing Ar and O2, as well as O2/O3, was also investigated. Finally, an energetic comparison among these different techniques was performed, focused on an industrial application of some of them.

Catalysis↗
PubMed2002

Development and evaluation of an immunoassay for biological monitoring chlorophenols in urine as potential indicators of occupational exposure.

Trichlorophenols (TCP) eliminated by the urine can be considered as potential biomarkers of exposure of many chemicals (chlorophenols, chlorophenoxy acid herbicides, prochloraz, lindane, hexachlorobenzene, etc). High-throughput screening methods are necessary to carry out efficient monitoring programs that may help to prevent certain occupational health diseases. For this purpose, an indirect enzyme-linked immunosorbent assay (ELISA) for 2,4,6-trichlorophenol detection has been developed using polyclonal antisera raised against 3-(3-hydroxy-2,4,6-trichlorophenyl)propanoic acid (hapten 5) covalently coupled by the mixed anhydride (MA) method to keyhole limpet hemocyanin (KLH). The indirect ELISA uses a heterologous coating antigen prepared by conjugation of 3-(2-hydroxy-3,6-dichlorophenyl)propanoic acid (hapten 4) to bovine serum albumin (BSA) using the active ester (AE) method. The optimum hapten density for the coating antigen was found to be 3 mol of hapten/mol of protein. The assay shows a limit of detection of 0.245 +/- 0.116 microg L(-1), and it is performed on 96-well microtiter plates in about 1.5 h. The ELISA reported recognizes on a much less extent other chlorinated phenols, such as 2,3,4,6-tetrachlorophenol (2,3,4,6-TtCP, 21%), 2,4,5-TCP (12%) and 2,3,5-TCP (15%); however, brominated phenols (BP) are even more recognized than the corresponding chlorinated analogues (ex. 2,4,6-TBP, 710%; 2,4-DBP, 119%). With the aim of finding an explanation for this behavior, theoretical calculations have been performed for those and other halogenated phenols (2,4,6-triiodophenol and 2,4,6-trifluorophenol) to clarify which physicochemical parameter can explain better the recognition pattern observed. Finally, the assay has been adapted to the analysis of urine samples. The studies have shown that a limit of detection of 1 microg L(-1) can be accomplished on this biological matrix by combining the ELISA procedure with a C18 solid-phase extraction method.

Chlorophenols↗
PubMed2002

In situ removal of 2-chlorophenol from unsaturated soils by ozonation.

A mathematical model considering mass transfer process at the gas-liquid interface in soil ozonation was developed and validated with laboratory column experiments. Experimental data, specifically, concentration profiles of the organic contaminant and the ozone breakthrough curves, were obtained. In this model, the mass flux of ozone transferred from the gas phase into the liquid phase was described by the two-film theory incorporated with an enhancement factor approach as to account for chemical reactions. With the enhancement factor, the ozone gas transport in the experimental column can be described by an advection-dispersion-reaction equation with pseudo-second-order kinetics in the liquid film. This greatly simplifies the governing equations of the system. Results show that parameters such as degradation yield factor, diffusion coefficients, thickness of liquid film, ozone gas concentration, and gas-liquid interfacial area play an important role on the soil ozonation process. Using the scaled model, important universal dimensionless variables were obtained. The Stanton number (St) is the most important parameter in controlling the performance of system. When St approaches zero, the process is reaction-controlled. Conversely, when St is large, it is convection-controlled. Only when the system is convection-controlled (i.e., large St values) can an increase of ozone flow rate enhance the removal of soil contaminants such as 2-chlorophenol.

Air Movements↗
PubMed2002

TiO2-based photocatalytic degradation of 2-chlorophenol adsorbed on hydrophobic clay.

