Allyl chloride
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| Names | |||
|---|---|---|---|
| IUPAC name
3-Chloropropene
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| Properties | |||
| C3H5Cl | |||
| Molar mass | 76.52 g·mol−1 | ||
| Density | 0.94 g/mL | ||
| Melting point | −135 °C (−211 °F; 138 K) | ||
| Boiling point | 45 °C (113 °F; 318 K) | ||
| 0.36 g/100 mL (20 °C) | |||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| Flash point | −32 °C | ||
| Explosive limits | 2.9–11.2% | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene.
Production
Allyl chloride is prepared by the reaction of propylene with chlorine. At lower temperatures, the main product is 1,2-dichloropropane, but at 500 °C, allyl chloride predominates, being formed via a free radical reaction:
- CH3CH=CH2 + Cl2 → ClCH2CH=CH2 + HCl
An estimated 800M kg are produced in this way annually.[1]
Reactions and uses
The great majority of allyl chloride is converted to epichlorohydrin.[1] Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil)[1] and allylsilane.
In the laboratory, allyl chloride is a common alkylating agent, useful in the manufacture of pharmaceuticals and pesticides. Illustrative of its reactivity include its cyanation to allyl cyanide (CH2=CHCH2CN),[2] reductive coupling to give diallyl, oxidative addition to palladium to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2, and dehydrohalogenation to cyclopropene.
Safety
Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision.[3]
References
- ^ a b c Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June 2000. Cite error: The named reference "Ullmann" was defined multiple times with different content (see the help page).
- ^ J. V. Supniewski and P. L. Salzberg (1941). "Allyl Cyanide". Organic Syntheses; Collected Volumes, vol. 1, p. 46.
- ^ International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Safety Cards. © IPCS CEC 1993. Retrieved 13 February 2012.
External links
- International Chemical Safety Card 0010
- NIOSH Pocket Guide to Chemical Hazards. "#0018". National Institute for Occupational Safety and Health (NIOSH).
- IARC Monograph *Allyl chloride.