Hexachloronaphthalene

334.826

331.82900

215-641-3

0997

DTXSID60872604

White solid|White to yellow solid.

0

6.76020

Hexachloronaphthalene is a white solid with an aromatic odor. (NTP, 1992)

1.78 g/cm³

137 °C

344-388 °C

199.6ºC

1.676

Solubility in water: none

Storage and handling: ... Materials...which can decompose into toxic components due to contact with heat ... acids, or acid fumes, should be stored in cool, well-ventilated place, out of direct rays of sun, away from ... Fire hazard, and should be periodically inspected and monitored. Incompatible materials ... isolated from each other.

<1 mm

Relative vapour density (air = 1): 11.6

Aromatic odor.

Henry's Law constant = 8.7X10-5 atm-cu m/mol @ 25 °C /Estimated/

Flame resistant and have high dielectric constants. Their high degree of chemical stability is indicated by their resistance to most acids and alkalies as well as to dehydrochlorination. They are also resistant to attack by fungi and insects. /Chloronaphthalenes/|Hydroxyl radical reaction rate constant = 1.8X10-13 cu cm/molec-sec @ 25 °C /Estimated/|10 possible isomers

Insoluble in water.

Aryl Halides

HEXACHLORONAPHTHALENE is generally unreactive. May be incompatible with strong oxidizing and reducing agents. May be incompatible with some amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Noncombustible Solid

QJ7350000

Separated from strong oxidants and food and feedstuffs.

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))

Hexachloronaphthalene reacts with strong oxidizing agents.|Strong oxidizers.

Literature sources indicate that this compound is nonflammable. (NTP, 1992)|Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]|P260, P264, P270, P314, and P501|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P260, P264, P270, P280, P302+P352, P305+P351+P338, P314, P321, P332+P313, P337+P313, P362, and P501

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 store this material in a refrigerator. (NTP, 1992)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. (NIOSH, 2016)|/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 hexachloronaphthalene or its fumes.|Employes should be provided with and required to use splash-proof safety goggles where there is any possibility of molten Halowax 1014, /solid Halowax 1014 or liquids containing Halowax 1014/ contacting the eyes.|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 HEXACHLORONAPHTHALENE (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.

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.|Collect spilled material in the most convenient and safe manner for reclamation or disposal... . Liquids containing hexachloronaphthalene should be absorbed in vermiculite, dry sand, or a similar material.

Clothing contaminated with hexachloronaphthalene should be removed immediately and placed in closed containers until it can be discarded or until provision is made for the removal of hexachloronaphthalene from the clothing.|/Hexachloronaphthalene/ can effect the body if it is inhaled, comes in contact with the eyes or skin, or is swallowed. Every effort should be made to prevent skin, eye, oral, or inhalation contact with this material.|Eating and smoking should not be permitted in areas where /hexachloronaphthalene/ is handled, processed, or stored.|Workers subject to skin contact with /hexachloronaphthalene/ should wash with soap or mild detergent and water any areas of the body which may have contacted /hexachloronaphthalene/ at the end of each work day.|For more Preventive Measures (Complete) data for HEXACHLORONAPHTHALENE (12 total), please visit the HSDB record page.

This compound is highly toxic by inhalation. It is a strong irritant... /to/ the skin.

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 0.2 mg/cu m. Skin Designation.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 0.2 mg/cu m, skin.

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

Separated from strong oxidants and food and feedstuffs.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.

The substance is irritating to the eyes and skin.

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

PREVENT DISPERSION OF DUST! STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Hexachloronaphthalene was qualitatively detected in stack gas emissions and fly ash from municipal waste incinerators(1-3).

