Chlordecone: Difference between revisions
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'''Kepone''', also known as '''chlordecone''', is an [[organochlorine compound]]. It is a colourless solid. This compound is a controversial [[insecticide]] related to [[Mirex]] and [[DDT]]. Its use was so disastrous that it is now prohibited in the western world, but only after many millions of kilograms had been produced.<ref name=Ullmann2>Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Wienheim, 2002. {{DOI|10.1002/14356007.a14_263}}</ref> |
'''Kepone''', also known as '''chlordecone''', is an [[organochlorine compound]]. It is a colourless solid. This compound is a controversial [[insecticide]] related to [[Mirex]] and [[DDT]]. Its use was so disastrous that it is now prohibited in the western world, but only after many millions of kilograms had been produced.<ref name=Ullmann2>Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Wienheim, 2002. {{DOI|10.1002/14356007.a14_263}}</ref> Kepone is a known [[persistent organic pollutants]] (POP), classified among the "dirty dozen" and banned globally by the [[Stockholm Convention on Persistent Organic Pollutants]] as of 2011. |
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== Toxicology == |
== Toxicology == |
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Revision as of 21:18, 30 April 2014
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| Names | |
|---|---|
| IUPAC name
decachloropentacyclo[5.3.0.02.6.03.9.04.8]decan-5-one[1]
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| Other names
Chlordecone
Clordecone Merex CAS name: 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalen-2-one | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.093 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C10Cl10O | |
| Molar mass | 490.633 g/mol |
| Appearance | tan to white crystalline solid |
| Odor | odorless |
| Density | 1.6 g/cm3 |
| Melting point | 349 °C (660 °F; 622 K) |
| 0.27 g/100 mL | |
| Solubility | soluble in acetone, ketone, acetic acid slightly soluble in benzene, hexane |
| log P | 5.41 |
| Vapor pressure | 3.10−7 kPa |
| Thermochemistry | |
Std molar
entropy (S⦵298) |
764 J/K mol |
Std enthalpy of
formation (ΔfH⦵298) |
-225.9 kJ/mol |
| Hazards | |
| Flash point | Non-flammable |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
95 mg/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Kepone, also known as chlordecone, is an organochlorine compound. It is a colourless solid. This compound is a controversial insecticide related to Mirex and DDT. Its use was so disastrous that it is now prohibited in the western world, but only after many millions of kilograms had been produced.[2] Kepone is a known persistent organic pollutants (POP), classified among the "dirty dozen" and banned globally by the Stockholm Convention on Persistent Organic Pollutants as of 2011.
Toxicology
The LC50 (LC = lethal concentration) is 0.022 – 0.095 mg/kg for blue gill and trout. Kepone bioaccumulates in animals by a factors up to a million-fold. Workers with repeated exposure suffer severe convulsions resulting from degradation of the synaptic junctions.[2]
History
In the US, kepone was produced by Allied Signal Company and LifeSciences Product Company in Hopewell, Virginia. The improper handling and dumping of the substance into the nearby James River (U.S.) in the 1960s and 1970s drew national attention to its toxic effects on wildlife. The product is similar to DDT and is a degradation product of Mirex.[2] The history of Kepone incidents are reviewed in Who's Poisoning America?: Corporate Polluters and Their Victims in the Chemical Age (1982). In 2009, Kepone was included in the Stockholm Convention on persistent organic pollutants, which bans its production and use worldwide.[citation needed]
Case studies
James River estuary
Due to the pollution risks, many businesses and restaurants along the river suffered economic losses. In 1975 Governor Mills Godwin Jr. shut down the James River to fishing for 100 miles, from Richmond to the Chesapeake Bay. This ban remained in effect for 13 years, until efforts to clean up the river began to get results.[3]
French Antilles
The French island of Martinique is heavily contaminated with kepone,[4] following years of its unrestricted use on banana plantations. Despite a 1990 ban of the substance by France, the economically powerful planter community lobbied intensively to gain the power to continue using kepone until 1993. They had argued that no alternative pesticide was available, which has since been disputed. Similarly, the nearby island of Guadeloupe is also contaminated, but to a lesser extent. Since 2003, the local authorities restricted cultivation of crops because the soil has been seriously contaminated by kepone. Guadeloupe has one of the highest prostate cancer rates in the world.[5]
In popular culture
- Kepone was the name of an American indie rock band from Richmond, Virginia formed in 1991.
- The Dead Kennedys recorded a song named "Kepone Factory", a satire of the controversy surrounding Allied Signal and their negligence regarding employee safety, for their 1981 album In God We Trust, Inc.. Written in 1978, the song was originally titled "Kepone Kids".
References
- ^ IUPAC Agrochemical information (http://sitem.herts.ac.uk/aeru/iupac/1293.htm)
- ^ a b c Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263
- ^ JACK COOKSEY, "What's in the Water?", Richmond Magazine, June 2007, accessed 13 June 2012
- ^ French Documentary
- ^ European Journal, Deutsche Welle, 26 May 2010.[1]