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Encyclopedia > Trichloroethylene
Properties

Image File history File links Download high resolution version (952x814, 11 KB) Summary Description: Skeletal formula of trichloroethene (C2HCl3). ... Image File history File links Trichloroethylene_Space_filling. ...

General

Name Trichloroethylene
Chemical formula ClCH=CCl2
Appearance Colorless liquid

Physical A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... Color is an important part of the visual arts. ...

Formula weight 131.4 g/mol
Melting point 200 K (-73 °C)
Boiling point 360 K (87 °C)
Density 1460 kg/m3 (liquid)
Solubility insoluble in water

Thermochemistry ... The gram or gramme, symbol g, is a unit of mass. ... The mole and its simple conversions into different units of measurements. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The kelvin (symbol: K) is the SI unit of temperature, and is one of the seven SI base units. ... A degree Celsius (°C) is a unit of temperature named after the Swedish astronomer Anders Celsius (1701-1744), who first proposed a similar system in 1742. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... The international prototype, made of platinum-iridium, which is kept at the BIPM under conditions specified by the 1st CGPM in 1889. ... The Metre (or Meter) is the base fundamental unit of length in the metric measurement system as defined originally by the French Academy of Sciences during the French Revolutionary–Napoleonic war era, and subsequently adopted by various successive International Standards Committees as the utility, elegance, and self-consistency of the... A substance is soluble in a fluid if it dissolves in that fluid. ...

ΔfH0gas -7.78 kJ/mol
ΔfH0liquid -42.3 kJ/mol
ΔfH0solid ? kJ/mol
S0gas, 100 kPa ? J/(mol·K)
S0liquid, 100 kPa ? J/(mol·K)
S0solid ? J/(mol·K)

Safety The standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of a substance in its standard state from its constituent elements in their standard states (the most stable form of the element at 1 atmosphere... The joule (symbol: J) is the SI unit of energy, or work with base units of kg·m2/s2. ... The standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of a substance in its standard state from its constituent elements in their standard states (the most stable form of the element at 1 atmosphere... The standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of a substance in its standard state from its constituent elements in their standard states (the most stable form of the element at 1 atmosphere... In chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure. ... The joule (symbol: J) is the SI unit of energy, or work with base units of kg·m2/s2. ... In chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure. ... In chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure. ...

Ingestion May cause nausea, stomach irritation. Inhaling vapors from stomach into lungs causes symptoms like those of inhalation.
Inhalation Can cause dizziness, drowsiness, confusion, unconsciousness, and cardiac failure. May irritate mucous membranes.
Skin May cause skin irritation. Prolonged exposure may lead to chronic irritation.
Eyes May cause burning sensation, watering.
More info Hazardous Chemical Database

SI units were used where possible. Unless otherwise stated, standard conditions were used. In psychology, sensation is the first stage in the chain of biochemical and neurologic events that begins with the impinging of a stimulus upon the receptor cells of a sensory organ, which then leads to perception, the mental state that is reflected in statements like I see a uniformly blue... Cover of brochure The International System of Units. ... Temperature and air pressure can vary from one place to another on the Earth, and can also vary in the same place with time. ...


Disclaimer and references This page refers to the data given in chemical compound property tables. ...

The chemical compound trichloroethylene is a chlorinated hydrocarbon commonly used as an industrial solvent. It is a clear non-flammable liquid with a sweet smell. A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Hydrocarbons are refined at oil refineries and chemical plants In chemistr, a hydrocarbon is any chemical compound that consists only of the elements carbon (C) and hydrogen (H). ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ...


Its IUPAC name is trichloroethene. In industry, it is informally referred to by the abbreviations TCE and tri, and it is sold under a variety of trade names. In medicine, it was commonly referred to as trilene and trimar during its use as a general anesthetic. The International Union of Pure and Applied Chemistry (IUPAC) is an international non-governmental organization devoted to the advancement of chemistry. ... A general anaesthetic drug is an anaesthetic (or anesthetic AE) drug that brings about a reversible loss of consciousness. ...

