CAS name: 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalen-2-one
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||490.633 g/mol|
|Appearance||tan to white crystalline solid|
|Melting point||349 °C (660 °F; 622 K) (decomposes)|
|0.27 g/100 mL|
|Solubility||soluble in acetone, ketone, acetic acid |
slightly soluble in benzene, hexane
|Vapor pressure||3.10−7 kPa|
|764 J/K mol|
Std enthalpy of
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|95 mg/kg (rat, oral)|
|NIOSH (US health exposure limits):|
|Ca TWA 0.001 mg/m3|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Kepone, also known as chlordecone, is an organochlorine compound and a colourless solid. This compound is an obsolete 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. Kepone is a known persistent organic pollutant (POP), classified among the "dirty dozen" and banned globally by the Stockholm Convention on Persistent Organic Pollutants as of 2011.
The LC50 (LC = lethal concentration) is 35 μg/ L for Etroplus maculatus, 0.022–0.095 mg/kg for blue gill and trout. Kepone bioaccumulates in animals by factors up to a million-fold. Workers with repeated exposure suffer severe convulsions resulting from degradation of the synaptic junctions. Chronic lower level exposure causes prostate cancer.
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 humans and wildlife. The product is similar to DDT and is a degradation product of Mirex. 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.
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 show results.
Due to the pollution risks, many fishermen, marinas, seafood businesses, and restaurants, along with their employees along the river suffered economic losses. In 1981, a large group of these entities sued Allied Chemical in federal district court (Eastern District of Virginia), claiming special economic damages from Allied's negligent damage to the fish and wildlife. In a case that sometimes appears in law school courses on Remedies, the court rejected the traditional "economic-loss rule", which requires physical impact causing personal injury or property damage to receive economic damages, and instead allowed a limited group of the plaintiffs—the fishing boat owners, the marinas, and the bait and tackle shops—to recover economic damages from Allied Chemical.
The French island of Martinique is heavily contaminated with kepone, 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. The nearby island of Guadeloupe is also contaminated, but to a lesser extent. Since 2003, local authorities have restricted cultivation of crops because the soil has been seriously contaminated by kepone. Guadeloupe has one of the highest prostate cancer diagnosis rates in the world.