Allyl chloride
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| Names | |||
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| IUPAC name
3-Chloropropene
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| Other names | |||
| Identifiers | |||
107-05-1  |
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| ChEMBL | ChEMBL451126 |
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| ChemSpider | 13836674 |
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| EC Number | 209-675-8 | ||
| Jmol 3D model | Interactive image | ||
| PubChem | 7850 | ||
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| Properties | |||
| C3H5Cl | |||
| Molar mass | 76.52 g·mol−1 | ||
| Appearance | Colorless, brown, yellow, or purple liquid[1] | ||
| Odor | pungent, unpleasant[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) | |||
| Solubility | soluble in ether, acetone, benzene, chloroform | ||
| Vapor pressure | 295 mmHg[1] | ||
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Refractive index (nD)
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1.4055 | ||
| Vapor pressure | {{{value}}} | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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. It is an alkylating agent, which makes it both useful and hazardous to handle.[2]
Contents
Production
Laboratory scale
Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting allyl alcohol with phosphorus trichloride.[2] Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride.[3]
Industrial scale
Allyl chloride is produced by the chlorination of propylene. 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 were produced this way in 1997.[2]
Reactions and uses
The great majority of allyl chloride is converted to epichlorohydrin.[2] Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil)[4] and allylsilane.
As an alkylating agent, it is useful in the manufacture of pharmaceuticals and pesticides, such as mustard oil. Illustrative of its reactivity is its cyanation to allyl cyanide (CH2=CHCH2CN),[5] 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.[6]
See also
External links
- International Chemical Safety Card 0010
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- IARC Monograph *Allyl chloride.
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Cite error: Invalid
<ref>tag; no text was provided for refs namedNIOSH - ↑ 2.0 2.1 2.2 2.3 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.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ F. Romanowski, H. Klenk "Thiocyanates and Isothiocyanates, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim. doi:10.1002/14356007.a26_749
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
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