Tetrachloroethylene

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Tetrachloroethylene
Tetrachloroethylene Tetrachloroethylene.svg
Tetrachloroethylene
Tetrachloroethylene Tetrachloroethylene-3D-vdW.png
Tetrachloroethylene
   Carbon, C
   Chlorine, Cl
Tetrakloroetilen2.jpg
Names
Preferred IUPAC name
Tetrachloroethene
Other names
Carbon bichloride; Carbon dichloride (Carboneum Dichloratum); Ethylene tetrachloride; Perchlor; Perchloroethene; Perchloroethylene;
Identifiers
3D model (JSmol)
AbbreviationsPCE; Perc; Per
1304635
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.388 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-825-9
101142
KEGG
PubChem CID
RTECS number
  • KX3850000
UNII
UN number 1897
  • InChI=1S/C2Cl4/c3-1(4)2(5)6 Yes check.svgY
    Key: CYTYCFOTNPOANT-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2Cl4/c3-1(4)2(5)6
    Key: CYTYCFOTNPOANT-UHFFFAOYAO
  • ClC(Cl)=C(Cl)Cl
Properties
C2Cl4
Molar mass 165.82 g/mol
AppearanceClear, very refractive, colorless liquid
Odor Mild, sharp and sweetish [1]
Density 1.622 g/cm3
Melting point −22.0 to −22.7 °C (−7.6 to −8.9 °F; 251.2 to 250.5 K)
Boiling point 121.1 °C (250.0 °F; 394.2 K)
0.15 g/L (25 °C)
Vapor pressure 14 mmHg (20 °C) [1]
−81.6·10−6 cm3/mol
1.505
Viscosity 0.89  cP at 25 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Inhalation of vapours can cause anaesthesia and respiratory irritation. Causes irritation in contact with skin and eyes with no residual injury.
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H351, H411
P201, P202, P273, P281, P308+P313, P391, P405, P501
NFPA 704 (fire diamond)
[2]
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Flash point Not flammable
Lethal dose or concentration (LD, LC):
3420 mg/kg (oral, rat) [3]
2629 mg/kg (oral, rat), >10000 mg/kg (dermal, rat) [4]
4000 ppm (rat, 4 hr)
5200 ppm (mouse, 4 hr)
4964 ppm (rat, 8 hr) [5]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm
C 200 ppm (for 5 minutes in any 3-hour period), with a maximum peak of 300 ppm [1]
REL (Recommended)
Ca Minimize workplace exposure concentrations. [1]
IDLH (Immediate danger)
Ca [150 ppm] [1]
Safety data sheet (SDS) External MSDS
Related compounds
Related analogous organohalides
Tetrafluoroethylene
Tetrabromoethylene
Tetraiodoethylene
Related compounds
 Trichloroethylene
Dichloroethylene
1,1,2,2-Tetrachloroethane
Carbon tetrachloride
Supplementary data page
Tetrachloroethylene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Tetrachloroethylene, also known as perchloroethylene [a] or under the systematic name tetrachloroethene, and abbreviations such as perc (or PERC), and PCE, is a chlorocarbon with the formula Cl2C=CCl2. It is a non-flammable, stable, colorless and heavy liquid widely used for dry cleaning of fabrics. It also has its uses as an effective automotive brake cleaner. It has a mild sweet, sharp odor, detectable by most people at a concentration of 50 ppm. [6]

Tetrachloroethylene is regarded as a toxic substance, a human health hazard, and an environmental hazard. [2] [7] In 2020, the United States Environmental Protection Agency stated that "tetrachloroethylene exposure may harm the nervous system, liver, kidneys, and reproductive system, and may be harmful to unborn children", and reported that numerous toxicology agencies regard it as a carcinogen. [8]

History and production

French chemist Henri Victor Regnault first synthesized tetrachloroethylene in 1839 by thermal decomposition of hexachloroethane following Michael Faraday's 1820 synthesis of protochloride of carbon (carbon tetrachloride).