Contents


Production

Prior to the early 1970s, 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 The chemical compound and unsaturated hydrocarbon acetylene, also known under IUPAC nomenclature (see IUPAC nomenclature of organic chemistry) as ethyne, was discovered in 1836 by Edmund Davy, in England. ... Iron(III) chloride, generically called ferric chloride, is an iron-based salt of chemical formula FeCl3. ... A catalyst (Greek: καταλύτης, catalytÄ“s) is a substance that accelerates the rate (speed) of a chemical reaction (see also catalysis). ... A chemical equation is a symbolic representation of a chemical reaction. ...

HC≡CH + 2 Cl2 → Cl2CHCHCl2

The 1,1,2,2-tetrachloroethane is then dehydrochlorinated to give trichloroethylene. This can either be accomplished with an aqueous solution of calcium hydroxide The chemical compound and unsaturated hydrocarbon acetylene, also known under IUPAC nomenclature (see IUPAC nomenclature of organic chemistry) as ethyne, was discovered in 1836 by Edmund Davy, in England. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Calcium hydroxide Calcium hydroxide is a chemical compound with the chemical formula Ca(OH)2. ...

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 Calcium hydroxide Calcium hydroxide is a chemical compound with the chemical formula Ca(OH)2. ... R-phrases S-phrases , , RTECS number EV9800000, anhydrous EV9810000, dihydrate EV9830000, hexahydrate Supplementary data page Structure & properties n, εr, etc. ... Barium chloride (BaCl2) is a salt of barium and chlorine. ... R-phrases S-phrases , , RTECS number EV9800000, anhydrous EV9810000, dihydrate EV9830000, hexahydrate Supplementary data page Structure & properties n, εr, etc. ...

Cl2CHCHCl2 → ClCH=CCl2 + HCl

Today, however, most trichloroethylene is produced from ethylene. First, ethylene is chlorinated over a ferric chloride catalyst to produce 1,2-dichloroethane. The chemical substance hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride (HCl) gas. ... R-phrases R12, R67 S-phrases S2, S9, S16, S33, S46 Flash point Flammable gas Explosive limits 2. ... Iron(III) chloride, generically called ferric chloride, is an iron-based salt of chemical formula FeCl3. ... Flash point  ? °C R/S statement R: ? S: ? RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ...

CH2=CH2 + Cl2 → ClCH2CH2Cl

When heated to around 400 °C with additional chlorine, 1,2-dichloroethane is converted to trichloroethylene R-phrases R12, R67 S-phrases S2, S9, S16, S33, S46 Flash point Flammable gas Explosive limits 2. ... Flash point  ? °C R/S statement R: ? S: ? RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ...

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. The chemical compound potassium chloride (KCl) is a metal halide composed of potassium and chlorine. ... Aluminium chloride (AlCl3) is a compound of aluminium and chlorine. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... Tetrachloroethylene Cl2C=CCl2 is a manufactured chemical that is widely used for the dry cleaning of fabrics and for metal-degreasing. ... Strathisla whisky distillery in Keith, Scotland Distillation is a method of separation of substances based on differences in their vapour pressures. ...


Uses

Trichloroethylene is a good solvent for a variety of organic materials. When it 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 and the preparation of flavoring extracts from hops and spices. It was also used as a dry cleaning solvent, although tetrachloroethylene (also known as perchloroethylene) surpassed it in this role in the 1950s. A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Organic chemistry is that part of chemistry concerned with the composition, structure, properties, reactions and synthesis of organic compounds. ... It has been suggested that this article or section be merged with cooking oil. ... Binomial name Glycine max Soybeans (US) or soya beans (UK) (Glycine max) are a high-protein legume (Family Fabaceae) grown as food for both humans and livestock. ... Binomial name Cocos nucifera L. The Coconut Palm (Cocos nucifera), is a member of the Family Arecaceae (palm family). ... Genera Many; see list of Arecaceae genera Arecaceae (also known as Palmae or Palmaceae), the palm family, is a family of flowering plants, belonging to the monocot order Arecales. ... Coffee in beverage form. ... Decaffeination is the act of removing caffeine from coffee beans and tea. ... Hop flower in a Hallertau hopgarden Hops are the flowers of Humulus lupulus used as a flavouring and stability agent in beer since the seventeenth century. ... Screen shot of Spice OPUS, a fork of Berkeley SPICE SPICE (Simulation Program with Integrated Circuits Emphasis) is a general purpose analog circuit simulator. ... This article is in need of attention from an expert on the subject. ... Tetrachloroethylene Cl2C=CCl2 is a manufactured chemical that is widely used for the dry cleaning of fabrics and for metal-degreasing. ...