SEDIMENT: Hexachloronaphthalene concns of 30-250 ng/kg were detected in surface sediments collected from 10 lakes in central Finland in 1988(1); sediments from eight other lakes had no detectable levels (detection limit not reported) of hexachloronaphthalene(1). The compound was detected in sediments collected in 1995 from 5 sites selected in the Venice Lagoon, Italy (pg/g, use characteristic): Giudeca Island - 17.20, heavy boat traffic and sewage; Peelestrina - 4.24, undeveloped; Chioggia Harbor - 7.46, harbor activity; Porto Marghera - 102.93, chemical and oil refining plants; and Dese River - 9.45, agricultural impact(2). Water exchange is with the Adriatic Sea(2). Hexachloronaphthalene was also detected in sediments collected in 1995 from 4 sites selected in the Orbetallo Lagoon, Italy, which drains to the Mediterranean Sea(2). Concentrations were as follows (pg/g, use characteristic): Santa Liberata - 5.63, connecting channel; Orbetello - 67.78, sewage treatment plant; fish farm station - 0.90; and Albegua River - 2.13, undeveloped(2). Hexachloronaphthalene was detected in sediment samples from the River Eman, River Dalalven, River Gota and Lake Vanern, Sweden at concns ranging from not detected (detection limit not specified) to 37 ng/g dry weight(3).

Near point sources, concentrations in ... /air/ ... can range as high as 2.9 ug/cu m.|SOURCE DOMINATED: Hexachloronaphthalene was detected in six of eight sampling sites around a resource recovery facility at Augsburg, Germany between June 1992 and February 1993, prior to startup, with concns ranging from 0.033 to 0.47 fg/cu m for the filter and from 0.22 to 0.41 fg/cu m for the XAD cartridge samplers(1).

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 impregnates 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. 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 concentration 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 concentration up to 150 pg/cu m at semi-rural sites and 1-40 pg/cu m at remote sites. Chlorinated naphthalenes can be absorbed via oral, inhalative and dermal routes, with absorption and distribution over the whole body after oral administration. Chlorinated naphthalenes, especially the dioxin like congeners, have been detected in adipose tissue, liver, blood and breast milk samples from the general population at concentration 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. The polychlorinated naphthalenes congener/isomer pattern found in human samples was significantly different from the commercial polychlorinated naphthalenes mixtures. Two dominating congeners were 1,2,3,5,7/1,2,5,6,7-hexachloronapthalene. Analyses of human tissue samples and fluids confirmed the high retention potency of the 1,2,3,4,6,7-/1,2,3,5,6,7-hexachloronaphthalene isomers. Chlorinated naphthalenes can be absorbed via oral, inhalative and dermal routes, with absorption and distribution over the e badministeredoy after oral admin. The main target organs are the liver and fat tissue (besides the kidney and lung) showing a high retention, especially for the higher chlorinated congeners The amount of bioaccumulation observed incr with the degree of chlorination of the chlorinated naphthalenes. Elimination of the parent compounds and/or metabolites occurs via feces and urine. Lower chlorinated naphthalenes are less toxic than the higher chlorinated naphthalenes. Long term and carcinogenicity studies with chlorinated naphthalenes have not been performed. Like related cmpd, chlorinated naphthalenes have been demonstrated to be inducers of the cytochrome p450 (CYP) dependent microsomal enzymes. 1,2,3,4,6,7-Hexachloronaphthalene has been found to accelerate the onset of spermatogenesis in male offspring of rats. Cattle developed severe hyperkeratosis during a 5 to 10 day oral exposure of purified hexachloronaphthalenes. Hexachlorinated naphthalenes showed hyperkeratoic activity in the rabbit ear test and in hairless mice. Rats fed a mixture of penta/hexachloronaphthalenes dosed on alternate days for 26 days showed moderate liver changes (swollen and vacoulated liver cells, as well as necrosis and degeneration of scattered cells.Inhalation of a mixture containing penta-/hexachloronaphthalenes resulted in slight histological liver damage in rats. 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. Two hexa-isomers , which are minor components of Halowax 1014 were given single oral doses of Halowax 1014 or a mixture of hexachloronaphthalenes (consisting of equal amounts of 1,2,3,5,6,7-hexachloronaphthalene and 1,2,3,4,6,7-hexachloronaphthalene and a third unidentified hexachloronapthalene) One day after exposure the polychlorinated naphthalene patadministeredtn adipose tissue of animals admin Halowax 1014 was similar to that of the technical product. In 10 days the two hexa-isomers were dominant and after 120 days, they were the only cogeners detected, their concn beings still above 50% of the measured after day 1. In liver samples this selective retention lasted 1 day. Rats dosed with the hexachloronaphthalene mixture showed a strong similar retention of the 1,2,3,5,6,7- and 1,2,3,4,6,7-hexachloronaphthalene (the other unidentified hexachloronaphthalene could not be detected. 1,2,3,4,6,7-Hexachloronaphthalene transfer from dam to offspring has been studied in Wistar rats. Concn of this isomer were noted in the fat of female offspring. Short term exposure to higher chlorinated naphthalenes resulted in mortality, liver damage, degeneration of the kidneys etc in rats, rabbits and cattle. Inhalation of a penta/hexachloronaphthalene mixture for 143 days resulted in a slight to moderate histological liver damage in rats. 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, Halowaxes, Higher Chlorinated Naphthalenes/

