Pentachloroaniline Research Articles

Experimental study of relaxation dynamics in solid solutions of benzene, hexa-substituted benzenes. II

In continuation with Part I of current study, we present here the orientationally disordered materials pentachloroaniline (PCA), bromopentamethylbenzene (BPMB), and their solid solutions with hexachlorobenzene (HCB) and hexamethylbenzene (HMB), respectively, encompassing the entire concentration range, studied employing dielectric spectroscopy, differential scanning calorimetry, and powder X-ray spectroscopy. The α- relaxation in these systems gets closer to Debye behaviour on non-polar rich side and is analyzed employing Havriliak-Negami equation, whereas the β- relaxation is found to be symmetric everywhere and follows Cole–Cole equation. In both the systems studied here, the temperature dependence of relaxation rates could be described by Arrhenius equation. The β- relaxation evidenced in these two binary systems appears to originate from the different microscopic mechanism that is discussed based on their spectral behaviour. Further, we probe the liquid glasses of very dilute concentrations of dipolar HSB solutes in OTP matrix, and compare it with the spectral features of the dilute dipolar solid solutions of HSBs.

Reductive dehalogenation activity of indigenous microorganism in sediments of the Hackensack River, New Jersey

Organohalogen pollutants are of concern in many river and estuarine environments, such as the New York-New Jersey Harbor estuary and its tributaries. The Hackensack River is contaminated with various metals, hydrocarbons and halogenated organics, including polychlorinated biphenyls (PCBs) and polychlorinated dibenzo-p-dioxins. In order to examine the potential for microbial reductive dechlorination by indigenous microorganisms, sediment samples were collected from five different estuarine locations along the Hackensack River. Hexachlorobenzene (HCB), hexabromobenzene (HBB), and pentachloroaniline (PCA) were selected as model organohalogen pollutants to assess anaerobic dehalogenating potential. Dechlorinating activity of HCB and PCA was observed in sediment microcosms for all sampling sites. HCB was dechlorinated via pentachlorobenzene (PeCB) and trichlorobenzene (TriCB) to dichlorobenzene (DCB). PCA was dechlorinated via tetrachloroaniline (TeCA), trichloroanilines (TriCA), and dichloroanilines (DCA) to monochloroaniline (MCA). No HBB debromination was observed over 12 months of incubation. However, with HCB as a co-substrate slow HBB debromination was observed with production of tetrabromobenzene (TeBB) and tribromobenzene (TriBB). Chloroflexi specific 16S rRNA gene PCR-DGGE followed by sequence analysis detected Dehalococcoides species in sediments of the freshwater location, but not in the estuarine site. Analysis targeting 12 putative reductive dehalogenase (rdh) genes showed that these were enriched concomitant with HCB or PCA dechlorination in freshwater sediment microcosms.

Influence of quaternary ammonium compounds on the microbial reductive dechlorination of pentachloroaniline

The inhibitory effect of two widely used quaternary ammonium compounds (QACs) – alkyl benzyl dimethyl (AB) and hexadecyl trimethyl (HD) ammonium chloride – on fermentation, methanogenesis and pentachloroaniline (PCA) dechlorination was assessed using a mixed, methanogenic, PCA-dechlorinating culture amended with AB or HD at a concentration range from 5 to 70 μM. PCA dechlorination was inhibited at 5 μM AB and was completely inhibited at 25 or 5 μM by AB or HD, respectively. However, the PCA dechlorination pathway was the same in both the QACs-free and QACs-amended culture series. Fermentation (acidogenesis) and methanogenesis were inhibited by both AB and HD at and above 25 μM but to a lesser degree than PCA dechlorination. Overall, HD resulted in a more severe inhibition of the mixed culture than AB. Adsorption of both QACs to the mixed culture biomass followed the Freundlich isotherm model. The adsorption affinity of HD for the mixed culture biomass was significantly higher than that of AB, which may be related to the observed higher inhibitory effects of HD compared to AB. Both AB and HD were not degraded in the mixed, dechlorinating culture used in this study.

