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1,2,3,4-Tetrachloronaphthalene

HCID 29910
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
1335-88-2
Standard-SMILES
Clc1c(Cl)c(Cl)c2ccccc2c1Cl
InChIKey
NAQWICRLNQSPPW-UHFFFAOYSA-N
Summenformel
C10H4Cl4
Durchschnittliche Molmasse
265,9 g/mol
Monoisotopische Masse
263,906711

Überblick

Tetrachloronaphthalene is a colorless to pale-yellow solid with an intense aromatic odor. Melting Point :182 C. Presents an environmental danger. Used in lubricants and in the manufacture of insulation for electrical wire. 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 tetrachloronaphthalene in its various isomers together with (mainly) trichloro- pentachloro- and hexa-chloronapthalenes in their various isomers.

Namen und Bezeichner

Bevorzugter Name
1,2,3,4-Tetrachloronaphthalene
IUPAC
1,2,3,4-tetrachloronaphthalene
Englischer Name
1,2,3,4-Tetrachloronaphthalene
Summenformel
C10H4Cl4
Molmasse
265.95

Namen und Synonyme

1,2,3,4-TETRACHLORONAPHTHALENE20020-02-4Naphthalene, 1,2,3,4-tetrachloro-CCRIS 5937HSDB 4283Napthalene, 1,2,3,4-tetrachloro-NSC 524443UNII-365DE4737QAI3-26504365DE4737QNSC-524443DTXSID5026095
Weitere Namen anzeigen
PCN-271,2,3,4- tetrachloroTetrachloronapthalene.Naphthalene,1,2,3,4-tetrachloro-1,2,3,4-Tetrachloronaphthalene in toluene1,2,3,4-Tetrachloronaphthalene in isooctane1,2,3,4-Tetrachloronaphthalene 100 μg/mL in Nonane1,2,3,4-Tetrachloronaphthalene 10 μg/mL in Isooctane1,2,3,4-Tetrachloronaphthalene 100 μg/mL in Cyclohexane
TETRACHLORONAPHTHALENE, 1,2,3,4-1,2,3,4-TETRACHLORONAPHTHALENE [HSDB]RefChem:71291DTXCID306095Naphthalene, 1,2,3,4tetrachloro1,2,3,4-TETRACHLORONAPTHALENE622-398-0InChI=1/C10H4Cl4/c11-7-5-3-1-2-4-6(5)8(12)10(14)9(7)13/h1-4

Datenbank-Bezeichner

CAS
1335-88-2、20020-02-4

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,7
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
14
Formalladung
0
Komplexität
186

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Halowaxes

Other Classes -> Halowaxes

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 4 Einträge

log Kow = 5.86 (average of 6 isomers)

log Kow= 5.95

5.75-6.19

5.75

OdorAromatic odor
Density · 5 Einträge

1.59 to 1.65 (NIOSH, 2024)

1.59 to 1.65 (water= 1)

1.6 g/cm³

1.59-1.65

1.59-1.65

Color/FormColorless to pale yellow solid
Solubility · 6 Einträge

Insoluble (NIOSH, 2024)

less than 1 mg/mL at 63.5 °F (NTP, 1992)

In water, 0.0056 mg/l @ 25 °C (average of 6 isomers)

In water, 0.00426 mg/l @ 25 °C

Solubility in water: none

Insoluble

Flash Point · 6 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

Gefahrenhinweise

Regulatory Information · 3 Einträge

Hazard Traits - Bioaccumulation; Environmental Persistence

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

Substance: 1,2,3,4-TETRACHLORONAPHTHALENE

Fire Hazards · 2 Einträge

The flash point of this compound has not been determined, but it is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health Hazards · 2 Einträge

Excerpt from NIOSH Pocket Guide for Tetrachloronaphthalene:

SYMPTOMS: Exposure to this chemical may cause acneform dermatitis, headache, fatigue, anorexia and vertigo. It may also cause jaundice and other symptoms of liver failure.

