Hexachloroethane

Hexachloroethane
Names
	IUPAC name Hexachloroethane
	Other names Carbon hexachloride, Ethane hexachloride, Perchloroethane
Identifiers
CAS Number	67-72-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:39227 ;
ChEMBL	ChEMBL160929 ;
ChemSpider	5979 ;
ECHA InfoCard	100.000.606
EC Number	200-666-4;
KEGG	C19248 ;
PubChem CID	6214;
UNII	G30K3QQT4J ;
CompTox Dashboard (EPA)	DTXSID7020689 ;
	InChI InChI=1S/C2Cl6/c3-1(4,5)2(6,7)8 Key: VHHHONWQHHHLTI-UHFFFAOYSA-N ; InChI=1/C2Cl6/c3-1(4,5)2(6,7)8 Key: VHHHONWQHHHLTI-UHFFFAOYAD;
	SMILES ClC(Cl)(Cl)C(Cl)(Cl)Cl;
Properties
Chemical formula	C2Cl6
Molar mass	236.74 g/mol
Appearance	colorless crystals[1]
Odor	camphor-like[1]
Density	2.091 g/mL at 25 °C
Melting point	sublimes
Boiling point	183 to 185 °C (361 to 365 °F; 456 to 458 K)
Solubility in water	0.005% (22.2 °C)[1]
Vapor pressure	0.2 mmHg (20 °C)[1]
Magnetic susceptibility (χ)	-112.7·10−6 cm3/mol
Hazards
Main hazards	Probable carcinogen, dangerous CNS depression
NFPA 704 (fire diamond)	0 2 0
Flash point	noncombustible[1]
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	4460 mg/kg (rat, oral); 4970 mg/kg (guinea pig, oral) [2]
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 1 ppm (10 mg/m3) [skin][1]
REL (Recommended)	Ca TWA 1 ppm (10 mg/m3) [skin][1]
IDLH (Immediate danger)	Ca [300 ppm][1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Hexachloroethane, also known as perchloroethane (PCA), C₂ Cl₆, is a white crystalline solid at room temperature with a camphor-like odor.[3] It has been used by the military in smoke compositions, such as base-eject smoke munitions (smoke grenades).

Manufacture

Hexachloroethane is a byproduct of many industrial chlorination processes.[3] It is currently being manufactured directly in India.[4] The overall reaction is shown below. This reaction occurs stepwise.

C₂H₆ + 6 Cl₂ → C₂Cl₆ + 6 HCl

Applications

Hexachloroethane has been used in the formulation of extreme pressure lubricants. It has also been used as a chain transfer agent in the emulsion polymerization of propylene tetrafluoroethylene copolymer. Hexachloroethane has been used as an anthelmintic in veterinary medicine, a rubber accelerator, a component of fungicidal and insecticidal formulations as well as a moth repellant and a plasticizer for cellulose esters.[3]

Smoke grenades, called hexachloroethane (HCE) smoke or HC smoke, utilize a mixture containing roughly equal parts of HCE and zinc oxide and approximately 6% granular aluminium. These smokes are toxic, which is attributed to the production of zinc chloride (ZnCl₂).[5]

Hexachloroethane has been used in the manufacture of degassing pellets to remove hydrogen gas bubbles from molten aluminum in aluminum foundries. This use, as well as similar uses in magnesium, is being phased out in the European Union. It was phased out as early as 1999 in the United States.[4]

Toxicity

Hexachlorethane is not particularly toxic when taken orally,[6] but is considered to be quite toxic by skin adsorption. The primary effect is depression of the central nervous system.[3] The IDLH is given as 300 ppm and the OSHA PEL is 1 ppm (skin).[6] It is reasonably anticipated to be a carcinogen.[4]

References

NIOSH Pocket Guide to Chemical Hazards. "#0316". National Institute for Occupational Safety and Health (NIOSH).
"Hexachloroethane". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Snedecor, Gayle (1999). "Hexachloroethane". In Kroschwitz, Jacqueline I. (ed.). Kirk-Othmer Concise Encylclopedia of Chemical Technology (4th ed.). New York: John Wiley & Sons, Inc. p. 428. ISBN 978-0471419617.
"Report on Carcinogens, Twelfth Edition, Hexachloroethane" (PDF). NIH. 2011. Retrieved 2012-10-04.
"Appendix E: Smoke And Masking Agents" (PDF). Australian Department of Veteran Affairs. December 2003. p. E-3. Archived from the original (PDF) on 2014-02-13. Retrieved 2012-10-04.
"Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) Hexachloroethane". NIOSH. May 1994. Retrieved 2012-10-04.

External links

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[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0316". National Institute for Occupational Safety and Health (NIOSH).

[2] "Hexachloroethane". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Kirk-Othmer-3] Snedecor, Gayle (1999). "Hexachloroethane". In Kroschwitz, Jacqueline I. (ed.). Kirk-Othmer Concise Encylclopedia of Chemical Technology (4th ed.). New York: John Wiley & Sons, Inc. p. 428. ISBN 978-0471419617.

[NIH-4] "Report on Carcinogens, Twelfth Edition, Hexachloroethane" (PDF). NIH. 2011. Retrieved 2012-10-04.

[5] "Appendix E: Smoke And Masking Agents" (PDF). Australian Department of Veteran Affairs. December 2003. p. E-3. Archived from the original (PDF) on 2014-02-13. Retrieved 2012-10-04.

[CDC-6] "Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) Hexachloroethane". NIOSH. May 1994. Retrieved 2012-10-04.