C2Cl6 → C2Cl4 + Cl2

Faraday was previously falsely credited for the synthesis of tetrachloroethylene, which in reality, was carbon tetrachloride.[ non-primary source needed ] While trying to make Faraday's "protochloride of carbon", Regnault found that his compound was different from Faraday's. Victor Regnault stated "According to Faraday, the chloride of carbon boiled around 70 °C (158 °F) to 77 °C (171 °F) degrees Celsius but mine did not begin to boil until 120 °C (248 °F)". [9]

Tetrachloroethylene can be made by passing chloroform vapour through a red-hot tube, the side products include hexachlorobenzene and hexachloroethane, as reported in 1886. [10]

Most tetrachloroethylene is produced by high-temperature chlorinolysis of light hydrocarbons. The method is related to Faraday's method since hexachloroethane is generated and thermally decomposes. [11] Side products include carbon tetrachloride, hydrogen chloride, and hexachlorobutadiene.

Several other methods have been developed. When 1,2-dichloroethane is heated to 400 °C with chlorine, tetrachloroethylene is produced:

ClCH2CH2Cl + 3 Cl2 → Cl2C=CCl2 + 4 HCl

This reaction can be catalyzed by a mixture of potassium chloride and aluminium chloride or by activated carbon. Trichloroethylene is a major byproduct, which is separated by distillation.

Worldwide production was about 1 million metric tons (980,000 long tons; 1,100,000 short tons) in 1985. [11]

Although in very small amounts, tetrachloroethylene occurs naturally in volcanoes along with trichloroethylene. [12]

Uses

Tetrachloroethylene is an excellent nonpolar solvent for organic materials. Additionally, it is volatile, highly stable (easily recycled) and nonflammable, and has low toxicity. For these reasons, it has been widely used in dry cleaning worldwide since the 1930s. The chemist Sylvia Stoesser (1901–1991) had suggested tetrachloroethylene to be used in dry cleaning as an alternative to highly flammable dry cleaning solvents such as naphtha. [13]

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 strippers, aerosol preparations and spot removers.

Historical applications

Tetrachloroethylene was once extensively used as an intermediate in the manufacture of HFC-134a and related refrigerants.

In the early 20th century, tetrachloroethene was used for the treatment of hookworm infestation. [14] [15] In 1925, American veterinarian Maurice Crowther Hall (1881–1938), working on anthelmintics, demonstrated the effectiveness of tetrachloroethylene in the treatment of ancylostomiasis caused by hookworm infestation in humans and animals. Before Hall tested tetrachloroethylene on himself, in 1921 he discovered the powerful effect of carbon tetrachloride on intestinal parasites and was nominated for the Nobel Prize in Physiology or Medicine, but a few years later he found tetrachloroethylene to be more effective and safer. [16] Tetrachloroethylene treatment has played a vital role in eradicating hookworms in the United States and abroad.[ citation needed ] Hall's innovation was considered a breakthrough in medicine.[ citation needed ] It was given orally as a liquid or in capsules along with magnesium sulfate to get rid of the Necator americanus parasite in humans. [17]

Chemical properties and reactions

Tetrachloroethylene is a derivative of ethylene with all hydrogens replaced by chlorine. 14.49% of the molecular weight of tetrachloroethylene consists of carbon and the remaining 85.5% is chlorine. It is the most stable compound among all chlorinated derivatives of ethane and ethylene. It is resistant to hydrolysis and less corrosive than other chlorinated solvents. [11] It does not tend to polymerise like fluorine analogue tetrafluoroethylene, C2F4.

Tetrachloroethylene may react violently with alkali or alkaline earth metals, alkalis (sodium hydroxide and potassium hydroxide), nitric acid, beryllium, barium and aluminium. [18]

Oxidation

Oxidation of tetrachloroethylene by ultraviolet radiation in air produces trichloroacetyl chloride and phosgene:

4 C2Cl4 + 3 O2 → 2 CCl3COCl + 4 COCl2

This reaction can be halted by using amines and phenols (usually N-methylpyrrole and N-methylmorpholine) as stabilisers. But the reaction can be done intentionally to produce trichloroacetyl chloride. [11]

Chlorination

Hexachloroethane is formed when tetrachloroethylene reacts with chlorine at 50–80 °C in the presence of a small amount of iron(III) chloride (0.1%) as a catalyst: [19]