/BIRDS and MAMMALS/ Black cormorants, Phalacrocorax carbo sinensis (the breast muscles and liver) originating from the colony near Katy Rybackie on the south coast of the Gulf of Gdansk, Baltic Sea, were collected in 1992 and analysed for polychlorinated naphthalenes. PCNs were determined employing a multi-residue procedure including a non-destructive wide-bore open-tube extraction step, cleanup using semipermeable polyethylene membrane, HPLC fractionation of planar compounds on activated carbon column and final separation and identification and quantification with HRGC/HRMS. Tetra- to hepta-CNs were found in all samples examined, and penta- and next tetra-CNs were dominating homologue groups. Dominating members in the fingerprint of PCNs in black cormorants were 1,2,3,5,7-/1,2,4,6,7-P5CN (no. 52/60); 1,2,4,6,8-P5CN (no. 61); 1,2,3,4,6,7-/1,2,3,5,6,7-H6CN (no. 66/67); 1,2,4,6-/1,2,4,7-/1,2,5,7-T4CN (no. 33/34/37); 1,2,4,5,7-P5CN (no. 58); and 1,2,4,7,8-P5CN (no. 62). When related to potential food items, black cormorants biomagnify in their body many PCNs and the congeners no. 42 and 66/67 show highest biomagnification factor (BMF) values.

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

Hexachloronaphthalene has been detected in stack gas emissions and fly ash from municipal incinerators(1-3) which, as such, may result in direct release to the environment(SRC). Technical polychloronaphthalenes have physical and chemical properties similar to those of PCBs and therefore have similar industrial applications such as dielectrics for flame proofing and insulating in energy, electric and automobile industries, preservatives for wood, paper, and textiles, engine additives, heat exchange fluids, casting materials, and electroplating(4). As a class, chloronaphthalenes are considered ubiquitous global pollutants(4). Hexachloronaphthalene reached a concn of 750 ng/g over 4 hours in thermal experiments with model mixtures at 300 °C; Mg-Al-silicate, 4% charcoal, 7% Cl-, 1% CuCl2.H2O(5). U.S. demand for chloronaphthalenes has declined steadily; manufacturing of chloronaphthalene products ceased in 1977(6).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.7X10+4(SRC), determined from a structure estimation method(2), indicates that hexachloronaphthalene is expected to be immobile in soil(SRC). Volatilization of hexachloronaphthalene from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 8.7X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Hexachloronaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.3X10-6 mm Hg(SRC), determined from a fragment constant method(4). According to a UN-ECE POP (United Nations Economic Commission for Europe Persistent Organic Pollutants) criteria, hexachloronaphthalene is classified as being resistant to biodegradation with half-lives in soil being greater than 6 months(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.7X10+4(SRC), determined from a structure estimation method(2), indicates that hexachloronaphthalene 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 8.7X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 17 hrs and 11 days, respectively. 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 5,700 yrs if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 240,000(SRC), from an estimated log Kow of 7.0(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Hexachloronaphthalene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). According to a UN-ECE POP (United Nations Economic Commission for Europe Persistent Organic Pollutants) criteria, hexachloronaphthalene is classified as being resistant to biodegradation with half-lives in water or sediment being great than 6 months(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexachloronaphthalene, which has an estimated vapor pressure of 3.3X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase hexachloronaphthalene 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 86 days(SRC), calculated from its rate constant of 1.8X10-13 cu cm/molecule-sec at 25 °C(3). Particulate-phase hexachloronaphthalene may be removed from the air by wet and dry deposition(SRC). Hexachloronaphthalene is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