Due to concerns about its toxicity, the use of trichloroethylene in the food and pharmaceutical industries has been banned in much of the world since the 1970s.


For most of its history, trichloroethylene has been widely used as a degreaser for metal parts. In the late 1950s, the demand for trichloroethylene as a degreaser began to decline 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, and as a result trichloroethylene has experienced a resurgence in use. It has also been used for drying out the last bit of water for production of 100% ethanol. The chemical compound 1,1,1-trichloroethane is a chlorinated hydrocarbon that was until recently widely used as an industrial solvent. ... The Montreal Protocol on Substances That Deplete the Ozone Layer is an international treaty designed to protect the ozone layer by phasing out the production of a number of substances believed to be responsible for ozone depletion. ...


Supplanting chloroform and ether for a significant period of time, trichloroethylene demonstrated superior efficacy in induction times and cost-effectiveness. Pioneered by ICI in Britain, its development was hailed as a revolution: lacking the great hepatotoxic liability of chloroform and the unpleasant pungency and flammability of ether, it nonetheless had several pitfalls, including the sensitization of the myocardium to epinephrine, potentially acting in an arrhythmogenic manner. Its low volatility demanded the employment of carefully regulated heat in its vaporization. Research demonstrating its transient elevation of LFTs (Liver Function Tests) raised concerns regarding its hepatoxic potential; several deaths occurred as a result, though the incidence was comparable to that of halothane hepatitis. Incompatibility with soda lime (the CO2 adsorbent utilized in closed-circuit, low-flow rebreathing systems) presented dangers: it was readily decomposed into 1,2-dichloroacetylene, a neurotoxic compound potentially responsible for its hepatoxic potential, though its metabolite trichloroacetic acid is more probably the etiological source of the latter. Halothane usurped a great portion of its market in 1956, with its total abandonment not achieved until the 1980s, when its use as an analgesic in obstetrics was implicated in foetal death. Concerns of its carcinogenic potential were raised simultaneously. PEL-TWA (OSHA) 50 ppm (240 mg/m3) IDLH (NIOSH) 500 ppm Flash point non-flammable RTECS number FS9100000 Supplementary data page Structure & properties n, εr, etc. ... Flash point -45 °C Autoignition temperature 170 °C R/S statement RTECS number KI5775000 Supplementary data page Structure and properties n, εr, etc. ... Imperial Chemical Industries (ICI) is a British chemical company, based in London. ... Hepatotoxicity (from hepatic toxicity) is chemical-driven liver damage. ... PEL-TWA (OSHA) 50 ppm (240 mg/m3) IDLH (NIOSH) 500 ppm Flash point non-flammable RTECS number FS9100000 Supplementary data page Structure & properties n, εr, etc. ... Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... Myocardium is the muscular tissue of the heart. ... Epinephrine (INN), also epinephrin (both pronounced ep-i-NEF-rin), or adrenaline (BAN) is a hormone and a neurotransmitter. ... Structural formula of halothane Halothane vapour is an inhalational general anaesthetic. ... Structural formula of halothane Halothane vapour is an inhalational general anaesthetic. ...


The active metabolite of trichloroethylene is trichloroethanol, identical to that of chloral hydrate. Therefore, concerns of the carcinogenicity of the latter have been raised, and is subject to on-going debate. Chloral hydrate is a sedative and hypnotic drug, also known as trichloroacetaldehyde monohydrate, 2,2,2-trichloro-1,1-ethanediol, and the tradenames Aquachloral, Novo-Chlorhydrate, Somnos, Noctec, and Somnote. ...