C2Cl4 + Cl2 → C2Cl6

CFC-113 is produced by the reaction of tetrachloroethylene with chlorine and HF in the presence of antimony pentafluoride: [20]

C2Cl4 + 3 HF + Cl2 → CClF2CCl2F + 3 HCl

Nitration

Tetrachlorodinitroethane can be obtained by nitration of tetrachloroethylene with fuming nitric acid (conc. HNO3 rich in nitrogen oxides) or nitrogen tetroxide: [21]

Cl2CCCl2 + N2O4 → NO2Cl2CCCl2NO2

The preparation of this crystalline solid compound from Tetrachloroethylene and nitrogen tetroxide was first described by Hermann Kolbe in 1869. [21]

Thermal decomposition

Tetrachloroethylene begins to thermally decompose at 400 °C, decomposition accelerates around 600 °C, and completely decomposes at 800 °C. Organic decomposition products identified were trichlorobutene, 1,3-dichloro-2-propanone, tetrachlorobutadiene, dichlorocyclopentane, dichloropentene, methyl trichloroacetate, tetrachloroacetone, tetrachloropropene, trichlorocyclopentane, trichloropentene, hexachloroethane, pentachloropropene, hexachloropropene, hexachlorobutadiene. [22]

Health and safety

Tetrachloroethylene is considered to be a toxin. [7] It is identified as a health hazard and environmental hazard. [2] Exposure to tetrachloroethylene, especially over a long term, may harm the nervous system, other organs, and increase the risk of getting cancer. [8] It may also have effects on pregnancy and the fetus. [8]

Reports of human injury are uncommon despite its wide usage in dry cleaning and degreasing. [23] Although limited by its low volatility, tetrachloroethylene has potent anaesthetic effects upon inhalation. [8] [24] The risk depends on whether exposure is over minutes or hours, or over years. [8]

Despite the advantages of tetrachloroethylene, cancer research and government environmental agencies have called for its replacement from widespread commercial use. [8] It is described as a possible neurotoxicant, liver and kidney toxicant and reproductive and developmental toxicant (...) a potential occupational carcinogen. [7] [8] [25] On the other hand, dry cleaning industry emphasizes minimal risk because modern machinery use closed systems to avoid any vapour escape and to optimize recycling. [11]

Metabolism

Tetrachloroethylene's biological half-life is approximately 3 days. [26] About 98% of the inhaled tetrachloroethylene is exhaled unchanged and only about 1–3% is metabolised to tetrachloroethylene oxide which rapidly isomerises into trichloroacetyl chloride. Trichloroacetyl chloride hydrolyses to trichloroacetic acid. [27] [26]

Neurotoxicity

Tetrachloroethylene can harm the nervous system, cause developmental deficits in children, impair vision, and increase the risk of psychiatric diagnoses. [7] [28] [29]

Carcinogenicity

Tetrachloroethylene has been classified as "Group 2A: Probably Carcinogenic" by the International Agency for Research on Cancer (IARC) due to sufficient evidence in experimental animals and limited evidence in humans for non-Hodgkin lymphoma, urinary bladder cancers, and cancers of the esophagus and cervix. [30] : 32 

Evidence from cohort and case-controlled epidemiologic studies demonstrates a positive association between cumulative exposures to tetrachloroethylene and the prevalence of bladder cancer, non-Hodgkin lymphoma, and multiple myeloma in adults. Some limited evidence of increased prevalence of kidney, lung, liver, and breast cancers with exposure to tetrachloroethylene has been found in epidemiologic research, but data quality limitations have produced variable results across studies. [30] : 326  [31] : § 4.2.1.3  [32] : 237 

Several modes of action are hypothesized for the carcinogenicity of tetrachloroethylene in humans, though existing data is insufficient for adequate characterization. [31] : § 4.2.4, § 4.3.4  Markers of oxidative metabolism of tetrachloroethylene and increased prevalence of abnormal hepatic sonographs have been observed in dry-cleaners and laundry workers exposed to tetrachloroethylene, [33] [34] which suggests a potential for hepatocellular damage through the formation of reactive intermediates from glutathione conjugates during metabolization. [30] : 328  [32] : 10, 189–193  Although most genotoxicity assays of tetrachloroethylene produced negative findings for genotoxicity and mutagenicity, modest genotoxic effects and mutagenic effects have been identified under certain metabolic activation conditions, and several of tetrachloroethylene's metabolites have been shown to be mutagenic. [31] : § 4.10.3  [32] : 172–178 

