2-Chloronaphthalene

Other Classes -> Halowaxes

Volatile Organic Compound (VOC) and(or) Semi-Volatile Organic Compound (SVOC)

log Kow = 3.90

4.2

4.07

1.1377 at 160 °F (NTP, 1992) - Denser than water; will sink

1.1377 /cu cm at 71 °C

1.18 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

1.1377 @ 71°C

Monoclinic plates, leaflets from dil alcohol

Leaflets from ethanol (aq)

less than 1 mg/mL at 68.9 °F (NTP, 1992)

Sol in alcohol, ether, benzene, chloroform, carbon disulfide

In water, 11.7 mg/l @ 25 °C

Solubility in water, g/100ml: (none)

493 °F at 760 mmHg (NTP, 1992)

256 °C @ 760 mm Hg; 132.6 °C @ 20 mm Hg; 119.7 °C @ 11 mm Hg

at 101kPa: 259 °C

256 °C @760 [mm Hg]

139.1 °F (NTP, 1992)

59.5 deg C

59.5 °C

58 °C

This chemical does not meet GHS hazard criteria for 60% (3 of 5) of all reports.

Warning

H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard Traits - Respiratory Toxicity

SP - indicates a substance that is identified in a proposed Significant New Use Rule.

Substance: 2-chloronaphthalene

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

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.

Symptoms of chronic exposure to this class of compounds include chloracne, cysts, headache, fatigue, vertigo, anorexia and jaundice. This compound is a strong irritant. It may be absorbed through the skin.; [CAMEO] May cause irritation; [MSDSonline] See CHLORINATED NAPHTHALENES.

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.

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).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Naphthalene, 2-chloro- is included on this list.

Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use foam, dry powder, carbon dioxide.

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).

Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.

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.

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.

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.

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.

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.

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/

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).

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/

/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/

Bird eggs of 15 species were collected in the Baikal region (Selenga River estuary) in Russia(1). 2-Chloronaphthalene concentrations in combined egg yoke and white ranged from 232 ug/kg dry weight in the eggs of the tufted duck (Aythya fuligula) to <3 ug/kg dry weight in the eggs of the pochard (Aythya ferina), domestic fowl (Gallus gallus), heron (Ardea cinerea), black headed gull (Larus ridibundus), and liapwing (Vanellus vanellus)(1).

Cough.

Redness.

Redness.

Sore throat. Nausea.

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).

The substance is toxic to aquatic organisms. Bioaccumulation of this chemical may occur in fish. The substance may cause long-term effects in the aquatic environment. It is strongly advised not to let the chemical enter into the environment.

beta-Chloronaphthalene

Hepatic

8 x 10 ^-2 mg/kg-day

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.

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).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Naphthalene, 2-chloro- is included on this list.

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).

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.

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 ... .

Used for chemical resistant gage fluids and instrument seals; as heat exchange fluids; in high-boiling specialty solvents; in color dispersions; as a crank case additive to dissolve sludge and gums; as ingredients in motor tune-up compounds; a component of Halowax 1031; in the production of electric condensers; in the insulation of electric cables and wires; as an additive to extreme pressure lubricants; as supports for storage batteries; as a coating in foundry use; as a solvent; as an immersion liquid in microscopy; as a raw material for dyes; as a wood preservative; Chlorinated naphthalenes have not been manufactured in the US since 1977; [HSDB]

Shakeout, Cleaning, and Finishing [Category: Foundry]

The manufacturing of chlorinated naphthalenes (Halowax) has been discontinued in the USA since 1977.

... Except in special cases, chlorinated naphthalenes are no longer used in capacitors or electric cable coverings. Their use as lubricants has also been largely discontinued. Practice in individual countries varies, however. In the USA, for example, chlorinated naphthalenes are no longer used as wood preservatives. /Chlorinated naphthalenes/ /SRP: Former Use/

Monochloronaphthalenes have been used for chemical resistant gage fluids and instrument seals, as heat exchange fluids, high boiling specialty solvents, color dispersions, as crank case additives to dissolve sludge and gums, and as ingredients in motor tune-up compounds. /SRP: Former Use/

A component of Halowax 1031. /SRP: Former Use/

(1975) NOT PRODUCED COMMERCIALLY IN USA

(1977) NOT PRODUCED COMMERCIALLY IN USA

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.

Naphthalene, 2-chloro-: ACTIVE

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.