Trichloroethylene

Last updated
Trichloroethylene
Trikloreten.svg
Trichloroethylene.png
Trichloroethylene-3D-vdW.png
Trichloroethene.jpg
sample of Trichloroethylene
Names
Preferred IUPAC name
Trichloroethene
Other names
1-Chloro-2,2-dichloroethylene; 1,1-Dichloro-2-chloroethylene; Acetylene Trichloride; Anamenth; HCO-1120; TCE; Trethylene; Triclene; Tri; Trico; Trilene; Trimar;
Terchlorethylene; Chloréthérise (archaic)
Identifiers
3D model (JSmol)
AbbreviationsTCE
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.062 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-167-4
KEGG
PubChem CID
RTECS number
  • KX4550000
UNII
UN number 1710
  • InChI=1S/C2HCl3/c3-1-2(4)5/h1H Yes check.svgY
    Key: XSTXAVWGXDQKEL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2HCl3/c3-1-2(4)5/h1H
  • Cl\C=C(/Cl)Cl
  • Cl\C=C(/Cl)Cl
  • ClC=C(Cl)Cl
Properties
C2HCl3
Molar mass 131.38 g·mol−1
AppearanceColorless liquid
Odor pleasant, chloroform-like
Density 1.46 g/cm3 at 20 °C
Melting point −84.8 °C (−120.6 °F; 188.3 K) [1]
Boiling point 86.7 °C (188.1 °F; 359.8 K) [2]
1.280 g/L [2]
Solubility Ether, ethanol, chloroform
log P 2.26 [3]
Vapor pressure 58 mmHg (0.076 atm) at 20 °C [4]
−65.8·10−6 cm3/mol
1.4777 at 19.8 °C
Viscosity 0.532 mPa·s [5]
Pharmacology
N01AB05 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Acute exposure can cause dizziness and loss of consciousness, chronic exposure can increase cancer risk. Unstable in presence of sunlight and caustic soda.
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-exclam.svg
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
420 °C (788 °F; 693 K)
Explosive limits 8-10.5% [4]
Lethal dose or concentration (LD, LC):
4920 mg/kg (oral, rat), 29000 mg/kg (dermal, rabbit) [6]
8450 ppm (mouse, 4 hr)
26300 (rat, 1 hr) [7]
2900 ppm (human)
37,200 ppm (guinea pig, 40 min)
5952 ppm (cat, 2 hr)
8000 ppm (rat, 4 hr)
11,000 (rabbit) [7]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm C 200 ppm 300 ppm (5-minute maximum peak in any 2 hours) [4]
REL (Recommended)
Ca [4]
IDLH (Immediate danger)
Ca [1000 ppm] [4]
Safety data sheet (SDS) Carl Roth
Legal status
  • BR: Class B1 (Psychoactive drugs) [8]
  • US:banned for medical use (1977)
Related compounds
Related vinyl halides
Vinyl chloride
Tetrachloroethylene
Trifluoroethylene
Related compounds
 Chloroform
1,1,1-Trichloroethane
1,1,2-Trichloroethane
Chloral
Supplementary data page
Trichloroethylene (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 ?)

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 [4] and sweet taste. [9] 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.

Contents

History

The earliest record of trichloroethylene synthesis dates back to 1836. It was obtained from the action of potassium hydroxide on 1,1,2,2-tetrachloroethane and 1,1,1,2-tetrachloroethane by Auguste Laurent and notated as C4HCl3 (then the atomic weight of carbon was thought to be the half of it really was). Laurent did not investigate the compound further. [10] [11]

Trichloroethylene's discovery is widely attributed to E. Fischer who made it in 1864 via the reduction of hexachloroethane with hydrogen. Fischer investigated TCE and noted its boiling point as between 87 and 90 degrees Celsius. [12] [13] [14] Commercial production began in Germany, in 1920 and in the US in 1925. [15]

The use of trichloroethylene in the food and pharmaceutical industries has been banned in much of the world since the 1970s due to concerns about its toxicity. Legislation has forced the replacement of trichloroethylene in many processes in Europe as the chemical was classified as a carcinogen carrying an R45 risk phrase, May cause cancer. Many degreasing chemical alternatives are being promoted such as Ensolv and Leksol; however, each of these is based on n-propyl bromide which carries an R60 risk phrase of May impair fertility, and would not be a legally acceptable substitute.