Mechanochemical destruction of pentachloronitrobenzene with reactive iron powder

Pentachloronitrobenzene (PCNB) has been identified as a potential persistent organic pollutant, and received concerns from many countries for regulation due to its impurities such as dioxins and furans. Considering the need for its disposal, the mechanochemical destruction approach was investigated for the applicability. PCNB was co-ground with reactive iron powder in a high energy planetary ball mill at room temperature. PCNB was found to be destructed finally, and the Dioxins and coplanar-PCBs concentrations in PCNB had been degraded from 1146 ng-TEQ/kg to 0.04 ng-TEQ/kg finally. Pentachloroaniline (PCA), 2,3,5,6-tetrachloroaniline (2,3,5,6-TeCBA) and 3,4,5,6-tetrachloroaniline (3,4,5,6-TeCBA) were detected as intermediates during the ball milling process and were destructed completely after 8 h milling. The amount of water soluble chlorides (Cl −) reached 95.8% of the theoretical amount of chlorine in original PCNB sample after 12 h ball milling. The solvent acetone might play a role as the main hydrogen donor, which gives rise to the amination reaction of nitro-group. Metastable structures with high molecular were proposed to be formed during the ball milling process as intermediates. Carbonization was confirmed by Raman spectrum as the final degradation product of PCNB.

Life cycle assessment comparison of substrates for the bioremediation of pentachloroaniline under acidogenic/methanogenic conditions

Purpose In general, pentachloroaniline (PCA) biodechlorination is specific to the conditions of a system; such conditions include the type and concentration of electron donors and oxidizing agents as well as nutrient availability, pH, and temperature. In the bioremediation of contaminated sediments and soil, most researchers have focused on the ability of various electron donors to remove target compounds. However, the amended electron donors and the byproduct of the anoxic/anaerobic systems may cause more environmental impact. Therefore, methods for consistently evaluating the environmental effects of such electron donors and byproducts are highly needed. Accordingly, life cycle assessment (LCA) was carried out to estimate the environmental effect of PCA biodechlorination under acidogenic/methanogenic conditions through laboratory-scale experiments. Four scenarios, intended to assess the influence of electron donors on the environment and develop laboratory experimental research, were compared. In these scenarios, four compounds were used: acetate, lactate, methanol, and glucose + methanol.

Microbial transformation of pentachloronitrobenzene under nitrate reducing conditions

The effect of pentachloronitrobenzene (PCNB) on denitrification was assessed with two denitrifying cultures (PCNB-free control and PCNB-acclimated) developed from a contaminated estuarine sediment. PCNB was transformed to pentachloroaniline (PCA) in the PCNB-acclimated culture repeatedly amended with 0.1 muM PCNB, but further dechlorination or degradation of PCA was not observed for almost 1 year. The effect of PCNB on denitrification was also investigated with the PCNB-free control culture. PCNB at an initial concentration of 13 muM was transformed to PCA simultaneously with nitrate reduction but only after the nitrate concentration was at or below 20 mg N/l. PCNB addition at an initial concentration of 13 muM to the control denitrifying culture developed as PCNB-free culture resulted in a transient accumulation of nitric oxide (NO) and nitrous oxide (N(2)O). Similarly to the PCNB-acclimated culture, PCNB transformation to PCA started when the nitrate concentration decreased to about 20 mg N/l. A low degree of nitro group removal resulting in the formation of pentachlorobenzene (PeCB) was also observed in the control culture when amended with 13 muM PCNB. Further transformation or degradation of PCA was not observed in all cultures maintained under active nitrate reducing conditions. Based on the results of this study, the presence of nitrate at low concentrations in anoxic/anaerobic soil and sediments is not expected to negatively affect the biotransformation of PCNB to PCA, but dechlorination or degradation of PCA is not expected under active nitrate reducing conditions.

Theoretical investigation of the sequential reductive dechlorination pathways of chlorobenzenes and chloroanilines

The distribution of product isomers during the sequential reductive dechlorination of pentachloroaniline (PCA) and pentachlorobenzene (PeCB) was examined based on calculated thermodynamic, chromatographic, and electronic properties and then compared to the product distribution achieved by enrichment cultures. The dechlorination pathway analysis based on free energy considerations matched 78% and 67% of the experimental results for the sequential reductive dechlorination of chlorobenzenes (CBs) and chloroanilines (CAs), respectively. Chromatographic properties of CBs and CAs were able to explain some but not all of the reactions in the observed dechlorination pathways. Correlations between the observed dechlorination pattern and electronic properties of the parent compounds were able to explain most of the formation of the observed products. Experimentally observed sequential reductive dechlorination of CBs and CAs were similar to predicted dechlorination pathways based on the charge differential values calculated for the carbon-chloride bonds. Chlorine atoms were removed from the carbon atom that has the highest charge differential or the second highest charge differential. However, although thermodynamic, electronic as well as chromatographic properties of the CBs and CAs are certainly important factors, they may not be sufficient to completely describe the sequential microbial reductive dechlorination. Enzymatic specificity, as well as other factors (i.e., culture acclimation, environmental factors) should be considered for the interpretation of observed sequential reductive dehalogenation pathways of haloorganic compounds. This work provides the most comprehensive analysis to date of theoretical factors that control the sequential reductive chlorination of two homologous series of single-ring chloroaromatic species.

