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Home > Encyclopedia > Octachlorostyrene

Octachlorostyrene

Octachlorostyrene structure

Octachlorostyrene 

structure
  • CAS No:

    29082-74-4

  • Formula:

    C8Cl8

  • Chemical Name:

    Octachlorostyrene

  • Synonyms:

    Benzene,1,2,3,4,5-pentachloro-6-(1,2,2-trichloroethenyl)-;Benzene,pentachloro(trichloroethenyl)-;Styrene,octachloro-;1,2,3,4,5-Pentachloro-6-(1,2,2-trichloroethenyl)benzene;Perchlorostyrene;Trichlorovinylpentachlorobenzene;Octachlorostyrene;OCS;Octachlorostyrol;1,2,3,4,5-Pentachloro-6-(trichloroethenyl)benzene

  • Categories:

    Analytical Chemistry  >  Standard

Description

Octachlorostyrene (OCS) is a by-product of the normal industrial chemical processes such as PVC recycling activities, Aluminum refining operations, metal-chlorinated solvent degreasing operations and many others. These materials are known to be highly toxic and when released to the environment are extremely persistent.


Octachlorostyrene (OCS) is a by-product of the normal industrial chemical processes such as PVC recycling activities, Aluminum refining operations, metal-chlorinated solvent degreasing operations and many others. These materials are known to be highly toxic and when released to the environment are extremely persistent.


Octachlorostyrene (OCS) is a by-product of the normal industrial chemical processes such as PVC recycling activities, Aluminum refining operations, metal-chlorinated solvent degreasing operations and many others. These materials are known to be highly toxic and when released to the environment are extremely persistent.|Octachlorostyrene is an organochlorine compound.

Octachlorostyrene Basic Attributes

379.71

379.71

304368U4VH

DTXSID2021074

2903999090

Characteristics

0

7.29610

1.799g/cm3

92.5-96.5 °C

411.1ºC at 760 mmHg

2 °C

1.629

APPROX 4°C

LD orl-rat: >3710 mg/kg JTEHD6 10,285,82

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

Hydrocarbons, Aliphatic Unsaturated

Safety Information

UN16483/PG2

3

11-20/21/22-36-50/53

16-26-36-61-60

F,Xn,N

P273-P501

H410

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 41 companies from 2 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]|P260, P264, P270, P273, P314, P391, and P501

Waste water from the sedimentation basin of an aluminum smelt treated with hexachloroethane and chlorine gas contained octachlorostyrene at a concn of 230 ug/l(1). Waste water from the showering device of an aluminum smelt treated with dichloroethane and Freon gas contained octachlorostyrene at a concn of 230 ug/l(1). Waste waters from the chlorination and distillation processes of niobium and tantalum production both contained octachlorostyrene at a concn of 27 ug/l(1). Sewage sludge from the filterpress of an aluminum smelt treated with dichloroethane and Freon gas contained octachlorostyrene at a concn of 560 ug/kg(1). Octachlorostyrene was contained in the sewage sludges of several municipal and industrial plants that discharge their purified loads directly into the Necker River, Germany at concns ranging from 12 to 2500 ug/kg(2).|Two of six sewers from the Dow Chemical plant along the St. Clair River contained octachlorostyrene in their waste water effluents at concns of 0.038 and 0.16 ug/l(1). Treated leachate from the Dow Scott Rd landfill at Sarnia, Canada, Dow Chemical's disposal site for chlorinated tars, contained octachlorostyrene at a concn of 0.21 ug/l(2). Waste water from an Esso refinery contained octachlorostyrene at a concn of 0.002 ug/l(4). Octachlorostyrene was identified as a constituent in the fly ash of waste incinerators(2).

