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hexachloroethane ( CASNO:67-72-1 )

Identification and Related Records
Name:
hexachloroethane
CAS Registry number:
67-72-1
Iupac name:
1,1,1,2,2,2-hexachloroethane
Synonyms:
1,1,1,2,2,2-hexachloroethane
avlothane
distokal
distopan
distopin
carbon hexachloride
egitol
ethane hexachloride
ethylene hexachloride
falkitol
fasciolin
HCE
mottenhexe
perchloroethane
phenohep
EINECS(EC#):
200-666-4
Molecular Formula:
C2Cl6
Molecular Weight:
236.74
Inchi:
InChI=1/C2Cl6/c3-1(4,5)2(6,7)8
Canonical SMILES:
C(C(Cl)(Cl)Cl)(Cl)(Cl)Cl
Chemical and Physical Properties
Appearance:
white crystalline powder
Density:
2.091
Melting Point:
184-190℃
Boiling Point:
186℃
Refractive Index:
1.533
Flash Point:
61.3 °C
Water:
0.05 g/L (22℃)
Solubilities:
0.05 g/L (22 °C) in water
Color/Form:
Colorless crystals
Crystal structure: rhombic 71 deg C
Stability:
Stable. Non-combustible. May react with hot metals, strong oxidizing agents.
Storage temp:
2-8°C
Spectral properties:
SADTLER REF NUMBER: 4546 (IR, PRISM)
IR: 411 (Sadtler Research Laboratories IR Grating Collection)
MASS: 61377 (NIST/EPA/MSDC Mass Spectral database, 1990 version); 716 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Raman: 309 (Sadtler Research Laboratories spectral collection)
Computed Properties:
Molecular Weight:236.7394 [g/mol]
Molecular Formula:C2Cl6
XLogP3:4.1
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:0
Exact Mass:235.810166
MonoIsotopic Mass:233.813116
Topological Polar Surface Area:0
Heavy Atom Count:8
Formal Charge:0
Complexity:61.5
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:1
Safety and Handling
Hazard Codes:
Xn:Harmful
Risk Statements:
R36/37/38;R40;R51/53
Safety Statements:
S26;S36/37/39;S45;S61
HazardClass:
9
Safety:
Confirmed carcinogen with experimental carcinogenic data. A poison by intravenous route. Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Experimental reproductive effects. Mutation data reported. Liver injury has resulted from exposure to this material. An insecticide. Slightly explosive by spontaneous chemical reaction. Dehalogenation of this material by reaction with alkalies, metals, etc., will produce spontaneously explosive chloroacetylenes. When heated to decomposition it emits highly toxic fumes of Cl? and phosgene.?
Hazard Codes:?Xn,?N,?T,?F
Risk Statements: 40-51/53-36/37/38-39/23/24/25-36/38-23/24/25-11?
R40:Limited evidence of a carcinogenic effect.?
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R39/23/24/25:Danger of very serious irreversible effects and Toxic by inhalation, in contact with skin and if swallowed.?
R36/38:Irritating to eyes and skin.?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R12:Extremely flammable.
Safety Statements: 36/37-61-45-36/37/39-26-24-16-7?
S36/37:Wear suitable protective clothing and gloves.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S24:Avoid contact with skin.?
S16:Keep away from sources of ignition.?
S7:Keep container tightly closed.
RIDADR: UN 9037
WGK Germany: 3
RTECS: KI4025000
HazardClass: 9
PackingGroup: III
PackingGroup:
III
Skin, Eye, and Respiratory Irritations:
Mucous membranes, skin, lung, and cornea irritation.
approximatelyIt is irritating to the skin, eyes, mucous membranes, and upper respiratory tract.
Cleanup Methods:
1. Ventilate area of spill; 2. Collect spilled material in the most convenient and safe manner for reclamation or for disposal. ... Liquid containing hexachloroethane should be absorbed in vermiculite, dry sand, earth or a similar material.
