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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
3-Chloropropylene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.144
EC Number
  • 209-675-8
KEGG
PubChem CID
RTECS number
  • UC7350000
UNII
UN number 1100
  • InChI=1S/C3H5Cl/c1-2-3-4/h2H,1,3H2 checkY
    Key: OSDWBNJEKMUWAV-UHFFFAOYSA-N checkY
  • InChI=1/C3H5Cl/c1-2-3-4/h2H,1,3H2
    Key: OSDWBNJEKMUWAV-UHFFFAOYAQ
  • C=CCCl
Properties
C3H5Cl
Molar mass 76.52 g·mol−1
Appearance Colorless, brown, yellow, or purple liquid
Odor pungent, unpleasant
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
1.4055
Viscosity 0.3130 mPa·s
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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)
3
3
1
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)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1 ppm (3 mg/m3)
REL (Recommended)
TWA 1 ppm (3 mg/m3)
ST 2 ppm (6 mg/m3)
IDLH (Immediate danger)
250 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.

Production

Laboratory scale

Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting allyl alcohol with phosphorus trichloride. Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride.

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:

CH3CH=CH2 + Cl2 → ClCH2CH=CH2 + HCl

An estimated 800,000 tonnes were produced this way in 1997.

Reactions and uses

The great majority of allyl chloride is converted to epichlorohydrin. Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil), 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). Being a reactive alkyl halide, it undergoes reductive coupling to give diallyl:

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

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

See also

External links


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