2-Chloronaphthalene
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2-Chloronaphthalene
structure -
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CAS No:
91-58-7
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Formula:
C10H7Cl
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Chemical Name:
2-Chloronaphthalene
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Synonyms:
Naphthalene,2-chloro-;2-Chloronaphthalene;β-Chloronaphthalene;PCN 2
- Categories:
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CAS No:
Description
WHITE TO ALMOST WHITE CRYSTALLINE POWDER The chlorinated naphthalenes in which one or more hydrogen atoms have been replaced by chlorine to form wax-like substances, beginning with monochloronaphthalene and going on to the octachlor derivatives.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: Haz
Monoclinic plates or off-white crystalline powder. Melting point 59.5°C.|WHITE CRYSTALLINE POWDER.
Monoclinic plates or off-white crystalline powder. Melting point 59.5°C.
2-Chloronaphthalene Basic Attributes
162.62
162.62
202-079-9
49O81U3ITI
1708
3077
DTXSID8023971
Monoclinic plates, leaflets from dil alcohol|Leaflets from ethanol (aq)
29039990
Characteristics
0
4.2
White to almost white Crystalline Powder
1.1377
59.5 °C
119.7 °C @ Press: 11 Torr
125 °C
1.643
H2O: insoluble
2-8°C
Vapour pressure, Pa at 25°C: 1
Relative vapour density (air = 1): 5.6
Oral-Rat LD50: 2078 mg/kg; Oral-Mouse LD50: 886 mg/kg
Flammable, decomposes toxic chloride gas when burning
3.20e-04 atm-m3/mole
... Physical properties of ... chlorinated naphthalenes are generally dependent on the degree of chlorination. ... As the degree of chlorination increases the specific gravity, boiling point, fire and flash points all increase while ... vapor pressure and water solubility decrease. ... Chlorinated naphthalenes /also/ exhibit a high degree of chemical and thermal stability. /Chloronaphthalenes/|Mixtures of mono- and dichloronaphthalenes are generally liquids at room temperature ... .|Henry's Law Constant: 0.00032 atm-cu m/mol @ 25 °C|Physical state varies from oily liquids to crystalline solids, depending on the extent of chlorination /Chlorinated napthalene/
Insoluble in water.
Aryl Halides
2-CHLORONAPHTHALENE may react with strong oxidizing agents (NTP, 1992).
Safety Information
III
9
UN12303/PG2
3
36/37/38-39/23/24/25-23/24/25-11
37/39-26-45-36/37-16-7
QJ2275000
Xi,T,F
Warehouse low temperature, ventilated, dry
Stable under normal temperatures and pressures.
P210-P260-P280-P301 + P310-P311
H225-H301 + H311 + H331-H370
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U047, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.|Incinerate, 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. /Chloronaphthalenes/|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))|The following wastewater treatment technologies have been investigated for 2-chloronaphthalene: Concentration process: Chemical precipitation.
... /2-chloronaphthalene/ may react with strong oxidizers
USEPA; Ambient Water Quality Criteria Doc: Chlorinated Naphthalenes (1980) EPA 440/5-80-031.|Health and Welfare Canada; Chloronaphthalenes: An Environmental-Health Perspective (1982) 83-EHD-96.
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 160 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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 protect this material from exposure to light. Keep it away from oxidizing materials and store it under refrigerated temperatures. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|PREVENTION /OF CHLORACNE/ THROUGH USE OF PROTECTIVE CLOTHING, SHOWERS, & APPROPRIATE CLEAN CLOTHES & LOCKERS IS NECESSARY. /CHLORINATED NAPHTHALENES/
Incinerability: temperature for 99% destruction at 2.0 sec residence time under oxygen-starved reaction conditions: 975 °C.
Fires involving /2-chloronaphthalene/ ... can be controlled using a dry chemical, carbon dioxide or Halon extinguisher.