Testing for exposure

Tetrachloroethylene exposure can be evaluated by a breath test, analogous to breath-alcohol measurements. Also, for acute exposures, tetrachloroethylene in expired air can be measured. [35] Tetrachloroethylene can be detected in the breath for weeks following a heavy exposure. Tetrachloroethylene and its metabolite trichloroacetic acid, can be detected in the blood.

In the European Union, the Scientific Committee on Occupational Exposure Limits (SCOEL) recommends for tetrachloroethylene an occupational exposure limit (8-hour time-weighted average) of 20 ppm and a short-term exposure limit (15 min) of 40 ppm. [36]

Remediation and degradation

In principle, tetrachloroethylene contamination can be remediated by chemical treatment. Chemical treatment involves reducing metals such as iron powder. [37]

Bioremediation usually entails reductive dechlorination under anaerobic conditions by Dehalococcoides spp. [38] Under aerobic conditions, degradation may occur via co-metabolism by Pseudomonas sp. [39] Products of biological reductive dechlorination include trichloroethylene, cis-1,2-dichloroethylene, vinyl chloride, ethylene and chloride.

Explanatory notes

  1. ↑ Previously spelt as perchlorethylene

Related Research Articles

<span class="mw-page-title-main">Chlorine</span> Chemical element with atomic number 17 (Cl)

Chlorine is a chemical element; it has 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 between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

Chloroform, or trichloromethane, is an organochloride with the formula CHCl3 and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and PTFE. Chloroform was once used as an inhalational anesthetic between the 19th century and the first half of the 20th century. It is miscible with many solvents but it is only very slightly soluble in water.

<span class="mw-page-title-main">Dry cleaning</span> Cleaning of fabrics in non-aqueous solvents

Dry cleaning is any cleaning process for clothing and textiles using a solvent other than water. Clothes are instead soaked in a water-free liquid solvent. Perchloroethylene is the most commonly used solvent, although alternative solvents such as hydrocarbons, and supercritical CO2 are also used.

<span class="mw-page-title-main">Carbon tetrachloride</span> Carbon compound

Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a non-flammable, dense, colourless liquid with a "sweet" chloroform-like odour that can be detected at low levels. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, an anthelmintic and a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal.

<span class="mw-page-title-main">Dichloromethane</span> Chemical compound

Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.

<span class="mw-page-title-main">Vinyl chloride</span> Chemical compound

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). Vinyl chloride monomer is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States remains the largest vinyl chloride manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of vinyl chloride. Vinyl chloride is a flammable gas that has a sweet odor and is carcinogenic. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills. Before the 1970s, vinyl chloride was used as an aerosol propellant and refrigerant.

<span class="mw-page-title-main">1,1,1-Trichloroethane</span> Solvent, now banned for ozone depletion

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. A colourless and sweet-smelling liquid, it was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and as such use has declined since 1996. Trichloroethane should not be confused with the similar-sounding trichloroethene which is also commonly used as a solvent.

<span class="mw-page-title-main">Trichloroethylene</span> C2HCl3, widely used industrial solvent

Trichloroethylene (TCE) is a halocarbon with the formula C2HCl3, commonly used as an industrial metal degreasing solvent. It is a clear, colourless, non-flammable, volatile liquid with a chloroform-like pleasant mild smell and sweet taste. Its IUPAC name is trichloroethene. Trichloroethylene has been sold under a variety of trade names. Industrial abbreviations include TCE, trichlor, Trike, Tricky and tri. Under the trade names Trimar and Trilene, it was used as a volatile anesthetic and as an inhaled obstetrical analgesic. It should not be confused with the similar 1,1,1-trichloroethane, which was commonly known as chlorothene.

In organochlorine chemistry, reductive dechlorination describes any chemical reaction which cleaves the covalent bond between carbon and chlorine via reductants, to release chloride ions. Many modalities have been implemented, depending on the application. Reductive dechlorination is often applied to remediation of chlorinated pesticides or dry cleaning solvents. It is also used occasionally in the synthesis of organic compounds, e.g. as pharmaceuticals.

