Octachloronaphthalene
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Octachloronaphthalene
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CAS No:
2234-13-1
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Formula:
C10Cl8
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Chemical Name:
Octachloronaphthalene
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Synonyms:
Naphthalene,1,2,3,4,5,6,7,8-octachloro-;Naphthalene,octachloro-;1,2,3,4,5,6,7,8-Octachloronaphthalene;Perna;Halowax 1051;Perchloronaphthalene;Octachloronaphthalene;PCN 75;NSC 243655
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CAS No:
Description
The chlorinated naphthalenes in which one or more hydrogen atoms have been replaced by chlorine to form wax-like substances, beginning with monochloronaphthalene and going on to the octachlor derivatives. Their physical states vary from mobile liquids to waxysolids depending on the degree of chlorination; freezing/ melting points of the pure compounds range from 17C for 1-chloronaphthalene to 198C for 1,2,3,4- tetrachloronaphthalene. 1-Chloro-isomer: Hazard identification (based on NFPA-704 M R
Octachloronaphthalene is a pale yellow solid with an aromatic odor. (NTP, 1992)|WAXY YELLOW SOLID IN VARIOUS FORMS WITH CHARACTERISTIC ODOUR.|Waxy, pale-yellow solid with an aromatic odor.
Octachloronaphthalene is a pale yellow solid with an aromatic odor. (NTP, 1992)
Octachloronaphthalene Basic Attributes
403.73
403.73
218-778-7
BQ6EO9GJXE
1059
243655
DTXSID6025800
Crystals from cyclohexane|NEEDLES FROM BENZENE & CARBON TETRACHLORIDE|Waxy pale-yellow solid
2903999090
Characteristics
0
8.2
Octachloronaphthalene is a pale yellow solid with an aromatic odor. (NTP, 1992)
2.00 g/cm3 @ Temp: 25 °C
185-197 °C
246 °C @ Press: 0.50 Torr
-18 °C
1.684
H2O: Insoluble
APPROX 4°C
4.20 x 10 -7 mmHg at 25.00 °C (Lei et al., 1999)
13.9
Heitmuller et al. (1981) reported a NOEC of 560 ppm.
Flammable; burning produces toxic chloride gas
Aromatic odor
Softening point: 185-197 °C
Insoluble in water.
Aryl Halides
Contact with strong oxidizing agents may cause fire and explosion (NTP, 1992).
Noncombustible Solid
Safety Information
UN11453/PG2
3
22-67-65-50/53-38-11-20
36/39-62-61-60-33-25-16-9
QK0250000
Xn,N,F
Warehouse ventilated, low temperature and dry
P260, P264, P270, P273, P314, P501
H372
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.|Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced. Recommendable method: Incineration. Peer-review: Ensure plentiful supply of hydrocarbon fuel. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
Contact with strong oxidizing agents may cause fire and explosion.
Literature sources indicate that this chemical is nonflammable. (NTP, 1992)|Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 44 companies from 3 notifications to the ECHA C&L Inventory.|Danger|H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]|P260, P264, P270, P273, P314, and P501|P260, P264, P270, P314, and P501|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P260, P264, P280, P305+P351+P338, P314, P332+P313, P337+P313, and P501
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. (NIOSH, 2016)|Employees should be provided with and required to use impervious clothing, gloves, face shields (eight inch minimmum), and other appropriate protective clothing necessary to prevent: any possibility of skin contact with molten octachloronaphthalene, repeated or prolonged skin contact with solid octachloronaphthalene or liquids containing octachloronaphthalene, or skin contact with octachloronaphthalene vapors from heated material.|... Wear appropriate clothing to prevent any possibility of skin contact with molten material ... /or/ solutions. Wear eye protection ... /and/ wash promptly when skin ... is contaminated. /Chloronaphthalenes/|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|For more Personal Protective Equipment (PPE) (Complete) data for OCTACHLORONAPHTHALENE (7 total), please visit the HSDB record page.|(See protection codes)
Not combustible
In case of fire in the surroundings: all extinguishing agents allowed.
