Trichloroethylene
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sample of Trichloroethylene
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Names | |||
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Preferred IUPAC name
Trichloroethene | |||
Other names
1-Chloro-2,2-dichloroethylene; 1,1-Dichloro-2-chloroethylene; Acetylene Trichloride; Anamenth; HCC-1120; TCE; Trethylene; Triclene; Tri; Trico; Trilene; Trimar
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Identifiers | |||
3D model (
JSmol ) |
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Abbreviations | TCE | ||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.001.062 | ||
EC Number |
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KEGG | |||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1710 | ||
CompTox Dashboard (EPA)
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Properties | |||
C2HCl3 | |||
Molar mass | 131.38 g·mol−1 | ||
Appearance | Colorless liquid | ||
Odor | pleasant, chloroform-like | ||
Density | 1.46 g/cm3 at 20 °C | ||
Melting point | −84.8 °C (−120.6 °F; 188.3 K)[5] | ||
Boiling point | 86.7 °C (188.1 °F; 359.8 K)[1] | ||
1.280 g/L[1] | |||
Solubility | Ether, ethanol, chloroform | ||
log P | 2.26[2] | ||
Vapor pressure | 58 mmHg (0.076 atm) at 20 °C[3] | ||
−65.8·10−6 cm3/mol | |||
Refractive index (nD)
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1.4777 at 19.8 °C | ||
Viscosity | 0.532 mPa·s[4] | ||
Pharmacology | |||
N01AB05 (WHO) | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Acute exposure can cause dizziness and loss of consciousness, chronic exposure can increase cancer risk. Unstable in presence of light. | ||
GHS labelling: | |||
NFPA 704 (fire diamond) | |||
420 °C (788 °F; 693 K) | |||
Explosive limits
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8-10.5%[3] | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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4920 mg/kg (oral, rat), 29000 mg/kg (dermal, rabbit)[6] | ||
LC50 (median concentration)
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8450 ppm (mouse, 4 hr) 26300 (rat, 1 hr)[7] | ||
LCLo (lowest published)
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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)
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TWA 100 ppm C 200 ppm 300 ppm (5-minute maximum peak in any 2 hours)[3] | ||
REL (Recommended)
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Ca[3] | ||
IDLH (Immediate danger) |
Ca [1000 ppm][3] | ||
Safety data sheet (SDS) | Carl Roth | ||
Legal status | |||
Related compounds | |||
Related vinyl halides
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Vinyl chloride Tetrachloroethylene | ||
Related compounds
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Chloroform 1,1,1-Trichloroethane 1,1,2-Trichloroethane | ||
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).
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Trichloroethylene (TCE) is a
TCE is classified as a volatile organic compound.[9]
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]
Pioneered by
Originally thought to possess less
The introduction of halothane in 1956 greatly diminished the use of TCE as a general anesthetic. TCE was still used as an inhalation analgesic in childbirth given by self-administration. Fetal toxicity and concerns about the carcinogenic potential of TCE led to its abandonment in developed countries by the 1980s.
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
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
- 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
Uses
Trichloroethylene is an effective
When trichloroethylene was first widely produced in the 1920s, its major use was to extract
Anaesthesia
Pain Relief in Childbirth (1954), a short film by Imperial Chemical Industries explaining the use of nitrous oxide and trichloroethylene anaesthesia systems for childbirth. |
Trichloroethylene is a good analgesic at 0.35 to 0.5% concentrations.[21] Trichloroethylene was used in the treatment of trigeminal neuralgia beginning in 1916.[17]
From the 1940s through the 1980s, both in Europe and North America, trichloroethylene was used as a volatile anesthetic almost invariably administered with
TCE replaced earlier anesthetics chloroform and ether in the 1940s due to its lower toxicity than chloroform and being relatively non-flammable (unlike ether which is extremely flammable), but was itself replaced in the 1960s in developed countries with the introduction of halothane, which allowed much faster induction and recovery times and was considerably easier to administer. 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.[21] Its anaesthetic use was banned in the United States in 1977 but the anaesthetic use in the United Kingdom remained until the late 1980s.[17]
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.[23]
Trichloroethylene has been used in the production of halothane.[24]
Cleaning solvent
TCE has also been used as a dry cleaning solvent, although mostly replaced by tetrachloroethylene (also known as perchloroethylene), 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
Refrigerants
TCE is also used in the manufacture of a range of fluorocarbon refrigerants
Safety
Chemical instability
Despite its widespread use as a metal
Physiological effects
When inhaled, trichloroethylene produces
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.[35] 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.[35] A history of long-term exposure to high concentrations of trichloroethylene is a suspected environmental risk of Parkinson's disease.[36]
Metabolism
Trichloroethylene is metabolised to trichloroepoxyethane (TCE oxide) which rapidly isomerises to
were also detected as minor metabolites of TCE.Exposure and regulations
With a
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.[42] 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.[43]
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.[44] 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.[44] TCE levels above background have been found in homes undergoing renovation.[45]
Existing regulations in the United States and European Union
Until recent years[
State, federal, and international agencies classify trichloroethylene as a known or probable carcinogen. In 2014, the International Agency for Research on Cancer updated its classification of trichloroethylene to Group 1, indicating that sufficient evidence exists that it causes cancer of the kidney in humans as well as some evidence of cancer of the liver and non-Hodgkin's lymphoma.[46]
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).[47]
Existing EU legislation aimed at protection of workers against risks to their health (including Chemical Agents Directive 98/24/EC[48] and Carcinogens Directive 2004/37/EC[49]) 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
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.[54] Toluene dioxygenase has been reported to be involved in TCE degradation by Pseudomonas putida.[55] In some cases, Xanthobacter autotrophicus can convert up to 51% of TCE to CO and CO2.[55]
Society and culture
The 1995 non-fiction book
TCE has been used as a
References
- ^ a b "Trichloroethylene". Sigmaaldrich.com. Retrieved 20 October 2014.