The combination of adsorption and heterogeneous photocatalysis has been investigated as a promising technology for the removal of organic water pollutants. A laboratory study of the removal and decomposition of 2-chlorophenol (2-CP) as a toxic organic pollutant was carried out under various conditions with an organophilized clay mineral (hexadecylpyridinium chloride-modified montmorillonite; HDPM) as adsorbent and Degussa P25 TiO2 as photocatalyst. Three different oxidation processes leading to the degradation of 2-CP were compared: direct photolysis, heterogeneous photocatalysis in a TiO2 suspension, and the decomposition of substrate adsorbed on HDPM in the presence of TiO2. Both the degradation of 2-CP and the formation of intermediates were analyzed by HPLC, the total organic carbon content and the total organic and inorganic chloride contents were measured to monitor the mineralization process, and X-ray diffraction and thermoanalytical measurements were made to characterize the hydrophobic clay adsorbent. The heterogeneous photocatalytic degradation of dissolved (2-CP/UV/TiO2) and desorbed 2-CP (2-CP/HDPM/UV/TiO2) appeared to be equally efficient, whereas direct photolysis of 2-CP was far less efficient in the oxidative destruction. HDPM proved to be a suitable adsorbent, capable of adsorbing toxic organics from water. It was demonstrated that the adsorbent (at relatively high concentration) did not decrease the rate of mineralization of 2-CP. The results confirmed that the adsorbent retains its structure and composition during the mineralization process, and thus it can be reused without regeneration. The combination of adsorption and heterogeneous photocatalysis studied may be an efficient and economical means of accumulating, removing, and oxidizing organic water contaminants, and its application is in accordance with the growing environmental demands.

Adsorption↗
PubMed2003

Photochemistry of 4-chlorophenol on cellulose and silica.

The photochemistry of 4-chlorophenol (4-CP) was studied on silica and cellulose, using time-resolved diffuse reflectance techniques and product degradation analysis. The results have shown that the photochemistry of 4-CP depends on the support, on the concentration, and also on the sample preparation method. Transient absorption and photoproduct results can be understood by assuming the formation of the carbene 4-oxocyclohexa-2,5-dienylidene in both supports. On cellulose, at concentrations lower than 10 micromol g(-1), the carbene leads to the unsubstituted phenoxyl radical, and phenol is the main degradation product. At higher concentrations a new transient resulting from phenoxyl radicals coupling was also observed, and dihydroxybiphenyls are also formed. The reaction of the carbene with ground-state 4-CP was also detected through the formation of 5-chloro-2,4'-dihydroxybiphenyl. 4-Chlorophenoxyl radical and degradations products resulting from its coupling were also detected. Oxygen has little effect on the photochemistry of 4-CP on cellulose. On silica the transient benzoquinone O-oxide was formed in the presence of oxygen. Benzoquinone and hydroquinone are the main degradation products. In well-dried samples the formation of hydroquinone is reduced. At higher concentrations the same products as detected on cellulose were observed. 4-CP undergoes slow photochemical decomposition under solar radiation in both supports. The same main degradation products were observed in these conditions.

Adsorption↗
PubMed2004

Kinetics and mechanism of photoactivated periodate reaction with 4-chlorophenol in acidic solution.

The application of photoactivated periodate (UV/IO4-) to the degradation of 4-chlorophenol (4-CP) was explored in this study. Under low irradiation intensities (23 microW/cm2), wavelength of 266 nm, and pH 3, 4-CP was observed to degrade by pseudo-first-order reaction kinetics. The small reduction in 4-CP degradation in the presence of tert-butyl alcohol (t-BuOH) suggests that degradation of 4-CP by UV/IO4- was not dominated by an OH* pathway. O3 production was suppressed in the presence of t-BuOH under O2-limited environments and in the presence of 4-CP. Faster degradation of 4-CP in the presence of an OH* scavenger under nitrogen purging as compared to air-saturated conditions indicates that O(3P) is an important reactive species with 4-CP in this system. When 4-CP is added to the system, IO3- production is enhanced. On the basis of the elimination of potential reaction pathways, O(3P) and IO3* are suspected reactive species with 4-CP in this system.

Chlorophenols↗
PubMed2005

Temperature-dependent formation of polychlorinated naphthalenes and dibenzofurans from chlorophenols.