Influence of sulfate reduction on the microbial dechlorination of pentachloroaniline in a mixed anaerobic culture

The reductive dechlorination of pentachloroaniline (PCA) was investigated in the absence and presence of sulfate in batch assays using a PCA-dechlorinating mixed anaerobic culture with methanol as the external electron donor at neutral pH and 22 degrees C. PCA at an initial concentration of 7.8 microM was sequentially dechlorinated to dichlorinated anilines in the sulfate-free culture and the culture amended with 300 mg sulfate-S/L. At an initial concentration of 890 mg sulfate-S/L, a higher sulfate reduction rate was achieved, but PCA dechlorination was not observed until the sulfate concentration dropped to about 100 mg S/L. The transient inhibition of PCA is attributed to competition between sulfate reducing and dechlorinating species for electron donor, more likely for H(2) resulting from methanol fermentation. A long-term (118 days) PCA dechlorination assay with the sulfate-amended culture, which included five feeding cycles, resulted in accumulation of both sulfide (886 mg S/L) and acetate (1,900 mg COD/L). Under these conditions, the sulfate reducers were inhibited, while the rate and pathway of PCA dechlorination were not affected. The results of this study show that the rate of sulfate reduction rather than the sulfate concentration alone dictates the outcome of the competition between sulfate reducers and either dechlorinators or methanogens. The findings of the present study have significant implications relative to the fate and transport of PCA and its dechlorination products in sulfate-laden subsurface systems.

Effect of Nitrate Reduction on the Microbial Reductive Transformation of Pentachloronitrobenzene

The effect of nitrate reduction onthe reductive biotransformation of pentachloronitrobenzene (PCNB), an organochlorine fungicide, was assessed with a mixed fermentative/methanogenic culture enriched from a contaminated estuarine sediment. Glucose and methanol served asthe electron and carbon source. PCNB at an initial concentration of 3 microM was transformed to pentachloroaniline (PCA) simultaneously with nitrate reduction in cultures amended with 10 to 200 mg N/L nitrate. PCA sequentially dechlorinated to dichlorinated anilines (mainly 2,5-DCA) in the nitrate-free control culture, and the culture which was amended with 10 mg N/L nitrate. PCA partially dechlorinated to tetrachloroanilines (TeCAs), and methanogenesis was completely inhibited in the cultures amended with 50-200 mg N/L nitrate, whereas fermentation was only inhibited in the cultures amended with 200 mg N/L nitrate. The impact of nitrate reduction on the sequential dechlorination of PCA was attributed to the production of nitric oxide (NO) and nitrous oxide (N2O). Partial nitrate reduction to ammonia was observed in the cultures amended with 50, 100, or 200 mg N/L nitrate and PCNB (3 microM). Therefore, nitrate concentrations at or above 50 mg N/L lead to accumulation of toxic compounds such as highly chlorinated anilines (i.e., PCA, TeCAs) and denitrification intermediates (i.e., NO, N2O). These findings have significant environmental implications in terms of the fate and transformation of PCNB in subsurface environments where nitrate is present.

Efficient removal of the organochlorine pesticide and heavy-metal residues inEpimedium brevicornum Maxim by supercritical fluid extraction

