4-Chlorophenol

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

WATER, SPRAY, MIST, FOG, FOAM, DRY CHEMICAL

Use dry chemical, carbon dioxide, or foam extinguishers. Vapors are heavier than air and well collect in low areas. ... Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. ...From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. /Monochlorophenols/

Use dry chemical foam, carbon dioxide, or water spray. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Use water spray to keep fire-exposed containers cool.

Store in tightly closed containers in a cool, well ventilated area. Metal containers involving the transfer of this chemical should be grounded and bonded. Where possible, automatically pump liquid from drums or other storage containers to precess containers. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard. /Monochlorophenols/

Phenolic cmpd in wastewater are oxidized with hydrogen peroxide catalyzed by iron(3+)-iron(2+). When the wt ratio of phenol:hydrogen peroxide is 1:3 and iron 5-100 ppm, more than 95% of the phenols are removed in 30 min from a 500 ppm phenol soln at pH 5-6 and 25-50 °C. /Phenolic cmpd/

Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. /Monochlorophenols/

Shovel into suitable dry container.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Chemical Treatability of p-Chlorophenol; Concentration Process: Biological Treatment; Chemical Classification: Phenols; Scale of Study: Unknown; Type of Wastewater Used: Pure Compound (one solute in a solvent); Results of Study: 96% reduction based on chemical oxygen demand, rate of biodegradation 11 mg/g hr; (Activated Sludge Process).

Chemical Treatability of p-Chlorophenol; Concentration Process: Biological Treatment; Chemical Classification: Phenols; Scale of Study: Laboratory Scale; Type of Wastewater Used: Pure Compound (one solute in a solvent); Results of Study: 100% reduction in 33 hours; (Biodegradation by mutant pseudomonas species).

This work presents the results of the application of an optimally controlled influent flow rate strategy to biodegrade, in a discontinuous reactor, high concentrations of 4-chlorophenol used as toxic compound model. The influent is fed into the reactor in such a way as to obtain the maximal degradation rate, thus avoiding the inhibition of the microorganisms. The optimal strategy was able to manage increments of toxic concentrations in the influent up to 7,000 mg 4CP/L without any problem. It was shown not only that higher concentrations of toxic could be treated, but also that a reduction in degradation time (around 52%) and in the supplied air volume was obtained.

For more Disposal Methods (Complete) data for 4-CHLOROPHENOL (10 total), please visit the HSDB record page.

Personal protection: chemical protection suit and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Wash contaminated areas of skin with concentrated soap solution without delay. Contaminated gloves, clothing, shoes should be immediately removed and disposed of in an incinerator.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Avoid dilution following oral exposure; instead, administer charcoal as a slurry. Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. If the exposure occurs through eye contact, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove phenol with undiluted polyethylene glycol 300 to 400 or isopropyl alcohol prior to washing, if readily available. Wash exposed areas twice or for at least 10 minutes with large quantities of soapy water. Water alone may be harmful. (T36)

Male mice were administered 4-Chlorophenol (4-CP), 1.5 mmol/kg body weight, ip, and were killed at 10, 20, 30 and 50 min after drug injection. Either i.p. or oral 4-CP administration significantly lowered total liver thiol levels by 20-30% after 30 min and 3 hr respectively. This time-dependent effect of 4-CP after ip treatment was enhanced when mice were pretreated with hepatic microsomal enzyme inducers (phenobarbital, 40 mg/kg body weight, b.i.d., 7 days; and beta-naphthoflavone, 80 mg/kg body weight once daily, 4 days). Further, the microsomal cytochrome P-450 inhibitor, SKF 525-A, 75 mg/kg body weight injected i.p. to mice 30 min prior to 4-CP administration, blocked the reduction of liver thiol content produced by 4-CP. The results suggest that a chemically reactive intermediate of 4-CP may be formed in liver which is responsible for the observed decrease in liver thiol content. Other investigations were done to characterize the in vitro irreversible binding of [14C]4-CP. [14C]4-CP was bound irreversibly to mouse liver microsomal proteins in a concentration-dependent manner. Binding was NADPH dependent and gave a maximal binding of 12.0 nmol/mg protein/20 min and an apparent binding constant of 0.222 mM. [14C]-Binding of 4-CP was increased by 155 and 127% in liver microsomes of phenobarbital- and beta-naphthoflavone. SKF 525-A, and CO:O2 (4:1, v/v)] and selected nucleophilic compounds (glutathione, L-cysteine or L-lysine) significantly reduced [14C]4-CP binding to mouse liver microsomes. An epoxide hydrolase inhibitor, cyclohexene oxide, did not alter the extent of irreversible binding, whereas scavengers of superoxide anions or agents that are reported to reduce accumulation of active semiquinone and quinone species (L-ascorbic acid, superoxide dismutase or epinephrine) decreased the binding of [14C]4-CP to mouse liver microsomal proteins by 56, 31 and 92% respectively...