First remove all sources of ignition, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.|1. VENTILATE AREA OF SPILL. 2. COLLECT SPILLED MATERIAL IN MOST CONVENIENT & SAFE MANNER FOR RECLAMATION OR FOR DISPOSAL IN SECURED SANITARY LANDFILL. LIQ ... SHOULD BE ABSORBED IN VERMICULITE, DRY SAND, EARTH, OR A SIMILAR MATERIA
Non-impervious clothing which becomes contaminated with molten or solid octachloronaphthalene or liquids containing octachloronaphthalene should be removed promptly and not reworn until the octachloronaphthalene is removed from the clothing.|If employess' clothing may have become contaminated with solid octachloronaphthalene, employees should change into uncontaminated clothing before leaving the work premises.|Clothing contaminated with octachloronaphthalene should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of octachloronaphthalene from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the octachloronaphthalene, the person performing the operation should be informed of octachloronaphthalene's hazardous properties.|CONDENSER IMPREGNATION & OTHER OPERATIONS INVOLVING MELTING OF CHLORONAPHTHALENE SHOULD BE ENCLOSED OR PROVIDED WITH EFFECTIVE LOCAL EXHAUST VENTILATION. /CHLORONAPHTHALENES/|For more Preventive Measures (Complete) data for OCTACHLORONAPHTHALENE (10 total), please visit the HSDB record page.
Toxic by Inhalation and skin contact.
Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 0.1 mg/cu m. Skin Designation.|Vacated 1989 OSHA PEL TWA 0.1 mg/cu m; STEL 0.3 mg/cu m, skin designation, is still enforced in some states.
Recommended Exposure Limit: 10 Hr Time-Weighted avg: 0.1 mg/cu m; skin.|Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 0.3 mg/cu m; skin.
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.
The substance may cause effects on the liver. This may result in tissue lesions.
The substance may have effects on the liver.
STRICT HYGIENE!
Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear safety goggles, face shield or eye protection in combination with breathing protection.
Octachloronaphthalene concns of 50-130 ug/L were detected in industrial wastewaters from aluminum smelting processes that used either hexachloroethane-chlorine gas or dichloroethane-Freon gas treatments(1). Stack gas samples were collected from five different municipal waste incinerators in Spain; octachloronaphthalene represented the lowest contribution to the total polychlorinated naphthalenes, 0.14-2.88%, and concentrations varied from 0.002 to 0.12 ng.cu m(2). Octachloronaphthalene was not detected in the crude, purified, and flue gases of waste gasification and combustion of a pilot plant(3).Octachloronaphthalene concentrations in the purified gas after addition of PVC and polyester were 700 and 20 g/cu m, respectively(3).
SEDIMENT: Although analyzed for, octachloronaphthalene was not detected (detection limit of several ng/kg) in surface sediments collected from 18 lakes in central Finland in 1988(1); tetra-, penta-, and hexachloronaphthalenes were detected, but hepta- and octachloronaphthalene were not(1). Analysis of sediment samples taken from an industrial outfall in the Calcasieu River, LA (sampling date not reported), found octachloronaphthalene concns of 12 ug/g in the bottom sediment and 0.81 ug/g in the suspended sediment(2); octachloronaphthalene was not detected (detection limit not reported) in the water-only phase(2). Surface sediments (upper 5 cm) from two polluted Mediterranean lagoons in Italy, Venice and Orbetello, were sampled in 1995 and analyzed for polychlorinated naphthalenes; octachloronaphthalene concentrations ranged from 0.95-9.31 pg/g dry weight for five sites in Venice, and from not quantified-1.78 pg/g dry weight for three sites in Orbetello(3). A site at the Albegua River was selected as a control and had an octachloronaphthalene concentration in surface sediments of 1.06 pg/g dry weight(3). In this study octachloronaphthalene made up 1.6% of the total polychlorinated naphthalenes(3). Concentrations of octachloronaphthalene ranged from <0.001 to 1.29 ng/g dry weight in surface sediments (0-30 cm) collected in Jun 1998 from the upper Detroit River at nine sites; from 0.007 to 0.01 ng/g dry weight from three sites in Lake Michigan; and 0.247 pg/g dry weight from one site in the upper Rouge River(4).
