Allyl chloride

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Allyl chloride
Allyl chloride.svg
Allyl-chloride-3D-balls.png
Allyl-chloride-3D-vdW.png
Names
IUPAC name
3-Chloropropene
Other names
1-Chloro-2-propene[1]
3-Chloropropylene[1]
Identifiers
107-05-1 YesY
ChEMBL ChEMBL451126 YesY
ChemSpider 13836674 YesY
EC number 209-675-8
Jmol-3D images Image
PubChem 7850
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]
1.4055
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
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −32 °C (−26 °F; 241 K)
390 °C (734 °F; 663 K)
Explosive limits 2.9–11.2%
US health exposure limits (NIOSH):
TWA 1 ppm (3 mg/m3)[1]
TWA 1 ppm (3 mg/m3)
ST 2 ppm (6 mg/m3)[1]
250 ppm[1]
Except where noted otherwise, data is 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.

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.[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[edit]

Today 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 were produced this way in 1997.[2]

Reactions and uses[edit]

The great majority of allyl chloride is converted to epichlorohydrin.[2] Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil)[2] 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),[4] reductive coupling to give diallyl, oxidative addition to palladium to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2, and dehydrohalogenation to cyclopropene.

Safety[edit]

Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision.[5]

See also[edit]

External links[edit]

References[edit]

  1. ^ a b c d e f g h "NIOSH Pocket Guide to Chemical Hazards #0018". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ 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.
  3. ^ Furniss, Brian; Hannaford, Antony; Smith, Peter; and Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry 5th Ed. London: Longman Science & Technical. p. 558. ISBN 9780582462366. 
  4. ^ J. V. Supniewski and P. L. Salzberg (1941). "Allyl Cyanide". Org. Synth. ; Coll. Vol. 1, p. 46 
  5. ^ International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Safety Cards. © IPCS CEC 1993. Retrieved 13 February 2012.