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 An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class ( alkanes with one or more hydrogens substituted by chlo ...

with the formula Cl₂C=CCl₂ . It is a colorless liquid widely used for

dry cleaning Dry cleaning is any cleaning process for clothing and textiles using a solvent other than water. Dry cleaning still involves liquid, but clothes are instead soaked in a water-free liquid solvent. Tetrachloroethylene (perchloroethylene), known in ...

of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a sweet odor detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about in 1985.M. Rossberg et al. "Chlorinated Hydrocarbons" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2006, Wiley-VCH, Weinheim.

Production

British

physicist A physicist is a scientist who specializes in the field of physics, which encompasses the interactions of matter and energy at all length and time scales in the physical universe. Physicists generally are interested in the root or ultimate caus ...

and

chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties. Chemists carefully describe th ...

Michael Faraday Michael Faraday (; 22 September 1791 – 25 August 1867) was an English scientist who contributed to the study of electromagnetism and electrochemistry. His main discoveries include the principles underlying electromagnetic inducti ...

first synthesized tetrachloroethylene in 1821 by thermal decomposition of

hexachloroethane 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 compositions, such as base-eject ...

. :C₂Cl₆ → C₂Cl₄ + Cl₂ Most tetrachloroethylene is produced by high temperature chlorinolysis of light hydrocarbons. The method is related to Faraday's discovery since hexachloroethane is generated and thermally decomposes. Side products include

carbon tetrachloride Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVAC ...

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...

, and

hexachlorobutadiene Hexachlorobutadiene, Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlo ...

. Several other methods have been developed. When

1,2-dichloroethane The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl ...

is heated to 400 °C with

chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...

, tetrachloroethylene is produced by the

chemical reaction A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the pos ...

: :ClCH₂CH₂Cl + 3 Cl₂ → Cl₂C=CCl₂ + 4

HCl HCL may refer to: Science and medicine * Hairy cell leukemia, an uncommon and slowly progressing B cell leukemia * Harvard Cyclotron Laboratory, from 1961 to 2002, a proton accelerator used for research and development * Hollow-cathode lamp, a spe ...

This reaction can be

catalyzed Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

by a mixture of

potassium chloride Potassium chloride (KCl, or potassium salt) is a metal halide salt composed of potassium and chlorine. It is odorless and has a white or colorless vitreous crystal appearance. The solid dissolves readily in water, and its solutions have a salt ...

and

aluminium chloride Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contam ...

or by activated

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...

Trichloroethylene The chemical compound trichloroethylene is a halocarbon commonly used as an industrial solvent. It is a clear, colourless non-flammable liquid with a chloroform-like sweet smell. It should not be confused with the similar 1,1,1-trichloroethane, ...

is a major byproduct, which is separated by

distillation Distillation, or classical distillation, is the process of separation process, separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distilla ...

Uses

Tetrachloroethylene is an excellent

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

for

organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...

materials. Otherwise it is volatile, highly stable, and

nonflammable A combustible material is something that can burn (i.e., ''combust'') in air. A combustible material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort and a flammable mat ...

. For these reasons, it is widely used in

. It is also used to degrease metal parts in the automotive and other metalworking industries, usually as a mixture with other chlorocarbons. It appears in a few consumer products including

paint stripper Paint stripper, or paint remover, is a chemical product designed to remove paint, finishes, and coatings, while also cleaning the underlying surface. The product's material safety data sheet provides more safety information than its product la ...

s and spot removers. It is also used in aerosol preparations.

Historical applications

Tetrachloroethylene was once extensively used as an intermediate in the manufacture of

HFC-134a 1,1,1,2-Tetrafluoroethane (also known as norflurane ( INN), R-134a, Freon 134a, Forane 134a, Genetron 134a, Green Gas, Florasol 134a, Suva 134a, or HFC-134a) is a hydrofluorocarbon (HFC) and haloalkane refrigerant with thermodynamic properties s ...

and related

refrigerant A refrigerant is a working fluid used in the heat pump and refrigeration cycle, refrigeration cycle of air conditioning systems and heat pumps where in most cases they undergo a repeated phase transition from a liquid to a gas and back again. Ref ...

s. In the early 20th century, tetrachloroethene was used for the treatment of

hookworm Hookworms are intestinal, blood-feeding, parasitic roundworms that cause types of infection known as helminthiases. Hookworm infection is found in many parts of the world, and is common in areas with poor access to adequate water, sanitation, an ...

infestation.