URBAN/SUBURBAN: The mean concentration of the combined tri- to octachloronaphthalenes in ambient air monitored from Jun 1992 to Feb 1993 was 60 pg/cu m from seven stations in Augsburg, Germany and 24 pg/cu m at the rural background station 15 km northwest of Augsburg(1). Octachloronaphthalene made up 0.10% of the total polychlorinated naphthalenes measured at Augsburg(1).|RURAL/REMOTE: The mean concentration of the combined tri- to octachloronaphthalene in ambient air monitored from Jun 1992 to Feb 1993 was 24 pg/cu m at the rural background station 15 km northwest of Augsburg, Germany(1).
Toxicity
moderately toxic
IDENTIFICATION: There are 75 possible congeners of chlorinated naphthalenes. Commercial products are generally mixtures of several congeners and range from thin liquids to hard waxes to high melting point solids. The higher chlorinated naphthalene products have been used as impregnants for condensers and capacitors and dipping encapsulating cmpd in electronic and automotive applications and as temporary binders in the manufacture of ceramic components, in paper coating and in precision casting of alloys, in electroplating, stop-off cmpd, as additive in gear oils and cutting cmpd, in flame proofing and insulation of electrical cable and conductors and moisture proof sealants, as separators in batteries, in refractive index testing oils, masking cmpd in electroplating and in grinding wheel lubricants. HUMAN EXPOSURE: The major sources of release of chlorinated naphthalenes into the environment are likely from waste incineration and disposal of items containing chlorinated naphthalenes to landfill. In the past, chlorinated naphthalene concn of up to 14.5 mg/cu m have been measured in the workplace, while levels of 25-2900 ng/cu m have been recorded in out door air in vicinity of manufacturing sites. More recently, monitoring studies have revealed chlorinated naphthalene concn up to 150 pg/cu m at semirural sites and 1-40 pg/cu m at remote sites. Chlorinated naphthalenes can be absorbed via oral, inhalative and dermal routes, with absorption and distribution over the whole body after oral admin. Chlorinated naphthalenes, especially the dioxin like congeners, have been detected in adipose tissue, liver, blood and breast milk samples from the general population at concn in the ng/kg lipid range. Severe skin reactions (chloracne) and liver disease have been reported after occupational exposure to chlorinated naphthalenes. Chloracne was common among workers who handling chlorinated naphthalenes in the 1930's to 1940's. A cohort study on workers exposed to chlorinated naphthalenes at a cable manufacturing plant found an excess of deaths from cirrhosis of the liver. However, individuals with chloracne did not show a higher mortality due to liver cirrhosis compared with other workers. The mortality from all cancers was slightly but significantly elevated among all exposed men (standardized mortality ratio =1.18), but was not more elevated in the subcohort with chloracne. This subcohort showed statistically significant excess mortality from cancer of the esophagus and from benign and unspecified neoplasms. Symptoms described in workers exposed to chlorinated naphthalenes included irritation of the eyes, fatigue, headache, anemia, hematuria, impotency, anorexia, vomiting and severe abdominal pain. ANIMAL STUDIES: Chlorinated naphthalenes have been shown to be highly bioaccumulative in fish, but less so in shrimp and algae. The amount of bioaccumulation observed incr with the degree of chlorination of the chlorinated naphthalenes. The most highly chlorinated naphthalenes do not appear to bioaccumulate. Chlorinated naphthalene concn in fish range up to a maximum of around 300 ug/kg lipid weight. 1,2,3,4-Tetrachloronaphthalene has demonstrated no mutagenicity in the Salmonella Ames test. Monitoring studies with seabird eggs have revealed a decr in chlorinated naphthalene levels between 1974 and 1987. Hydroxy metabolites have been identified mostly for the lower chlorinated naphthalenes (mono- to tetra-) in experimental animals. Cattle developed severe systemic disease (bovine hyperkeratosis) during a 5-10 day oral exposure to 1.7-2.4 mg/kg bw/day of penta-, hexa-hepta- or octachlorinated naphthalenes. There are also preliminary indications for the occurrence of methylthio- or methyl sulfoxide chloronaphthalene metabolites in the feces of rats. Elimination of the parent compounds and/or metabolites occurs via feces and urine. The higher chlorinated congeners appeared to be more toxic than the lower chlorinated ones. Long term and carcinogenicity studies with chlorinated naphthalenes have not been performed. Like related cmpd, chlorinated naphthalenes have been demonstrated to be inducers of the cytochrome p450 (CYP) dependent microsomal