Aldrin
| Aldrin | |
|---|---|
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1,2,3,4,10,10-Hexachloro- |
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| Identifiers | |
| CAS number | 309-00-2  |
| ChemSpider | 10292747 |
| UNII | OZE3CLY605 |
| KEGG | C07552 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C12H8Cl6 |
| Molar mass | 364.91 g mol−1 |
| Appearance | colorless solid |
| Melting point |
104 °C, 377 K, 219 °F |
| Solubility in water | slightly soluble |
| Vapor pressure | 7.5 × 10−5 mmHg @ 20 °C |
| Hazards | |
| NFPA 704 |
 0
2
0
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| Flash point | 66 °C (151 °F) |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 |
[edit] Production
Aldrin is produced by combining hexachlorocyclopentadiene with norbornadiene in a Diels-Alder reaction to give the adduct.[2]
Similarly, an isomer of aldrin, known as isodrin is produced by reaction of hexachloronobornadiene with cyclopentadiene.[3]
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.
[edit] 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. [4]
[edit] Safety and environmental aspects
Aldrin has rat LD50 of 39 to 60 mg/kg (oral in rats). For fish however, it is extremely toxic, with an LC50 of 0.006– 0.01 for trout and blue gill.[1]
[edit] References
- ^ a b Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263
- ^ Jubb, A. H. (1975). Basic Organic Chemistry, Part 5 Industrial products. London: Wiley. ISBN 0-471-85014-4.
- ^ Bird, C. W.; Cookson, R. C.; Crundwell, E. (1961). "946. Cyclisations and rearrangements in the isodrin?aldrin series". Journal of the Chemical Society (Resumed): 4809. doi:10.1039/JR9610004809.
- ^ Chemicals Regulation Directorate. "Banned and Non-Authorised Pesticides in the United Kingdom". Retrieved 1 December 2009.