Despite the use of solvent extraction as a means of separating organic materials, its application to wastewater treatment generally has been limited to removal of phenol & its compounds present at high concentrations. This paper provides a systematic methodology of the extraction problem, which may be used to establish the treatability criteria for organic priority pollutants. The treatabilities are calculated based on distribution coefficients & extraction column models in the literature. Distribution coefficients (estimated) for 2-chloronaphthalene & other pollutants in various solvents are given.|Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contamin- ated surfaces with 60-70% ethanol 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.
IN MFR, HAZARD IS NOT CONFINED TO FINAL PRODUCT, BUT ALSO BOUND UP WITH BASE CHEMICALS USED (CHLORINE & NAPHTHALENE OR DIPHENYL) ALL OF WHICH ARE TOXIC; THE FOLLOWING PRECAUTIONS ... /SHOULD BE CONSIDERED/: (A) MFR PROCESSES ... ENCLOSED OR EXHAUST VENTILATION HOODS ... USED; (B) WORKROOMS ... TIDY & FREE OF DUST ... C) LIBERAL WASHING FACILITIES & 2-LOCKER SYSTEM FOR ORDINARY & WORKING CLOTHES SHOULD BE PROVIDED ... . /CHLORONAPHTHALENES/|... Work clothing should be changed daily if it is possible that clothing is contaminated. /Chloronaphthalenes/|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. /Chloronaphthalenes/
Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Provision to contain effluent from fire extinguishing. Separated from strong oxidants. Store in an area without drain or sewer access.
A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
The substance is irritating to the eyes, skin and respiratory tract.
The substance may have effects on the liver. This may result in impaired functions.
NO open flames.
PREVENT GENERATION OF MISTS!
Use ventilation, local exhaust or breathing protection.
Protective gloves.
Wear safety spectacles.
U047; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
U047; As stipulated in 40 CFR 261.33, when beta-chloronaphthalene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
According to the EPA's STORET database, 1255 sampling stations reported that unspecified isomers of chloronaphthalene were present in effluents, of which 1.4% contained detectable levels of the chemical with a median concentration of less than 10.0 ug/l(1). Wastewater from the gaseous diffusion facility operated by Union Carbide at Oak Ridge, TN contained 2-chloronaphthalene in the volatile fraction(2). Leachate from Hooker Chemical and Plastics Corp disposal site at Love Canal, NY contained 2-chloronaphthalene(3). Pyrolysis of vinylidene chloride polymer, which is used as wrapping material, released 2-chloronaphthalene to the atmosphere(4). Municipal waste incinerators can emit 2-chloronaphthalene to ambient air(5). 2-Chloronaphthalene was not detected in tire leachate water; the detection limit was 1 ug/l(6). 2-Chloronaphthalene was not detected in ashes obtained from about one-fourth of the operating municipal refuse incinerators in the U.S. (7). The detection limit was 3 ppb for sample of fly ash and 30 ppb for samples of combined fly and bottom ash(7).
SOIL: 2-Chloronaphthalene was found in groundwater and soil/sediments samples from 91 waste sites at 18 U.S. Department of Energy (DOE) facilities with a frequency of <3(1). On-site soil concentrations of 2-chloronaphthalene from the Lipari landfill in Mantua Township, Gloucester County New Jersey collected in 1987 were 3,185 (average) and 12,000 (maximum) ug/kg(2).|SEDIMENT: According to the EPA's STORET database, 340 sampling stations reported that unspecified isomers of chloronaphthalene were present in sediments, of which 0.3% contained detectable levels of the chemical with a median concentration of less than 500.0 ug/kg by dry weight(3). Ground water sediment samples from nearby the Hooker Chemical and Plastics Corp disposal site at Love Canal, NY contained 2-chloronaphthalene(1). 2-Chloronaphthalene was detected at concn equal to or less than 2.0 ug/kg in surficial bed material at Racoon Creek at Bridgeport, NJ on Jan 8, 1981(2). 2-Chloronaphthalene was not detected at 516 sites sampled to assess the occurrence of semivolatile organic compounds in streambed sediments form 20 major river basins across the United States from 1992-1995(4). Water and suspended solids samples were collected during June and August 1988 at four stations along the Rainy River on the Canada-Minnesota boarder and from two pulp and paper mill final effluents and analyzed for a variety of organic contaminates (5). 2-Chloronaphthalene was detected in the suspended solids from one of the pulp and paper mill final effluent at 18.0 and 21.0 ng/g in June and August, respectively(5). 2-Chloronaphthalene was not detected at the other five sites; the detection limit was 10.0 ng/g(5). 2-Chloronaphthalene was found in groundwater and soil/sediments from 91 waste sites at 18 U.S. Department of Energy (DOE) facilities with a frequency of <3(6).
