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| | Chlordecone Basic information |
| Product Name: | Chlordecone | | Synonyms: | 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2h-cyclobuta(cd)pe;1,1a,3,3a,4,5,5,5a,5b,6-Decachlorooctahydro-1,3,4-metheno-2H-cyclobuta(cd)pentalen-2-one;1,1a,3,3a,4,5,5,5a,5b,6-decachloro-octahydro-1,3,4-metheno-2h-cyclobuta[cd]pen;1,2,3,4,5,5,6,7,8,9,10,10-dodecachlorooctahydro-1,3,4-metheno-2-cyclobuta-(c,d);1,2,3,5,6,7,8,9,10,10-decachloro(5.2.1.0(sup2,6).0(sup3,9).0(sup5,8))decan;1,2,3,5,6,7,8,9,10,10-Decachloro(5.2.1.02,6.03,9 .05,8)decan-4-one;1,3,4-Metheno-2H-cyclobuta(cd)pentalen-2-one, 1,1a,3,3a,4,5,5,5a,5b,6-decachloroctahydro-;decachloropentacyclo(5.2.1.0(2,6).0(3,9).0(5),(8))decan-4-one | | CAS: | 143-50-0 | | MF: | C10Cl10O | | MW: | 490.64 | | EINECS: | 205-601-3 | | Product Categories: | | | Mol File: | 143-50-0.mol |  |
| | Chlordecone Chemical Properties |
| Melting point | 350℃ (DEC.) | | Boiling point | 450.5±45.0 °C(Predicted) | | density | 2.27 | | vapor pressure | 2.25 x 10-7 mmHg at 25 °C (Kilzer et al., 1979) | | Fp | >100 °C | | storage temp. | 0-6°C | | solubility | Soluble in acetic acid, alcohols, and ketones (Windholz et al., 1983) | | form | Tan to white crystalline solid | | Water Solubility | (mg/L):
7.600 at 24 °C (shake flask-nephelometry, Hollifield, 1979)
2.7 at 20–25 °C (Kilzer et al., 1979) | | Merck | 13,2098 | | Henry's Law Constant | (x 10-2 atm?m3/mol):
3.11 at 25 °C (approximate - calculated from experimentally determined water solubility and
vapor pressure values) | | Exposure limits | NIOSH REL: TWA 1 mg/m3. | | IARC | 2B (Vol. 20, Sup 7) 1987 | | EPA Substance Registry System | Chlordecone (143-50-0) |
| | Chlordecone Usage And Synthesis |
| Description | Chemically, kepone is a chlorinated polycyclic insecticide and fungicide. Chlordecone was used as an insecticide for leaf-eating insects, ants, and cockroaches; as a larvicide for flies; and for control of insects that attack structures. Chlordecone was also used on bananas, nonbearing citrus trees, tobacco, ornamental shrubs, lawns, turf, and flowers. The dry powder is readily absorbed through the skin and respiratory tract. Occupational workers handling kepone without appropriate workplace safety dress and PPE suffered chemical poisoning. The symptoms included, tremors, jerky eye movements, memory loss, headaches, slurred speech, unsteadiness, lack of coordination, loss of weight, rash, enlarged liver, decreased libido, sterility, chest pain, and arthralgia (sharp pain, extending along a nerve or group of nerves, experienced in a joint and/or joints). Chlordecone was first introduced as a pesticide in 1958 and was used until 1978, when its use in the United States was discontinued (NCI 1976, IARC 1979, HSDB 2009). | | Chemical Properties | Kerosene is a white to pale yellow, flammable liquid that has wide use in household and industrial activities. For instance, in heating, as cooking fuel, in cleaning, degreasing, as a solvent, for paints, enamels, polishes, varnishes, and in asphalt coating. | | Chemical Properties | Kepone is a tan to white, odorless crystalline
solid. | | Physical properties | Colorless to tan, odorless, noncombustible, crystalline solid | | Uses | Insecticide; fungicide. | | Uses | Formerly as insecticide, fungicide. | | Uses | Chlordecone, a chlorinated dicyclodiene compound, was
introduced under the trade name Kepone in 1958. In the
United States, Kepone found use as an ant and cockroach
poison. Outside the United States, it was used primarily as a
pesticide against the banana root borer. The compound is the
ketone analog of mirex; it is a contaminant of mirex and is