Chemical instability

Although it has proven useful as a metal degreaser, trichloroetylene itself is unstable in the presence of metal over prolonged exposure. As early as the 1961 this phenomenon was clearly recognized by the manufacturing industry, since an additive was instilled in the commercial formulation of trichloroethylene. The reactive instability is accentuated by higher temperatures, so that the search for stabilizing additives is conducted by heating trichloroethylene to its boiling point in a reflux condenser and observing decomposition. The first widely used stabilizing additive was dioxane; however, its use was patented by Dow Chemical Company and could not be used by other manufacturers. Considerable research took place in the 1960s to develope alternative stabilizers for trichlorethylene. The principle family of chemicals that showed promise was the ketone family, such as methyl ethyl ketone. 1,4-Dioxane, often just called dioxane, is a clear, colorless organic compound which is a liquid at room temperature and pressure. ... The Dow Chemical Company (NYSE: DOW)(TYO: 4850 ) is a multinational corporation headquartered in Midland, Michigan, USA. In terms of market capitalization, it is the largest chemical company in the world, followed closely by DuPont. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... 2-Butanone is a manufactured organic chemical but it is also present in the environment from natural sources. ...


Health effects

Organochlorine compounds such as trichloroethylene present a potentially serious environmental liability given their great resistance to natural degradation and their high marine toxicity. An organochlorine compound is an organic compound of chlorine. ...


When inhaled, trichloroethylene depresses the central nervous system. Its symptoms are similar to those of alcohol intoxication, beginning with headache, dizziness, and confusion and progressing with increasing exposure to unconsciousness and death. Caution should be exercised anywhere a high concentration of trichloroethylene vapors may be present, because it quickly desensitizes the nose to its scent, and it is possible to unknowingly inhale harmful or even lethal amounts of the vapor -- that is, it has poor warning properties. A diagram showing the CNS: 1. ... ...


The long-term effects of trichloroethylene on human beings are unknown. In animal studies, chronic trichloroethylene exposure has produced liver cancer in mice, but not in rats. Studies on its effects on reproduction in animals have been similarly inconsistent, and so no conclusive statements about its ability to cause birth defects in humans can be made. Recent studies have shown a correlation between male fertility and exposure to trichloroethylene. Trichloroethylene has been shown to reduce sperm counts in some cases. Hepatocellular carcinoma (HCC, also called hepatoma or liver cancer) is a primary malignancy (cancer) of the liver. ... For other uses, see Reproduction (disambiguation) Reproduction is the biological process by which new individual organisms are produced. ... A congenital disorder is a medical condition or defect that is present at or before birth (for example, congenital heart disease). ...


More recent analyses indicate low-level evidence of a mutagenic or teratogenic effect; thus, it is known that it promotes the formation of tumors, though the exact pathway is not well-understood. Its long-term safe use as a surgical anesthetic did not lead to an increased incidence of cancer as compared to background levels, indicating that any such effect is most probably extremely low-level. It is current categorized as IARC 2A, analogous to trichloromethanereasonably anticipated to be a human carcinogen. More information on the carcinogenic potential of organochlorine compounds may be gleaned from the report on carcinogens. In biology, a mutagen (Latin, literally origin of change) is an agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ... Teratogenesis is a medical term from the Greek, literally meaning monster-making. ... PEL-TWA (OSHA) 50 ppm (240 mg/m3) IDLH (NIOSH) 500 ppm Flash point non-flammable RTECS number FS9100000 Supplementary data page Structure & properties n, εr, etc. ...


The Environmental Protection Agency mounted a major effort in the 1990s to assess how dangerous trichloroethylene was to human health. Following four years of study, senior EPA scientists concluded in 2001 that it 2 to 40 times more likely to cause cancer than the EPA had previously believed. EPA redirects here. ...


Existing regulation

Until recent years, the US Agency for Toxic Substances and Disease Registry (ATSDR) contended that trichloroethylene was had little-to-no carcinogenic potential, and was probably a co-carcinogen—that is, it acted in concert with other substances to promote the formation of tumors.