Anaesthesia

Trichloroethylene is a good analgesic at 0.35 to 0.5% concentrations. [16] Trichloroethylene was used in the treatment of trigeminal neuralgia beginning in 1916. [17]

Pioneered by Imperial Chemical Industries in Britain, under the trade name "Trilene" (from trichloroethylene) , its development was hailed as an anesthetic revolution. It was mostly known as "Trimar" in the United States. The –mar suffix indicates study and development at the University of Maryland, e.g., "Fluoromar" for fluroxene and "Vinamar" for ethyl vinyl ether". [18] From the 1940s through the 1980s, both in Europe and North America, trichloroethylene was used as a volatile anesthetic almost invariably administered with nitrous oxide. Marketed in the UK by Imperial Chemical Industries under the trade name Trilene it was coloured blue (with a dye called waxoline blue in 1:200,000 concentration) [19] to avoid confusion with the similar-smelling chloroform. Trilene was stabilised with 0.01% thymol. [19]

Cyprane handheld anaesthetic device for trichloroethylene, made in the UK, 1947. This device was designed for self-administration by the patient. Cyprane Trilene inhaler.png
Cyprane handheld anaesthetic device for trichloroethylene, made in the UK, 1947. This device was designed for self-administration by the patient.

Originally thought to possess less hepatotoxicity than chloroform, and without the unpleasant pungency and flammability of ether, TCE replaced earlier anesthetics chloroform and ether in the 1940s. TCE use was nonetheless soon found to have several pitfalls. These included promotion of cardiac arrhythmias, low volatility and high solubility preventing quick anesthetic induction, reactions with soda lime used in carbon dioxide absorbing systems, prolonged neurologic dysfunction when used with soda lime, and evidence of hepatotoxicity as had been found with chloroform. Alkali components of carbon dioxide absorbers reacted with trichloroethylene and released dichloroacetylene, a neurotoxin.

The introduction of halothane in 1956 greatly diminished the use of TCE as a general anesthetic in the 1960s, as halothane allowed much faster induction and recovery times and was considerably easier to administer. Trichloroethylene has been used in the production of halothane. [20]

Bottle of trichloroethylene for anesthesia by ICI Bottle of trichloroethylene, England, 1940-1960 Wellcome L0065373.jpg
Bottle of trichloroethylene for anesthesia by ICI
Inhaler used for Trilene, 1961-1970 Trilene inhaler, London, England, 1961-1970 Wellcome L0065862.jpg
Inhaler used for Trilene, 1961-1970
Pain Relief in Childbirth (1954)
Nuvola apps kaboodle.svg

Trilene was also used as an inhaled analgesic, mainly during childbirth, often self-applied by the patient. Trichloroethylene was introduced for obstetrical anaesthesia in 1943, and used until the 1980s. [16] Its anaesthetic use was banned in the United States in 1977 but the anaesthetic use in the United Kingdom remained until the late 1980s (especially for childbirth). [17] Fetal toxicity and concerns about the carcinogenic potential of TCE led to its abandonment in developed countries by the 1980s. TCE was used with halothane in the tri-service field anaesthetic apparatus used by the UK armed forces under field conditions. As of 2000, TCE was still in use as an anesthetic in Africa. [21]

Production

Today, most trichloroethylene is produced from ethylene. First, ethylene is chlorinated over a ferric chloride catalyst to produce 1,2-dichloroethane:

CH2=CH2 + Cl2 → ClCH2CH2Cl

When heated to around 400 °C with additional chlorine, 1,2-dichloroethane is converted to trichloroethylene:

ClCH2CH2Cl + 2 Cl2 → ClCH=CCl2 + 3 HCl

This reaction can be catalyzed by a variety of substances. The most commonly used catalyst is a mixture of potassium chloride and aluminum chloride. However, various forms of porous carbon can also be used. This reaction produces tetrachloroethylene as a byproduct and depending on the amount of chlorine fed to the reaction, tetrachloroethylene can even be the major product. Typically, trichloroethylene and tetrachloroethylene are collected together and then separated by distillation.

