Dichlorodiphenyl dichloroethane
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Dichlorodiphenyl dichloroethane | |||||||||||||||
other names |
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Molecular formula | C 14 H 10 Cl 4 | |||||||||||||||
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properties | ||||||||||||||||
Molar mass | 320.04 g mol −1 | |||||||||||||||
Physical state |
firmly |
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density |
1.476 g cm −3 (20 ° C) |
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Melting point |
109.5 ° C |
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boiling point |
350 ° C |
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Vapor pressure |
1.35 10 −6 mmHg (25 ° C) |
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solubility |
practically insoluble in water (0.09 mg l −1 at 25 ° C) |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
p , p ′ -Dichlorodiphenyldichloroethane ( p , p ′ -DDD ) is a chemical compound . It was used as an insecticide and is also a metabolite of the related insecticide DDT .
history
In the 1940s and 1950s, p , p ′ -DDD was used to control the larvae of the mosquito species Clear Lake gnat in the waters of Clear Lake , California . The applications only resulted in a concentration of a few ppb p , p ′ -DDD in the lake water and killed around 99% of the mosquito larvae in the sea mud. However, the released p , p ′ -DDD accumulated through biomagnification via the food chain and led to the collapse of the racing divers population at this lake. The p , p ′ -DDD concentration in plankton was already around 265 times higher than in water, and in predatory fish and birds it was increased by a factor of around 85,000. Analyzed body fat from dead racing divers contained around 1600 ppm p , p ′ -DDD.
- Reductive dechlorination of DDT to DDD
Extraction and presentation
p , p ′ -DDD was produced by the condensation of dichloroacetaldehyde with chlorobenzene . Technical DDT contains p , p ′ -DDD at 0.3% or <4%, depending on the source.
use
p , p ′ -DDD was used as an insecticide. Production figures are not known, but it was of little significance.
The isomeric o , p ′ -DDD is used in veterinary medicine under the active ingredient name Mitotane for the treatment of Cushing's syndrome in dogs , but is becoming increasingly less important than more modern drugs due to its toxic properties.
Individual evidence
- ↑ a b c Entry on 1,1-dichloro-2,2-bis (4-chlorophenyl) ethane in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .
- ↑ a b c d e Entry on dichlorodiphenyldichloroethane in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on March 3, 2019.
- ^ Thomas R. Dunlap, DDT: Scientists, Citizens and Public Policy . Princeton University Press, 1981, ISBN 0-691-04680-8 , pp. 94-96.
- ↑ a b U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry: Toxicological profile for DDT, DDE and DDD. (PDF; 4.0 MB) , 2002.
- ^ Advisory committee for existing substances of the Society of German Chemists : DDT and derivatives - model substances to describe endocrine effects relevant to reproduction . BUA-Stoffbericht 216, S. Hirzel Verlag, August 1998, ISBN 3-7776-0961-7 .