4-chlorophenol is corrosive to epithelial tissue. It produce effects ranging from slight hyperemia to severe corrosion when applied to the corneas. Acute inhalation exposure may lead to hemorrhage in the lungs and tachypnea. Oral exposure to 2-chlorophenol can produce a variety of neurological effects, including tremors, myoclonic convulsions, a hunched posture, dyspnea, collapse, and coma (L159).

EC50; Species: Chlorella vulgaris (Green algae, exponential growth phase, 50000 cells/mL); Conditions: freshwater, static, 21 °C; Concentration: 29000 ug/L for 96 hr; Effect: growth, general /formulated product/

EC50; Species: Pseudokirchneriella subcapitata (Green algae, exponential growth phase, 50000 cells/mL); Conditions: freshwater, static, 21 °C; Concentration: 38000 ug/L for 96 hr; Effect: growth, general /formulated product/

EC50; Species: Pseudokirchneriella subcapitata (Green algae, exponential growth phase); Conditions: saltwater, static; Concentration: 400 uM for 72 hr (95% confidence interval: 340-510 uM); Effect: decreased population growth rate /formulated product/

EC50; Species: Lemna gibba (Inflated duckweed, age 3 frond); Conditions: freshwater, static, 27.5 °C; Concentration: 183 uM for 7 days; Effect: decreased vegetative frond reproduction /formulated product/

For more Ecotoxicity Values (Complete) data for 4-CHLOROPHENOL (47 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an experimental Koc value range of 70 to 485.6(2-4), indicates that 4-chlorophenol is expected to have high to moderate mobility in soil(SRC). The pKa of 4-chlorophenol is 9.41(5), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). Volatilization of 4-chlorophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-7 atm-cu m/mole for the neutral species(SRC) derived from its vapor pressure, 8.90X10-2 mm Hg(7), and water solubility, 2.40X10+4 mg/L(8). 4-Chlorophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.2X10-2 mm Hg(7). 4-Chlorophenol reached 2% of its theoretical BOD using activated sludge in the Japanese MITI test(9) while complete degradation was reported within 3 days in acclimated sludges(10,11). 4-Chlorophenol degraded in clay and silt loams soils from 84-100% in 3-16 days(12-14) and 22.2% and 35% in 1 and 10 weeks, respectively, in para-brown soil(15). These data suggest that biodegradation of 4-chlorophenol in soils is variable depending on conditions(SRC).

AQUATIC FATE: Based on a classification scheme(1), an experimental Koc value range of 70 to 485.6(2-4), indicates that 4-chlorophenol may exhibit low to moderate absorption to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of 6.3X10-7 atm-cu m/mole for the neutral species(SRC) derived from its vapor pressure, 8.90X10-2 mm Hg(6), and water solubility, 2.40X10+4 mg/L(7). According to a classification scheme(8), a BCF range of 6.0-18(6,9, 10) suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Chlorophenol undergoes flash-induced aquatic photolysis in both aerated and non-aerated solns(11) and photolytic oxidation by UV/ozone(12). Biodegradation of 4-chlorophenol in water varies depending on the conditions. Complete removals have been reported in water after 13 days for acclimated water(13) and 30 days in farm stream sediment(14), 44% degradation after 5 days(15) and 33% after 25 days in non-acclimated water(13). These data suggest that biodegradation will vary depending on the conditions(SRC). Since the pKa of 4-chlorophenol is 9.41(16), it will exist in water and sediment in a partially dissociated state which may effect its transport and reactivity in water and sediment(SRC). The suggested half-life of 4-chlorophenol in water is 55 hours(6), although it is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(17).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-chlorophenol, which has a vapor pressure of 8.90X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-chlorophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.3 days(SRC), calculated from its rate constant of 9.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The quantum yield for the disappearance of 4-chlorophenol was 0.25 when it was irradiated at 296 nm in aqueous solution at pH 1-13; products of photolysis included hydroquinone(4).