Prior to the early 1970s, however, most trichloroethylene was produced in a two-step process from acetylene. First, acetylene was treated with chlorine using a ferric chloride catalyst at 90 °C to produce 1,1,2,2-tetrachloroethane according to the chemical equation:

HC≡CH + 2 Cl2 → Cl2CHCHCl2

The 1,1,2,2-tetrachloroethane is then dehydrochlorinated to give trichloroethylene. This can be accomplished either with an aqueous solution of calcium hydroxide:

2 Cl2CHCHCl2 + Ca(OH)2 → 2 ClCH=CCl2 + CaCl2 + 2 H2O

or in the vapor phase by heating it to 300–500 °C on a barium chloride or calcium chloride catalyst:

Cl2CHCHCl2 → ClCH=CCl2 + HCl

Common impurities in reagent and technical grade TCE are methyl chloroform, carbon tetrachloride, ethylene dichloride, tetrachloroethanes, benzene and phenol. However, these compounds are present in very small amounts and do not possess any risk. [17]

Uses

Trichloroethylene is an effective solvent for a variety of organic materials. It is mainly used for cleaning. Trichloroethylene is an ingredient in various printing ink, varnishes and industrial paint formulations, as an active ingredient. [22] [17] Other uses include dyeing and finishing operations, adhesive formulations, the rubber industry, adhesives, lacquers, and paint strippers. It is applied before plating, anodizing, and painting. [23]

When trichloroethylene was first widely produced in the 1920s, its major use was to extract vegetable oils from plant materials such as soy, coconut, and palm. Other uses in the food industry included coffee decaffeination (removal of caffeine) and the preparation of flavoring extracts from hops and spices. [17] TCE was used a freezing point depressant in carbon tetrachloride fire extinguishers. [17]

Trichloroethylene is also a chain terminator for polyvinyl chloride. [17] Chlorination gives pentachloroethane.

Cleaning solvent

TCE has also been used as a dry cleaning solvent, although mostly replaced by tetrachloroethylene, except for spot cleaning where it is still used under the trade name Picrin.[ citation needed ]

Perhaps the greatest use of TCE is as a degreaser for metal parts. It has been widely used in degreasing and cleaning since the 1920s because of its low cost, low flammability, low toxicity and high effectivity as a solvent. The demand for TCE as a degreaser began to decline in the 1950s in favor of the less toxic 1,1,1-trichloroethane. However, 1,1,1-trichloroethane production has been phased out in most of the world under the terms of the Montreal Protocol due to its effect of ozone depletion. As a result, trichloroethylene has experienced some resurgence in use as a degreaser. [17]

Trichloroethylene is used to remove grease and lanolin from wool before weaving. [17]

TCE has also been used in the United States to clean kerosene-fueled rocket engines (TCE was not used to clean hydrogen-fueled engines such as the Space Shuttle Main Engine). During static firing, the RP-1 fuel would leave hydrocarbon deposits and vapors in the engine. These deposits had to be flushed from the engine to avoid the possibility of explosion during engine handling and future firing. TCE was used to flush the engine's fuel system immediately before and after each test firing. The flushing procedure involved pumping TCE through the engine's fuel system and letting the solvent overflow for a period ranging from several seconds to 30–35 minutes, depending upon the engine. For some engines, the engine's gas generator and liquid oxygen (LOX) dome were also flushed with TCE before test firing. [24] [25] The F-1 rocket engine had its LOX dome, gas generator, and thrust chamber fuel jacket flushed with TCE during launch preparations. [25]

Refrigerants

TCE is also used in the manufacture of a range of fluorocarbon refrigerants [26] such as 1,1,1,2-tetrafluoroethane more commonly known as HFC 134a. TCE was also used in industrial refrigeration applications due to its high heat transfer capabilities and its low-temperature specification.

