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Home > Encyclopedia > Trichloronaphthalene

Trichloronaphthalene

Trichloronaphthalene structure

Trichloronaphthalene 

structure
  • CAS No:

    1321-65-9

  • Formula:

    C10H5Cl3

  • Chemical Name:

    Trichloronaphthalene

  • Synonyms:

    Naphthalene,trichloro-;Trichloronaphthalene

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The chlorinated naphthalenes in which one or more hydrogen atoms have been replaced by chlorine to form wax-like substances, beginning with monochloronaphthalene and going on to the octachlor derivatives.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


Trichloronaphthalene is a colorless to pale-yellow solid with an aromatic odor. mp: 93°C; bp: 304-354°C. Used in lubricants and in the manufacture of insulation for electrical wire. Presents an environmental danger. If released into the environment, bioaccumulation takes place in fish. Will persist in the environment causing long-term adverse effects. The halowaxes are technical-grade chlorinated naphthalenes containing trichloronaphthalene in its various isomers together with (mainly) tetrachloro-, pentachloro-, and hexa-chloronapthalenes in their various isomers.|COLOURLESS-TO-YELLOW SOLID IN VARIOUS FORMS WITH CHARACTERISTIC ODOUR.|Colorless to pale-yellow solid with an aromatic odor.


Trichloronaphthalene is a colorless to pale-yellow solid with an aromatic odor. mp: 93°C; bp: 304-354°C. Used in lubricants and in the manufacture of insulation for electrical wire. Presents an environmental danger. If released into the environment, bioaccumulation takes place in fish. Will persist in the environment causing long-term adverse effects. The halowaxes are technical-grade chlorinated naphthalenes containing trichloronaphthalene in its various isomers together with (mainly) tetrachloro-, pentachloro-, and hexa-chloronapthalenes in their various isomers.

Trichloronaphthalene Basic Attributes

231.5057

229.94600

215-321-3

0962

2811

DTXSID80198454

Colorless to pale-yellow solid.

Characteristics

4.80000

1.58 g/cm3

93 °C

304-354 °C

228.5ºC

1.6030 (estimate)

Insoluble (NIOSH, 2016)|Water solubility: 0.017-0.064 mg/l at 25 °C /Trichloronaphthalene isomers/|Solubility in water: none|Insoluble

2.00e-05 mmHg

8.0 (Air= 1 at boiling point of trichloronaphthalene)|Relative vapor density (air = 1): 8

Aromatic odor

No rapid reaction with air No rapid reaction with water

Aryl Halides

TRICHLORONAPHTHALENE is non-flammable, but combustible. Gives off irritating or toxic gases in a fire. Incompatible with strong oxidizing agents. Reacts violently with liquid oxygen. Also can react violently with aluminum and with bases.

Combustible Solid

Safety Information

UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

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))

Incompatibilities: Contact with strong oxidizing agents may cause fires and explosions.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P301+P312, P314, P330, and P501|P260, P264, P270, P301+P312, P305+P351+P338, P314, P330, P332+P313, P337+P313, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

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. 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)|/Persons/ should be provided with and required to use impervious clothing, gloves, faceshields (eight inch minimum) and other appropriate clothing to prevent skin contact with liquid or molten trichloronaphthalene or its fumes.|... 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 TRICHLORONAPHTHALENE (7 total), please visit the HSDB record page.|(See protection codes)

Extinguishant: Foam, carbon dioxide, dry chemical. Also wear a self-contained breathing apparatus (SCBA) with a full facepiece operated in the pressure demand or other positive pressure mode.

Sweep spilled substance into containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. Do not let this chemical enter the environment.|1. Remove all ignition sources. 2. Ventilate area of spill. 3. For small quantities, sweep onto paper or other flammable material, place in an appropriate container, and burn in a safe place, such as a fume hood.

