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Hexachloroethane, also known as perchloroethane is the organochlorine compound with the chemical formula . It is white solid at room temperature with a camphor-like odor. It has been used by the military in
smoke composition A smoke composition is a pyrotechnic composition designed primarily to generate smoke. Smoke compositions are used as obscurants or for generation of signaling smokes. Some are used as a payload of smoke bombs and smoke grenades. Obscurants Smok ...
s, such as base-eject smoke munitions ( smoke grenades).


Manufacture

Chlorination of
tetrachloroethylene Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and many other names (and abbreviations such as "perc" or "PERC", and "PCE"), is a chlorocarbon with the formula Cl2C=CCl2 . It is a colorless li ...
at 100–140 °C with the presence of
ferric chloride Iron(III) chloride is the inorganic compound with the formula . Also called ferric chloride, it is a common compound of iron in the +3 oxidation state. The anhydrous compound is a crystalline solid with a melting point of 307.6 °C. The col ...
is the most commonly used commercial production method, however several other methods exist. A high purity form can be produced in a small scale by reacting chlorine together with barium carbide. In September 1997, it was reported as no longer being produced in the United States for commercial distribution, but was produced as a by-product of industrial chlorination process. :


Applications

Hexachloroethane has been used in the formulation of extreme pressure
lubricants A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, t ...
. It has also been used as a
chain transfer agent Chain transfer is a polymerization reaction by which the activity of a growing polymer chain is transferred to another molecule. :P• + XR' → PX + R'• Chain transfer reactions reduce the average molecular weight of the final polymer. Chain ...
in the emulsion polymerization of propylene tetrafluoroethylene copolymer. Hexachloroethane has been used as an
anthelmintic Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may ...
in
veterinary medicine Veterinary medicine is the branch of medicine that deals with the prevention, management, diagnosis, and treatment of disease, disorder, and injury in animals. Along with this, it deals with animal rearing, husbandry, breeding, research on nutri ...
, a rubber accelerator, a component of fungicidal and insecticidal formulations as well as a moth repellant and a plasticizer for cellulose esters. 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 Magnesium is a chemical element with the symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 of the periodic ...
, is being phased out in the
European Union The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are located primarily in Europe, Europe. The union has a total area of ...
.


Use as smoke agent

Smoke grenades, called hexachloroethane smoke or HC smoke, utilize a mixture containing roughly equal parts of hexachloroethane and
zinc oxide Zinc oxide is an inorganic compound with the formula . It is a white powder that is insoluble in water. ZnO is used as an additive in numerous materials and products including cosmetics, food supplements, rubbers, plastics, ceramics, glass, cement ...
and approximately 6% granular
aluminium Aluminium (aluminum in American and Canadian English) is a chemical element with the symbol Al and atomic number 13. Aluminium has a density lower than those of other common metals, at approximately one third that of steel. It ha ...
. These smokes are toxic, which is attributed to the production of
zinc chloride Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. This salt is hygroscopic ...
(). According to Steinritz et al., "Due to its potential pulmonary toxicity," zinc chloride producing smoke grenades "have been discharged from the armory of most western countries (...)."


Use as a riot control agent

HC smoke grenades, often used as smoke agents in combat, were used against protesters in Portland by
Federal Protective Services Federal or foederal (archaic) may refer to: Politics General *Federal monarchy, a federation of monarchies *Federation, or ''Federal state'' (federal system), a type of government characterized by both a central (federal) government and states or ...
and the
Department of Homeland Security The United States Department of Homeland Security (DHS) is the U.S. federal executive department responsible for public security, roughly comparable to the interior or home ministries of other countries. Its stated missions involve anti-ter ...
in Portland, Oregon during protests against police brutality. HC smoke began to be used more often by federal forces during Operation Diligent Valor. Despite numerous smoke canisters labeled "HC" being photographed by journalists and unusual levels of zinc and chloride, the two dominant combustion elements in HC smoke canisters, being found at protest locations, Rob Sperling, communications director for the Federal Protective Services denied the use of HC, claiming, "FPS doesn't have any items that contain HC." The Portland Bureau of Environmental Services requested safety data sheets from FPS regarding the use of HC smoke. The request was denied. While HC smoke has been most extensively used by FPS in Portland, Or during 2020-21 protests, police departments in other American cities, such as
Milwaukee Milwaukee ( ), officially the City of Milwaukee, is both the most populous and most densely populated city in the U.S. state of Wisconsin and the county seat of Milwaukee County. With a population of 577,222 at the 2020 census, Milwaukee i ...
, Wi and
Denver Denver () is a consolidated city and county, the capital, and most populous city of the U.S. state of Colorado. Its population was 715,522 at the 2020 census, a 19.22% increase since 2010. It is the 19th-most populous city in the Unit ...
, Co have also purchased HC smoke canisters. Most documented uses of HC smoke as a riot control agent occurred in the United States, with little being known about its use by other governments.


Health effects

Many protesters reported vomiting and a continued loss of appetite when exposed to the toxic smoke. Some have also reported changes in menstrual cycles. Despite its continued use by FPS as a riot control agent, the Department of Defense has begun to phase out the use of HC smoke after a 1994 report by the U.S. Army Biomedical Research and Development Laboratory due to ensure the safety of US soldiers, noting that, "Exposure of unprotected soldiers to high concentrations of HC smoke for even a few minutes has resulted in injuries and fatalities." While HC related injuries have been common in Portland, Or, no deaths due to the use of HC smoke have been reported.


Toxicity

Hexachloroethane is not particularly toxic when taken orally, but is considered to be quite toxic by skin adsorption. The primary effect is depression of the central nervous system. The concentration that is immediately dangerous to life or health is 300 ppm and the
permissible exposure limit The permissible exposure limit (PEL or OSHA PEL) is a legal limit in the United States for exposure of an employee to a chemical substance or physical agent such as high level noise. Permissible exposure limits are established by the Occupationa ...
according to the
Occupational Safety and Health Administration The Occupational Safety and Health Administration'' (OSHA ) is a large regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. Congress established the agen ...
is 1 ppm (skin). It is reasonably anticipated to be a carcinogen.


References


External links


US Government Agency for Toxic Substances and Disease Registry ToxFAQs for Hexachloroethane



Scorecard.org chemical profile

US EPA Hexachloroethane fact sheet
{{Authority control Chloroalkanes IARC Group 2B carcinogens