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Epichlorohydrin

(±)-Epichlorohydrin
Epichlorohydrin
The rear section of ball-and-stick model of the epichlorohydrin molecule
Ball-and-stick model of the epichlorohydrin molecule
Names
Preferred IUPAC name
2-(Chloromethyl)oxirane
Other names
(Chloromethyl)oxirane
Epichlorohydrin
1-Chloro-2,3-epoxypropane
γ-Chloropropylene oxide
Glycidyl chloride
Identifiers
106-89-8 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:37144 YesY
ChemSpider 13837112 YesY
ECHA InfoCard 100.003.128
KEGG C14449 YesY
PubChem 7835
UNII 08OOR508C0 YesY
Properties
C3H5ClO
Molar mass 92.52 g/mol
Appearance colorless liquid
Odor garlic or chloroform-like
Density 1.1812 g/cm3
Melting point −25.6 °C (−14.1 °F; 247.6 K)
Boiling point 117.9 °C (244.2 °F; 391.0 K)
7% (20°C)
Vapor pressure 13 mmHg (20°C)
Hazards
Safety data sheet External MSDS
Toxic T
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 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 32 °C (90 °F; 305 K)
Explosive limits 3.8%-21%
Lethal dose or concentration (LD, LC):
3617 ppm (rat, 1 hr)
2165 ppm (rat, 1 hr)
250 ppm (rat, 8 hr)
244 ppm (rat, 8 hr)
360 ppm (rat, 6 hr)
250 ppm (rat, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 5 ppm (19 mg/m3) [skin]
REL (Recommended)
 Carcinogen
IDLH (Immediate danger)
 Ca [75 ppm]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive compound and is used in the production of glycerol, plastics, epoxy glues and resins, and elastomers. In contact with water, epichlorohydrin hydrolyzes to 3-MCPD, a carcinogen found in food.

Epichlorohydrin was first described in 1848 by Marcellin Berthelot. The compound was isolated during studies on reactions between glycerol and gaseous hydrogen chloride.

Epichlorohydrin is manufactured from allyl chloride in two steps, beginning with the addition of hypochlorous acid, which affords a mixture of two alcohols:

In the second step, this mixture is treated with base to give the epoxide:

In this way, more than 800,000 tons (1997) of epichlorohydrin are produced annually.

Glycerol is a co-product of biodiesel produced on a large scale. The conversion of glycerol into other building block chemicals is of interest because glycerol is otherwise hard to dispose of. Dow and Solvay are building glycerol-to-epichlorohydrin (GTE) plants in Shanghai and Thailand, respectively. In Dow's process, glycerol is dichlorinated with hydrogen chloride with the help of a carboxylic acid catalyst. The mixture of dichlorohydroxypropanes is treated with base to form epichlorohydrin.


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