Hazards Summary · 2 Einträge

Chlorinated naphthalenes may be absorbed through the skin. They cause liver injury and hyperkeratosis in experimental animals. Penta- and hexachloronaphthalene may cause in exposed workers acne-like lesions that itch severely. Tri-, tetra-, and octachloronaphthalene are non-acnegenic under the conditions of industrial use. Nine occupational fatalities from chlorinated naphthalene poisoning have been reported. Most cases of intoxication among cable workers, assemblers, and laborers involve either penta- or hexachloronaphthalene. A nonfatal case of toxic hepatitis was reported in an 18 year old female who was soldering electrical condensers. [ACGIH] Acne-form dermatitis is listed as an adverse effect for all of the halowaxes except trichloronaphthalene in the NIOSH Pocket Guide. May cause liver injury; [ICSC]

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

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/

Metabolism/Metabolites · 3 Einträge

Tetrachloronaphthalene undergoes oxidn & conjugation in rabbits. Metabolites are glucuronic acids, acid sulfates & mercapturates. /from table/

When rats were given a single oral dose of 1 g of tetrachloronaphthalene, 45% was recovered in the urine in the next four days. The compound was partly metabolized into sulfate (4%), mercapturic acid (3%), and glucuronic acid (38%). The rest of the dose was not accounted for.

When administered to pig, 1,2,3,4-tetrachloronaphthalene gave phenolic metabolites - 5,6,7,8-tetrachloro-naphthol and 5,6,7,8-tetrachloro-2-naphthol.

Absorption, Distribution and Excretion · 2 Einträge

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 ... .

After chronic oral administration of 1,2,3,4-tetrachloronaphthalene with food to rats, accum in adipose tissue. Concentrations in blood and adipose tissue reached max in first 3 wk and reached equilibrium value within 5 wk.

Verwendung und Herstellung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
29910
DTXSID
DTXSID5026095
UNII
365DE4737Q
EC Number
215-642-9、622-398-0
Nikkaji
J94.938H

410 °F (NIOSH, 2024)

210 °C

210 °C (Open Cup)

210 °C o.c.

410 °F (open cup)

(oc) 410 °F

Boiling Point · 5 Einträge

599 to 680 °F at 760 mmHg (NIOSH, 2024)

311.5 to 360 °C

312-360 °C

599-680 °F

599-680 °F

DecompositionWhen heated to decomposition it emits highly toxic fumes of /hydrogen chloride/.
Melting Point · 6 Einträge

360 °F (NIOSH, 2024)

360 °F (NTP, 1992)

115 °C

199 °C

182 °C

360 °F

Vapor Density · 2 Einträge

9.2 (Air= 1 at bp of tetrachloronaphthalene)

Relative vapor density (air = 1): 9.2

Physikochemische Eigenschaften

Schmelzpunkt
196 °C · 196°C
Siedepunkt
362.3 · 362.3±37.0 °C(Predicted)
Dichte
1.552 · 1.552±0.06 g/cm3(Predicted)
Flammpunkt
-18 °C · -18 °C
storage temp.
2 · 2-8°C
Henry's Law Constant
4.1 · 4.1×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Stabilität
Stable. Incompatible with strong oxidizing agents.
EPA chemische Informationen
1 · 1,2,3,4-Tetrachloronaphthalene (20020-02-4)

Exposure to this chemical may cause acneiform dermatitis, headache, fatigue, anorexia and vertigo. It may also cause jaundice and other symptoms of liver failure. [HSDB] Toxic by inhalation, ingestion, and skin absorption; Strongly irritating; [CAMEO] An eye irritant; [MSDSonline] See CHLORINATED NAPHTHALENES.

Reactive Group · 2 Einträge

Aryl Halides

Aryl Halides

TSCA Requirements · 1 Eintrag

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. Tetrachloronaphthalene is included on this list.

OSHA StandardsPermissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 2 mg/cu m. Skin Designation.
Reactivity Profile · 2 Einträge

TETRACHLORONAPHTHALENE is non-flammable, but combustible. Gives off irritating or toxic gases in a fire. Incompatible with strong oxidizing agents. Reacts violently with aluminum, with bases, and with liquid O2.

Simple aromatic halogenated organic compounds, such as 1,2,3,4-TETRACHLORONAPHTHALENE, are very unreactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Chemical DangersDecomposes on burning. This produces toxic gases of hydrogen chloride and phosgene. Reacts with strong oxidants. This generates fire and explosion hazard.
Flammable LimitsCombustible Solid
Air and Water Reactions · 2 Einträge

No rapid reaction with air. No rapid reaction with water.

Insoluble in water.

Toxic Combustion Products · 2 Einträge

Toxic gases and vapors (such as hydrogen chloride, phosgene, and carbon monoxide) may be released in a fire involving tetrachloronaphthalene.