Safety

Chemical instability

Despite its widespread use as a metal degreaser, trichloroethylene itself is unstable in the presence of metal over prolonged exposure. As early as 1961 this phenomenon was recognized by the manufacturing industry when stabilizing additives were added to the commercial formulation. Since the reactive instability is accentuated by higher temperatures, the search for stabilizing additives was conducted by heating trichloroethylene to its boiling point under a reflux condenser and observing decomposition. Definitive documentation of 1,4-dioxane as a stabilizing agent for TCE is scant due to the lack of specificity in early patent literature describing TCE formulations. [27] [28] Epichlorohydrin, butylene oxide, N-methylpyrrole and ethyl acetate are common stabilisers for TCE, with epichlorohydrin being the most persistent and effective. [29] Other chemical stabilizers include ketones such as methyl ethyl ketone.

Du Pont Triclene D 1947.png
Trimar 1952 Ohio Chemical.png
Two advertisements for trichloroethylene in two different uses, metal degreasing (1947) and anaesthesia (1952)

Physiological effects

When inhaled, trichloroethylene produces central nervous system depression resulting in general anesthesia. These effects may be mediated by trichloroethylene acting as a positive allosteric modulator of inhibitory GABAA and glycine receptors. [30] [31] Its high blood solubility results in a less desirable slower induction of anesthesia. At low concentrations, it is relatively non-irritating to the respiratory tract. Higher concentrations result in tachypnea. Many types of cardiac arrhythmias can occur and are exacerbated by epinephrine (adrenaline). It was noted in the 1940s that TCE reacted with carbon dioxide (CO2) absorbing systems (soda lime) to produce dichloroacetylene by dehydrochlorination and phosgene. [32] Cranial nerve dysfunction (especially the fifth cranial nerve) was common when TCE anesthesia was given using CO2 absorbing systems. Muscle relaxation with TCE anesthesia sufficient for surgery was poor. For these reasons as well as problems with hepatotoxicity, TCE lost popularity in North America and Europe to more potent anesthetics such as halothane by the 1960s. [33]

The symptoms of acute non-medical exposure are similar to those of alcohol intoxication, beginning with headache, dizziness, and confusion and progressing with increasing exposure to unconsciousness. [34] Much of what is known about the chronic human health effects of trichloroethylene is based on occupational exposures. Besides the effects to the central nervous system, workplace exposure to trichloroethylene has been associated with toxic effects in the liver and kidney. [34] A history of long-term exposure to high concentrations of trichloroethylene is a suspected environmental risk of Parkinson's disease. [35]

Metabolism

Trichloroethylene is metabolised to trichloroepoxyethane (TCE oxide) which rapidly isomerises to trichloroacetaldehyde (chloral). [36] Chloral hydrates to chloral hydrate in the body. Chloral hydrate is either reduced to 2,2,2-trichloroethanol or oxidised to trichloroacetic acid. Monochloroacetic acid, [37] dichloroacetic acid [38] and trichloromethane [37] [39] [40] were also detected as minor metabolites of TCE.

Exposure and regulations

With a specific gravity greater than 1 (denser than water), trichloroethylene can be present as a dense non-aqueous phase liquid (DNAPL) if sufficient quantities are spilt in the environment.