enzymes. Chlorinated naphthalenes were also found to change lipid peroxidation and antioxidant enzyme activities in rats in a manner indicative of oxidative stress. At least some of the biological and toxic responses of chlorinated naphthalenes are believed to be mediated via the cytosolic Ah receptor, resembling those of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and related cmpd. All chlorinated naphthalenes tested cause skin irritations in laboratory animals. Chlorinated napthalenes appear to be of moderate to high acute toxicity to aquatic organisms. The amount of bioaccumulation observed increases with the amount of chlorination of the chlorinated naphthalenes, but the most highly chlorinated naphthalenes (octachloronaphthalene) do not appear to bioaccumulate. /Chlorinated naphthalenes, Higher Chlorinated Naphthalenes/
/AQUATIC SPECIES/ In the food chain important to humans, bioaccumulation takes place, specifically in fish. It is strongly advised not to let the chemical enter into the environment because it persists in the environment.
Polychlorinated naphthalenes do not occur naturally in the environment(1).
Octachloronaphthalene's production and use in fireproofing and waterproofing in cable insulation and as a lubricant additive(1) may have resulted in its release to the environment through various waste streams(SRC). Polychlorinated naphthalenes are no longer produced(2).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.1X10+5(SRC), determined from a structure estimation method(2), indicates that octachloronaphthalene is expected to be immobile in soil(SRC). Volatilization of octachloronaphthalene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 0.000731 atm-cu m/mole(SRC), derived from its vapor pressure of 1.1X10-8 mm Hg(4) and water solubility of 8X10-5 mg/l(5). However, volatilization is expected to be attenuated by adsorption to soil(SRC). Octachloronaphthalene is not expected to volatilize from dry soil surfaces(SRC), based upon a vapor pressure of 1.1X10-8 mm Hg(4). Octachloronaphthalene is reported to have "poor" biodegradability(6). Tetra to hexachlorinated naphthalenes showed no biodegradation during 28 day aerobic biodegradation experiments(7). In addition, a predictive method based upon evaluated biodegradation data and the fact that octachloronaphthalene contains 8 aromatic chlorine substructures predicts that octachloronaphthalene has a low probability of biodegrading fast in the environment(8).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.1X10+5(SRC), determined from a structure estimation method(2), indicates that octachloronaphthalene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 0.000731 atm-cu m/mole(SRC), derived from its vapor pressure, 1.1X10-8 mm Hg(4) and water solubility, 8X10-5 mg/l(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8.2 hours and 8.7 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). Octachloronaphthalene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(13). Octachloronaphthalene absorbs light with wavelengths >290 nm(4), and may be susceptible to direct photolysis by sunlight(SRC). According to a classification scheme(6), a BCF of 330(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, in another experiment no uptake of octachloronaphthalene was observed, and it was proposed that the lack of uptake was due to the size of the octachloronaphthalene molecule and its inability to permeate through the membrane(8,9). Octachloronaphthalene is reported to have "poor" biodegradability(10). Tetra to hexachlorinated naphthalenes showed no biodegradation during 28 day aerobic biodegradation experiments(11). In addition, a predictive method based upon evaluated biodegradation data and the fact that octachloronaphthalene contains 8 aromatic chlorine substructures predicts that octachloronaphthalene has a low probability of biodegrading fast in the environment(12).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), octachloronaphthalene, which has a vapor pressure of 1.1X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase octachloronaphthalene 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 830 days(SRC), calculated from its rate constant of 3.8X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase octachloronaphthalene may be removed from the air by wet and dry deposition(SRC). Octachloronaphthalene absorbs light with wavelengths >290 nm(4), and may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of octachloronaphthalene with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 830 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Octachloronaphthalene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Octachloronaphthalene absorbs light with wavelengths >290 nm(4), and may be susceptible to direct photolysis by sunlight(SRC).