RURAL/REMOTE: A survey of organic chemicals contained in the ambient air of New Bedford, MA was taken on Sept 3, and 6, 1982(1). 2-Chloronaphthalene was not detected(1). Thirty-four polynuclear aromatic hydrocarbons, including 2-chloronaphthalene, were measured in ambient air samples around the Great Lakes between January and November 1990; however, 2-chloronaphthalene was not detected(2).
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. Their main uses have been in cable insulation, wood preservation, engine oil additives, electroplating masking compounds, capacitors and refractive index testing oils and as a feedstock for dye production. 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. A single study on chlorinated tap water revealed 0.44 ng monochloronaphthalene/l. 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. Monochloronaphthalenes appear to be readily degradable by soil and water microorganisms under aerobic conditions. Chlorinated naphthalene concn in fish range up to a maximum of around 300 ug/kg lipid weight. 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. 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. 1-Monochloronaphthalene was not mutagenic in the Salmonella Ames test. 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. /Chlorinated naphthalenes, Monochloronaphthalenes/
LD50 Mouse oral 886 mg/kg|LD50 Rat oral 2078 mg/kg
/AQUATIC SPECIES/ Results from bioassays ... show that the monochloro-isomer is more acutely toxic than the octachloro-isomer for a freshwater plant, a freshwater invertebrate species, a freshwater vertebrate species, and a saltwater species. /Monochloronaphthalene/
Lab experiments have shown that chloronaphthalenes may be formed from naphthalenes (an observed aquatic pollutant) under conditions similar to those used to disinfect drinking water and waste water. This observation has led to the speculation that treatment activities may be a continuing source of chloronaphthalenes in the environment. /Chloronaphthalenes/|Leachate from hazardous waste sites can release 2-chloronaphthalene to ground and surface waters(1). Pyrolysis of vinylidene chloride polymer, which is used as wrapping material, may release 2-chloronaphthalene to the atmosphere(2). Municipal waste incinerators can emit 2-chloronaphthalene to ambient air(3). 2-Chloronaphthalene may be formed as a product of chlorination during water treatment(4) and therefore, it may be released in cooling water discharges and to drinking water supplies(SRC).|2-Chloronaphthalene's past production and use along with other monochloronaphthalenes for chemical-resistant gauge fluids and as heat-exchange fluids, color dispersions, engine crackcase additives to dissolve sludges and gums, and ingredients in motor tune-up compounds(1), may have resulted in its release to the environment through various waste streams(SRC). The sole U.S. producer ceased manufacturing chloronaphthalene products in 1977(2). 2-Chloronaphthalene may also be released to the environment via effluents from gaseous diffusion facilities(3).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3000(SRC), determined from a structure estimation method(2), indicates that 2-chloronaphthalene is expected to have slight mobility in soil(SRC). Volatilization of 2-chloronaphthalene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 0.00032 atm-cu m/mole(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 2-Chloronaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0122 mm Hg(4). Biodegradation half-lives were 59 and 79 days for 2-chloronaphthalene contained in a mixture of oil sludge that was added to soil columns along with nitrogen and phosphorus(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3000(SRC), determined from a structure estimation method(2), indicates that 2-chloronaphthalene 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 0.00032 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.2 hours and 6.1 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). The estimated volatilization half-life from a model pond is 38 days if adsorption is considered(7). According to a classification scheme(5), a BCF of 4300(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). A number of aerobic biological screening studies, which utilized settled waste water, sewage, or activated sludge for inocula, have demonstrated that 2-chloronaphthalene should biodegrade slowly in aquatic systems(8-11). The hydrolysis of 2-chloronaphthalene is not environmentally important(12). The neutral rate constant for the hydrolysis of 2-chloronaphthalene in water at 25 °C is 9.5X10-6, which corresponds to a half-life of 8.3 years(12).