Allyl chloride
| Allyl chloride | |
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3-Chloropropene |
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| Properties | |
| Molecular formula | C3H5Cl |
| Molar mass | 76.52 g mol−1 |
| Density | 0.94 g/mL |
| Melting point |
-135 °C, 138 K, -211 °F |
| Boiling point |
45 °C, 318 K, 113 °F |
| Solubility in water | 0.36 g/100 mL (20 °C) |
| Hazards | |
| EU Index | 602-029-00-X |
| EU classification | Flammable (F) Harmful (Xn) Carc. Cat. 3 Muta. Cat. 3 Dangerous for the environment (N) |
| R-phrases | R11 R20/21/22 R36/37/38 R40 R40 R48/20 R68 R50 |
| S-phrases | (S2) S16 S25 S26 S36/37 S46 S61 |
| NFPA 704 |
 3
3
1
|
| Flash point | −32 °C |
| Autoignition temperature |
390 °C |
| Explosive limits | 2.9–11.2% |
 (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 | |
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.
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[edit] 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]
[edit] 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.
[edit] Safety
Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision.[3]
[edit] 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.
- ^ J. V. Supniewski and P. L. Salzberg (1941), "Allyl Cyanide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0046; Coll. Vol. 1: 46
- ^ International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Saftey Cards. © IPCS CEC 1993. http://siri.org/msds/mf/cards/file/0010.html. Retrieved 13 February 2012.