- ^ "Trichloroethylene". www.chemsrc.com.
- ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0629". National Institute for Occupational Safety and Health (NIOSH).
- ISSN 0021-9568.
- ^ "Safety Data Sheet". Retrieved 23 February 2022.
- ^ FischerSci Trichloroethylene SDS
- ^ a b "Trichloroethylene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ 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.
- ^ ATSDR
- ^ Essai sur l'Action du Chlore sur la Liqueur des Hollandais et sur quelques Ethers in Annal. de Chimie, LXIII. (1836) page 379
- ^ The so-called Perchloride of Formyl, Gmelin, L. (translated in 1855). Hand-book of Chemistry: Organic chemistry. UK: Cavendish Society. pages 200–201
- ^ Ueber die Einwirkung von Wasserstoff auf Einfach-Chlorkohlenstoff, Fischer, E. (1864) in Zeitschrift für Chemie. page 268
- ^ Waters EM, Gerstner HB, Huff JE. Trichloroethylene. I. An overview. J Toxicol Environ Health. 1977 Jan;2(3):671-707. doi: 10.1080/15287397709529469. PMID 403297.
- ^ 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
- ^ Mertens JA (1993). Chlorocarbons and chlorohydrocarbons. In: Kirk-Othmer Encyclopedia of Chemical Technology, 4th Ed. Kroschwitz JI, Howe-Grant M, editors. New York: John Wiley & Sons, pp. 40–50.
- ^ A Portrait of Medical History and Current Medical Problem (1962), p. 130
- ^ a b c d e f g h i Chapter 4: Trichloroethylene, Morrison, R. D., Murphy, B. L. (2015). Chlorinated Solvents: A Forensic Evaluation: Royal Society of Chemistry.
- ^ Subramanian, Indu (20 Nov 2023). "Is Most Parkinson's Disease Man-Made?". Medscape. Retrieved 29 Nov 2023.
- PMID 22309908.
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- ^ a b Textbook of Obstetric Anaesthesia. (2002). UK: Greenwich Medical Media. Pages 64-65
- ^ a b Current Researches in Anesthesia & Analgesia. (1951). USA: International Anesthesia Research Society. p.278
- ^ P. Fenton (2000). "Volatile Anaesthetic Agents". Archived from the original on 2012-01-07. Retrieved 2012-02-11.
- ^ Suckling et al.,"PROCESS FOR THE PREPARATION OF 1,1,1-TRIFLUORO-2-BROMO-2-CHLOROETHANE", US patent 2921098, granted January 1960 , assigned to Imperial Chemical Industries
- ^ "Santa Susana Field Laboratory : The Use of Trichloroethylene at NASA's SSFL Sites" (PDF). Ssfl.msfc.nasa.gov. Archived from the original (PDF) on 14 November 2013. Retrieved 22 February 2015.
- ^ a b "F-1 Rocket Engine Operating Instructions". Ntrs.nasa.gov. Retrieved 20 October 2014.
- ^ "Production of R-134a" (PDF). Nd.edu. Archived from the original (PDF) on 11 July 2009. Retrieved 21 February 2015.
- ISBN 978-0124047075.
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- ^ Morrison, R. D., Murphy, B. L. (2013). Chlorinated Solvents: A Forensic Evaluation. UK Royal Society of Chemistry.
- PMID 10825391.)
{{cite journal}}
: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link - PMID 10683198.
- ^ Orkin, F. K. (1986) Anesthesia Systems (Chapter 5). In R. D. Miller (Ed.), Anesthesia (second edition). New York, NY: Churchill Livingstone.[page needed]
- ^ Stevens, W.C. and Kingston H. G. G. (1989) Inhalation Anesthesia (Chapter 11). In P. G. Barash et al. (Eds.) Clinical Anesthesia. Philadelphia, PA: Lippincott.[page needed]
- ^ a b "Trichloroethylene | Technology Transfer Network Air Toxics Web site | US EPA". Epa.gov. Retrieved 2013-10-05.