Toxic gases and vapors (such as hydrogen chloride, phosgene, and carbon monoxide) may be released in a fire involving tetrachloronaphthalene.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4 Einträge

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.

Rinse mouth. Rest. Refer for medical attention .

First Aid · 3 Einträge

Excerpt from NIOSH Pocket Guide for Tetrachloronaphthalene:

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.

(General first aid procedures)

Safe StorageSeparated from strong oxidants and food and feedstuffs. Keep in a well-ventilated room.
Exposure Control and Personal Protection · 2 Einträge

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Fire Fighting Procedures · 2 Einträge

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.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher.

Storage Conditions · 2 Einträge

Materials which are toxic as stored or which decompose into toxic components due to contact with heat ... should be stored in cool, well-ventilated place, out of direct rays of sun, away from areas of high fire hazard, and ... periodically inspected and monitored.

This material should be stored in a refrigerator.

Cleanup Methods · 2 Einträge

If you spill this chemical, dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tigh plastic bag for eventual disposal. Solvent-wash all contaminated surfaces wit toluene followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

1. Ventilate area of spill. 2. Collect spilled material in the most convenient and safe manner for reclamation or for disposal in a secured sanitary landfill. Liquids containing tetrachloronaphthalene should be absorbed in vermiculite, dry sand, earth, or a similar material.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a strong 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.

Disposal Methods · 5 Einträge

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))

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.

You should dispose of all waste and contaminated materials associated with this chemical as specified by existing local, state and federal regulations concerning hazardous waste disposal. It is suggested that your contaminated materials should be destroyed by incineration in a special, high temperature ( >2000 degrees F), chemical incinerator facility.

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))

Spillage Disposal · 1 Eintrag

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 sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder.

Preventive Measures · 6 Einträge

If employees' clothing may have become contaminated with solid tetrachloronaphthalene, employees should change into uncontaminated clothing before leaving the work premises.

Clothing contaminated with tetrachloronaphthalene should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of tetrachloronaphthalene from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the tetrachloronaphthalene, the person performing the operation should be informed of tetrachloronaphthalene's hazardous properties.

Non-impervious clothing which becomes contaminated with molten tetrachloronaphthalene should be removed immediately and not reworn until the tetrachloronaphthalene is removed from the clothing.

Employees should be provided with and required to use impervious clothing, gloves, face shields (eight-inch minimum), and other appropriate protective clothing necessary to: prevent any possibility of skin contact with molten tetrachloronaphthalene; prevent repeated or prolonged skin contact with solid tetrachloronaphthalene or liquids containing tetrachloronaphthalene; or prevent skin contact with tetrachloronaphthalene fumes from heated material.

For more Preventive Measures (Complete) data for TETRACHLORONAPHTHALENE (10 total), please visit the HSDB record page.

CONDENSER IMPREGNATION & OTHER OPERATIONS INVOLVING MELTING OF CHLORONAPHTHALENE SHOULD BE ENCLOSED OR PROVIDED WITH EFFECTIVE LOCAL EXHAUST VENTILATION. /CHLORONAPHTHALENES/

Toxikologische Informationen

Target OrgansLiver, skin, central nervous system
Ecotoxicity Values · 2 Einträge

LC50 Shrimp 69-90 ug/l water Tri/Tetrachloronapthalene mixture for 4 days /Tri-Tetrachloronaphthalene/

LC50 Shrimp 74 ug/l Tetra/penta mixture for 4 days /Tetra-Pentachloronaphthalenes/