To investigate the gas-phase formation of polychlorinated naphthalenes (PCNs) and dibenzofurans (PCDFs) from chlorinated phenols in combustion exhaust gas, experiments were performed with each of the three chlorophenols in a laminar flow reactor over the range of 550-750 degrees C under oxidative conditions. Maximum PCN and PCDF yields were observed between 625 and 725 degrees C. The degree of chlorination of naphthalene and dibenzofuran products decreased as temperature increased, and on average, the naphthalene congeners were less chlorinated than the dibenzofuran congeners. Congener distributions are consistent with proposed PCN and PCDF formation pathways, both involving phenoxy radical coupling at unchlorinated ortho-carbon sites to form a dihydroxybiphenyl keto tautomer intermediate. Tautomerization of this intermediate and subsequent fusion via H2O loss results in PCDF formation, whereas CO elimination and subsequent fusion with hydrogen and/or chlorine loss leads to PCN formation. PCDF isomer distributions were found to be weakly dependent on temperature. PCN isomer distributions were found to be more temperature sensitive, however, with selectivity to particular isomers decreasing with increasing temperature. These results contribute to the understanding of PCN and PCDF formation in combustion and provide information on how to predict and minimize these emissions.

Air Pollutants↗
PubMed2005

Role of phenoxyl radicals in DNA adduction by chlorophenol xenobiotics following peroxidase activation.

Chlorophenol (CP) toxins are classified as probable human carcinogens and are known to undergo bioactivation to generate benzoquinone (BQ) electrophiles that react covalently with biopolymers. Recently, we characterized the ability of pentachlorophenol (PCP) to react covalently with deoxyguanosine (dG) following treatment with horseradish peroxidase (HRP)/H2O2 or myeloperoxidase to yield a C8-dG oxygen (O)-adduct that suggested the intermediacy of the pentachlorophenoxyl radical in covalent bond formation [Dai, J., Wright, M. W., and Manderville, R. A. (2003) Chem. Res. Toxicol. 16, 817-821]. Investigations currently focus on a wider range of CP substrates (PCP, 2,4,6-trichlorophenol (2,4,6-TCP), 2,4,5-TCP, and 2,4-dichlorophenol (2,4-DCP)) to establish their reactivity toward dG and duplex DNA (calf thymus (CT)) following activation by HRP/H2O2, as a representative peroxidase system. Our data show that chlorophenoxyl radicals may either react directly with dG and CT-DNA to form C8-dG O-adducts in an irreversible process or couple to yield 1,4-BQ electrophiles that react with dG to afford adducts of the benzetheno variety. These results are the first to establish the in vitro relevance of C8-dG O-adducts of phenolic toxins. The 1H NMR chemical shifts and reactivity of the benzetheno adducts favor 4' '-hydroxy-1,N2-benzetheno-dG adduct assignment, which is in contrast to other literature which has assigned the 1,4-BQ-dG adduct as 3' '-hydroxy-1,N2-benzetheno-dG. Overall, the results from this current study have provided new insights into peroxidase-mediated activation of CP substrates and have strengthened the hypothesis that direct reactions of phenoxyl radicals with DNA contribute to peroxidase-driven toxic effects of phenolic xenobiotics.

Carcinogens↗
PubMed2006

Group philicity and electrophilicity as possible descriptors for modeling ecotoxicity applied to chlorophenols.

The search for the best quantitative structure-activity relationship (QSAR) models in ecotoxicology is an ever-topical research activity. Hence, the development of new descriptors and applying them successfully in QSAR studies seems demanding in ecotoxicology. In the present work, group philicities are utilized for the first time in QSAR analysis for ecotoxicological studies on chlorophenols (CPs). It is important to point out that group philicities are capable of providing the best QSAR model for the toxicity of CPs against Daphnia magna. Furthermore, global electrophilicity and group philicities together give the best QSAR models for Brachydanio rerio and Bacillus with the maximum value of coefficient of determination and high internal predictive ability. The developed QSAR models clearly show the importance of the selected density functional reactivity indices as descriptors in ecotoxicological studies.