A method involving depuration of 12 organochlorine pesticides (OCPs) and 7 heavy metals from Epimedium brevicomum Maxim was developed using supercritical fluid extraction (SPE). The pesticides in the study consisted of alpha, beta-, gamma-, and delta-Benzene hexachloride, Pentachloronitrobenzene (PCNB), Pentachloroaniline (PCA), Heptachlor (HEPT), Methyl -pentachlorophenyl sulfide (MPCPS), pp'-DDE[1,1-dichloro-2, 2-bis (p-chlorophenyl) ethylene], op'-DDT [1,1,1-trichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane], pp'-DDD [1,1-dichloro-2-2-bis(p-chlorophenyl)]ethane, pp'-DDT [1,1,1-trichloro-2,2-bis(p-chlorophenyl) ethane]. A series of experiments was conducted to optimize the final extraction conditions as following: pure CO2, extraction pressure of 15 Mpa, extration temperature of 60 degrees C, extraction time of 10 min, flow rate at 55 kg/h. A GC method with electron capture detection was employed to determination of the OCPs, and an atomic absorption spectrometry (AAS) was designed for the determination of 7 heavy metals including of Pb, Cd, Cu, Fe, Zn, As, Hg in Epimedium brevicomum Maxim. A HPLC method was developed for the quantitative determination of active constituents. The SFE was used to remove the organochlorine pesticide and heavy metals from Epimedium brevicornum Maxim, receiving high decontamination rate of pesticide residue and low loss of active constituents.

Influence of Dissolved Organic Matter and Fe(II) on the Abiotic Reduction of Pentachloronitrobenzene

Nitroaromatic pesticides (NAPs) are hydrophobic contaminants that can accumulate in sediments by the deposition of suspended solids from surface waters. Fe(II) and dissolved organic matter (DOM), present in suboxic and anoxic zones of freshwater sediments, can transform NAPs in natural systems. We studied the reduction of pentachloronitrobenzene (PCNB) to pentachloroaniline (PCA) in controlled studies using Fe(II) and surface water DOM isolates from Pony Lake, Antarctica, and Suwannee River, GA, in unfiltered and 0.45 microm filtered solutions. We observed rapid reduction of PCNB to PCA in the presence of Fe(II) and DOM (t(1/2) approximately = 30 min to 4 h) and very limited reduction in DOM-only systems. DOM in unfiltered systems inhibited iron colloid formation and potentially limited the formation of reactive Fe(ll)-iron colloid surface complexes, causing reductive transformation in Fe(II)-DOM media to be slower in some cases relative to Fe(ll)-only controls. Conversely, in 0.45 microm filtered solutions, PCNB reduction in Fe(III)-DOM media was faster than the Fe(II)-only controls, suggesting that DOM enhances the reductive capacity of Fe(ll) in the absence of iron colloids. This work shows that DOM may significantly affect the reactivity of Fe(ll) toward NAPs under suboxic and anoxic conditions in natural wetland sediments.

Temperature and pH Effect on the Microbial Reductive Transformation of Pentachloronitrobenzene

The effect of pH and temperature on the microbial reductive transformation of pentachloronitrobenzene (PCNB), an organochlorine fungicide, was investigated with a mixed fermentative/methanogenic culture developed from a contaminated estuarine sediment. Culture series were incubated at a temperature range from 4 to 45 degrees C at pH 6.9+/-0.1 and at a pH range from 2.7+/-0.1 to 7.6+/-0.1 at 22 degrees C. Significant differences were observed in terms of biotransformation rate, extent, and products as a function of temperature. Incubation at different pH values resulted in differences in biotransformation rate and extent, but not in terms of products formed. PCNB (3 microM) was transformed to pentachloroaniline (PCA) in all culture series. However, sequential dechlorination of PCA was observed only at a temperature range from 4 to 35 degrees C and at a pH range from 6.2+/-0.1 to 7.6+/-0.1. The highest PCA dechlorination rate was observed at 22 degrees C and at pH 7.6+/-0.1. The effect of temperature on the PCA dechlorination rate was modeled using an Arrhenius relationship, which accounts for both enzyme activation and deactivation. The dechlorination of PCA and chlorinated aniline intermediates was simulated using a branched-chain Michaelis-Menten model, and kinetic constants were determined.

The influence of iron reduction on the reductive biotransformation of pentachloronitrobenzene