Environmental Fate · 6 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 13,700(SRC), determined from a structure estimation method(2), indicates that tetrachloronaphthalene is expected to be immobile in soil(SRC). Volatilization of tetrachloronaphthalene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3); however, adsorption may attenuate this process(SRC). Tetrachloronaphthalene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-5 mm Hg(SRC), determined from a fragment constant method(4). No data were located regarding the biodegradation of tetrachloronaphthalene in soil, but it has been reported that higher polychlorinated naphthalenes such as tetrachloronaphthalene are slow to biodegrade(5,6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 13,700(SRC), determined from a structure estimation method(2), indicates that tetrachloronaphthalene 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 1.6X10-4 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 7 hours and 9 days, respectively if adsorption is ignored(SRC). The volatilization half-life from a model pond is 9 months if adsorption is considered(5). According to a classification scheme(6), BCF values measured in fish of 5,100-33,000(7,8) suggests bioconcentration in aquatic organisms is very high(SRC). Halogenated aromatics are generally resistant to aqueous environmental hydrolysis(3); therefore, tetrachloronaphthalene is not expected to hydrolyze in water(SRC). No data were located regarding the biodegradation of tetrachloronaphthalene in water, but it has been reported that higher polychlorinated naphthalenes such as tetrachloronaphthalene are slow to biodegrade(9,10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetrachloronaphthalene, which has an estimated vapor pressure of 4.8X10-5 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 tetrachloronaphthalene 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 35 days(SRC), calculated from its rate constant of 9.1X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase tetrachloronaphthalene may be removed from the air by wet and dry deposition(SRC). Naphthalene and structurally related chemicals absorb light greater than 290 nm and are susceptible to photolysis(4); however the rate of this potential reaction is not known for tetrachloronaphthalene(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 14,000(SRC), determined from a structure estimation method(2), indicates that 1,2,3,4-tetrachloronaphthalene is expected to be immobile in soil(SRC). Volatilization of 1,2,3,4-tetrachloronaphthlene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.38X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 2.9X10-6 mm Hg(4), and water solubility, 0.00426 mg/l(5). However, adsorption to soil is expected to attenuate volatilization(SRC). 1,2,3,4-Tetrachloronaphthalene is not expected to volatilize from dry soil surfaces(SRC), based upon a vapor pressure of 2.9X10-6 mm Hg(4). 1,2,3,4-Tetrachloronaphthalene's chemical structure suggests that it will not biodegrade quickly, because of the large number of aromatic chloride substituents(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 14,000(SRC), determined from a structure estimation method(2), indicates that 1,2,3,4-tetrachloronaphthalene 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 0.000238 atm-cu m/mole(SRC), derived from its vapor pressure 2.9X10-6 mm Hg(4), and water solubility, 0.00426 mg/l(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 11 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(SRC). The estimated volatilization half-life from a model pond is 11 years if adsorption is considered(9). According to a classification scheme(6), BCF values in the range of 5,100(7) to 33,000(5), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). 1,2,3,4-Tetrachloronaphthalene's highly chlorinated chemical structure suggests that it will not biodegrade quickly(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2,3,4-tetrachloronaphthalene, which has a vapor pressure of 2.9X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases. Vapor-phase 1,2,3,4-tetrachloronaphthalene 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 35 days(SRC), calculated from its rate constant of 9.1X10-13 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Particulate-phase 1,2,3,4-tetrachloronaphthalene may be removed from the air by wet and dry deposition(SRC). 1,2,3,4-Tetrachloronaphthalene may absorb light with wavelengths >290 nm, and may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Primary hepatotoxins: the toxic effect to the liver is the principal adverse effect of the chemical.
Exposure Routes · 2 Einträge

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

Toxicity Summary · 2 Einträge

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. There are no known commercial uses for purified tetrachloronaphthalenes. 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 cogeners in out door air were tri- and tetrachloronaphthalene. 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. 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. 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, Tetrachloronaphthalenes and higher Chlorinated Naphthalenes/

Animal Concentrations · 3 Einträge

Tetrachloronaphthalene was detected in rabbit and reindeer from Sweden at a concns of 1.4 and 0.19 ng/g, respectively(1). Tetrachloronaphthalene was detected in seals and osprey at concns of 0.016 and 13 ng/g, respectively(1). Tetrachloronaphthalene was identified as a constituent of the total polychlorinated naphthalene concentration in herring gulls and herring gull eggs near Lake Huron and Lake Superior(2).