The first known report of TCE in groundwater was given in 1949 by two English public chemists who described two separate instances of well contamination by industrial releases of TCE. [41] Based on available federal and state surveys, between 9% and 34% of the drinking water supply sources tested in the US may have some TCE contamination, though EPA has reported that most water supplies comply with the maximum contaminant level (MCL) of 5 ppb. [42]

Generally, atmospheric levels of TCE are highest in areas of concentrated industry and population. Atmospheric levels tend to be lowest in rural and remote regions. Average TCE concentrations measured in air across the United States are generally between 0.01 ppb and 0.3 ppb, although mean levels as high as 3.4 ppb have been reported. [43] TCE levels in the low parts per billion range have been measured in food; however, levels as high as 140 ppb were measured in a few samples of food. [43] TCE levels above background[ how? ] have been found in homes undergoing renovation. [44]

Existing regulations

State, federal, and international agencies classify trichloroethylene as a known or probable carcinogen for humans. In 2014, the International Agency for Research on Cancer updated its classification of trichloroethylene to Group 1, indicating that sufficient evidence exists that it can cause cancer of the kidney in humans as well as some evidence of cancer of the liver and non-Hodgkin's lymphoma. [45]

In the European Union, the Scientific Committee on Occupational Exposure Limit Values (SCOEL) recommends an exposure limit for workers exposed to trichloroethylene of 10 ppm (54.7 mg/m3) for 8-hour TWA and of 30 ppm (164.1 mg/m3) for STEL (15 minutes). [46]

Existing EU legislation aimed at protection of workers against risks to their health (including Chemical Agents Directive 98/24/EC [47] and Carcinogens Directive 2004/37/EC [48] ) currently do not impose binding minimum requirements for controlling risks to workers' health during the use phase or throughout the life cycle of trichloroethylene.

In 2023, the United States United States Environmental Protection Agency (EPA) determined that trichloroethylene presents a risk of injury to human health in various uses, including during manufacturing, processing, mixing, recycling, vapor degreasing, as a lubricant, adhesive, sealant, cleaning product, and spray. It is dangerous from both inhalation and dermal exposure and was most strongly associated with immunosuppressive effects for acute exposure, as well as autoimmune effects for chronic exposures. [49] As of June 1, 2023, two U.S. states (Minnesota and New York) have acted on the EPA's findings and banned trichloroethylene in all cases but research and development. [50] [51] According to the US EPA, in October 2023 it "proposed to ban the manufacture (including import), processing, and distribution in commerce of TCE for all uses, with longer compliance time frames and workplace controls (including an exposure limit) for some processing and industrial and commercial uses until the prohibitions come into effect"[ needs update ] to "protect everyone including bystanders from the harmful health effects of TCE". [52]

Remediation

Recent research has focused on the in-place remediation of trichloroethylene in soil and groundwater using potassium permanganate instead of removal for off-site treatment and disposal. Naturally occurring bacteria have been identified with the ability to degrade TCE. Dehalococcoides sp. degrade trichloroethylene by reductive dechlorination under anaerobic conditions. Under aerobic conditions, Pseudomonas fluorescens can co-metabolize TCE. Soil and groundwater contamination by TCE has also been successfully remediated by chemical treatment and extraction. The bacteria Nitrosomonas europaea can degrade a variety of halogenated compounds including trichloroethylene. [53] Toluene dioxygenase has been reported to be involved in TCE degradation by Pseudomonas putida . [54] In some cases, Xanthobacter autotrophicus can convert up to 51% of TCE to CO and CO2. [54]

Society and culture

Groundwater and drinking water contamination from industrial discharge including trichloroethylene is a major concern for human health and has precipitated numerous incidents and lawsuits in the United States.

The 1995 non-fiction book A Civil Action was written about a lawsuit ( Anderson v. Cryovac ) against following the increase in cancer cases after trichloroethylene pollution incidents and it was adapted to cinema in 1998.

