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
107-05-1 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL451126 YesY
ChemSpider 13836674 YesY
ECHA InfoCard 100.003.144
EC Number 209-675-8
PubChem 7850
UNII V2RFT0R50S N
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 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%
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 of its reactivity is its cyanation to allyl cyanide (CH2=CHCH2CN),[7] 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.[8]

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 and P. L. Salzberg (1941). "Allyl Cyanide". Org. Synth. ; Coll. Vol., 1, p. 46 
  8. ^ International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". International Chemical Safety Cards. © IPCS CEC 1993. Retrieved 13 February 2012.