A chlor-alkali plant that is located in southeastern coastal Georgia, near Brunswick, GA, and operated from 1955 to 1994, disposed of its process wastes into large holding pits near the top of the marsh and directly into the marsh and tidal creek(1). The concentration of 1,2,3,4- and 1,2,3,6-tetrachloronaphthalene combined in a composite muscle tissue sample of two boat-tailed grackle (Quiscalus major) collected in August 1995 in Purvis Creek, 1-2 km from a Chlor-Alkali facility were <3 pg/g wet weight(1). The concentration of 1,2,3,4- and 1,2,3,6-tetrachloronaphthalene combined in a composite heptopancreases tissue sample of blue crabs (Callinectes sapidus) collected in March 1997 in the same location was 45 pg/g wet weight(1). Combined 1,2,3,4-, 1,2,3,7-, and 1,2,6,7-tetrachloronaphthalene concentrations were 31 (male), 29 (male), 50 (female), and 57 (female) pg/g lipid weight for the four porpoise blubber samples collected in the southern part of the Baltic Sea between 1991 and 1993(2). Breast muscle, liver, and adipose tissue samples from five white-tailed sea eagles (Haliaeetus albicilla) found dead in 1991-1992 in north- and southwestern Poland were analyzed for polychlorinated naphthalenes(3). Concentrations of 1,2,3,4-, 1,2,3,7-, and 1,2,6,7-tetrachloronaphthalene (pg/g lipid weight) combined ranged from 210 to 740 in muscle tissue, 260 to 1100 in liver tissue, and 520 to 580 in adipose tissue(3). Three black cormorants (Phalacrocorax carbo sinensis) originating from the colony near Katy Rybackie on the south coast of the Gulf of Gdansk, Baltic Sea were collected in 1992 and analyzed for polychlorinated naphthalenes(4). Concentrations of 1,2,3,4-, 1,2,3,7-, and 1,2,6,7-tetrachloronaphthalene combined in muscle and liver were 0.18, 0.13, and 0.029, and 0.25, 0.25, and 0.24 ng/g lipid weight, respectively(4). Polychlorinated naphthalenes were analyzed in blubber, nuchal fat, liver, muscle, kidney, and brain of three male harbor porpoises (Phocoena phocoena) from the west coast of Sweden(5). Mean concentrations of 1,2,3,4- and 1,2,3,6-tetrachloronaphthalene combined in blubber samples taken from six anatomical sites ranged from 2.9 to 9.8 pg/g wet weight(5). Mean concentrations of 1,2,3,4- and 1,2,3,6-tetrachloronaphthalene combined in nuchal fat, liver, kidney, muscle, and brain were 2.5, 3.9, 1.0, 1.1, and 0.66 pg/g wet weight, respectively(5).

A chlor-alkali plant that is located in southeastern coastal Georgia, near Brunswick, GA, and operated from 1955 to 1994, disposed of its process wastes into large holding pits near the top of the marsh and directly into the marsh and tidal creek(1). The concentration of 1,2,3,4- and 1,2,3,6-tetrachloronaphthalene combined in a composite muscle tissue sample of two boat-tailed grackle (Quiscalus major) collected in August 1995 in Purvis Creek, 1-2 km from a Chlor-Alkali facility were <3 pg/g wet weight(1). The concentration of 1,2,3,4- and 1,2,3,6-tetrachloronaphthalene combined in a composite heptopancreases tissue sample of blue crabs (Callinectes sapidus) collected in March 1997 in the same location was 45 pg/g wet weight(1). Combined 1,2,3,4-, 1,2,3,7-, and 1,2,6,7-tetrachloronaphthalene concentrations were 31 (male), 29 (male), 50 (female), and 57 (female) pg/g lipid weight for the four porpoise blubber samples collected in the southern part of the Baltic Sea between 1991 and 1993(2). Breast muscle, liver, and adipose tissue samples from five white-tailed sea eagles (Haliaeetus albicilla) found dead in 1991-1992 in north- and southwestern Poland were analyzed for polychlorinated naphthalenes(3). Concentrations of 1,2,3,4-, 1,2,3,7-, and 1,2,6,7-tetrachloronaphthalene (pg/g lipid weight) combined ranged from 210 to 740 in muscle tissue, 260 to 1100 in liver tissue, and 520 to 580 in adipose tissue(3). Three black cormorants (Phalacrocorax carbo sinensis) originating from the colony near Katy Rybackie on the south coast of the Gulf of Gdansk, Baltic Sea were collected in 1992 and analyzed for polychlorinated naphthalenes(4). Concentrations of 1,2,3,4-, 1,2,3,7-, and 1,2,6,7-tetrachloronaphthalene combined in muscle and liver were 0.18, 0.13, and 0.029, and 0.25, 0.25, and 0.24 ng/g lipid weight, respectively(4). Polychlorinated naphthalenes were analyzed in blubber, nuchal fat, liver, muscle, kidney, and brain of three male harbor porpoises (Phocoena phocoena) from the west coast of Sweden(5). Mean concentrations of 1,2,3,4- and 1,2,3,6-tetrachloronaphthalene combined in blubber samples taken from six anatomical sites ranged from 2.9 to 9.8 pg/g wet weight(5). Mean concentrations of 1,2,3,4- and 1,2,3,6-tetrachloronaphthalene combined in nuchal fat, liver, kidney, muscle, and brain were 2.5, 3.9, 1.0, 1.1, and 0.66 pg/g wet weight, respectively(5).