Clothing contaminated with trichloronaphthalene should be removed immediately and placed in closed containers until it can be discarded or until provision is made for the removal of trichloronaphthalene from the clothing.|Employees who handle trichloronaphthalene should wash their hands throughly with soap or mild detergent and water before eating, smoking, or using toilet facilities.|CONDENSER IMPREGNATION & OTHER OPERATIONS INVOLVING MELTING OF CHLORONAPHTHALENE SHOULD BE ENCLOSED OR PROVIDED WITH EFFECTIVE LOCAL EXHAUST VENTILATION. /CHLORONAPHTHALENES/|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|For more Preventive Measures (Complete) data for TRICHLORONAPHTHALENE (9 total), please visit the HSDB record page.

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 5 mg/cu m. Skin Designation.

Recommended Exposure Limit: 10 Hr Time-Weighted avg: 5 mg/cu m; skin.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from strong oxidants and food and feedstuffs.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

The substance is mildly irritating to the eyes and skin.

The substance may have effects on the liver. This may result in liver impairment.

NO open flames.

PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles.

Trichloronaphthalene was detected in 1 of 3 sediment samples from sites adjacent to hazardous waste disposal areas in Niagara Falls, NY, 1979, at a concn of 6 ppm(1).

Toxicity

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. Predominant cogners in out door air were tri- and tetrachloronaphthalenes. Recent monitoring studies 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. 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. Longterm 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. Tetra- and pentachloronaphthalene congeners tend to predominate in the biota. /Chlorinated naphthalenes, Higher Chlorinated Naphthalenes/

/BIRDS and MAMMALS/ Effects of a German wood preservative were studied in heifers. Two calves were placed in a shed built with treated wood and compared with heifers kept in an untreated building. A blanket holding preservative treated material was kept in place on the animal's back for 9 months. Seven calves were fed the wood preservative or active fractions isolated from it. Plasma vitamin-A concentrations were determined. Gas chromatography was also used on fractions of the preservative to determine composition. Contact exposures with the wood and blanket produced definite skin lesions in 3 weeks. The harmful action spread beyond the area covered by the blanket. Despite skin lesions, the animals remained in good condition. Calves fed the wood preservative or active fractions showed all symptoms and lesions of hyperkeratosis. Lacrimation, depression, and emaciation were manifested in 3-6 weeks. Plasma vitamin-A concentrations were consistently lower in animals kept in the shed built of treated wood, but no severe deficiency was seen in these animals or in the animals which wore the treated blanket. However, the calves fed small amounts of preservative suffered severe vitamin-A deficiency and marked internal lesions. Gas chromatographic determination showed the active fraction to contain trichloronaphthalene and some more highly chlorinated naphthalenes. ...|/AQUATIC SPECIES/ This substance may be hazardous to the environment; special attention should be given to crustacea. 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. The substance may cause long-term effects in the aquatic environment.

Polychlorinated naphthalenes do not occur naturally in the environment(1).

