Allyl chloride
| Allyl chloride | |
|---|---|
| File:Allyl chloride.png | |
| 1-Chloroprop-2-ene | |
| style="background: #F8EABA; text-align: center;" colspan="2" | 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) |
| style="background: #F8EABA; text-align: center;" colspan="2" | 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 | |
| Flash point | −32 °C |
| Autoignition temperature |
390 °C |
| Explosive limits | 2.9–11.2% |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 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.
Contents
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.
Mapping of industrial releases in the United States
One tool that maps the most recent release information for allyl chloride [1] to particular locations in the United States[3] and also provides additional information about such releases is TOXMAP. TOXMAP is a Geographic Information System (GIS) from the Division of Specialized Information Services of the United States National Library of Medicine (NLM) that uses maps of the United States to help users visually explore data from the United States Environmental Protection Agency's (EPA) Toxics Release Inventory and Superfund Basic Research Programs. TOXMAP is a resource funded by the US Federal Government. TOXMAP's chemical and environmental health information is taken from NLM's Toxicology Data Network (TOXNET)[4] and PubMed, and from other authoritative sources.
References
- ↑ 1.0 1.1 1.2 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.; Coll. Vol., 1: 46 Missing or empty
|title=(help) - ↑ "TRI Releases Map". Toxmap.nlm.nih.gov. Retrieved 2010-03-23.
- ↑ TOXNET - Databases on toxicology, hazardous chemicals, environmental health, and toxic releases
External links
- International Chemical Safety Card 0010
- NIOSH Pocket Guide to Chemical Hazards 0018
- IARC Monograph *Allyl chloride.de:Allylchlorid
et:Allüülkloriid fr:Chlorure d'allyle nl:Allylchloride ja:塩化アリル no:Allylklorid pl:Chlorek allilu sv:Allylklorid vi:Allyl clorua zh:烯丙基氯
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