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Inhalation (L159) ; oral (L159) ; dermal (L159)

4-chlorophenol works as a weak uncoupler of oxidative phosphorylation and inhibitors of cellular respiration. The ability of chlorophenols to uncouple oxidative phosphorylation increases with increasing chlorination. In fact, studies indicate a concentration-dependent triphasic effect of chlorophenols on phosphorylation and cellular respiration. At low concentrations, uncoupling produces stimulation of the resting state respiration as a result of increased adenosine triphosphatase (ATPase) activity in the absence of a phosphate acceptor.Inhibition of active respiration is also observed. At moderate concentrations, resting respiration is neither stimulated nor inhibited. Significant inhibition of respiration, associated with a breakdown of the electron transport process and decreased ATPase activity, occurs at very high concentrations. Uncoupling activity has been attributed to a protonophoric effect (a disruption of the energy gradient across the mitochondrial membrane resulting from distribution of chlorophenols in the phospholipid bilayer of the membrane), whereas inhibition of cellular respiration has been attributed to a direct action on intracellular proteins (L159).

/AQUATIC SPECIES/ ...The response of enclosed marine plankton to chlorophenol additions /was monitored/, and /it was/ determined that exposure to chlorophenols affected algal biomass, composition, and activity. In the first of 3 studies, 1 mg 4-MCP or 2,4-DCP/L prevented the increase in algal biomass (as chlorophyll) that occurred in control enclosures. Large flagellates made up a greater proportion of the algal community in 1 mg/L-treated enclosures compared with controls, perhaps because grazing was reduced. Primary productivity generally parallelled the dynamics of algal biomass, as it was reduced by exposure to 1 mg 4-MCP/L; however, the addition of 1 mg 2,4-DCP/litre did not affect photosynthetic radiolabelled dissolved inorganic carbon (DIC) uptake. Results were generally similar during the 2 subsequent manipulations, though the magnitude and timing of the effects varied.

/AQUATIC SPECIES/ Marine zooplankton were strongly affected by chlorophenol additions during field studies in 1500-L plastic enclosures. While the zooplankton communities in the control enclosures and those treated with 0.1 mg 4-MCP/L or 0.1 mg 2,4-DCP/L displayed similar dynamics, total biomass and production in enclosures treated with 1 mg 4-MCP/L and 1 mg 2,4-DCP/L were reduced relative to controls throughout the first three-quarters of the study. All life-history stages of several copepod species were similarly affected. Results in subsequent studies were generally similar, though the magnitude of the impact varied.

/AQUATIC SPECIES/ Toxicity and metabolism of para-chlorophenol (p-CP) in the marine microalga Tetraselmis marina have been studied. The inhibition constant EC(50) for p-CP was 272+/-17 uM (34.8+/-2.2 mg/L) under the experimental conditions. Two metabolites were detected in the growth medium in the presence of p-CP by reverse phase HPLC and their concentrations increased at the expense of p-CP. The two metabolites, which were found to be more polar than p-CP, were isolated by a C18 column. They were identified as p-chlorophenyl-beta-D-glucopyranoside (p-CPG) and p-chlorophenyl-beta-D-(6-O-malonyl)-glucopyranoside (p-CPGM) by electrospray ionization-mass spectrometric analysis in a negative ion mode. The molecular structures of p-CPG and p-CPGM were further confirmed by enzymatic and alkaline hydrolyses. Treatment with beta-glucosidase released free p-CP and glucose from p-CPG, whereas p-CPGM was completely resistant. Alkaline hydrolysis completely cleaved the esteric bond of the malonylated glucoconjugate and yielded p-CPG and malonic acid. It was concluded that the pathway of p-CP metabolism in T. marina involves an initial conjugation of p-CP to glucose to form p-chlorophenyl-beta-d-glucopyranoside, followed by acylation of the glucoconjugate to form p-chlorophenyl-beta-D-(6-O-malonyl)-glucopyranoside. The metabolism of p-CP in T. marina was mainly driven by photosynthesis, and to a lesser extent by anabolic metabolism in the dark. Accordingly, the detoxification rate under light was about seven times higher than in the darkness. This work provides the first evidence that microalgae can adopt a combined glucosyl transfer and malonyl transfer process as a survival strategy for detoxification of such xenobiotics as p-CP.