Evacuate and restrict persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste.
Transport:
UN 9037
Fire Fighting Procedures:
If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.
Fire Potential:
Not flammable by standard tests in air.
Formulations/Preparations:
Purity: 98.0% minimum
Smoke mixture with US Army designation HC, type C is composed of ca 6.7 wt% grained aluminum, 46.7 wt% zinc oxide, and 46.7 wt% hexachloroethane.
Reactivities and Incompatibilities:
Hexachloroethane was among a number of chemicals studied for vigorous reactions with zinc, cadmium, or mercury.
Alkalis; metals such as zinc, cadmium, aluminum, hot iron and mercury.
Other Preventative Measures:
If materials not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.
Personnel protection: Avoid breathing vapors. If contact with the material anticipated, wear appropriate chemical protective clothing. Avoid breathing fumes from burning material. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Avoid bodily contact with the material.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
If the use of respirators is necessary, the only respirators permitted are those that have been approved by the Mine Safety and Health Administration (formerly Mining Enforcement and Safety Administration) or by the National Institute for Occupational Safety and Health. In addition to respirator selection, a complete respiratory protection program should be instituted which includes regular training, maintenance, inspection, cleaning, and evaluation.
If employees' clothing may have become contaminated with solid hexachloroethane or liquids containing hexachloroethane, employees should change into uncontaminated clothing before leaving the work premises.
Clothing contaminated with solid hexachloroethane or liquids containing hexachloroethane should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of hexachloroethane from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the hexachloroethane, the person performing the operation should be informed of hexachloroethane's hazardous properties. Non-impervious clothing which becomes contaminated with solid hexachloroethane or liquids containing hexachloroethane should be removed immediately and not reworn until the hexachloroethane is removed from the clothing.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers.
Workers subject to skin contact with solid hexachloroethane or liquids containing hexachloroethane should wash with soap or mild detergent and water any areas of the body which may have contacted hexachloroethane at the end of each work day.
Employees who handle solid hexachloroethane or liquids containing hexachloroethane should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities.
Eating and smoking should not be permitted in areas where solid hexachloroethane or liquids containing hexachloroethane is handled, processed, or stored.
The worker should immediately wash the skin when it becomes contaminated.
The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
Protective Equipment and Clothing:
Wear thick working gloves, safety goggles, universal gas mask.
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 solid hexachloroethane or liquids containing hexachloroethane.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Respirator Recommendations: At concentrations above the NIOSH REL, or where there is no REL, at any detectable concentration: Assigned Protection Factor (APF) Respirator Recommendation APF = 10,000 Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. APF = 10,000 Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape conditions: Assigned Protection Factor (APF) Respirator Recommendation APF = 50 Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister/Any appropriate escape-type, self-contained breathing apparatus.
Specification:
?Hexachloroethane , its cas register number is 67-72-1. It also can be called?1,1,1,2,2,2-Hexachloroethane ; Avlothane ; Distokal ; Egitol ; Ethane hexachloride ; Ethane, hexachloro- ; Ethylene hexachloride ; Falkitol ; Hexachlor-aethan ; Mottenhexe ; Perchloroethane ; Phenohep ; Ethane, 1,1,1,2,2,2-hexachloro- .It is a?colorless, crystalline solid with a camphor-like odor.It?may cause illness from inhalation or ingestion and may irritate skin, eyes and mucous membranes. When heated to high temperatures it may emit toxic fumes. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. It?insoluble in water.It?can react with hot iron, zinc and aluminum.
Octanol/Water Partition Coefficient:
log Kow = 4.14
Disposal Methods:
[40 CFR 240-280, 300-306, 702-799 (7/1/2006)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number D034 & U131, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U131, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids.