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-chloronaphthalene, which has a vapor pressure of 0.0122 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-chloronaphthalene 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 2.1 days(SRC), calculated from its rate constant of 1.5X10-11 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). 2-Chloronaphthalene 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 2-chloronaphthalene with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.1 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Chloronaphthalene absorbs light with wavelengths >290 nm(2), and may be susceptible to direct photolysis by sunlight(SRC).|The hydrolysis of 2-chloronaphthalene is not environmentally important(1). The neutral rate constant for the hydrolysis of 2-chloronaphthalene in water at 25 °C is 9.5X10-6 hr-1, which corresponds to a half-life of 8.3 years(1). Data regarding direct photolysis of 2-chloronaphthalene in air or water were not located in the available literature. 2-Chloronaphthalene does absorb UV light in the environmentally relevant range (greater than 290 nm) with lambda max in methanol of 307 and 321 nm(2). Therefore, 2-chloronaphthalene has the potential to undergo photolysis in the environment. The rate constant for the vapor-phase reaction of 2-chloronaphthalene with photochemically produced hydroxyl radicals has been estimated to be 1.65X10-11 cu cm/molecule-sec at 25 °C; which corresponds to an atmospheric half-life of about 23 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(3).
4.27e+03|After 7 days exposure to water concn ranging from about 100 to 750 ug/l, the bioconcentration factor of 2-chloronaphthalene in the tissue of one year old, female guppies (Poecillia reticulata) was 4300(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-chloronaphthalene can be estimated to be 3,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-chloronaphthalene is expected to have slight mobility in soil.
The Henry's Law constant for 2-chloronaphthalene is 0.00032 atm-cu m/mole(1). This Henry's Law constant indicates that 2-chloronaphthalene is expected to volatilize from water surfaces(2). 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)(2) is estimated as 7.2 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)(2) is estimated as 6.1 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 38 days if adsorption is considered(4). 2-Chloronaphthlene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, adsorption to soil is expected to attenuate volatilization(SRC). 2-Chloronaphthalene is not expected to volatilize from dry soil surfaces(SRC), based upon a vapor pressure of 0.0122 mm Hg(3) 2-Chloronaphthalene was found to disappear from two soils, Captina silt loam and McLaurin sandy loam, adjusted to 80% water holding capacity, with a half-life of 11.3 days(5). For 2-chloronaphthalene it was found that soil type and condition (sterile, nonsterile) had no significant effect on the disappearance rate(5).
GROUNDWATER: Groundwater samples from nearby the Hooker Chemical and Plastics Corp disposal site at Love Canal, NY contained 2-chloronaphthalene(1). 2-Chloronaphthalene was not detected in well water collected September 1980 from well water samples in Bristol, Rhode Island(2). Groundwater monitoring data (1981-1986) from 500 disposal site investigations in the United States were evaluated to determine the frequency of certain contaminates(3). The frequency of detection of 2-chloronaphthalene in groundwater in EPA region 6 was 1.4 and 2-chloronaphthalene was not detected in the other seven regions tested(3). 2-Chloronaphthalene was found in groundwater and soil/sediments samples from 91 waste sites at 18 U.S. Department of Energy (DOE) facilities with a frequency of <3(4). Maximum concentrations of 2-chloronaphthalene were reported as below the detection limit in three groundwater collected September 1983, September 1984, and March 1986 from the Lipari landfill in Mantua Township, Gloucester County New Jersey, respectively(5). Maximum concentrations were reported as <200, <40, and <50 ppb for the September 1983, September 1984, and March 1986 samples(5).