SEDIMENTS: Octachlorostyrene was detected in the bottom sediments of the Bayou d'Inde along the Calcasieu River, LA at a concn of 56.0 ug/g(1). An octachlorostyrene concn of 5.6 ug/g was detected in the suspended sediments of the Bayou d'Inde along the Calcasieu River, LA(1). Bottom sediments of the St. Clair River contained octachlorostyrene at concns ranging from undetected levels to 79.5 ug/kg dry weight with an average 14.8 ug/kg for 21 samples(2). Bottom sediments of the Lake St. Clair contained octachlorostyrene at concn ranging from undetected levels to 79.5 ug/kg dry weight with an average 14.8 ug/kg for 21 samples(2). Bottom sediments of the Detroit River contained octachlorostyrene at concn ranging from undetected levels to 3.5 ug/kg dry weight with an average 1.0 ug/kg for 8 samples(2). Octachlorostyrene was detected in 10 of 13 sediment samples from western Lake Ontario at concn ranging from trace amounts to 49 ppb with an average of 13.6 ppb(3). The concn of octachlorostyrene ranged from 2.5 to 4.1 ng/g dry weight for 6 sediment samples from Lake Ontario near the Niagara River(4).|SEDIMENTS: Suspended particulate matter from the St. Clair River contained octachlorostyrene ranging in concn from 1.1 to 3300 ng/g with an average concn of 448 ng/g for 19 samples(1). Bottom sediments of southern Lake Huron contained octachlorostyrene at concn sranging from 0.02 to 0.1 ng/g dry weight with an average of 0.06 ng/g dry weight for 9 samples(2). Bottom sediments of Lake St. Clair contained octachlorostyrene at concns ranging from 5.1 to 11.0 ng/g dry weight with an average of 8.1 ng/g dry weight for 2 samples(2). Bottom sediments of western Lake Erie contained octachlorostyrene at concns ranging from 0.8 to 5.9 ng/g dry weight with an average of 2.3 ng/g dry weight for 9 samples(2). Bottom sediments of central Lake Erie contained octachlorostyrene at concn ranging from undetectable levels to 0.5 ng/g dry weight with an average of 0.2 ng/g dry weight for 22 samples(2) Bottom sediments of eastern Lake Erie contained octachlorostyrene at concn ranging from undetectable levels to 0.3 ng/g dry weight with an average of 0.2 ng/g dry weight for 15 samples(2). Sediment samples were collected at the head and mouth of the St. Clair River from 1987 to 1989(3). Year to year comparisons showed a substantial reduction in concns of octachlorostyrene in suspended sediments(3). The mean concn of octachlorostyrene in suspended sediment from Port Lambton (at St. Clair River) was 21.1 ng/g (range, 1.18-108.6 ng/g)(3).|A sediment core from the St. Clair River contained octachlorostyrene at concns of 210, 9, 11, 150 and 74 ppb at interval lengths of 0-3, 3-8, 8-13, 13-18 and 18-24 cm, respectively(1). Sediment traps at Lake St. Clair contained octachlorostyrene at an average concn of 3 ng/g for 9 sites, each with 3 samples(2). Surficial sediment at Lake St. Clair contained octachlorostyrene at an average concn of 4 ng/g for 33 samples(2).|SOILS: The concentration of octachlorostyrene in River Elbe (Germany) floodplain soils ranged from 1-696 ug/kg(1).

REMOTE: The mean concn of octachlorosytrene in air samples taken from Egbert, Ontario, Canada from Jul 1988 to Sept 1989 was 0.71 pg/cu m (range, <0.1 (detection limit)-31 pg/cu m; 48 of 143 samples >0.1 pg/cu m)(1).

Toxicity

Octachlorostyrene is not produced commercially for any application(1). In addition to the lower chlorinated styrenes, octachlorostyrene is mainly an accidental by-product of high temperature industrial processes involving chlorine such as the electrolytic production of chlorine gas or magnesium, the refining and degassing of an aluminum smelt, and the chlorination and distillation processes of niobium and tantalum production(1,2). Release of octachlorostyrene into the environment has been shown to occur largely through the waste water effluents of these operations(1-3). Octachlorostyrene has also been released to ground water via leachate from a landfill where chlorinated tars were deposited(4). Waste incinerators can emit fly ash containing octachlorostyrene to the atmosphere(5).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 200,000 to 10,000,000(2), indicates that octachlorostyrene is expected to be immobile in soil(SRC). Volatilization of octachlorostyrene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, volatilization from water surfaces is expected to be attenuated by adsorption to soil(SRC). Octachlorostyrene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-5 mm Hg(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 200,000 to 10,000,000(2), indicates that octachlorostyrene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.3X10-4 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 13 hrs and 10 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 volatilation half-life from a model pond is 670 yrs if adsorption is considered(5). According to a classification scheme(6), BCF values ranging from 8,100 to 1,400,000(7,8), suggests bioconcentration in aquatic organisms is very high(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), octachlorostyrene, which has an estimated vapor pressure of 1.3X10-5 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(SRC). Vapor-phase octachlorostyrene 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 15 days(SRC), calculated from its rate constant of 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase octachlorostyrene may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of octachlorostyrene with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Octachlorostyrene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Octachlorostyrene weakly adsorbs UV light between 295 and 310 nm with slow photolysis(3). Heptachlorostyrene and two isomers of hexachlorostyrene were identified as the major transformation products of photolysis(3). Minor photolytic transformation products include pentachlorostyrene and tetrachlorostyrene(3).