Signs and Symptoms · 4 Einträge

Redness.

Redness. Pain.

Abdominal pain. Headache. Nausea. Vomiting.

Acne-form dermatitis; headache, lassitude (weakness, exhaustion), anorexia, dizziness; jaundice, liver injury

Effluent Concentrations1,2,3,4-Tetrachloronaphthalene was found in air-dried fly ash from a municipal incinerator(1).
ICSC Environmental DataBioaccumulation of this chemical may occur in fish. It is strongly advised not to let the chemical enter into the environment. The substance may cause long-term effects in the aquatic environment.
Soil Adsorption/Mobility · 2 Einträge

Using a structure estimation method based on molecular connectivity indices(1), the Koc for tetrachloronaphthalene can be estimated to be 13,700(SRC). According to a classification scheme(2), this estimated Koc value suggests that tetrachloronaphthalene is expected to be immobile in soil(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1,2,3,4-tetrachloronaphthlene can be estimated to be 14,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,2,3,4-tetrachloronaphthalene is expected to be immobile in soil.

Natural Pollution SourcesPolychlorinated naphthalenes do not occur naturally in the environment(1).

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

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. Tetrachloronaphthalene is included on this list.

Clean Water Act Requirements · 2 Einträge

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Chlorinated Naphthalene/

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Chlorinated Naphthalene/

Sicherheitsdaten

ridadr
UN 1145 3/PG 2
risk_code
11-38-50/53-65-67-20
hazard_code
Xi,N,Xn,F
safety_code
60-61-62-33-25-16-9
hazard_class
IRRITANT
Giftige Stoffe Daten
20020-02-4(Hazardous Substances Data)
Uses · 6 Einträge

There are no known commercial uses for purified individual isomers of di-, tri-, tetra-, penta-, hexa-, or heptachloronaphthalene. [HSDB]

No known commercial uses for purified tetrachloronaphthalenes; [HSDB] See CHLORINATED NAPHTHALENES.

Not manufactured in the US since 1977; No longer used in capacitors or electric cable coverings; Largely discontinued as lubricants; No longer used as wood preservatives in the US; [HSDB]

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/

Tetrachloronaphthalene is used in electrical insulating materials, as a component of resins or polymers for coating or impregnating textiles, wood and paper, and as an additive in cutting oils.

U.S. Production · 4 Einträge

... Exact yearly or total production figures are obscure. In 1972, the estimated market for PCNs was less than 2300 metric tons. /Polychlorinated naphthalenes/

(1977) MORE THAN 2.3X10+6 G-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/

Methods of Manufacturing · 3 Einträge

PARTIAL CHLORINATION OF NAPHTHALENE IN PRESENCE OF FERRIC OR ANTIMONY CHLORIDE CATALYST.

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

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

Formulations/PreparationsThere 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. /Chlorinated naphthalenes/
General Manufacturing Information · 6 Einträge

Naphthalene, tetrachloro-: ACTIVE

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 waxes, 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/

Koppers Co, Inc., the sole U.S. producer, ceased manufacturing their chloronaphthalene products (Halowax) in 1977.

Polychlorinated naphthalenes are halogenated aromatic hydrocarbons that are no longer produced.

Anwendungen · 1 Eintrag

Verwenden1,2,3,4-Tetrachloronaphthalene is a standard for environmental testing and research. Substance for the studies on the pollutant concentration in the placenta: Unborn children are exposed to environmental pollutants via placenta, and there is causal relationship between maternal intake of pollutants and fetal exposure

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

2-Chlornaphthalin

Anbieter1 Anbieter

DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]

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. There are no known commercial uses for purified tetrachloronaphthalenes. 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 cogeners in out door air were tri- and tetrachloronaphthalene. 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. 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. 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, Tetrachloronaphthalenes and higher Chlorinated Naphthalenes/