Allyl chloride
Chemical compound
From Wikipedia, the free encyclopedia
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.[4]
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| Names | |||
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| Preferred IUPAC name
3-Chloroprop-1-ene | |||
| Other names | |||
| Identifiers | |||
3D model (JSmol) |
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| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.144 | ||
| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |||
| UN number | 1100 | ||
CompTox Dashboard (EPA) |
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| Properties | |||
| C3H5Cl | |||
| Molar mass | 76.52 g·molâ1 | ||
| Appearance | Colorless, brown, yellow, or purple liquid[1] | ||
| Odor | pungent, unpleasant[1] | ||
| Density | 0.94 g/mL | ||
| Melting point | â135 °C (â211 °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] | ||
Refractive index (nD) |
1.4055 | ||
| Viscosity | 0.3130 mPa·s[2] | ||
| Hazards | |||
| GHS labelling: | |||
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| Danger | |||
| H225, H302, H312, H315, H319, H332, H335, H341, H351, H373, H400 | |||
| P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | â32 °C (â26 °F; 241 K) | ||
| 390 °C (734 °F; 663 K) | |||
| Explosive limits | 2.9â11.2% | ||
| Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration) |
11000 mg/m3 (rat, 2 hr) 11500 mg/m3 (mouse, 2 hr) 5800 mg/m3 (guinea pig, 2 hr) 22500 mg/m3 (rabbit, 2 hr) 10500 mg/m3 (cat, 2 hr)[3] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) |
TWA 1 ppm (3 mg/m3)[1] | ||
REL (Recommended) |
TWA 1 ppm (3 mg/m3) ST 2 ppm (6 mg/m3)[1] | ||
IDLH (Immediate danger) |
250 ppm[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production
Laboratory scale
Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting allyl alcohol with phosphorus trichloride.[5][4] Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride.[6]
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:
![{\displaystyle {\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}\mathrm {CH} {=}\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {Cl} {\vphantom {A}}_{\smash[{t}]{2}}{}\mathrel {\longrightarrow } {}\mathrm {ClCH} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {CH} {=}\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {HCl} }}](http://wikimedia.org/api/rest_v1/media/math/render/svg/49a2aa3447a82e549c5c5634089dd5a814f31e8a)
An estimated 800,000 tonnes were produced this way in 1997.[4]
Reactions and uses
The great majority of allyl chloride is converted to epichlorohydrin.[4] Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil),[7] and 1-bromo-3-chloropropane.
As an alkylating agent, it is useful in the manufacture of pharmaceuticals and pesticides, such as mustard oil.
Illustrative reactions
Illustrative of its reactivity is its cyanation to allyl cyanide (CH2=CHCH2CN).[8] Being a reactive alkyl halide, it undergoes reductive coupling to give diallyl:[9]
![{\displaystyle {2\,\mathrm {ClCH} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {CH} {=}\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {Mg} {}\mathrel {\longrightarrow } {}(\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{2}}){\vphantom {A}}_{\smash[{t}]{2}}(\mathrm {CH} {=}\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{2}}){\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {MgCl} {\vphantom {A}}_{\smash[{t}]{2}}}}](http://wikimedia.org/api/rest_v1/media/math/render/svg/1ba62f2439cfd4b1cd79ade8dc9035a4c5f7aca0)
It undergoes oxidative addition to palladium(0) to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2. Dehydrohalogenation gives cyclopropene.
Safety
See also
External links
- International Chemical Safety Card 0010
- NIOSH Pocket Guide to Chemical Hazards. "#0018". National Institute for Occupational Safety and Health (NIOSH).
- IARC Monograph *Allyl chloride.