Chemical Treatability of Hexachloroethane; Concentration Process: Activated carbon; Chemical Classification: Halocarbons; Scale of Study: Batch Flow/Laboratory Scale; Type of Wastewater Used: Pure Compound; Influent Concentration: 100 ppb; Results of Study: 100% removal; 98% desorbed from carbon by elutriation with solvent (Filtrasorb 300 used solvent included pentane-acetone, diethylether, methylene chloride-acteone, methyl chloride-acetone, and acetone).
Chemical Treatability of Hexachloroethane; Concentration Process: Resin Adsorption; Chemical Classification: Halocarbons; Scale of Study: Batch Flow/Laboratory Scale; Type of Wastewater Used: Pure Compound; Influent Concentration: 100 ppb; Results of Study: 100% removal; 55% desorption from resin by elutriation with solvent (Amberlite XAD-2 used solvents included pentane-acetone, diethyl ether, methylene chloride-acetone, methyl chloride-acetone, and acetone).
Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/
Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/
The codisposal of selected organic priority pollutants with municipal refuse was investigated with four pilot-scale simulated landfill cells operated under the influence of single pass leaching or leachate recycle. ... During a 15-month period, little evidence of release of trichloroethane, and hexachloroethane was obtained even after elution of as much as 20 bed volumes in the recycle cells.
Incineration 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: Excess hydrocarbon fuels should be used due to the high chlorine content. (Peer review conclusions of an IRPTC expert consultation (May 1985))
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

By-product from the chlorination of ethylene and propylene with excess chlorine in vapor phase at 550-650 deg C without a catalyst.
In the presence of catalysts, trichloroethylene is readily chlorinated to hexachloroethane.
Ethylene dichloride + chlorine (chlorination; byproduct of trichloroethylene/perchloroethylene production)
Ethane/propane + chlorine (chlorinolysis; byproduct of perchloroethylene/carbon tetrachloride production)
A primary source for hexachloroethane is from the production of tetrachloroethylene and carbon tetrachloride by chlorinolysis of hydrocarbons and chlorinated hydrocarbon residues. It can be separated from the residues by distillation and fractionated crystallization. For the intentional production of hexachloroethane, tetrachloroethylene is chlorinated batchwise in the presence of iron chloride. The hexachloroethane crystallizes from the mother liquor and is isolated. The mother liquor is recycled and again chlorinated.
U.S. Imports

(1978) 7.88X10+8 G
(1982) 5.10X10+8 G
(1984) 6.51X10+8 g
(1986) 4.47X10+6 lb
U.S. Production

(1977) AT LEAST 9.58X10+8 G
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >10 million - 50 million 1990 >1 million - 10 million 1994 >10 million - 50 million 1998 >500 thousand - 1 million 2002 10 thousand - 500 thousand
Hexachloroethane is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Consumption Patterns

According to USA distributors, hexachloroethane had three major applications within the United States prior to 1979: 50% used by the military in the production of smoke bombs and other smoke munitions. 30-40% in the manufacture of degassing pellets to be used in aluminum foundries to force air bubbles out of molten ore. 10-20% as an anthelmintic for the control of sheep flukes.
Sampling Procedures:
A modified Grob closed-loop-stripping device is used to concentrate organic contaminants from drinking water.
A representative sample is collected in a glass container equipped with a Teflon-lined cap. Care is taken to avoid sample contact with any plastic.
EPA Method 1625 - Extractables by GC/MS: Collect water samples in municipal and industrial discharges in glass containers and extract with methylene chloride.
Biomedical Effects and Toxicity
Pharmacological Action:
- Agents destructive to parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
Therapeutic Uses:
MEDICATION (VET): Exptl use: Hexachloroethane was evaluated as a fasciolicide in dairy cattle under field conditions. After treatment with hexachloroethane, Fasciola hepatica infected cows had a significant average daily milk yield incr (90 to 120 days after treatment) of 4.2 kg/day over daily yields of the previous lactation. A 73% efficacy was observed against egg production by Fasciola hepatica after a single treatment of 90 g of hexachloroethane/animal. After a two to three month interval, a second treatment produced a combined treatment efficacy against fluke egg production of 92.11%. [Randall WF, Bradley RE; Am J Vet Res 41 (2): 262-3 (1980)]
Biomedical Effects and Toxicity:
Orally admin hexachloroethane is absorbed and appears rapidly in the systemic circulation. It is distributed widely throughout the body, the highest concn being found in the fat, the lowest in muscle.