TCE has been used as a recreational drug. [55] Common methods of taking trichloroethylene recreationally include inhalation from a rag (similar to taking an inhalational anaesthetic) and drinking. [56] Most TCE abusers were young people and workers who use the chemical in their workplace. The main reason for abuse is TCE's euphoriant and slight hallucinogenic effect. [56] Some workers had become addicted to TCE. [57]

Related Research Articles

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">Halothane</span> General anaesthetic

Halothane, sold under the brand name Fluothane among others, is a general anaesthetic. It can be used to induce or maintain anaesthesia. One of its benefits is that it does not increase the production of saliva, which can be particularly useful in those who are difficult to intubate. It is given by inhalation.

<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">Tetrachloroethylene</span> Chemical compound in very wide use

Tetrachloroethylene, also known as perchloroethylene or under the systematic name tetrachloroethene, and abbreviations such as 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.

<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.

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.

<span class="mw-page-title-main">Inhalational anesthetic</span> Volatile or gaseous anesthetic compound delivered by inhalation

An inhalational anesthetic is a chemical compound possessing general anesthetic properties that is delivered via inhalation. They are administered through a face mask, laryngeal mask airway or tracheal tube connected to an anesthetic vaporiser and an anesthetic delivery system. Agents of significant contemporary clinical interest include volatile anesthetic agents such as isoflurane, sevoflurane and desflurane, as well as certain anesthetic gases such as nitrous oxide and xenon.

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 chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water and other chlorocarbons.

<span class="mw-page-title-main">Halogenated ether</span> Subcategory of ether used in anesthesiology

A halogenated ether is a subcategory of a larger group of chemicals known as ethers. An ether is an organic chemical that contains an ether group—an oxygen atom connected to two (substituted) alkyl groups. A good example of an ether is the solvent diethyl ether. What differentiates a halogenated ether from other types of ethers is the substitution (halogenation) of one or more hydrogen atoms with a halogen atom. Halogen atoms include fluorine, chlorine, bromine, and iodine.

1,1-Dichloroethane is a chlorinated hydrocarbon. It is a colorless oily liquid with a chloroform-like odor. It is not easily soluble in water, but miscible with most organic solvents.

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.

<span class="mw-page-title-main">Methoxychlor</span> Synthetic organochloride insecticide, now obsolete.

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<span class="mw-page-title-main">View-Master factory supply well</span>

The View-Master factory supply well in Beaverton, Oregon, was evaluated for public health effects by the Oregon Department of Human Services (ODHS) under a cooperative agreement with the Agency for Toxic Substances and Disease Registry (ATSDR). Workers there were potentially exposed to the industrial solvent trichloroethylene (TCE), classified by the International Agency for Research on Cancer (IARC) as a probable human carcinogen. At the factory, which closed in 2001, it had been estimated by ODHS that up to 25,000 workers may have been exposed to TCE via the factory's drinking water, which was drawn from a well on-site. However, further investigation showed that the actual number of employees who can be identified from employment records for the site is approximately half that number. In addition, the number of employees identified as having worked at the site for more than five years is likely to be less than 1,000. The site is now considered safe.

<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">1,1,1,2-Tetrachloroethane</span> Chemical compound

1,1,1,2-Tetrachloroethane is a chlorinated hydrocarbon. It is a colorless liquid with a sweet chloroform-like odor. It is used as a solvent and in the production of wood stains and varnishes. It is an isomer of 1,1,2,2-tetrachloroethane.

The Omega Chemical Corporation was a refrigerant and solvent recycling company that operated from 1976 to 1991 in Whittier, California. Due to improper waste handling and removal, the soil and groundwater beneath the property became contaminated and the area is now referred to as the Omega Chemical Superfund Site. Cleanup of the site began in 1995 with the removal of hazardous waste receptacles and a multimillion-dollar soil vaporization detoxifying system.

The Orange Valley Regional Groundwater Superfund site is a group of wells in Orange and West Orange, two municipalities in Essex County, New Jersey, United States. The groundwater in the public wells are contaminated with the hazardous chemicals of Trichloroethylene (TCE), Dichloroethene (DCE), Tetrachloroethylene (Perchloroethene), 1,1-Dichloroethene (1,1-DCE), and 1,2-Dichloroethene (1,2-DCE). These chemicals pose a huge risk to the towns nearby population, as the wells are a source of public drinking water. In March 2012, the site was added to the National Priorities List (NPL) of the United States Environmental Protection Agency (EPA) Superfund site list.