The effect of iron reduction on the microbial reductive transformation of pentachloronitrobenzene (PCNB), an organochlorine fungicide, was investigated with a mixed, methanogenic culture enriched from a contaminated sediment. Fe(III)EDTA, Fe(III)citrate (completely bioavailable) and FeOOH (less bioavailable) were used as the iron source. PCNB was transformed to pentachloroaniline (PCA), but dechlorination of PCA and methanogenesis were not observed in cultures amended with Fe(III)EDTA until all of the added Fe(III) was reduced to Fe(II). Although PCA dechlorination did not take place, low rate methanogenesis was observed simultaneously with iron reduction in the culture amended with Fe(III)citrate. In contrast, both methanogenesis and PCA dechlorination took place at the same time with iron reduction in the same mixed, methanogenic culture amended with FeOOH, but at a lower rate compared to the Fe(III)-free control culture. Addition of anthraquinone 2,6-disulfonate (AQDS) to the culture amended with FeOOH resulted in a higher iron reduction rate, as compared to cultures devoid of AQDS, and a lower rate of both PCA dechlorination and methanogenesis. Therefore, the reductive dechlorination of PCA is adversely impacted under conditions favoring high iron reduction rates. The interaction of these potentially competing processes (i.e. iron reduction, methanogenesis, and dechlorination) can significantly influence the environmental fate of PCNB and its transformation products, especially in soil and sediments.

Kinetics of the Microbial Reductive Dechlorination of Pentachloroaniline

The microbial reductive dechlorination kinetics of pentachloroaniline (PCA) and less chlorinated anilines (CAs) were investigated with a mixed, fermentative/ methanogenic culture. Batch dechlorination assays were performed with all available CAs at an initial concentration of 3 microM, and an incubation temperature of 22 degrees C. Dechlorination of PCA, two tetrachloroanilines (2,3,4,5- and 2,3,5,6-TeCA), five trichloroanilines (2,3,4-, 2,3,5-, 2,4,5-, 2,4,6-, and 3,4,5-TrCA), and one dichloroaniline (3,5-DCA; low extent) was observed but none of the five remaining dichloroanilines and three monochloroanilines were dechlorinated by the enrichment culture during batch assays. The dechlorination rates (k') and half-saturation coefficients (Kc) were measured using nonlinear regression based on the integrated Michaelis-Menten equation under conditions of electron donor saturation and assuming constant biomass concentration over the relatively short batch incubation period. At an initial concentration of CAs of about 3 microM, the values of k' and Kc ranged from 0.25 to 1.19 microM/day and from 0.11 to 1.72 microM, respectively, corresponding to half-lives in the range of 1.5-8.5 days. Model simulations of the sequential dechlorination reactions based on a branched-chain Michaelis-Menten model and using independently measured k' and Kc values matched the experimental data very well.

Decontamination of organochlorine pesticides in Radix Codonopsis by supercritical fluid extractions and determination by gas chromatography

A method involving depuration of 12 organochlorine pesticides (OCPs) from Radix codonopsis was developed using supercritical fluid extraction (SFE). The pesticides investigated in the study included alpha-, beta-, gamma- and delta-benzene hexachloride, PCNB (pentachloro-nitrobenzene), PCA (pentachloroaniline), HEPT (heptachlor), MPCPS (methyl-pentachlorophenyl sulfide), pp'-DDE [1,1-dichloro-2, 2-bis(p-chlorophenyl) ethylene], op'-DDT [1,1,1-trichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane], pp'-DDD [1,1-dichloro-2-2-bis(p-chlorophenyl)ethane] and pp'-DDT [1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane]. A series of experiments was conducted to optimize the final extraction conditions as follows: pure CO2, extraction pressure 15 MPa, extraction temperature 60 degrees C, extraction time 20 min and flow rate 55 mL/h. A GC method with electron capture detection was employed for the determination of the OCPs in Radix codonopsis. An HPLC method was developed for the quantitative determination of active constituents. SFE was used to remove the organochlorine pesticide from Radix codonopsis. The results showed that at least 93.5% of the organochlorine pesticide residues in the herb sample were removed by SPE, while 95.0% of the active constituent marker (atractylenoide III) remained.

Microbial Reductive Transformation of Pentachloronitrobenzene under Methanogenic Conditions