380.19|Bioconcentration factor in Oncorhynchus mykiss, exposure concentration 1.3 x 10(-2) ug/L, 330|In a continuous flow through system, an octachloronaphthalene BCF of 0 was measured in guppies (Poecillia reticula) over a 7-day exposure period(1,2); it was proposed that the lack of uptake was due to the size of the octachloronaphthalene molecule and its inability to permeate through the membrane(1,2). In a static system, a mean BCF of 330 was measured in rainbow trout over a 96-day exposure period(3). According to a classification scheme(4), BCF values of <30 are low and from 100-1000 are high.|Uptake rate constants by fish of di-, tetra-, hexa-, octa-, and decachlorobiphenyls are independent of the solute's hydrophobicity. By combining a 2-compartment bioconcentration model with a modified membrane permeation model, simple relationships between uptake rate constants into fish and the solutes' hydrophobicities and molecular configurations are obtained. The observed lack of uptake by fish of hexabromobenzene, octachloronaphthalene, and octachlorodibenzo-p-dioxin is not due to insufficient exposure concn, since the exposure concn of these compounds in the continuous flow water saturation system were significantly higher than those of some PCB congeners. The lack of uptake of these chemicals can be explained by proposing a influence of membrane permeation on the mechanism of bioconcentration. For these compounds, the size rather than octan-1-ol/water partition coefficients or aqueous solubility causes a lack of uptake by fish(1).
7.76e+05 L/kg|Using a structure estimation method based on molecular connectivity indices(1), the Koc for octachloronaphthalene can be estimated to be 1.1X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that octachloronaphthalene is expected to be immobile in soil.
The Henry's Law constant for octachloronaphthalene is 0.000731 atm-cu m/mole(SRC), derived from its vapor pressure, 1.1X10-8 mm Hg(1), and water solubility, 8X10-5 mg/l(2). This Henry's Law constant indicates that octachloronaphthalene is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 8.2 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 8.7 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4800 years if adsorption is considered(4). Octachloronaphthalene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Octachloronaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1.1X10-8 mm Hg(1).
Total polychlorinated naphthalenes decreased form 3,081 to 483 pg/g milk fat in breast milk of women living in Stockholm, Sweden from 1972-1992; octachloronaphthalene was not detected in any samples(1).
