Allyl chloride
McGraw-Hill Science & Technology Dictionary:
Top
allyl chloride
(′al·əl ′klör′īd)
(organic chemistry) CH2CHCH2Cl A volatile, pungent, toxic, flammable, colorless liquid, boiling at 46°C; insoluble in water; made by chlorination of propylene at high temperatures.
Related Videos:
Top
Allyl chloride
Wikipedia on Answers.com:
Top
Allyl chloride
| Allyl chloride | |
|---|---|
 |
|
 |
 |
|
3-Chloropropene |
|
| 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) |
|
| 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. 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.
- ^ 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 Safety Cards. © IPCS CEC 1993. http://siri.org/msds/mf/cards/file/0010.html. Retrieved 13 February 2012.
External links
This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)
Post a question - any question - to the WikiAnswers community:
Copyrights:
McGraw-Hill Science & Technology Dictionary
McGraw-Hill Dictionary of Scientific and Technical Terms. Copyright © 2003, 1994, 1989, 1984, 1978, 1976, 1974 by McGraw-Hill Companies, Inc. All rights reserved.
Read more