8.13e+03|Fish accumulated ... octachlorostyrene ... in an area polluted by industrial effluents.|In order to compare the degree of accumulation of residues /polychlorinated biphenyls, 1,1-dichloro-2,2-bis(p-chlorophenyl)ethene, 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane, hexachlorobenzene, pentachlorobenzene & octachlorostyrene/ in different animal species from different locations ... the levels of 5 pollutants in the samples of aquatic biota from two locations in the Oslo Fjord area, 1 from the Frierfjord & another from Ora, located at the estuary of the Glomma River /were analyzed/. ... Hexachlorobenzene, pentachlorobenzene & octachlorostyrene were present more often. ... The concn of 1,1-dichloro-2,2-bis(p-chlorophenyl)ethene, polychlorinated biphenyls, & pentachlorobenzene lend support to the idea that direct uptake from water by way of the respiratory organs or the general body surface is the most important route of entry. Feeding habits are also of importance; detritus-feeding brittle star had higher residue levels than the rock dwelling sea star & snail.|A field BCF of 1,400,000 for octachlorostyrene was determined from the average concn contained in the tissues of 10 Lake Ontario rainbow trout (Salmo gairdneri) and the average octachlorostyrene concn in Lake Ontario water(1). However dietary uptake also contributed to this field BCF value(SRC). Experimental BCF values of 8,100 and 33,000 have been reported for octachlorostyrene in rainbow trout (Salmo gairdneri)(1) and fathead minnow (Pimephales promelas), respectively(2). According to a classification scheme(3), these BCFs suggest bioconcentration in aquatic organisms is very high(SRC). The BCF for oligochaetes was 16(4).

The Koc for octachlorostyrene ranges from 200,000 to 10,000,000 for sediments from the St. Clair River(1). According to a classification scheme(2), these Koc values suggest that octachlorostyrene will be immobile in soil(SRC).

The Henry's Law constant for octachlorostyrene is estimated as 2.3X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that octachlorostyrene 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 13 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 10 days(SRC). Octachlorostyrene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from moist soil water surfaces is expected to be attenuated by adsorption(SRC). The estimated volatilization half-life from a model pond is 670 yrs if adsorption is considered(3). Octachlorostyrene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-5 mm Hg(SRC), determined from a fragment constant method(4).

SURFACE WATER: Octachlorostyrene was detected at 9 of 13 sampling stations along the St. Clair River at concns ranging from 1 to 2 ng/l(1). Octachlorostyrene was listed as a contaminant present in the waters of Lakes Ontario, Erie, Huron and St. Clair(2). St. Clair River water contained octachlorostyrene ranging in concns from 0.02 to 7.20 ng/l with an average concn of 1.0 ng/l for 20 samples(3). The average octachlorostyrene concn for 8 offshore water samples from Lake Ontario was 4.6 ng/l(4). Octachlorostyrene was detected in the surface film water of the Frierfjord, S Norway(5). Octachlorostyrene was detected at concns ranging from 0.013 to 0.063 ng/l for 6 of 13 samples from the St. Clair River on Aug 7, 1985(6). Octachlorostyrene was detected at concns ranging from 0.011 to 0.085 ng/l of 7 of 13 samples from the St. Clair River on Aug 27, 1985)(6). Octachlorostyrene was detected at concn ranging from 0.030 to 0.048 ng/l for 3 of 13 samples from St. Clair of Sept 23, 1985(6). Octachlorostyrene was detected at concns ranging from 0.012 to 0.0283 ng/l for 5 of 13 samples from the St. Clair River on Oct 17, 1985(6).

Octachlorostyrene was listed as a contaminant found in the milk of non-occupationally exposed humans(1,2). Human milk (497 samples) representing donors from across Canada were analyzed for octachlorostyrene(3); the mean concn of octachlorostyrene in whole milk and milk fat were 0.05 and 2.16 ng/g, respectively, with a frequency of 7% for the 497 samples(3).

Occupational exposure to octachlorostyrene may occur through inhalation of dust and dermal contact with this compound at workplaces where octachlorostyrene is produced indirectly(SRC). Foundry workers, who use hexachloroethane as a degassing agent for aluminum, are exposed to octachlorostyrene which is formed by complex reactions(2). A greater than 70-fold increase of mean octachlorostyrene in blood was found among exposed subjects compared with controls (control, 0.7 ng/g lipid; exposed, 54.6 ng/g lipid)(2). Monitoring data indicate that the general population may be exposed to octachlorostyrene via ingestion of fish and seafood containing octachlorostyrene(SRC).