Occupational exposure to octachloronaphthalene may occur through inhalation and dermal contact with this compound at workplaces where octachloronaphthalene was produced or used. Monitoring data indicate that the general population may be exposed to octachloronaphthalene via inhalation of ambient air. (SRC)
Drug Information
One day after a single intraperitoneal injection in mice of 1 mg per animal the highest concentration of octachloronaphthalene was found in the adipose tissue: 2.1% of the dose. Lower concentrations were found in the liver (1.9%), spleen (0.80%), and kidneys (0.32%). The concentration in adipose tissue increased gradually up to day 7.|Tissue distribution and biological half lives of 1,8-dichloronaphthalene), 2,7-dichloronaphthalene, and octachloronaphthalene were investigated in mice. Pathogen free male JCL/ICR mice were given a single ip dose of 1 mg of 5 mg/ml 1,8-dichloronaphthalene, 2,7-dichloronaphthalene, or octachloronaphthalene dissolved in olive oil. Controls were injected with vehicle only. Animals were killed by cervical dislocation 3 and 6 hr and 1, 3, 7, 14, and 28 days after injection. The brain, heart, lungs, liver, kidneys, testes, spleen, and adipose tissues were removed and the chloronaphthalenes were estimated by gas chromatography of tissue extracts. Biological half lives were calculated from elimination data. The highest percentage of each chloronaphthalene was found in the adipose tissue, attributable to lipophilic properties of chloronaphthalenes, and the lowest percentage was found in heart and brain tissues. The concentration of chloronaphthalenes in other tissues showed no fixed relationship. Octachloronaphthalene was present mostly in the adipose tissue, where little 1,8-dichloronaphthalene was present. The concentration of the three chloronaphthalenes, except for octachloronaphthalene in adipose tissues, increased to a maximum within 3 hr after dosing and decreased exponentially thereafter. The concentration of octachloronaphthalene increased gradually in adipose tissue up to day 7. The biological half life of 2,7-dichloronaphthalene was longer than that of 1,8-dichloronaphthalene in most of the tissues. It was concluded that the biological half life may be affected by the substituted position of chlorine in the chloronaphthalenes and that higher chlorinated naphthalenes are metabolized more slowly than lower chlorinated naphthalenes.|The uptake and elimination of three superlipophilic compounds (hexabromobenzene, PCB153, and octachloronaphthalene) after dietary uptake was studied in earthworms (Eisenia andrei). All three compounds were taken up from the food, although they did not significantly accumulate despite their hydrophobicity. Both uptake efficiencies (E) and biomagnification factors (BMF) were low. E varied between 0.70 and 7.5%, while BMF values were all below 0.17. The elimination of the compounds was slow, with elimination rate constants k2 varying between 0.04 and 0.09/day.
41.69 Days|... /A/ study comparing di- and octachloronaphthalenes found higher half-lives for octachloronaphthalene (3.72 days) than for 1,8-dichloronaphthalene (0.27 days) or 2,7- dichloronaphthalene (0.80 days) in adipose tissue of mice, if calculated from tissue levels at various time points up to 28 days. Nevertheless, the half-life observed for octachloronaphthalene is unexpectedly short for such a highly chlorinated, lipophilic compound.|Several biological half-life times /in mice/ were calculated during the exponential elimination phase/after single ip injection/: 3.72 days for the adipose tissue, 3.39 days for the testes, 2.25 days for the spleen, 2.20 for the kidneys and as the fastest: 1.51 days for the lungs. The investigators did not recover 100% of the amount injected, probably a part remained at the site of injection.