References

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  2. 1 2 "Trichloroethylene". Sigmaaldrich.com. Retrieved 20 October 2014.
  3. ↑ "Trichloroethylene". www.chemsrc.com.
  4. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0629". National Institute for Occupational Safety and Health (NIOSH).
  5. ↑ Venkatesulu, D.; Venkatesu, P.; Rao, M. V. Prabhakara (1997). "Viscosities and Densities of Trichloroethylene or Tetrachloroethylene with 2-Alkoxyethanols at 303.15 K and 313.15 K". Journal of Chemical & Engineering Data. 42 (2): 365–367. doi:10.1021/je960316f. ISSN   0021-9568.
  6. ↑ FischerSci Trichloroethylene SDS
  7. 1 2 "Trichloroethylene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  8. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  9. ↑ Trichloroethylene (TCE) on ATSDR
  10. ↑ Essai sur l'Action du Chlore sur la Liqueur des Hollandais et sur quelques Ethers in Annal. de Chimie, LXIII. (1836) page 379
  11. ↑ The so-called Perchloride of Formyl, Gmelin, L. (translated in 1855). Hand-book of Chemistry: Organic chemistry. UK: Cavendish Society. pages 200–201
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  13. ↑ Waters, E. M.; Gerstner, H. B.; Huff, J. E. (January 1977). "Trichloroethylene. I. An overview". Journal of Toxicology and Environmental Health. 2 (3): 671–707. doi:10.1080/15287397709529469. ISSN   0098-4108.
  14. ↑ Hardie DWF (1964). Chlorocarbons and chlorohydrocarbons. 1,1,2,2-Tetrachloroethane. In: Encyclopedia of Chemical Technology. Kirk RE, Othmer DF, editors. New York: John Wiley & Sons, pp. 159–164
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  18. ↑ John C. Krantz, Jr (1962). A Portrait of Medical History and Current Medical Problems. The John D. Lucas Printing Company. p. 160.
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  22. ↑ Subramanian, Indu (20 Nov 2023). "Is Most Parkinson's Disease Man-Made?". Medscape. Retrieved 29 Nov 2023.
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  25. 1 2 "F-1 Rocket Engine Operating Instructions". Ntrs.nasa.gov. Retrieved 20 October 2014.
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  27. ↑ Murphy, Brian L; Morrison, Robert D. (2015). "9. Source Identification and Age Dating of Chlorinated Solvents". Introduction to environmental forensics (3rd ed.). Academic Press. sec. 9.2.2.1 1,4-Dioxane. ISBN   978-0124047075.
  28. ↑ Mohr, Thomas K. G. (2010). "Historical Use of Chlorinated Solvents and Their Stabilizing Compounds". Environmental investigation and remediation: 1,4-dioxane and other solvent stabilizers. CRC Press. p. 53 "Was 1,4-Dioxane a Stabilizer for Trichloroethylene?". ISBN   978-1566706629.
  29. ↑ Morrison, R. D., Murphy, B. L. (2013). Chlorinated Solvents: A Forensic Evaluation. UK Royal Society of Chemistry.
  30. ↑ M. J. Beckstead, J. L. Weiner, E. I. 2nd Eger, D. H. Gong & S. J. Mihic (2000). "Glycine and gamma-aminobutyric acid(A) receptor function is enhanced by inhaled drugs of abuse". Molecular Pharmacology . 57 (6): 1199–1205. PMID   10825391.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  31. ↑ M. D. Krasowski & N. L. Harrison (2000). "The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations". British Journal of Pharmacology . 129 (4): 731–743. doi:10.1038/sj.bjp.0703087. PMC   1571881 . PMID   10683198.