The reductive transformation of pentachloronitrobenzene (PCNB), an organochlorine fungicide, was investigated with a mixed, methanogenic culture developed from a contaminated estuarine sediment. Batch assays performed with this enrichment culture resulted in the biotransformation of PCNB to pentachloroaniline (PCA), which was then sequentially dechlorinated as follows: PCA --> 2,3,4,5- and 2,3,5,6-tetrachloroaniline (TeCA) --> 2,4,5- and 2,3,5-trichloroaniline (TrCA) --> 2,4-, 2,5-, and 3,5-dichloroaniline (DCA) --> 3- and 4-chloroaniline (CA) (low levels). Glucose fermentation, methanogenesis, and dechlorination were not inhibited at an initial PCNB concentration up to 40 microM, which is 27 times higher than its aqueous solubility. The addition of 25 mM 2-bromoethanesulfonate (BES) to the PCNB-amended culture resulted in the complete inhibition of methanogenesis, but the biotransformation of PCNB to PCA and its sequential dechlorination pathway were not affected. The addition of sodium azide (200 mg/L) to the PCNB-amended culture resulted in complete inhibition of methanogenesis, but did not inhibit the transformation of PCNB to PCA; however, PCA dechlorination was not observed. PCNB was also abiotically transformed to PCA in autoclaved culture media but at much lower rates as compared to the biotic assays. In contrast, the rate of PCNB to PCA transformation in autoclaved culture controls was similar to the rates observed in the azide-amended culture and the active enrichment culture, indicating that biotically derived reductants facilitated the observed transformation of PCNB to PCA. Dechlorination of PCA was not observed in any of the abiotic controls. These findings have significant environmental implications in terms of the fate and transport of PCNB, PCA, and its dechlorination products in subsurface systems.

Supercritical fluid extraction for the separation of organochlorine pesticides residue in Angelica sinensis.

A method involving the simultaneous extraction and separation of 12 organochlorine pesticides (OCPs) from Angelicae sinensis was developed using supercritical fluid extraction (SFE). The pesticides in the study were alpha-, beta-, gamma- and delta-benzene hexachloride, PCNB (pentachloro- nitrobenzene), PCA (pentachloroaniline), HEPT (heptachlor), MPCPS (methyl-pentachlorophenyl sulfide), pp'-DDE [1,1-dichloro-2,2-bis (p-chlorophenyl) ethylene], op'-DDT [1,1,1,-trichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl) ethane], pp'-DDD [1,1-dichloro-2,2-bis(p-chlorophenyl) ethane], and pp'-DDT [1,1,1,-trichloro-2,2-bis (p-chlorophenyl)ethane]. The extraction conditions were optimized as follows: pure CO(2), extraction pressure 15 MPa, extraction temperature 60 degrees C, extraction time 20 min, and flow-rate 1.5 mL/min. A GC method with electron capture detection was employed to determine the OCPs in Angelicae sinensis. An HPLC method was developed for the quantitative determination of active constituents. The SFE provided high decontamination rate of OCPs and low loss of active constituents in Angelicae sinensis.

Reductive Dehalogenation of Chloroanilines in Anaerobic Estuarine Sediment

The reductive dehalogenation of chloroanilines (CAs) was investigated in anaerobic sediment/water systems. The sulfate content of the interstitial and overlaying waters was approximately 20 mmoles l−1 and the sediment was apparently sulfidogenic. The CAs exhibited first-order disappearance kinetics with the rate constants ranging from 0.012–0.005 day−1 or half-lives between 40 and 672 days. Pentachloroaniline (PeCA), 2,3,4,5-tetrachloroaniline (2,3,4,5-TeCA) and 3,4,5-trichloroaniline (3,4,5-TCA) were transformed by the sequential removal of halogen from the para and ortho positions. The disappearance of the parent compound and accumulation of metabolites were simulated using a first-order branched kinetic model.

Pollution by the fungicide pentachloronitrobenzene in an intensive farming area in Japan

Environmental pollution by pentachloronitrobenzene (PCNB) was investigated at Tsumagoi, an intensive farming area, where a great amount of PCNB has been applied. High concentrations of PCNB were detected in river water near an area of cabbage cultivation. Further, pentachloroaniline (PCA) and pentachlorothioanisole (PCTA), which are the principal biodegradation products of PCNB, were also detected, and their ratios to PCNB were higher in autumn than in summer. PCNB concentrations in soil were similar to those of river sediment, in which PCNB was concentrated 5000–10000 times over levels in river water. The biodegradation rate of PCNB in river water was higher than in river sediment and soil. The formation rates of PCA from PCNB were higher in river sediment and soil than in river water. It is considered that PCA remains for a long time in the environment and accumulates in river sediment and soil.

Raman and infrared spectra of pentachloroaniline

AbstractRaman spectra of crystalline pentachloroaniline (PCA) have been measured. The infrared spectra have also been recorded for solid and solutions in CCl4 between 4000–200 cm−1. An assignment of the observed frequencies has been proposed for a Cs molecular symmetry based on related halogen substituted benzene derivatives. The molecule does not appear to self‐associate in CCl4 solutions although there is some evidence for a weak hydrogen bonding in the solid state.