Administration of octachloronaphthalene to immature male Wistar rats resulted in a dose dependent increase in several enzymic, electrophoretic and spectral parameters associated with induction of the hepatic microsomal enzymes. Compared to corn oil treated animals (control) octachloronaphthalene (150 umol/kg) induced hepatic cytochrome p-450 (1.5 fold), benzo(a)pyrene hydroxylase (18-fold) and 4-chlorobiphenyl hydroxylase (18-fold) enzyme activities. In addition to increases in the relative peak intensities of the reduced microsomal cytochrome p-450:CO and ethylisocyanide difference spectra the peak maxima were observed at 448.5 and 452.2/428.0 nm, respectively. The effects of administering octachloronaphthalene to the rat were similar to those observed after pretreatment with 3-methylcholanthrene and electrophoresis of the induced microsomal proteins showed that both compounds enhanced heme-staining peptides with comparable electrophoretic mobilities. Coadministration of 3-methylcholanthrene (3 X 100 umol/kg) and octachloronaphthalene (2 X 150 umol/kg) indicated that their inductive effects were not additive. Octachloronaphthalene was an 3-methylcholanthrene type inducer of hepatic microsomal enzymes.|Octachloronaphthalene, a major component of halowax 1051, induces microsomal benzo(a)pyrene hydroxylase and dimethylaminoantipyrine n-demethylase activities and intensifies protein staining band on SDS polyacrylamide electrophoresis.|As observed for other halogenated aryl hydrocarbons, the relative induction potencies of PCNs appear to depend on the degree and position of chlorine substitution of the naphthalene ring ... In several different test systems, the most potent EROD and AHH inducers include 1,2,3,4,6,7/1,2,3,5,6,7-hexachloronaphthalene, 1,2,3,4,5,6,7-heptachloronaphthalene, and some unidentified congeners present in Halowax 1014. Octachloronaphthalene was also found to cause a dose-dependent AHH increase in microsomes of rats.|Of the individual PCN congeners tested, penta-, hexa-, and heptachloronaphthalenes gave full dose- response curves, whereas most of the lower chlorinated congeners as well as octachloronaphthalene were inactive in /the rat hepatoma H4IIE-luc cell (luciferase) assay . The most potent congener was 1,2,3,4,6,7-hexachloronaphthalene . Similar results have been obtained by another study testing individual PCN congeners using the luciferase (and the EROD) assay with recombinant H4IIE rat hepatoma cells. Again, hexa- and heptachloronaphthalenes tested were the most potent congeners, /followed by/ Pentachlorinated congeners .Tetra, tri-, di-, and monochloronaphthalenes were found to be less active. There was also a rank order of potency within the penta- and hexachloronaphthalene isomers, in a manner suggesting that the presence of meta-substituted chlorines is linked to decreased potency. For example, for hexachloronaphthalenes, an approximate ranking order was given as 1,2,3,6,7,8 greater than 1,2,3,4,6,7 greater than 1,2,3,5,6,7 greater than 1,2,3,5,6,8.
Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Acne-form dermatitis; liver damage, jaundice Target Organs: Skin, liver (NIOSH, 2016)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)
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.
NAPHTHALENE toxicosis caused by vapor inhalation can usually be managed simply by removing the individual to fresh air. Skin contamination should be removed promptly by washing with soap and water. Eye contamination should be removed by flushing with copious amounts of clear water. Irritation may be severe, and if it persists, should receive medical attention. SRP: /It may be helpful to empty stomach and administer dose of activated charcoal/ Examine the plasma for evidence of hemolysis: a reddish-brown tinge. Examine the blood smear for "ghosts" and Heinz bodies. If /hemolysis is/ present, monitor red blood cell count and hematocrit for anemia, urine for protein, and cells. Measure direct- and indirect-reacting bilirubin in the plasma. Monitor fluid balance and blood electrolytes. If possible, monitor urinary excretion of naphthol to assess severity of poisoning and clinical progress. If hemolysis is clinically significnt, administer intravenous fluids to accelerate urinary excretion of the naphthol metabolite and protect the kidney from products of hemolysis. Use Ringer's-lactate or sodium bicarbonate to keep urine pH above 7.5. Consider use of mannitol, or furosemide, to promote diuresis. If urine flow declines, intravenous infusions must be carefully monitored to avoid fluid overload. Institute hemodialysis. Consider charcoal hemoperfusion in tandem to extract naphthalene and end-products. If anemia is severe, blood transfusions may be needed. Hydrocortisone may be of some benefit if significant hemolysis is present. /Fumigant poisoning/
/HUMAN EXPOSURE STUDIES/ Until 1957 there was general agreement that as the degree of chlorination increased, so did the acneigenic properties and the systemic toxicity of the chloronaphthalenes. ... as a result /of/ ... experiments on human volunteers, the unexpected fact emerged that whereas tri-, tetra-, hepta-, and octachloronaphthalenes were entirely nonacneigenic, the penta- and hexachloro derivatives produced very severe chloracne indeed.|/SIGNS AND SYMPTOMS/ Overexposure to octachloronaphthalene may cause an acne like skin rash. It may also injure the liver, resulting in such effects as fatigue, dark urine, yellow jaundice, and possibly death.
octachloronaphthalene
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact
Acne-form dermatitis; liver damage, jaundice
MAY BE ABSORBED!