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- ^ Fishbein, L. (1977). Potential Industrial Carcinogens and Mutagens. Environmental Protection Agency, Office of Toxic Substances
- ^ a b 21.4.25: Trichloroethylene in Biological Monitoring: An Introduction. (1993). UK: Wiley.
- ^ Biologically Based Methods for Cancer Risk Assessment. (2013). Springer US.
- ^ Toxicological Profile for Trichloroethylene: Draft. (1995). U.S. Department of Health and Human Services.
- ^ Mutagenesis. (1978). page 268
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- ^ "Consumer Factsheet on: Trichloroethylene" (PDF). Epa.gov. Retrieved 22 February 2015.
- ^ a b "Trichloroethylene Toxicity: Where is Trichloroethylene Found? | Environmental Medicine | ATSDR". www.atsdr.cdc.gov. 2022-09-09. Retrieved 2023-03-02. This article incorporates text from this source, which is in the public domain.
- ^ "Trichloroethylene (tce) TEACH Chemical Summary - epa nepis".
- ^ Trichloroethylene (IARC Summary & Evaluation, Volume 106, 2014) (PDF). iarc.fr. Retrieved 2016-03-08.
- ^ "Recommendation from the Scientific Committee on Occupational Exposure Limits for Trichloroethylene (SCOEL/SUM/142)" (PDF). April 2009.
- ^ "Council Directive 98/24/EC" (PDF). Eur-lex.europa.eu. Retrieved 21 February 2015.
- ^ "Directive 2004/37/EC" (PDF). Eur-lex.europa.eu. Retrieved 21 February 2015.
- ^ US EPA, OCSPP (2020-02-12). "Final Risk Evaluation for Trichloroethylene" (PDF). www.epa.gov. Retrieved 2023-06-03.
- ^ "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.
- ^ "Minnesota Statutes". Environmental Protection, Chapter 116, Section 116.385, act No. 116.38 (also known as "White Bear Area Neighborhood Concerned Citizens Group Ban TCE Act") of 2022. Minnesota Legislature. Archived from the original on 6 September 2023.
- ^ "Risk Management for Trichloroethylene (TCE)". US EPA. 21 Nov 2023. Retrieved 23 Nov 2023.
- ^ "Nitrosomonas europaea". Genome.jgi-psf.org. 2015-02-05. Archived from the original on 2009-07-03. Retrieved 2015-02-21.
- ^ ISBN 978-1566765619. Retrieved 21 February 2015.
- ^ Trichloroethylene in Neurology in Clinical Practice, Daroff, R. B., Fenichel, G. M., Jankovic, J., Mazziotta, J. C. (2012).
- ^ a b Chapter 50: Trichloroethylene Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants.Barceloux, D. G. (2012).
- ^ 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
Further reading
- Agency for Toxic Substances and Disease Registry (ATSDR). 1997. Toxicological Profile for Trichloroethylene.
- Doherty, Richard E. (2000). "A History of the Production and Use of Carbon Tetrachloride, Tetrachloroethylene, Trichloroethylene and 1,1,1-Trichloroethane in the United States: Part 2 – Trichloroethylene and 1,1,1-Trichloroethane". Environmental Forensics. 1 (2): 83–93. S2CID 97370778.
- Lipworth, Loren; Tarone, Robert E.; McLaughlin, Joseph K. (2006). "The Epidemiology of Renal Cell Carcinoma". The Journal of Urology. 176 (6): 2353–2358. PMID 17085101.
- Matei, Adrienne (7 Apr 2021). "Rates of Parkinson's disease are exploding. A common chemical may be to blame". The Guardian.
- US Environmental Protection Agency (USEPA). 2011. Toxicological Review for Trichloroethylene
- US National Academy of Sciences (NAS). 2006. Assessing Human Health Risks of Trichloroethylene – Key Scientific Issues. Committee on Human Health Risks of Trichloroethylene, National Research Council.
- US National Toxicology Program (NTP). 2021. Trichloroethylene, in the 15th Annual Report of Carcinogens.
External links
- US EPA: Trichloroethylene – TCE information website – US Environmental Protection Agency(EPA)
- chlorinated-solvents.eu – Sustainable uses and industry recommendations, European Chlorinated Solvents Association
- Case Studies in Environmental Medicine: Trichloroethylene Toxicity – Department of Health and Human Services(public domain)
- Assessing Human Health Risks of Trichloroethylene – Key Scientific Issues – US National Academy of Sciences (NAS)
- US NIH: Fifteenth Report on Carcinogens: Trichloroethylene Monograph – US National Institutes of Health (NIH)
- Workplace Safety and Health Topics: Trichloroethylene – TCE – US National Institute for Occupational Safety and Health (NIOSH)