... A dose of 0.5 g/kg of body weight in a rabbit was slowly metabolized. Approximately 5 percent appeared in the urine in a period of 3 days and from 14 to 24 percent in the expired air.
Hexachloroethane (HCE) was fed to Fischer 344 rats at approximate doses of 0, 1, 15 or 62 mg/kg/day for 16 weeks. Selected tissues were assayed at termination for HCE content. Histopathological examination identified the kidney as the primary target organ with male rats more sensitive than female rats. The kidney concentration of HCE increased proportionately with dose in the males, but there were disproportionately small increases with dose in females. A group of male rats was given 62 mg/kg/day for 8 weeks to estimate tissue clearance. Clearance of HCE from fat, liver, kidney and blood occurred in an apparent first-order manner with a half-life of approximately 2.5 days. The apparent first-order elimination suggests that HCE metabolism and excretion were not saturated in rats given up to 62 mg/kg/day and suggests that, in the range of doses given, toxicity should be proportional to exposure concentration. [Gorzinski SJ et al; Drug Chem Toxicol 8 (3): 155-69 (1985)] PubMed Abstract
A small group (n = 12) of military white smoke munition workers provided blood plasma during a production break (S I) and after five weeks' production (S II) of a hexachloroethane (HCE)/titanium dioxide formula. Plasma was also obtained from a sex and age matched control group (n = 12) and a group (n = 13) of previously HCE-exposed workers, respectively. HCE in plasma (P-HCE) was determined with gas chromatography and electron capture detection. No HCE was found in the plasma samples from the two control groups. In the HCE exposed group the mean (+/- SD) P-HCE level increased almost two orders of magnitude from S I (0.08 +/- 0.14 microgram/L) to S II (7.30 +/- 6.04 micrograms/L) despite efforts to minimize the internal dose. [Selden A et al; Int Arch Occup Environ Health 65 (1 Suppl): S111-4 (1993)] PubMed Abstract
It is absorbed through the skin. It has high toxicity via intravenous and moderate via oral, intraperitoneal, and dermal routes.
Analyzed liver, kidneys, blood, and adipose tissue from rats fed hexachloroethane in a 110 d dietary feeding study. After 57 d?Reported that the "concentration of HCE in the kidneys of male rats was significantly higher at all dose levels when compared to females (mg HCE/g of kidney with increasing dose males: 1.4, 24.3, 95.1; females: 0.4, 0.7, 2.0).
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 1,380 to 2,360(2,3) indicate that hexachloroethane is expected to have low to slight mobility in soil(SRC). Volatilization of hexachloroethane from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 3.89X10-3 atm-cu m/mole(4). Hexachloroethane is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.4 mm Hg(5). The biodegradation half-life of hexachloroethane in a non-adapted aerobic sandy soil was reported as 25-48 days(5).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 1,380 to 2,360(2,3), indicate that hexachloroethane is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 3.89X10-3 atm-cu m/mole at 25 deg C(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 hours and 6 days, respectively(SRC). According to a classification scheme(6), BCF values ranging from 1.0 to 708(7-10) suggest the potential for bioconcentration in aquatic organisms is low to high(SRC). Hexachloroethane injected into a shallow sand aquifer was degraded with a half-life of 40 days in 10 deg C groundwater under anaerobic conditions(11).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexachloroethane, which has a vapor pressure of 0.4 mm Hg at 20 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Hexachloroethane does not contain functional groups that react with atmospheric oxidants such as hydroxyl radicals, nitrate radicals and ozone(3). Hexachloroethane does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
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