Skin, liver
Octachloronaphthalene Use and Manufacturing
Polychlorinated naphthalenes (PCNs) ... can be synthesized by the chlorination of naphthalene. /Polychlorinated naphthalenes/
Chemical research; organic synthesis. According to HSDB (1005), U.S. has discontinued manufacturing of chlorinated naphthalenes since 1977. Chlorinated naphthalenes were formerly used as a wood preservative, additives in cutting oils, and as an additive in fireproofing and waterproofing cable insulation.
... Exact yearly or total production figures are obscure. In 1972, the estimated market for PCNs was less than 2300 metric tons. /Polychlorinated naphthalenes/
Naphthalene, 1,2,3,4,5,6,7,8-octachloro-: ACTIVE|SP - indicates a substance that is identified in a proposed Significant New Use Rule.|Koppers Co, Inc., the sole U.S. producer, ceased manufacturing their chloronaphthalene products (Halowax) in 1977.|Commercial PCNs were produced by several companies, eg, Koppers Chemical Co., Halochem, Prodelec, Bayer, and ICI, and marketed under a number of trade names including Halowaxes, Nibren wasex, Seekay waxes, and Clonacire waxes. /Polychlorinated naphthalenes/|... Most of the commercial PCNs were complex mixtures of isomers and cogeners, although two products, namely monoPCN and Halowax 1051/N-Wax 80, contained primarily 1-chloronaphthalene and octachloronaphthalene, respectively. /Polychlorinated naphthalenes/
HPLC METHOD HAS BEEN USED TO CHARACTERIZE BEHAVIOR OF MIXTURES OF CHLORINATED NAPHTHALENES. RETENTION TIMES & UV SPECTRA WHICH ARE RECORDED ARE DEPENDENT ON THE NUMBER & THE POSITION OF THE CHLORINE ATOMS ON THE NUCLEUS. RESULTS FROM THIS SYSTEM WERE COMPARED WITH RESULTS FROM SEVERAL TLC SYSTEMS. PEAKS IN THE CHROMATOGRAMS FROM HALOWAXES HAVE BEEN ASSIGNED TO INDIVIDUAL CONSTITUENTS.|MIXTURES OF POLYCHLORINATEDBIPHENYLS & POLYCHLORINATED NAPHTHALENES CAN BE ANALYZED BY HPLC & GC AFTER THEIR CONVERSION TO FULLY CHLORINATED END PRODUCTS. HALOWAX, A MIXTURE OF OCTACHLORONAPHTHALENE & CHLORONAPHTHALENE CAN BE SUCCESSFULLY ANALYZED.|Method: NIOSH S97; Analyte: Octachloronaphthalene; Matrix: Air; Procedure: GC; Range: 0.055-0.215 mg/cu m.|EPA Method 8250. Packed Column GC/MS Technique for the determination of semivolatile organic compounds in extracts prepared from all types of solid waste matrices, soil, andgroundwater. This method is applicable to quantify most neutral, acidic, and basic organic compounds that are soluble in methylene chloride and capable of being eluted with derivatization as sharp peaks from a gas chromatographic packed column. Under the prescribed conditions, no detection limit was given. Precision and method accuracy were found to be directly related to the concentration of the analyte and essentially independent of the sample matrix.|For more Analytic Laboratory Methods (Complete) data for OCTACHLORONAPHTHALENE (6 total), please visit the HSDB record page.
Computed Properties
Molecular Weight:403.7
XLogP3:8.2
Exact Mass:403.744921
Monoisotopic Mass:399.750822
Heavy Atom Count:18
Complexity:254
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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