Dichlorodiphenyl dichloroethane

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Structural formula
Structure of dichlorodiphenyldichloroethane
General
Surname Dichlorodiphenyl dichloroethane
other names
  • DDD
  • p , p ′ -DDD
  • TDE
  • 1-chloro-4- [2,2-dichloro-1- (4-chlorophenyl) ethyl] benzene ( IUPAC )
Molecular formula C 14 H 10 Cl 4
External identifiers / databases
CAS number 72-54-8
EC number 200-783-0
ECHA InfoCard 100,000,712
PubChem 6294
Wikidata Q417682
properties
Molar mass 320.04 g mol −1
Physical state

firmly

density

1.476 g cm −3 (20 ° C)

Melting point

109.5 ° C

boiling point

350 ° C

Vapor pressure

1.35 10 −6 mmHg (25 ° C)

solubility

practically insoluble in water (0.09 mg l −1 at 25 ° C)

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 301-312-351-410
P: 273-280-301 + 310-501
Toxicological data

113 mg kg −1 ( LD 50 ,  rat ,  oral )

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

  1. ↑ 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) .
  2. ↑ 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.
  3. ^ Thomas R. Dunlap, DDT: Scientists, Citizens and Public Policy . Princeton University Press, 1981, ISBN 0-691-04680-8 , pp. 94-96.
  4. ↑ 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.
  5. ^ 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 .

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