Aldrin: Wikis

  
  

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Aldrin
Aldrin
Aldrin-from-xtal-3D-balls.png
IUPAC name
Identifiers
CAS number 309-00-2 Yes check.svgY
SMILES
InChI
InChI key QBYJBZPUGVGKQQ-SJJAEHHWBI
ChemSpider ID 10292747
Properties
Molecular formula C12H8Cl6
Molar mass 364.91 g mol−1
Melting point

104 °C

Vapor pressure 7.5 × 10−5 mmHg @ 20oC
Hazards
NFPA 704
NFPA 704.svg
0
2
0
 
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aldrin is an organochlorine insecticide that was widely used until the 1970s, when it was banned in most countries. It is a colourless solid. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.[1]

Contents

Production

Aldrin is produced by combining hexachlorocyclopentadiene with norbornadiene in a Diels-Alder reaction to give the adduct.[2]

Synthesis of Aldrin via a Diels-Alder reaction


Aldrin is named after the German chemist Kurt Alder, one of the coinventors of this kind of reaction. An estimated 270 million kilograms of aldrin and related cyclodiene pesticides were produced between 1946 and 1976.

In soil, on plant surfaces, or in the digestive tracts of insects, aldrin oxidizes to the epoxide dieldrin, which is more strongly insecticidal

Environmental impact and regulation

Like related polychlorinated pesticides, aldrin is highly lipophilic. Its solubility in water is only 0.027 mg/L, which exacerbates its persistence in the environment. It was banned by the Stockholm Convention on Persistent Organic Pollutants. In the U.S., aldrin was cancelled in 1974. The substance is banned from use for plant protection by the EU. [3]

Safety and environmental aspects

Aldrin has rat LD50 of 39 to 60 mg/kg (oral in rats).

References

  1. ^ Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263
  2. ^ Jubb, A. H. (1975). Basic Organic Chemistry, Part 5 Industrial products. London: Wiley. ISBN 0-471-85014-4.  
  3. ^ Chemicals Regulation Directorate. "Banned and Non-Authorised Pesticides in the United Kingdom". http://www.pesticides.gov.uk/approvals.asp?id=55. Retrieved 1 December 2009.  







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