Allyl chloride
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| Preferred IUPAC name
3-Chloroprop-1-ene | |||
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| Identifiers | |||
3D model (JSmol)
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| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.144 | ||
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| KEGG | |||
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·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] | ||
Refractive index (nD)
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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, P261, 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 | −32 °C (−26 °F; 241 K) | ||
| 390 °C (734 °F; 663 K) | |||
| Explosive limits | 2.9–11.2% | ||
| Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration)
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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)
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TWA 1 ppm (3 mg/m3)[1] | ||
REL (Recommended)
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TWA 1 ppm (3 mg/m3) ST 2 ppm (6 mg/m3)[1] | ||
IDLH (Immediate danger)
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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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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]
Production
[edit]Laboratory scale
[edit]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
[edit]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 800,000 tonnes were produced this way in 1997.[4]
Reactions and uses
[edit]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
[edit]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]
- 2 ClCH2CH=CH2 + Mg → (CH2)2(CH=CH2)2 + MgCl2
It undergoes oxidative addition to palladium(0) to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2. Dehydrohalogenation gives cyclopropene.
Safety
[edit]Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision.[10]
See also
[edit]External links
[edit]- International Chemical Safety Card 0010
- NIOSH Pocket Guide to Chemical Hazards. "#0018". National Institute for Occupational Safety and Health (NIOSH).
- IARC Monograph *Allyl chloride.
References
[edit]- ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0018". National Institute for Occupational Safety and Health (NIOSH).
- ^ Viswanath, D.S.; Natarajan, G. (1989). Data Book on the Viscosity of Liquids. Hemisphere Publishing Corporation. ISBN 0-89116-778-1.
- ^ "Allyl chloride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c d 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.
- ^ Hofmann. Augustus William and Cahours. Augustus (1857) "Researches on a new class of alcohols," Philosophical Transactions of the Royal Society of London, 147: 555–574 ; see pp. 558–559.
- ^ Furniss, Brian; Hannaford, Antony; Smith, Peter; Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry (5th ed.). London: Longman Science & Technical. pp. 558. ISBN 9780582462366.
- ^ 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
- ^ J. V. Supniewski & P. L. Salzberg (1941). "Allyl Cyanide". Organic Syntheses; Collected Volumes, vol. 1, p. 46.
- ^ Amos Turk; Henry Chanan (1947). "Biallyl". Org. Synth. 27: 7. doi:10.15227/orgsyn.027.0007.
- ^ International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Safety Cards. © IPCS CEC 1993. Archived from the original on 2016-03-04. Retrieved 13 February 2012.
| Authority control databases: National |
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