The investigators reported the detection of a large number of polychlorinated polynuclear aromatics, incl chlorinated naphthalenes, in flue gas samples from two coal-fired boilers and one municipal incinerator. ... Trichloronaphthalene was some of the major polychlorinated polynuclear aromatics cmpd emitted from the tested boilers.|Trichloronaphthalene consists of 14 individual isomers that may have been released to the environment through various waste streams when it was used in lubricants and in insulation for electrical wire. U.S. demand for chloronaphthalenes has declined steadily; manufacturing of chloronaphthalene products ceased in 1977(2).|Trichloronaphthalene was detected in the pyrolysis of polyvinylidene at concns of 4.56-306 ug/g(1). Trichloronaphthalene was identified in the soot of combusted dichlorobenzene-containing products(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8100(SRC), determined from a structure estimation method(2), indicates that trichloronaphthalene is expected to be immobile in soil(SRC). Volatilization of trichloronaphthalene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil may attenuate this process. Trichloronaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.1X10-4 mm Hg(SRC), determined from a fragment constant method(4). Monochloronaphthalenes appear to be readily degradeable by soil and water microorganisms under aerobic conditions(5). No information was found on the biodegradation of higher chlorinated congeners by microorganisms(5); however, the addition of chlorines to aromatic structures is known to decrease biodegradability(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8100(SRC), determined from a structure estimation method(2), indicates that trichloronaphthalene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.1X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hours and 8 days, respectively(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 141 days if adsorption is considered (5). According to a classification scheme(6), a measured BCF value of 27,000 for 1,3,7,-trichloronaphthalene in guppies(7), suggests bioconcentration in aquatic organisms is very high(SRC). Halogenated aromatics are generally resistant to aqueous environmental hydrolysis(3); therefore, trichloronaphthalene is not expected to hydrolyze in water(SRC). Monochloronaphthalenes appear to be readily degradeable by soil and water microorganisms under aerobic conditions(8). No information was found on the biodegradation of higher chlorinated congeners by microorganisms(8); however, the addition of chlorines to aromatic structures is known to decrease biodegradability(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trichloronaphthalene, which has an estimated vapor pressure of 3.1X10-4 mm Hg at 25 °C (SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase trichloronaphthalene 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 8 days(SRC), calculated from its rate constant of 2X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase trichloronaphthalene may be removed from the air by wet and dry deposition(SRC). Naphthalene and its derivatives absorb light in the environmental UV spectrum and may be susceptible to direct photolysis(4). However, the rate of this reaction is not known for trichloronaphthalene(SRC).

The rate constant for the vapor-phase reaction of trichloronaphthalene with photochemically-produced hydroxyl radicals has been estimated as 2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Halogenated aromatics are generally resistant to aqueous environmental hydrolysis(2); therefore, trichloronaphthalene is not expected to hydrolyze in water(SRC). Naphthalene and its derivatives absorb light in the environmental UV spectrum and are susceptible to direct photolysis(3). However, the rate of this reaction is not known for trichloronaphthalene(SRC).

Estimated BCF values of 7,300-10,900 were calculated for trichloronaphthalene(SRC), using log Kow values in the range of 5.12-5.35(1) and a regression-derived equation(2). The bioconcentration factor of 1,3,7,-trichloronaphthalene in guppies was reported as 27,000 in a flow through experiment(3). According to a classification scheme(4), these BCF values suggest 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 trichloronaphthalene can be estimated to be 8100(SRC). According to a classification scheme(2), this estimated Koc value suggests that trichloronaphthalene is expected to be immobile in soil(SRC).

The Henry's Law constant for trichloronaphthalene is estimated as 3.1X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trichloronaphthalene 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 5 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 8 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 141 days if adsorption is considered (3). Trichloronaphthalene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur, however adsorption may also attenuate this process(SRC). Trichloronaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.1X10-4 mm Hg(SRC), determined from a fragment constant method(4).

SURFACE WATER: Trichloronaphthalene was identified, not quantified, in Lake Ontario(1).

Occupational exposure to trichloronaphthalene may have occured through inhalation and dermal contact with this compound at workplaces where trichloronaphthalene was produced or used. (SRC)

Drug Information

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: Anorexia, nausea; dizziness; jaundice, liver injury Target Organs: Liver (NIOSH, 2016)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, wash the contaminated skin with soap and water. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