Health and safety

The acute toxicity of tetrachloroethylene "is moderate to low". "Reports of human injury are uncommon despite its wide usage in dry cleaning and degreasing". The

International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; french: Centre International de Recherche sur le Cancer, CIRC) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and ...

has classified tetrachloroethylene as a Group 2A carcinogen, which means that it is probably carcinogenic to humans. Like many

chlorinated hydrocarbons An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class ( alkanes with one or more hydrogens substituted by chlo ...

, tetrachloroethylene is a

central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all par ...

depressant and can enter the body through respiratory or dermal exposure. Tetrachloroethylene dissolves fats from the skin, potentially resulting in skin irritation. Animal studies and a study of 99 twins showed there is a "lot of circumstantial evidence" that exposure to tetrachloroethylene increases the risk of developing

Parkinson's disease Parkinson's disease (PD), or simply Parkinson's, is a long-term degenerative disorder of the central nervous system that mainly affects the motor system. The symptoms usually emerge slowly, and as the disease worsens, non-motor symptoms becom ...

ninefold. Larger population studies are planned. Also, tetrachloroethylene has been shown to cause liver tumors in mice and kidney tumors in male rats. At temperatures over , such as in welding, tetrachloroethylene can be oxidized into

phosgene Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, espe ...

, an extremely poisonous gas. The U.S.

National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the C ...

has compiled extensive health and safety information for tetrachloroethylene, including recommendations for dry cleaning establishments. Tetrachloroethylene exposure has been linked to pronounced acquired color vision deficiencies after chronic exposure.

Testing for exposure

Tetrachloroethylene exposure can be evaluated by a breath test, analogous to breath-alcohol measurements. Because it is stored in the body's fat and slowly released into the bloodstream, tetrachloroethylene can be detected in the breath for weeks following a heavy exposure. Tetrachloroethylene and

trichloroacetic acid Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Salts and esters of trichloroacetic acid are calle ...

(TCA), a breakdown product of tetrachloroethylene, can be detected in the

blood Blood is a body fluid in the circulatory system of humans and other vertebrates that delivers necessary substances such as nutrients and oxygen to the cells, and transports metabolic waste products away from those same cells. Blood in the c ...

. In Europe, the Scientific Committee on Occupational Exposure Limits (SCOEL) recommends for tetrachloroethylene an

occupational exposure limit An occupational exposure limit is an upper limit on the acceptable concentration of a hazardous substance in workplace air for a particular material or class of materials. It is typically set by competent national authorities and enforced by legi ...

(8 hour time-weighted average) of 20 ppm and a short-term exposure limit (15 min) of 40 ppm.

Remediation and degradation

In principle, tetrachloroethylene contamination can be remediated by chemical treatment or by

bioremediation Bioremediation broadly refers to any process wherein a biological system (typically bacteria, microalgae, fungi, and plants), living or dead, is employed for removing environmental pollutants from air, water, soil, flue gasses, industrial effluent ...

. Chemical treatment involves reducing metals such as iron powder. Bioremediation entails reductive dechlorination by ''Dehalococcoides'' sp. under aerobic conditions by cometabolism by ''Pseudomonas'' sp. In addition to bioremediation, TCE hydrolyzes on contact with soil. Products of biodegradation products include

trichloroethylene The chemical compound trichloroethylene is a halocarbon commonly used as an industrial solvent. It is a clear, colourless non-flammable liquid with a chloroform-like sweet smell. It should not be confused with the similar 1,1,1-trichloroethane, ...

, cis-

1,2-dichloroethene 1,2-Dichloroethene, commonly called 1,2-dichloroethylene or 1,2-DCE, is the name for a pair of organochlorine compounds with the molecular formula CHCl. They are both colorless liquids with a sweet odor. It can exist as either of two geometric ...

and

vinyl chloride Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC ...

; full degradation converts tetrachloroethylene to ethylene and chloride.

References

External links

ATSDR Case Studies in Environmental Medicine: Tetrachloroethylene Toxicity
U.S.

Department of Health and Human Services The United States Department of Health and Human Services (HHS) is a cabinet-level executive branch department of the U.S. federal government created to protect the health of all Americans and providing essential human services. Its motto is " ...

Tetrachloroethylene (Perchloroethylene)
U.S.

*Australia
National Pollutant Inventory (NPI)
page

by Julian Kesner, New York ''Daily News'', April 20, 2007.
Sustainable uses and Industry recommendations
{{Authority control Commodity chemicals Dry cleaning Halogenated solvents Hazardous air pollutants IARC Group 2A carcinogens Organochlorides