Octachlorostyrene was detected in the blood of 136 residents of Schhleswig-Holstein, Germany who ate contaminated fish from the River Elbe at concn ranging from less than 0.5 to 9.2 ng/l with an average of 1.5 ng/l(1). Human adipose tissue of 36 autopsy patients from Windsor and 21 autopsy patients from B Cornwall, Canada were both found to contain octachlorostyrene with an 8% frequency of occurrence(2). Octachlorostyrene was listed as a contaminant found in the adipose tissue and/or milk of non-occupationally exposed humans(3,4). The mean concn of octachlorostyrene in Canadian adipose tissue was 1 ng/g wt wet (N=108; max, 44 ng/g)(5). Human milk (497 samples) representing donors from across Canada were analyzed for octachlorostyrene(6); the mean concn of octachlorostyrene in whole milk and milk fat were 0.05 and 2.16 ng/g , respectively, with a frequency of 7% for the 497 samples(6).

Drug Information

IN RATS, (14)C-OCTACHLOROSTYRENE WAS ABSORBED IN THE GI TRACT AFTER ORAL ADMIN & DISTRIBUTED IN ALL TISSUES EXAMINED. THE HIGHEST CONCN WERE FOUND IN FAT FOLLOWED BY ADRENAL GLANDS, SKIN, & LUNG. DECAY OF RADIOACTIVITY IN THE TISSUES FOLLOWED 1ST-ORDER KINETICS. APPROX 8% OF AN IV DOSE WAS EXCRETED IN FECES DURING 7 DAYS AFTER ADMIN, WHILE NEGLIGIBLE AMOUNTS WERE FOUND IN THE URINE. MORE THAN 90% OF THE RADIOACTIVITY IN FECES WAS DUE TO THE UNCHANGED CMPD, WHILE PENTACHLOROPHENYLDICHLOROACETIC ACID & HEPTACHLOROSTYRENE IN EQUAL PROPORTIONS ACCOUNTED FOR THE REMAINING 10%. A SMALL AMOUNT (1%) OF THE DOSE WAS DETECTED IN EXPIRED AIR AS CARBON DIOXIDE.

MORE THAN 90% OF THE RADIOACTIVITY IN FECES WAS DUE TO THE UNCHANGED CMPD, WHILE PENTACHLOROPHENYLDICHLOROACETIC ACID & HEPTACHLOROSTYRENE IN EQUAL PROPORTIONS ACCOUNTED FOR THE REMAINING 10%. A SMALL AMOUNT (1%) OF THE DOSE WAS DETECTED IN EXPIRED AIR AS CARBON DIOXIDE.

109.65 Days

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/|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 pulmonary edema and treat if necessary ... . Monitor for shock 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 ... . /Aromatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

octachlorostyrene

Octachlorostyrene Use and Manufacturing

Octachlorostyrene was never produced for agricultural or any other application ... clearly has to be regarded as an industrial by-product accidentally formed.|Octachlorostyrene is mainly an accidental by-product of high temperature industrial processes involving chlorine such as the electrolytic production of chlorine gas or magnesium, the refining and degassing of an aluminum smelt, and the chlorination and distillation processes of niobium and tantalum production.

ERLD Method XENO: Analytical Procedures and Quality Assurance Plan for the Determination of Xenobiotic Chemical Contaminants in Fish. Detection limit = 2.5 ppb.

GAS CHROMATOGRAPHIC-MASS SPECTROMETRIC ANALYSIS OF TISSUE EXTRACTS FROM CORMORANTS FOUND DEAD IN THE FIELD, SHOWED PRESENCE OF 3 CHLOROSTYRENE DERIVATIVES, INCLUDING OCTACHLOROSTYRENE. THE TISSUES WERE EXTRACTED WITH PETROLEUM ETHER, & THE EXTRACTS WERE PURIFIED, CONCENTRATED, & ANALYZED. THE EFFLUENT EMERGING FROM THE COLUMN WAS SCANNED CONTINUOUSLY BY TAKING A MASS SPECTRUM EVERY 4 SEC.

Computed Properties

Molecular Weight:379.7
XLogP3:7.4
Rotatable Bond Count:1
Exact Mass:379.744921
Monoisotopic Mass:375.750822
Heavy Atom Count:16
Complexity:270
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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