|DRINKING WATER: 2-Chloronaphthalene was listed as a contaminant found in drinking water for a survey of US cities including Pomona, Escondido, Lake Tahoe and Orange Co, CA and Dallas, Washington, DC, Cincinnati, Philadelphia, Miami, New Orleans, Ottumwa, IA, and Seattle(1). For all samples taken from 11 water utilities of the Ohio River Valley, 2-chloronaphthalene was detected in 4 of 150 raw water extracts and 30 of 120 finished drinking water extracts, suggesting that 2-chloronaphthalene is formed as a product of chlorination during water treatment(2).|SURFACE WATER: According to the EPA's STORET database, 863 sampling stations reported that unspecified isomers of chloronaphthalene were present in ambient waters, of which 1.4% contained detectable levels of the chemical with a median concentration of less than 10.0 ug/l(2). 2-Chloronaphthalene is listed as a contaminant of Great Lakes Ontario and Erie(1). In July 1977 to June 1978, 2 of 18 raw water samples of Beaver River water at Beaver Falls, PA contained 2-chloronaphthalene at mean and maximum concn of 0.2 ug/l(3). 2-Chloronaphthalene was detected at <2 ug/l in the Potomac River at Quantico, Virginia, spring 1986(4).|RAIN/SNOW/FOG: Rain water from four storms during March to April 1982 at the Oregon Graduate Center about 12 km northwest of Portland, OR and that of 5 events in southeastern Portland did not contain 2-chloronaphthalene(1). Snow pack from 20 sampling plots in the city of St Marie, Canada contained 2-chloronaphthalene at concn less than 0.050 ug/l(2).
Occupational exposure to 2-chloronaphthalene may have occurred through inhalation and dermal contact with this compound at workplaces where 2-chloronaphthalene was produced or used. Monitoring data indicate that the general population may be exposed to 2-chloronaphthalene via inhalation of ambient air, ingestion of food and drinking water. (SRC)
Drug Information
In pigs 10 min after retrocarotid admin of 1-chloronaphthalene the blood concn was 5.1 ug/g & decreased with time. After admin of 2-chloronaphthalene, the concn was similar to 1-chloronaphthalene. Its metabolite, 3-chloro-naphthol, was detected in blood. 6-hr after admin of the chlorinated naphthalenes, they were found in the brain, kidney, liver, lung, skeletal muscle, heart & fat with highest concn in brain & kidney. Fat concn of 2-chloronaphthalene was low (0.6 ug/g). Chloronaphthalenes are distributed in various organs & tissues whereas metabolites were concentrated in urine, bile, kidney & liver.|Chloronaphthalenes can be absorbed through the skin, lung, and gut, and tend to deposit in fat depots. Accumulation occurs in pilosebaceous acini and adipose tissue and to a lesser degree in brain, kidney and other body tissues. Excretion occurs predominantly in urinary metabolites as well as in bile. /Chloronaphthalenes/|From studies on the metabolism of PCNs, it can be concluded that mono and dichloronaphthalenes (>80-90%) and tetrachloronaphthalenes (>45%) are well absorbed by the gastrointestinal tract. Higher chlorinated PCNs are less well absorbed, presumably very poorly absorbed ... .
2-chloronaphthalene in corn oil was admin by retrocarotid injection in pigs. Analysis of urine samples showed presence of monohydroxy compd, identified as 3-chloro-2-naphthol.|Yields (+)-trans-7-chloro-1,2-dihydro-1,2-dihydroxynaphthalene in pseudomonas. /from table/|Most of the metabolites identified in urine and/or feces of rats, pigs, and frogs after treatment with monochloronaphthalenes were hydroxylated PCNs (phenolic and conjugated forms), with evidence for metabolism via arene oxide.
... Possible impurities of ... /chloronaphthalenes/ ... may include biphenyls, fluorenes, pyrenes, anthracenes and dibenzofurans. /Chloronaphthalenes/
SYMPTOMS: Symptoms of chronic exposure to this class of compounds include chloracne, cysts, headache, fatigue, vertigo, anorexia and jaundice. ACUTE/CHRONIC HAZARDS: This compound is a strong irritant. It may be absorbed through the skin. When heated to decomposition it emits toxic fumes of chlorides. (NTP, 1992)
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)
Fresh air, rest. Seek medical attention if you feel unwell.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
Rinse with plenty of water (remove contact lenses if easily possible).