also a product of mirex degradation. | | Definition | ChEBI: An organochlorine compound with insecticidal activity. | | General Description | Odorless colorless crystalline solid. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | A halogenated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. | | Health Hazard | INHALATION AND INGESTION: These symptoms present in all affected patients - Neurologic Impairment - anxiety, irritability, memory disturbance, headache, tremors, opsiclonus, stuttering, slurred speech, and abnormal tandem gait. | | Health Hazard | Kerosene toxicity is variable and is based on the composition. It is rapidly absorbed by the skin and accidental ingestion results in mucous membrane irritation, gastrointestinal irritation, vomiting, diarrhea, pneumonitis, CNS depression, drowsiness, coma, and may lead to death. Prolonged contact is also known to cause skin blisters and dermatitis. Studies with non-human primates have demonstrated that aerosols and kerosene aspiration into the lungs cause cellular damage. Household activities and possible long-term exposures to kerosine require proper care to avoid skin contact and possible damage. Kerosene should never be sucked by mouth. | | Fire Hazard | Flash point data for KEPONE (TM) are not available; however, KEPONE (TM) is probably combustible. | | Potential Exposure | Kepone was registered for the control
of rootborers on bananas with a residue tolerance of
0.01 ppm. This constituted the only food or feed use
of Kepone. Nonfood uses included wireworm control in
tobacco fields and bait to control ants and other insects in
indoor and outdoor areas. A rebuttable presumption
against registration of chlordecone was issued by the
United States Environmental Protection Agency on
March 25, 1976 on the basis of oncogenicity. The trademarked Kepone and products of six formulations were the
subject of voluntary cancellation according to a United
States Environmental Protection Agency notice dated
July 27, 1977. In a series of decisions, the first of which
was issued on June 17, 1976, the EPA effectively
canceled all registered products containing Kepone as of
May 1, 1978. | | Carcinogenicity | Kepone (chlordecone) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. | | Environmental Fate | Photolytic. Kepone-contaminated soils from a site in Hopewell, VA were analyzed by
GC/MS. 8-Chloro and 9-chloro homologs identified suggested these were photodegradation
products of kepone (Borsetti and Roach, 1978). Products identified from the photolysis
of kepone in cyclohexane were 1,2,3,4,6,7,9,10,10-nonachloro-5,5-dihydroxypentacyclo[
5.3.0.02,6.03,9.04,8]decane for the hydrate and 1,2,3,4,6,7,9,10,10-nonachloro-5,5-
dimethoxypentacyclo[5.3.0.02,6.03,9.04,8]decane (Alley et al., 1974).
Chemical/Physical. Readily reacts with moisture forming hydrates (Hollifield, 1979).
Decomposes at 350°C (Windholz et al., 1983) probably emitting toxic chlorine fumes. | | Shipping | UN2761 Organochlorine pesticides, solid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials. | | Incompatibilities | Acids, acid fumes. | | Waste Disposal | A process has been developed
which effects chlordecone degradation by treatment of aqueous wastes with UV radiation in the presence of hydrogen in
aqueous sodium hydroxide solution. Up to 95% decomposition was effected by this process. Chlordecone previously
presented serious disposal problems because of its great
resistance to bio- and photo degradation in the environment.
It is highly toxic to normally occur in degrading microorganisms. Although it can undergo some photodecomposition
when exposed to sunlight to the dihydro compound (leaving
a compound with 8 chloro substituents) that degradation
product does not significantly reduce toxicity. Disposal by
incineration with HCl scrubbing is recommended.
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| | Chlordecone Preparation Products And Raw materials |
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