The rate constant for the vapor-phase reaction of hexachloronaphthalene with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-13 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 86 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hexachloronaphthalene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

An estimated BCF of 240,000 was calculated for hexachloronaphthalene(SRC), using an estimated log Kow of 7.0(1) and a regression-derived equation(2). According to a classification scheme(3), 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 hexachloronaphthalene can be estimated to be 3.7X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that hexachloronaphthalene is expected to be immobile in soil.

The Henry's Law constant for hexachloronaphthalene is estimated as 8.7X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that hexachloronaphthalene 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 17 hrs 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 11 days(SRC) Hexachloronaphthalene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(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 5,700 yrs if adsorption is considered(3). Hexachloronaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.3X10-6 mm Hg(SRC), determined from a fragment constant method(4).

GROUNDWATER: Hexachloronaphthalene was detected at 8 of 33 groundwater sampling points collected from an aquifer 10 km from the mouth of the Llobregat River near Barcelona, Spain between 1995 and mid-1996 at concentrations ranging from not detected (detection limit <0.1 ng/l) to 330 ng/l(1).

The concentrations of polychlorinated naphthalenes (PCNs) were determined together with polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs), 1,1-bis-(4-chlorophenyl)-2,2,2-trichloroethane (p,p'-DDT), 2,2-bis(4-chlorophenyl)-1,1-dichloroethylene (p,p'-DDE) and hexachlorobenzene (HCB) in milk, sampled in the course of 1972-92 from mothers living in Stockholm. ... The mean recoveries of seven chlorinated naphthalene (CN) congeners added to milk prior to extraction were 76-99%. ... The pattern of PCNs in milk differed to a great extent from that in the commercial PCN products. The dominating congeners in breast milk were 1,2,3,5,7-pentachloronaphthalene (CN-52), 1,2,3,4,6,7- and/or 1,2,3,5,6,7-hexachloronaphthalene (CN-66/ CN-67) and one unidentified tetrachloronaphthalene. There was a notable decrease in the concentrations of PCNs as was of the other organochlorine contaminants in milk from 1972 to 1992. During this time period the sum of CN congeners decreased from 3,081 to 483 pg/g milk fat and the sum of toxic equivalents of dioxin and dioxin-like compounds decreased from 100 to 39 pg/g milk fat.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 520 workers (52 of these are female) are potentially exposed to hexachloronaphthalene in the US(1). Occupational exposure to hexachloronaphthalene occurs through inhalation and dermal contact with this compound at workplaces where hexachloronaphthalene is produced(SRC). Monitoring data indicate that the general population may be exposed to hexachloronaphthalene via dermal contact with contaminated sediments or ingestion of fish products containing hexachloronaphthalene(SRC).

Human adipose tissues obtained during autopsies in Canadian muncipalities within the Great Lakes basin contained hexachloronaphthalene at overall mean concns of 0.43, 1.01, 0.57, 0.82, 0.74, 0.54, 0.86, and 1.04 ng/g fat from Cornwall, Kingston, London, Ottawa, St. Catharines, Toronto (two sample sets), and Windsor, respectively(1).|Significant associations (P < 0.05) between estimated fish intake and blood plasma levels have been found for 1,2,3,4,6,7/1,2,3,5,6,7-hexachloronaphthalene, but not for several other PCNs, including 1,3,5,7-tetrachloronaphthalene, in samples from 37 males selected according to varying intake of fish from the Baltic Sea; occupational exposure to PCNs was not known, but was possible in some cases. The blood plasma concentrations of 1,2,3,4,6,7/1,2,3,5,6,7-hexachloronaphthalene were found to be 2400 (no fish consumption, n = 9), 3800 (moderate fish consumption, n = 14), and 9400 (high fish consumption, n = 14) ng/kg wet weight. /Polychlorinated Naphthalenes/|Analyses of human tissues and fluids confirmed the high retention potency of the 1,2,3,4,6,7/1,2,3,5,6,7-hexachloronaphthalene isomers... Paired samples of liver and adipose tissue from seven subjects showed concentration ratios (on a lipid weight basis) from 0.5 to 20 for these hexa-isomers. The ratio of the sum of PCNs in liver to that in adipose tissue ranged from 0.7 to 10 (median 1.2).