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  34. 1 2 "Trichloroethylene | Technology Transfer Network Air Toxics Web site | US EPA". Epa.gov. Retrieved 2013-10-05.
  35. ↑ Dorsey ER, Zafar M, Lettenberger SE, et al. (2023). "Trichloroethylene: An Invisible Cause of Parkinson's Disease?". J Parkinsons Dis. 13 (2): 203–218. doi:10.3233/JPD-225047. PMC   10041423 . PMID   36938742.
  36. ↑ Fishbein, L. (1977). Potential Industrial Carcinogens and Mutagens. Environmental Protection Agency, Office of Toxic Substances
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  38. ↑ Biologically Based Methods for Cancer Risk Assessment. (2013). Springer US.
  39. ↑ Toxicological Profile for Trichloroethylene: Draft. (1995). U.S. Department of Health and Human Services.
  40. ↑ Mutagenesis. (1978). page 268
  41. ↑ Lyne FA, McLachlan T (1949). "Contamination of water by trichloroethylene" p. 513 in Lilliman, B.; Houlihan, J. E.; Lyne, F. A.; McLachlan, T. (1949). "Notes". The Analyst. 74 (882): 510–513. Bibcode:1949Ana....74..510L. doi:10.1039/AN9497400510.
  42. ↑ "Consumer Factsheet on: Trichloroethylene" (PDF). Epa.gov. Retrieved 22 February 2015.
  43. 1 2 "Trichloroethylene Toxicity: Where is Trichloroethylene Found? | Environmental Medicine | ATSDR". www.atsdr.cdc.gov. 2022-09-09. Retrieved 2023-03-02.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  44. ↑ "Trichloroethylene (tce) TEACH Chemical Summary - epa nepis".
  45. ↑ Trichloroethylene (IARC Summary & Evaluation, Volume 106, 2014) (PDF). iarc.fr. Retrieved 2016-03-08.
  46. ↑ "Recommendation from the Scientific Committee on Occupational Exposure Limits for Trichloroethylene (SCOEL/SUM/142)" (PDF). April 2009.
  47. ↑ Council Directive 98/24/EC of 7 April 1998 on the protection of the health and safety of workers from the risks related to chemical agents at work (fourteenth individual Directive within the meaning of Article 16(1) of Directive 89/391/EEC)
  48. ↑ Directive 2004/37/EC of the European Parliament and of the Council of 29 April 2004 on the protection of workers from the risks related to exposure to carcinogens, mutagens or reprotoxic substances at work (Sixth individual Directive within the meaning of Article 16(1) of Council Directive 89/391/EEC) (codified version)
  49. ↑ US EPA, OCSPP (2020-02-12). "Final Risk Evaluation for Trichloroethylene" (PDF). www.epa.gov. Retrieved 2023-06-03.
  50. ↑ "How Minnesota passed the country's first ban on trichloroethylene". www.pca.state.mn.us/news-and-stories. Minnesota Pollution Control Agency. 28 August 2023. Archived from the original on 6 September 2023. Retrieved 6 September 2023.
  51. ↑ Minnesota Statutes (act 116.38 (also known as "White Bear Area Neighborhood Concerned Citizens Group Ban TCE Act"), Environmental Protection, Chapter 116, Section 116.385). Minnesota Legislature. 2022. Archived from the original on 6 September 2023.
  52. ↑ "Risk Management for Trichloroethylene (TCE)". US EPA. 21 Nov 2023. Retrieved 23 Nov 2023.
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  55. ↑ Trichloroethylene in Neurology in Clinical Practice, Daroff, R. B., Fenichel, G. M., Jankovic, J., Mazziotta, J. C. (2012).
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  57. ↑ Trichlorethylene Addiction and its Effects (1972) Boleslaw Alapin M.D., M.R.C. Psych. British Journal of Addiction to Alcohol & Other DrugsVolume 68, Issue 4 p. 331-335 DOI

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