Halocarbon compounds are chemical compounds in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms resulting in the formation of organofluorine compounds, organochlorine compounds, organobromine compounds, and organoiodine compounds. Chlorine halocarbons are the most common and are called organochlorides.

Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds containing at least one covalently bonded atom of chlorine. The chloroalkane class includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

1,1-Dichloroethylene, commonly called vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula CCl2CH2. It is a colorless liquid with a sharp odor. Like most chlorocarbons, it is poorly soluble in water but soluble in organic solvents. 1,1-DCE was the precursor to the original clingwrap, Saran, for food, but this application has been phased out.

Hexachlorobenzene, or perchlorobenzene, is an aryl chloride and a six-substituted chlorobenzene with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the Stockholm Convention on Persistent Organic Pollutants.

<span class="mw-page-title-main">Thiophosgene</span> Chemical compound

Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.

<span class="mw-page-title-main">Hexachloroethane</span> Chemical compound

Hexachloroethane (perchloroethane) is an organochlorine compound with the chemical formula (CCl3)2. It is a white or colorless solid at room temperature with a camphor-like odor. It has been used by the military in smoke compositions, such as base-eject smoke munitions.

<span class="mw-page-title-main">1,1,2,2-Tetrachloroethane</span> Chemical compound

1,1,2,2-tetrachloroethane (TeCA), also known by the brand names Bonoform, Cellon and Westron, is an organic compound. It is colorless liquid and has a sweet odor. It is used as an industrial solvent and as a separation agent. TeCA is toxic and it can be inhaled, consumed or absorbed through the skin. After exposure, nausea, dizziness or even liver damage may occur.

<span class="mw-page-title-main">Hexachlorobutadiene</span> Chemical compound

Hexachlorobutadiene, (often abbreviated as "HCBD") 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 chlorine-containing compounds. Structurally, it has a 1,3-butadiene core, but fully substituted with chlorine atoms.

<span class="mw-page-title-main">Perchloromethyl mercaptan</span> Chemical compound

Perchloromethyl mercaptan is the organosulfur compound with the formula CCl3SCl. It is mainly used as an intermediate for the synthesis of dyes and fungicides (captan, folpet). It is a colorless oil, although commercial samples are yellowish. It is insoluble in water but soluble in organic solvents. It has a foul, unbearable, acrid odor. Perchloromethyl mercaptan is the original name. The systematic name is trichloromethanesulfenyl chloride, because the compound is a sulfenyl chloride, not a mercaptan.

<span class="mw-page-title-main">Pentachloroethane</span> Chemical compound

Pentachloroethane is a chemical compound of chlorine, hydrogen, and carbon with the chemical formula C2HCl5. It is a colourless non-flammable liquid that is used as a solvent for oil and grease, in metal cleaning, and in the separation of coal from impurities.

<span class="mw-page-title-main">Octachloropropane</span> Chemical compound

Octachloropropane or perchloropropane is the chemical compound with elemental formula C3Cl8 and structural formula Cl3C−CCl2−CCl3. Its molecule has a simple chain of three carbon atoms connected by single bonds, with chlorine atoms filling their remaining bonds. It is a chlorocarbon, specifically the third simplest perchloroalkane. It can be described as a derivative of propane C3H8, with all hydrogen atoms replaced by chlorine.

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  26. 1 2 Shane S. Que Hee, ed. (1993). "Biological Exposure Indices". Biological Monitoring: An Introduction. John Wiley & Sons. p. 470. ISBN   978-0-471-29083-4.
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  39. ↑ Ryoo, D.; Shim, H.; Arenghi, F. L. G.; Barbieri, P.; Wood, T. K. (2001). "Tetrachloroethylene, Trichloroethylene, and Chlorinated Phenols Induce Toluene-o-xylene Monooxoygenase Activity in Pseudomonas stutzeri OX1". Appl Microbiol Biotechnol. 56 (3–4): 545–549. doi:10.1007/s002530100675. PMID   11549035. S2CID   23770815.

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