Absorbed by skin.|Rats (Sprague-Dawley, female; n = 12) were given single oral doses of Halowax 1014 (20 mg/kg body weight) or of a mixture (0.053 mg/ kg body weight) of hexachloronaphthalenes (consisting of equal amounts of 1,2,3,5,6,7-hexachloronaphthalene, 1,2,3,4,6,7-hexachloronaphthalene, and a third unidentified hexachloronaphthalene). The hepatic and adipose residue levels were measured 1, 10, 30, and 120 days after dosing. One day after exposure, the PCN pattern in the adipose tissue of the animals administered Halowax 1014 was similar to that of the technical product, but the relative levels of hepta- and octachloronaphthalenes were lower, possibly due to a less effective absorption of these compounds. However, within 10 days, the two hexa-isomers (co-eluting in gas chromatography) were dominant; after 120 days, they were the only congeners detected, their concentrations being still about 50% of that measured after 1 day. In liver samples, this selective retention was seen after only 1 day. Rats dosed with the hexachloronaphthalene mixture also showed a strong, similar retention of the 1,2,3,5,6,7- and 1,2,3,4,6,7-hexachloronaphthalene (the other unidentified hexachloronaphthalene could not be detected). The concentration ratios (based on the total concentrations of the two hexa-isomers) for liver/adipose tissue were found to be remarkably high: 7.3, 1.1, 0.8, and 0.63 at 24 hr and 10, 35, and 120 days, respectively, based on the fresh weights, or 140, 23, 17, and 13, based on the lipid weights.|The transfer of 1,2,3,4,6,7-hexachloronaphthalene from dam to offspring has been studied in Wistar rats orally (gavage) dosed with 1 ug 1,2,3,4,6,7-hexachloronaphthalene/kg body weight per day (in corn oil) on gestation days 14-16. Concentrations of 1,2,3,4,6,7-hexachloronaphthalene in fat of female offspring were 22.18 +/- 6.59 ug/kg (corresponding to 1.5-1.6 ng/pup) at birth (postnatal day 0) and 9.78 +/- 2.86 ug/kg (corresponding to 13-26 ng/pup) at weaning (postnatal day 21), and concentrations in fat of dams were 5.75 +/- 2.81 ug/kg at weaning; 1,2,3,4,6,7-hexachloronaphthalene was not detected in the control.

/In the pig/ 1,2,3,4,5,6-Hexachloronaphthalene was not metabolized.

The half-lives were calculated to be 41 days in the adipose tissue and 26 days in the liver /of rats/.|Human blood samples from three individuals exposed to PCN-contaminated rice oil in 1979 in Taiwan were monitored for the 1,2,3,4,6,7/1,2,3,5,6,7-hexachloronaphthalenes over a period of about 10 years. The measured concentrations resulted in calculated half-lives of 1.5-2.4 years.|Rats (Sprague-Dawley, female; n = 12) were given a mixture (0.053 mg/kg body weight) of hexachloronaphthalenes (consisting of equal amounts of 1,2,3,5,6,7-hexachloronaphthalene, 1,2,3,4,6,7-hexachloronaphthalene, and a third unidentified hexachloronaphthalene)...The half-lives /for the two isomers, 1,2,3,5,6,7-hexachloronaphthalene and 1,2,3,4,6,7-hexachloronaphthalene/ were calculated to be 41 days in the adipose tissue and 26 days in the liver. This order of magnitude is comparable to that reported for slowly eliminated PCDF congeners in experimental animals.