Algorithms↗
PubMedDate not supplied

Enhancement of biodegradation of phenol and a nongrowth substrate 4-chlorophenol by medium augmentation with conventional carbon sources.

The enhancement of biodegradation of phenol and 4-chlorophenol (4-cp) as a cometabolised compound by Pseudomonas putida ATCC 49451 was accomplished by augmenting the medium with conventional carbon sources such as sodium glutamate and glucose. Compared with phenol as the sole carbon source, the addition of 1 gl(-1) sodium glutamate increased the toxicity tolerance of cells toward 4-cp and significantly improved the biodegradation rates of both phenol and 4-cp even when the initial concentration of 4-cp was as high as 200 mgl(-1). On the other hand, supplementation of glucose caused a significant drop in the medium pH from 7.2 to 4.3 resulting in a reduction of degradation rate, leaving a considerable amount of 4-cp undegraded when the initial concentration of 4-cp was higher than 100 mgl(-1). By regulating the pH of the medium, however, enhancement of degradation rates of phenol and 4-cp in the presence of glucose was achieved with a concomitant complete degradation of phenol and 4-cp.

Biodegradation, Environmental↗
PubMed1999

Facilitation of cometabolic degradation of 4-chlorophenol using glucose as an added growth substrate.

This paper reports on the feasibility of using glucose as an added substrate for cometabolic transformation of 4-chlorophenol (4-cp). When glucose was fed as the added growth substrate, only 78% and 43% of the initial 4-cp concentrations of 100 and 200 mg l-1, respectively, were transformed before the pH dropped to below 4.5 and stopped all reactions. By maintaining the medium pH, complete removal of 4-cp was achieved even at the high initial concentration of 200 mg l-1. Phenol induction prior to inoculation was not a prerequisite to ensure transformation of 4-cp when glucose was the added growth substrate. Compared with phenol as the added growth substrate, cells grown on glucose displayed a longer acclimation phase and, in general, a lower specific transformation rate. The volumetric transformation rate of 4-cp, however, was greatly enhanced due to the increased cell density. The results of this work suggest that 4-cp itself induced the enzymes necessary for its cometabolism. With NADH regenerated effectively through metabolism of glucose, 4-cp was transformed in the absence of added phenol. Consequently, the competitive inhibition involved in cometabolism was avoided and the risks associated with addition of toxic growth substrates such as phenol were eliminated.

Biodegradation, Environmental↗
PubMed2001

Biotransformation kinetics of Pseudomonas putida for cometabolism of phenol and 4-chlorophenol in the presence of sodium glutamate.

A kinetic model to describe the degradation of phenol and cometabolic transformation of 4-chlorophenol (4-cp) in the presence of sodium glutamate (SG) has been developed and validated experimentally. The integrated model accounts for cell growth, toxicity of 4-cp, cross-inhibitions among the three substrates, and the different roles of the specific growth substrate (phenol) and the conventional carbon source (SG) in the cometabolism of 4-cp. In this ternary substrate system, the overall phenol degradation and 4-cp transformation rates are greatly enhanced by the addition of SG since SG is able to attenuate the toxicity of 4-cp and therefore increase the cell growth rate. Model analysis indicates that the maximum specific degradation rate of phenol (0.819 mg (mg.h)(-1)) is lowered by SG by up to 46% whereas the specific transformation rate of 4-cp is not directly affected by the presence of SG. The competitive inhibition coefficient of 4-cp to phenol degradation (Ki,cp) and that of phenol to 4-cp transformation (Ki,ph) were determined to be 6.49 mg l(-1) and 0.193 mg l(-1), respectively, indicating that phenol imposes much larger competitive inhibition to 4-cp transformation than the converse. The model developed can simultaneously predict phenol degradation and 4-cp transformation, and is useful for dealing with cometabolism involving multiple substrates.