Half a dozen state, federal and international agencies now classify trichloroethylene as a probable carcinogen. California EPA regulators consider it a known carcinogen and issued their a risk assessment in 1999 that concluded that it was far more toxic than previous scientific studies had shown.


Proposed U.S. federal regulation

In 2001, a draft report of the Environmental Protection Agency (EPA) laid the groundwork for tough new standards to limit public exposure to trichloroethylene. The assessment set off a fight between the EPA and the Department of Defense (DoD), the Department of Energy, and NASA, who appealed directly to the White House. They argued that the EPA had produced junk science, its assumptions were badly flawed and that evidence exonerating the chemical was ignored. The United States Department of Defense, abbreviated DoD or DOD and sometimes called the Defense Department, is a civilian Cabinet organization of the United States government. ... The United States Department of Energy (DOE) is a Cabinet-level department of the United States government responsible for energy policy and nuclear safety. ... This article or section does not cite its references or sources. ...


The DoD has about 1,400 military properties nationwide that are polluted with trichloroethylene. The chemical has contaminated 23 sites in the Energy Department's nuclear weapons complex — including Lawrence Livermore National Laboratory in the San Francisco Bay area, and NASA centers, including the Jet Propulsion Laboratory in La Cañada Flintridge. Aerial view of the lab and surrounding area. ... The Caltech Jet Propulsion Laboratory (JPL), in La Cañada Flintridge, near Pasadena, California, USA, builds and operates unmanned spacecraft for the National Aeronautics and Space Administration (NASA). ... La Cañada Flintridge is a city located in Los Angeles County, California. ...


High-level political appointees in the EPA — notably research director Paul Gilman — sided with the Pentagon and agreed to pull back the risk assessment. In 2004, the National Academy of Sciences was given a a $680,00 contract to study the matter; it is due to issue a new report in the summer of 2006. President Harding and the National Academy of Sciences at the White House, Washington, DC, April 1921 The National Academy of Sciences (NAS) is a corporation in the United States whose members serve pro bono as advisers to the nation on science, engineering, and medicine. ...


Reduced production and remediation

In recent times, there has been a substantial reduction in the production output of trichloroethylene; alternatives for use in metal degreasing abound, chlorinated aliphatic hydrocarbons being phased out in a large majority of industries due to the potential for irreversible health effects and the legal liability that ensues as a result.


The U.S. military has virtually eliminated its use of the chemical, purchasing only 11 gallons last year. About 100 tons of it is used annually in the U.S. as of 2006.


Recent research has focussed on aerobic degradation pathways in order to reduce environmental pollution through the use of genetically modified bacteria. Limited success has been attained thus far; the intended application is for treatment and detoxification of industrial wastewater. The Lachine Canal, in Montreal, is badly polluted Pollution is the release of harmful environmental contaminants, or the substances so released. ... An iconic image of genetic engineering; this 1986 autoluminograph of a glowing transgenic tobacco plant bearing the luciferase gene of the firefly strikingly demonstrates the power and potential of genetic manipulation. ... Wastewater is any water that has been adversely affected in quality by any anthropogenic influence. ...


External links


  Results from FactBites:
 
Trichloroethylene - Wikipedia, the free encyclopedia (1264 words)
In the late 1950s, the demand for trichloroethylene as a degreaser began to decline in favor of the less toxic 1,1,1-trichloroethane.
The active metabolite of trichloroethylene is trichloroethanol, identical to that of chloral hydrate.
The weak association between trichloroethylene and cancer are responsible for its questionable status: until recent years, the US Agency for Toxic Substances and Disease Registry (ATSDR) contended that it was had little-to-no carcinogenic potential, and was probably a co-carcinogen—that is, it acted in concert with other substances to promote the formation of tumors.
ATSDR - ToxFAQs™: Trichloroethylene (TCE) (978 words)
Trichloroethylene (TCE) is a nonflammable, colorless liquid with a somewhat sweet odor and a sweet, burning taste.
Trichloroethylene is not thought to occur naturally in the environment.
Trichloroethylene quickly evaporates from surface water, so it is commonly found as a vapor in the air.
  More results at FactBites »

 
 

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