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

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/|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/ While some cases of chloracne have been reported, incidence & severity have been less when trichloronaphthalene was only material used than when penta- or hexachloronaphthalene was present.|/HUMAN EXPOSURE STUDIES/ Industrial experience with trichloronaphthalene (usually mixed with some tetrachloronaphthalene) has been favorable in comparison with the more highly chlorinated naphthalenes. ... Studies with human voluteers showed that the mist of trichloronaphthalene was entirely nonacneigenic as compared to that observed after exposure to the penta and hexachloro-derivatives, which produced severe chloroacne.|/HUMAN EXPOSURE STUDIES/ Until 1957 there was general agreement that as degree of chlorination incr so did acneigenic properties & systemic toxicity of the chloronaphthalenes. According to ... result of ... expt on human volunteers, the unexpected fact emerged that whereas tri-, tetra-, hepta-, & octachloronaphthalenes were entirely nonacneigenic, penta- & hexachloro derivatives produced very severe chloracne indeed.|/HUMAN EXPOSURE STUDIES/ Skin conditions resulting from exposure to certain chlorinated hydrocarbons were studied in electrical condenser employees. The 31 workers examined in two facilities that used a combination of trichloronaphthalene (1321659) and tetrachloronaphthalene (1335882) in the manufacture of condensers were all employed in the finishing departments. Exposure to the chlorinated naphthalenes resulted in acneform eruptions, characterized by pustules, papules, and comedones. Eruptions usually occurred within the first few months of employment. Incidence of acneform eruptions appeared to be higher in summer than in winter. Acneform eruptions differed from acne commonly found among adolescents. One case of permanent facial disfigurement in a young girl involved the deeper layers of skin. In severe cases, there was a tendency to secondary infection, especially when there was coexisting pruritus and if the worker scratched the lesions. In one case, furunculosis of the cheek, superimposed on a severe acneform eruption, resulted in death from septicemia. ...|For more Human Toxicity Excerpts (Complete) data for TRICHLORONAPHTHALENE (6 total), please visit the HSDB record page.

The substance can be absorbed into the body by inhalation of fume and through the skin.|inhalation, skin absorption, ingestion, skin and/or eye contact

anorexia, nausea; dizziness; jaundice, liver injury


Redness.


Redness. Pain.

Liver

Trichloronaphthalene Use and Manufacturing

Methods of Manufacturing

Polychlorinated naphthalenes (PCNs) ... can be synthesized by the chlorination of naphthalene. /Polychlorinated naphthalenes/

Uses

Wire coating, electrical insulations.

Production

(1977) MORE THAN 2.3X10+6 CHLORONAPHTHALENES|(1979) NOT PRODUCED COMMERCIALLY IN THE USA|... Exact yearly or total production figures are obscure. In 1972, the estimated market for PCNs was less than 2300 metric tons. /Polychlorinated naphthalenes/

Naphthalene, trichloro-: 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/

SAMPLES WERE ANALYZED BY QUADRUPLE GC/MS/COMPUTER IN MULTIPLE ION DETECTION MODE.|Method: NIOSH S128: Analyte: Trichloronaphthalene; Matrix: Air; Procedure: Gas chromatography; Range: 1.647 to 8.79 mg/cu m.|Chloronaphthalenes are analyzed by GLC, HPLC, and TLC. /Chloronaphthalenes/|EPA Method 8120. Gas Chromatographic Method with an electron capture detector for the detection of ppb levels of certain chlorinated hydrocarbons including chlorinated naphthalene, not otherwise specified. in solid waste using the solvent flush technique. Under the prescribed conditions for chlorinated naphthalene, not otherwise specified the method detection limit is not given. Prcision and method accuracy were found to be directly related to the concentration of the parameter and essentially independent of the sample matrix. /Chlorinated naphthalene, not otherwise specified/|EPA Method 8250. Packed Column Gas Chromatography/Mass Spectrometry Technique for the determination of semivolatile organic compounds in extracts prepared from all types of solid waste matrices, soil, and groundwater. 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, chlorinated naphthalene, not otherwise specified, detection limit not given. Precision and method accuracy were found to be directly related to the concentration of the analyte and essentially independent of the sample matrix. /Chlorinated naphthalene, not otherwise specified/

Computed Properties

Molecular Weight:231.5
XLogP3:5.1
Exact Mass:229.945683
Monoisotopic Mass:229.945683
Heavy Atom Count:13
Complexity:183
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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