Chapter 1: Introduction

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. It has a boiling point at
117.9 C.The most familiar epoxy resin is used as a coating on the inside of food and
beverage cans to prevent rusting. Epichlorohydrin is also used as a solvent and in the
synthesis of glycerol. Other uses include insect fumigation and as an intermediate for the
formation of glycidyl acrylate derivatives such as those used in the manufacture of eyeglass
lenses.

Commercial grade epichlorohydrin can be found listed as being of a minimum purity of

98.0 weight percent (with water content less than 0.1 weight percent), but more typically it is
listed as having a minimum purity of 99.9 weight percent (with water content less than
0.05 weight percent).

Epichlorohydrin is an important commercial chemical, with a global annual demand of well

over one million tons. Primary commercial applications are in the production of epoxy
resins, elastomers, and synthetic glycerol. Glycerol production has been on the decline as
byproduct glycerol from soap production and biodiesel have been able to meet most demand.
Dow is the only remaining known producer of synthetic glycerol, with production in Stade
Germany. Synthetic glycerol is only used when the highest purity is required, as in
pharmaceuticals and some food grade products. The availability of crude byproduct from
biodiesel production has not only given rise to a reduced requirement of glycerol from
epichlorohydrin but actually stimulated new world-scale epichlorohydrin plants based on
crude glycerol feedstock. These world-scale plants currently under construction and
scheduled to come on stream within the next three years will add to the existing smaller scale
glycerol to epichlorohydrin plants which have recently come on stream.
Chemical Equation of the Epichlorohydrin

Epichlorohydrin was first introduced commercially in the mid-1930s by Shell using a process
based on the high temperature chlorination of propylene to give allyl chloride and byproduct
hydrogen chloride (HCl) as shown below. (At lower temperatures, the predominant reaction
is the addition of chlorine to the double bond to give dichloropropane.).

Allyl chloride was then converted to glycerol chlorohydrin (dichloropropanol) by reaction

with hypochlorous acid (HOCl was obtained by reaction of chlorine and water, with
byproduct HCl also formed):

Dehydrohalogenation of the dichloropropanol with an alkali (base) such as calcium

hydroxide gave epichlorohydrin and byproduct calcium chloride:
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Physical and Chemical Properties

Epichlorohydrin is a colorless, mobile, liquid and has an irritating chloroform-like odor. It is

soluble in benzene, miscible with alcohol, ether, chloroform, trichloroethylene, and carbon
tetrachloride, and immiscible with petroleum hydrocarbons. It is not soluble in water
(Howard, 1990).

Properties Value

Molecular Weight 92.53

Boiling Point 116.5 oC
Melting Point -48.0 oC
Flash point, open cup 40 oC (105 oF)
Water solubility 65.8 at 20 oC
Vapor Density 3.29 (air=1)
Vapor Pressure 10 mm Hg at 16.6 oC
Density/Specific Gravity 1.1812 at 20/4 oC (water=1)
Log/Octanol Water Partition Coefficient 0.26
Conversion Factor 1 ppm = 3.78 mg/m3