Difference between revisions of "Allyl chloride"

Latest revision as of 09:58, 20 September 2010

Allyl chloride
File:Allyl chloride.png
File:Allyl-chloride-3D-balls.png	File:Allyl-chloride-3D-vdW.png
IUPAC name 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	75px 3 3 1
Flash point	−32 °C
Autoignition temperature	390 °C
Explosive limits	2.9–11.2%
Y (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.

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. ↑ ^{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.
2. ↑ J. V. Supniewski and P. L. Salzberg (1941), "Allyl Cyanide", Org. Synth. ; Coll. Vol., 1: 46  Missing or empty |title= (help)
3. ↑ "TRI Releases Map". Toxmap.nlm.nih.gov. Retrieved 2010-03-23. 
4. ↑ 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