Allyl chloride

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Allyl chloride
Allyl chloride.svg
Allyl-chloride-3D-balls.png
Allyl-chloride-3D-vdW.png
Names
Preferred IUPAC name
3-Chloroprop-1-ene
Other names
3-Chloropropene
1-Chloro-2-propene[1]
3-Chloropropylene[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.144
EC Number 209-675-8
UNII
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
Flammable (F)
Harmful (Xn)
Carc. Cat. 3
Muta. Cat. 3
Dangerous for
the environment (N)
R-phrases (outdated) R11 R20/21/22 R36/37/38 R40 R40 R48/20 R68 R50
S-phrases (outdated) (S2) S16 S25 S26 S36/37 S46 S61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%
Lethal dose or concentration (LD, LC):
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)[2]
US health exposure limits (NIOSH):
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).
N verify (what is YesYN ?)
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.[3]

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.[4][3] Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride.[5]

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 metric tons were produced this way in 1997.[3]

Reactions and uses[edit]

The great majority of allyl chloride is converted to epichlorohydrin.[3] Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil)[6] and allylsilane.

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).[7] Being a reactive alkyl halide, it undergoes reductive coupling to give diallyl:[8]

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.[9]

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. ^ "Allyl chloride". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ 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.
  4. ^ 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.
  5. ^ Furniss, Brian; Hannaford, Antony; Smith, Peter; Tatchell, Austin (1996). Vogel's Textbook of Practical Organic Chemistry (5th ed.). London: Longman Science & Technical. p. 558. ISBN 9780582462366. 
  6. ^ 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
  7. ^ J. V. Supniewski; P. L. Salzberg (1941). "Allyl Cyanide". Org. Synth. ; Coll. Vol., 1, p. 46 
  8. ^ Amos Turk; Henry Chanan (1947). "Biallyl". Org. Synth. 27: 7. doi:10.15227/orgsyn.027.0007. 
  9. ^ International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Safety Cards. © IPCS CEC 1993. Retrieved 13 February 2012.