Cough. Dizziness. Headache. Laboured breathing. Nausea. Sore throat. Vomiting. Weakness.

MAY BE ABSORBED! Redness. Pain.

Redness. Pain. Blurred vision.

Abdominal pain. Unconsciousness. Further see Inhalation.

Cough, shortness of breath and sore throat can result from inhalation of 2-chlorophenol. These symptoms may be delayed. Abdominal pain, drowsiness, weakness, and convulsions can result from ingestion as well as inhalation. moreover, ingestion of 2-chlorophenol can cause restlessness, tremors, or central nervous system depression to occur. Eye exposure to 2-chlorophenol can lead to redness, pain, and blurred vision, while dermal contact can lead to redness and pain of the skin. Moreover, the substance can be rapidily absorbed after derma exposure (L159).

The concentration of 4-chlorophenol, a by-product of wood pulp chlorination, in Canadian pulp mill effluents was determined to range from 90 to 93 ug/L(1). In Jacksonville, AR, industrial waste, the concentration of 4-chlorophenol was determined to be 1.7 ppm in January 1970, 14.3 ppm in March 1970, 22.9 ppm in April 1970, 22.4 ppm in May 1970, and 2.1 ppm in August 1970(3). 4-Chlorophenol was detected but not quantified in Love Canal, NY water, sediment, and/or soil(2). The average concentration of 4-chlorophenol in the sewage treatment effluents in England and Wales was 115.53 ug/L with a 10.9% frequency of detection(4).

Analysis of chlorinated sewage treatment plants ... 4-chlorophenol was found at a concn of 0.7 ug/l.

The concentration of 4-chlorophenol ranged from 0.1 to 46.7 ug/cu m in emissions from the Heinola plant of Kuusakoski Ltd, a metals reclamation in Finland, analyzed in December 1989 and January 1990(1).

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Chlorophenols is produced, as an intermediate or final product, by process units covered under this subpart. /Chlorophenols/

Used as a chemical intermediate for pesticides, dyestuffs, and pharmaceuticals; Also used as a denaturant for alcohol, selective solvent in refining mineral oils, antiseptic, soil sterilant, adhesion promoting agent, and local antibacterial agent in root canal therapy; [HSDB]

Working with Glues and Adhesives [Category: Other]

CHEM INT FOR THE ACARICIDE, OVEX, RODENTICIDE, PHOSACETIN, PHARMACEUTICALS; DENATURANT FOR ALCOHOL; SELECTIVE SOLVENT IN REFINING MINERAL OILS

Intermediate in synthesis of dyes and drugs; denaturant for alcohol; selective solvent in refining mineral oil

To produce 2,4-dichlorophenol, and a germicide, 4-chlorophenol-o-cresol.

In the synthesis of derivatives of quinizarin, anthraquinone dyes; in the synthesis of the biocide 2-benzyl-4-chlorophenol; in the synthesis of the fungicides dichlorophen and triadimefon; in the synthesis of the cholesterol-reducing drug ethyl-alpha,alpha-dimethyl-4-chlorophenoxy acetate

... Chlorinated 2-phenoxyphenols, chlorinated diphenylethers, and chlorinated dibenzofurans occur as impurities in technical grade of chlorophenols. /Chlorophenols/

The impurities include polychlorinated dibenzo-pdioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), polychlorinated phenoxyphenols, polychlorinated diphenyl ethers, polychlorinated benzenes, and polychlorinated biphenyls. Because the higher chlorinated phenols are produced at higher temperature, the contamination of the higher chlorinated phenols is greater than that of the lower chlorinated phenols. /Chlorophenols/

Chlorination of phenol; from chloroaniline through diazonium salt

... From diazotized p-chloroaniline by chlorination of phenol.

Mfr by selective reduction of chlorobromophenols..

From p-nitrosophenol by a modification of Sandmeyer reaction.

For more Methods of Manufacturing (Complete) data for 4-CHLOROPHENOL (6 total), please visit the HSDB record page.

Cosmetics -> Antimicrobial

Pharmaceuticals -> Transformation products

Environmental transformation -> Pesticide transformation products (metabolite, successor)

Phenol, 4-chloro-: ACTIVE

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