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Naphthalene and Related Compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Start an IV with lactated Ringer's. Adequate hydration must be maintained to prevent renal failure secondary to myoglobinuria unless signs of cerebral or pulmonary edema are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Naphthalene and related compounds/|Maintain an open air way and assist ventilation if necessary. Treat coma and seizures if they occur. Treat hemolysis and resulting hemoglobinuria if they occur by intravenous hydration and urinary alkalinization. There is no specific antidote. Administer activated charcoal if available. Do not induce vomiting, because of the risk of lethargy and seizures. Do not administer milk, fats or oils, which may enhance absorption /Naphthalene/
/HUMAN EXPOSURE STUDIES/ When cmpd...used in poorly ventilated areas & especially when heat is applied ...there may be significant systemic absorption of toxic vapors. Target organ is primarily the liver. Cases of fatal acute yellow atrophy /of the liver/ have been reported. /chlorinated naphthalenes/|/HUMAN EXPOSURE STUDIES/ Chlorinated...naphthalenes are potent inducers of chloracne which may develop after wk or mo of cutaneous exposure & commonly appears first lateral to eyebrows, on chin, cheeks, forehead, chest, abdomen, thighs, or buttocks. ... The lesions are primarily papules & yellowish cysts surrounded by mild erythema. ... Pruritis is common. /chlorinated naphthalenes/|/HUMAN EXPOSURE STUDIES/ ...Chloronaphthalenes have photosensitizing action on skin. /Chloronaphthalenes/|/SIGNS AND SYMPTOMS/ Systemic poisoning /from chloronaphthalenes/ has been reported after absorption through vapor inhalation, with digestive disturbances, irritation of eyes, impotence & hematuria. /chloronaphthalenes/|/SIGNS AND SYMPTOMS/ Symptoms of poisoning may include headache, fatigue, vertigo and anorexia. Jaundice may /also result/ from liver damage. /Chloronaphthalenes/
2-chloronaphthalene
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Cough.
Redness.
Redness.
2-Chloronaphthalene Use and Manufacturing
REACTION OF 2-NAPHTHOL WITH PHOSPHORUS PENTACHLORIDE.|PREPD FROM BETA-NAPHTHYLAMINE BY DIAZOTIZATION & SANDMEYER COPPER CHLORIDE REACTION... BY CHLORINATION OF GASEOUS NAPHTHALENE @ 530 °C IN PRESENCE OF IODINE, APPROX 50% OF PRODUCT BEING 1-CHLORONAPHTHALENE WHICH IS SEPARATED BY FRACTIONAL FREEZING.
Chlorinated naphthalenes were formerly used in the production of electric condensers, insulating electric condensers, electric cables, and wires; additive for high pressure lubricants.
(1975) NOT PRODUCED COMMERCIALLY IN USA|(1977) NOT PRODUCED COMMERCIALLY IN USA
Naphthalene, 2-chloro-: 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.|1-chloronaphthalene & 2-chloronaphthalene are major components of Halowax 1031.
Method: EPA-EAD 1625, Semivolatile Organic Compounds by Isotope Dilution GC/MS; Analyte: 2-Chloronaphthalene; Matrix: Water; Detection Level: 10 ug/l.|Method: EPA-OSW 8270D, Semivolatile Organic Compounds by GC/MS; Analyte: 2-Chloronaphthalene; Matrix: Solid waste matrices, soils, air sampling media and water samples; Detection Level: 10 ug/l.|Method: DOE, OM100R, Semivolatile Organic Compounds in Multimedia Samples by Capillary Column Ion Trap MS; Analyte: 2-Chloronaphthalene; Matrix: Solid waste matrices, soils and groundwater; Detection Level: 43 ug/l.|Method: EPA-NERL 625, Base/Neutrals and Acids; Analyte: 2-Chloronaphthalene; Matrix: Water; Detection Level: 1.9 ug/l.|For more Analytic Laboratory Methods (Complete) data for 2-CHLORONAPHTHALENE (6 total), please visit the HSDB record page.
Computed Properties
Molecular Weight:162.61
XLogP3:4.1
Exact Mass:162.0236279
Monoisotopic Mass:162.0236279
Heavy Atom Count:11
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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