At least some of the biochemical (e.g., drug-metabolizing enzyme induction, hormonal changes) and toxic (e.g., skin disorders, weight loss, hepatotoxicity, reproductive toxicity) responses of PCNs are believed to be mediated via the cytosolic Ah receptor . Due to the lack of sufficient experimental data up to now, PCNs are not included in an internationally agreed toxic equivalency factor (TEF) system, which estimates the overall dioxin-like toxicity of the compound relative to TCDD. However, some congeners, in particular those with a planar structure (four lateral chlorines at 2,3,6,7, i.e., congeners 2,3,6,7-tetrachloronaphthalene, 1,2,3,6,7-pentachloronaphthalene, 1,2,3,4,6,7-hexachloronaphthalene, 1,2,3,5,6,7-hexachloronaphthalene, 1,2,3,6,7,8-hexachloronaphthalene, 1,2,3,4,5,6,7-heptachloronaphthalene, and 1,2,3,4,5,6,7,8-octachloronaphthalene) similar to TCDD, may exert a toxicity comparable to the more toxic PCBs. /Polychlorinated naphthalenes/|Pretreatment of immature male wistar rats with 1,2,3,4,5,6-hexachloronaphthalene resulted in induction of several hepatic microsomal drug-metabolizing enzymes. The enzymic activities, reduced Cytochrome p450:co & ethylisocyanide binding difference spectra & electrophoretic mobilities of induced microsomal proteins were comparable to those observed after admin of the classical inducer of microsomal aryl hydrocarbon hydroxylase, 3-methylcholanthrene. The 1,2,3,4,5,6,7-heptachloronaphthalene congener, which is fully substituted in lateral 2,3,6 & 7 positions, was more potent than the 1,2,3,4,5,6,8-hepta- & the 1,2,3,4,5,6-hexachloronaphthalene congeners which contain only 3 lateral chloro substituents. The effect of structure on induction activities of the polychlorinated naphthalenes were similar to those observed for other halogenated Aryl hydrocarbons.|As observed for other halogenated aryl hydrocarbons, the relative induction potencies of PCNs appear to depend on the degree and position of chlorine substitution of the naphthalene ring ... In several different test systems, the most potent EROD and AHH inducers include 1,2,3,4,6,7/1,2,3,5,6,7-hexachloronaphthalene, 1,2,3,4,5,6,7-heptachloronaphthalene, and some unidentified congeners present in Halowax 1014. Octachloronaphthalene was also found to cause a dose-dependent AHH increase in microsomes of rats.|Of the individual PCN congeners tested, penta-, hexa-, and heptachloronaphthalenes gave full dose- response curves, whereas most of the lower chlorinated congeners as well as octachloronaphthalene were inactive in /the rat hepatoma H4IIE-luc cell (luciferase) assay . The most potent congener was 1,2,3,4,6,7-hexachloronaphthalene . Similar results have been obtained by another study testing individual PCN congeners using the luciferase (and the EROD) assay with recombinant H4IIE rat hepatoma cells. Again, hexa- and heptachloronaphthalenes tested were the most potent congeners, /followed by/ Pentachlorinated congeners .Tetra, tri-, di-, and monochloronaphthalenes were found to be less active. There was also a rank order of potency within the penta- and hexachloronaphthalene isomers, in a manner suggesting that the presence of meta-substituted chlorines is linked to decreased potency. For example, for hexachloronaphthalenes, an approximate ranking order was given as 1,2,3,6,7,8 greater than 1,2,3,4,6,7 greater than 1,2,3,5,6,7 greater than 1,2,3,5,6,8.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Acne-form dermatitis, nausea, confusion, jaundice, coma Target Organs: Skin, liver (NIOSH, 2016)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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: 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. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)

Fresh air, rest.

