Tetrachloroethylene

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Tetrachloroethylene
TetrachloroethyleneTetrachloroethylene
Identifiers
CAS number127-18-4 YesY
ChemSpider13837281 YesY
UNIITJ904HH8SN YesY
EC number204-825-9
UN number1897
KEGGC06789 YesY
ChEBICHEBI:17300 N
ChEMBLCHEMBL114062 YesY
RTECS numberKX3850000
Jmol-3D imagesImage 1
Properties
Molecular formulaC2Cl4
Molar mass165.83 g mol−1
AppearanceClear, colorless liquid
Density1.622 g/cm3
Melting point−19 °C (−2 °F; 254 K)
Boiling point121.1 °C (250.0 °F; 394.2 K)
Solubility in water0.015 g/100 mL (20 °C)
Viscosity0.89 cP at 25 °C
Hazards
MSDSExternal MSDS
R-phrasesR40 R51/53
S-phrasesS23 S36/37 S61
Main hazardsHarmful (Xn),
Dangerous for
the environment (N)
NFPA 704
Flash pointNot flammable
Related compounds
Related Related organohalidesTetrabromoethylene
Tetraiodoethylene
Related compoundsTrichloroethylene
Dichloroethene
Tetrachloroethane
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral dataUV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
 
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Tetrachloroethylene
TetrachloroethyleneTetrachloroethylene
Identifiers
CAS number127-18-4 YesY
ChemSpider13837281 YesY
UNIITJ904HH8SN YesY
EC number204-825-9
UN number1897
KEGGC06789 YesY
ChEBICHEBI:17300 N
ChEMBLCHEMBL114062 YesY
RTECS numberKX3850000
Jmol-3D imagesImage 1
Properties
Molecular formulaC2Cl4
Molar mass165.83 g mol−1
AppearanceClear, colorless liquid
Density1.622 g/cm3
Melting point−19 °C (−2 °F; 254 K)
Boiling point121.1 °C (250.0 °F; 394.2 K)
Solubility in water0.015 g/100 mL (20 °C)
Viscosity0.89 cP at 25 °C
Hazards
MSDSExternal MSDS
R-phrasesR40 R51/53
S-phrasesS23 S36/37 S61
Main hazardsHarmful (Xn),
Dangerous for
the environment (N)
NFPA 704
Flash pointNot flammable
Related compounds
Related Related organohalidesTetrabromoethylene
Tetraiodoethylene
Related compoundsTrichloroethylene
Dichloroethene
Tetrachloroethane
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral dataUV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene ("perc" or "PERC"), and many other names, is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid." It has a sweet odor detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about one million metric tons in 1985.[1]

Production[edit]

Michael Faraday first synthesized tetrachloroethylene in 1821 by thermal decomposition of hexachloroethane.

C2Cl6 → C2Cl4 + Cl2

Most tetrachloroethene is produced by high temperature chlorinolysis of light hydrocarbons. The method is related to Faraday's discovery since hexachloroethane is generated and thermally decomposes.[1] 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, tetrachloroethene is produced by the chemical reaction:

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.

According to an United States Environmental Protection Agency (EPA) report of 1976, the quantity of tetrachloroethylene produced in the United States in the 1973 totaled 320,000 metric tons (706 million lb).[2] By 1993, the volume produced in the United States had dropped to 123,000 metric tons (271 million lb).[3]

Uses[edit]

Tetrachloroethylene is an excellent solvent for organic materials. Otherwise it is volatile, highly stable, and nonflammable. For these reasons, it is widely used in dry cleaning. Usually as a mixture with other chlorocarbons, it is also used to degrease metal parts in the automotive and other metalworking industries. It appears in a few consumer products including paint strippers and spot removers.

Historical applications[edit]

Tetrachloroethene 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 for hookworm infestation.[4]

Health and safety[edit]

The International Agency for Research on Cancer has classified tetrachloroethene as a Group 2A carcinogen, which means that it is probably carcinogenic to humans.[5] Like many chlorinated hydrocarbons, tetrachloroethene is a central nervous system depressant and can enter the body through respiratory or dermal exposure.[6] Tetrachloroethene dissolves fats from the skin, potentially resulting in skin irritation.

Animal studies and a study of 99 twins showed there is a "lot of circumstantial evidence" that exposure to tetrachloroethene increases the risk of developing Parkinson's disease ninefold. Larger population studies are planned.[7]

At temperatures over 315 °C (599 °F), such as in welding, tetrachloroethylene can be oxidised into phosgene, an extremely poisonous gas.[8][9] Tetrachloroethylene should not be used near welding operations, flames, or hot surfaces.[10]

Testing for exposure[edit]

Tetrachloroethene exposure can be evaluated by a breath test, analogous to breath-alcohol measurements. Because it is stored in the body's fat and slowly released into the bloodstream, tetrachloroethene can be detected in the breath for weeks following a heavy exposure. Tetrachloroethylene and trichloroacetic acid (TCA), a breakdown product of tetrachloroethene, can be detected in the blood.