Algorithms↗
PubMed2003

Epifluorescence microscope methods for bacterial enumeration in a 4-chlorophenol degrading consortium.

Epifluorescence microscope methods, namely BacLight, direct epifluorescence filter technique and Rhodamine 123, consistently underestimated plate bacterial counts in a 4-chlorophenol degrading consortium. Cells capable of passing through 0.2 microm filters, referred as 'ultramicrocells', were found. Although cell counts were higher when traditional methods were used, BacLight and direct epifluorescence filter technique were convenient techniques for the systematic monitoring of bacteria involved in biodegradation processes, as results were consistent and available within a short time.

Bacteroidetes↗
PubMed2004

Chlorophenol removal from soil suspensions: effects of a specialised microbial inoculum and a degradable analogue.

Two soils of different contamination history were tested in slurry for their self-remediability towards mono-, di- and trisubstituted chlorophenols. The landfill soil showed poor ability in removing the compounds. Instead, the soil from the golf course, treated for many years with a 2,4,6-trichlorophenol derivative (Prochloraz), remediated different concentrations of the same 2,4,6TCP, 2,4-dichlorophenol and monochlorophenol isomers, singly and in mixtures, at varying degradation rates. Ralstonia eutropha TCP, a specialised microorganism capable of degrading 2,4,6TCP, proved highly efficient in removing the compound from both tested soils. The same microbial inoculum allowed total removal of the ternary mixture of monochlorophenol isomers from the golf course soil, but it did not accelerate the removal of the same compounds when singly supplied. The addition of phenol as a degradable analogue was more effective in co-metabolically removing not only the single monochlorophenols, but also their mixtures, the removal occurring faster and independently of the presence of the microbial inoculum. From the golf course soil, a microorganism, phenotypically and genetically identical to R. eutropha TCP, was isolated and classified as R. eutropha TCP II.

Biodegradation, Environmental↗
PubMedDate not supplied

Exposure of workers to 2,3,7,8-substituted polychlorinated dibenzo-p-dioxin (PCDD) and dibenzofuran (PCDF) compounds in sawmills previously using chlorophenol-containing antistain agents.

The use of chlorophenol-containing antistain agents (e.g., Ky5, a wood preservative) ceased in Finland at the end of the 1980s, after 5 decades of use. Exposure of workers to the impurities in these agents (i.e., polychlorinated dibenzo-p-dioxins [PCDDs] and dibenzofurans [PCDFs]) was assessed at three sawmills at which personnel used a sodium chlorophenate product as an antistain agent. Given that compounds accumulate in body fat and their half-lives in humans are long, we could determine 2,3,7,8-substituted PCDDs and PCDFs 5-9 y after the last exposure occurred. We used high-resolution gas chromatography/high-resolution mass spectrometry to determine PCDDs/PCDFs in plasma from 39 Ky5-exposed workers and 18 nonexposed workers. The average total plasma concentration of PCDD/PCDF of the Ky5-exposed workers at the three sawmills were 1018, 945, and 1165 pg/g fat, and corresponding concentrations in the nonexposed workers were 743, 1124, and 844 pg/g fat, respectively. We found no significant differences in total levels between Ky5-exposed workers and nonexposed workers. However, concentrations of the 1,2,3,4,6,7,8-HpCDF isomer were significantly higher (p < .01) among the Ky5-exposed workers at all three sawmills (averages of 224, 99, and 148 pg/g fat) than among their respective nonexposed workers (averages of 43, 48, and 44 pg/g fat). These results indicate that workers had handled Ky5. When we expressed concentration levels in international toxic equivalents (I-TEQs), the mean total I-TEQ PCDD/PCDF of Ky5-exposed workers was significantly lower at one of the sawmills (average = 42 pg I-TEQ/g) than at the other two sawmills (averages of 64 and 62 pg I-TEQ/g)(p < .05). Nevertheless, total concentrations at the sawmills studied were within the range of background levels in the general population.

Adult↗