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

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

Treatment (Vet): Treatment of hyperkeratosis is purely supportive. Antibiotics can be used to prevent bacterial infection. Vit A and C ...admin, along with B-complex vitamins. Corticosteroids may be of some benefit. Skin should be kept as pliable as possible and free from flies and ectoparasites. /Chlorinated naphthalenes/|If a fumigant liquid or solid has been ingested less than several hours prior to treatment, quantities remaining in the stomach must be removed as effectively as possible by gastric intubation, aspiration, and lavage, after all possible precautions have been taken to protect the respiratory tract from aspirated gastric contents. A. Put in place a cuffed endotracheal tube prior to gastric intubation. Administer oxygen, using a mechanical ventilator if respiration is depressed. B. Lavage the stomach with a slurry of activated charcoal in saline or water. Leave a volume of the slurry in the stomach with an appropriate dose of sorbitol as cathartic ... . C. If treatment is delayed and if the patient remains fully alert, administer activated charcoal and sorbitol orally. ... Repeated administration of charcoal at half or more the initial dosage every 2-4 hours may be beneficial. D. Do not give vegetable or animal fats or oils, which enhance gastrointestinal absorption of many of the fumigant compounds. Intravenous infusions of glucose are valuable in limiting the hepatotoxicity of many substances. Monitor central venous pressure to avoid precipitating, or aggravating, pulmonary edema by fluid overload. The victim should be watched closely for indications of delayed or recurrent pulmonary edema, and for bronchopneumonia. Fluid balance should be monitored, and urine sediment should be checked regularly for indications of tubular injury. Measure serum alkaline phosphatase, LDH, ALT, AST, and bilirubin to assess liver injury. Extracorporeal Hemodialysis may be needed to regulate extracellular fluid composition if renal failure supervenes. It is probably not very effective in removing lipophilic fumigant compounds from blood, but is, of course, effective in controlling extracellular fluid composition if renal failure occurs.|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/|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/ Causes severe acne-form eruptions and toxic /necrosis/ of the liver.|/HUMAN EXPOSURE STUDIES/ A quantity of 2 ml of a 3% solution of either Halowax 1014 or hexachloronaphthalene was applied on the skin of six Caucasian and four Negro male volunteers, daily for a minimum of 6 weeks to a maximum of 12 weeks. With both compounds dermal effects developed, from increase in number of epidermal cells (day 5), follicular involvement without erythema (day 10), follicular accentuation (day 14), small comedones (week 3 - 5), to large comedones (week 6 - 12). Pretreatment with vitamin A did not result in any amelioration of the effect.|/HUMAN EXPOSURE STUDIES/ A preliminary report of the dermatological and systemic effects of exposure to hexachloronaphthalene and chlorodiphenyl is presented. Studies were made of 118 workers in a plant who were exposed to the solid, liquid, or vapor state of these contaminants. Of these 78% were affected with dermatitis. A second group with dermatoses was selected to determine the presence of any systemic effect. No direct effects could be established, and blood studies did not reveal any appreciable changes. Dermatitis had a predilection for the face and extensor surfaces of the body.|/HUMAN EXPOSURE STUDIES/ Until 1957 there was general agreement that as the degree of chlorination increased, so did the acneigenic properties and the systemic toxicity of the chloronaphthalenes. ... as a result /of/ ... experiments on human volunteers, the unexpected fact emerged that whereas tri-, tetra-, hepta-, and octachloronaphthalenes were entirely nonacneigenic, the penta- and hexachloro derivatives produced very severe chloracne indeed.|For more Human Toxicity Excerpts (Complete) data for HEXACHLORONAPHTHALENE (9 total), please visit the HSDB record page.

1,2,3,4,5,6-hexachloronaphthalene

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

Acne-form dermatitis, nausea, confusion, jaundice, coma

MAY BE ABSORBED! Redness. Pain.

Redness. Pain.

Skin, liver

U.S. demand for chloronaphthalenes has declined steadily; manufacturing of chloronapthalene products ceased in 1977. /Chloronaphthalenes/

Koppers Co, Inc., the sole U.S. producer, ceased manufacturing their chloronaphthalene products (Halowax) in 1977.|The manufacturing of chlorinated naphthalenes (Halowax) has been discontinued in the USA since 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/

Method: NIOSH Method: S100; Analyte: Hexachloronaphthalene. Matrix: Air. Procedure: GC; Range: 0.104 - 0.459 mg/cu m.|EPA Method 8120. GC Method with an ECD 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. Precision 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 GC/MS 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/