In Europe, the Scientific Committee on Occupational Exposure Limits (SCOEL) recommends for tetrachloroethylene an occupational exposure limit (8h time-weighted average) of 20 ppm and a short-term exposure limit (15 min) of 40 ppm.[11]

Environmental contamination[edit]

Tetrachloroethene is a common soil contaminant. With a specific gravity greater than 1, tetrachloroethylene will be present as a dense nonaqueous phase liquid if sufficient quantities of liquid are spilled in the environment. Because of its mobility in groundwater, its toxicity at low levels, and its density (which causes it to sink below the water table), cleanup activities are more difficult than for oil spills. Recent research has focused on the in place remediation of soil and ground water pollution by tetrachloroethylene. Instead of excavation or extraction for above-ground treatment or disposal, tetrachloroethylene contamination has been successfully remediated by chemical treatment or bioremediation. Bioremediation has been successful under anaerobic conditions by reductive dechlorination by Dehalococcoides sp. and under aerobic conditions by cometabolism by Pseudomonas sp.[12][13] Partial degradation daughter products include trichloroethylene, cis-1,2-dichloroethene and vinyl chloride; full degradation converts tetrachloroethylene to ethene and hydrogen chloride dissolved in water.

Estimates state that 85% of tetrachloroethylene produced is released into the atmosphere; while models from OECD assumed that 90% is released into the air and 10% to water. Based on these models, its distribution in the environment is estimated to be in the air (76.39% - 99.69%), water (0.23% - 23.2%), soil (0.06-7%), with the remainder in the sediment and biota. Estimates of lifetime in the atmosphere vary, but a 1987 survey estimated the lifetime in the air has been estimated at about 2 months in the Southern Hemisphere and 5–6 months in the Northern Hemisphere. Degradation products observed in a laboratory include phosgene, trichloroacetyl chloride, hydrogen chloride, carbon dioxide, and carbon monoxide. Tetrachloroethylene is degraded by hydrolysis, and is also persistent under aerobic conditions. This compound is degraded by reductive dechlorination with anaerobic conditions present, with the degradation products like trichloroethene, dichloroethene, vinyl chloride, ethene, and ethane.[14]

References[edit]

  1. ^ a b M. Rossberg et al. “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_233.pub2
  2. ^ "Assessment of Hazardous Waste Practices: Organic Chemicals, Pesticides and Explosives Industries" prebpublication issue for EPA Libraries and Solid Waste Management Agencies under contract # 68-01-2919, USEPA 1976
  3. ^ "Toxicological Profile For Tetrachloroethylene". Atlanta, GA: Agency for Toxic Substances and Disease Registry. September 1997. p. 174. Retrieved 2012-09-16.  citing C&EN, 1994, Facts and Figures for the Chemical Industry, Chemical and Engineering News, July 4, 1994.
  4. ^ Young, M.D.; et al. (1960). "The Comparative Efficacy of Bephenium Hydroxynaphthoate and Tetrachloroethylene against Hookworm and other Parasites of Man". American Journal of Tropical Medicine and Hygiene 9 (5): 488–491. PMID 13787477. 
  5. ^ IARC monograph. Tetrachloroethylene, Vol. 63, p. 159. Last Updated May 20, 1997. Last retrieved June 22, 2007.
  6. ^ Control of Exposure to Perchloroethylene in Commercial Drycleaning. Hazard Controls: Publication 97-157. National Institute for Occupational Safety and Health.
  7. ^ Industrial Solvent Linked to Increased Risk of Parkinson's Disease
  8. ^ Medical Management Guidelines for Tetrachloroethylene
  9. ^ Common cleaners can turn into poison gas
  10. ^ Working safely with tetrachloroethylene
  11. ^ "SCOEL recommendations". 2011-04-22. Retrieved 2011-04-22. 
  12. ^ 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". Applied Microbiol Biotechnol 56 (3–4): 545–549. doi:10.1007/s002530100675. 
  13. ^ Deckard, L. A., Wills, J. C., Rivers, D. B. (1994). "Evidence for aerobic degradation of tetrachloroethylene by bacterial isolate". Biotechnol. Lett. 16 (11): 1221–1224. doi:10.1007/BF01020855. 
  14. ^ Watts P. (2006). Concise International Chemical Assessment Document 68: TETRACHLOROETHENE, World Health Organization

Further reading[edit]

External links[edit]