Epichlorohydrin

(±)-Epichlorohydrin[1]
IUPAC name	chloromethyloxirane
Other names	epichlorohydrin 1-chloro-2,3-epoxypropane γ-chloropropylene oxide glycidyl chloride
Identifiers
CAS number	106-89-8
SMILES	C1C2(O1)C2Cl
Properties
Molecular formula	C3H5ClO
Molar mass	92.52 g/mol
Density	1.1812 g/cm3
Melting point	-25.6 °C
Boiling point	117.9 °C
Hazards
MSDS	External MSDS
NFPA 704	3 3 2
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Epichlorohydrin is a reactive organic compound. It is an epoxide and an organochloride. It is a colorless liquid with a pungent, garlic-like odor that is insoluble in water, but miscible with most polar organic solvents.^[2] Epichlorohydrin is a highly reactive compound and will polymerize upon treatment with acid or strong base.

Epichlorohydrin is manufactured from propylene through the intermediacy of allyl chloride. A major industrial use of epichlorohydrin has been in the production of glycerin, though this application has become less attractive as glycerine is a major byproduct of biodiesel production. Indeed, at least three companies have announced plans to convert glycerine to epichlorohydrin, for instance Solvay and Dow.^{[citation needed]} "Epi" is also used as a building block in the manufacture of plastics, epoxy resins, phenoxy resins and other polymers. It used as a solvent for cellulose, resins and paints and it has found use as an insect fumigant.

Epichlorohydrin is a precursor to glycidyl nitrate, an energetic binder used in explosive and propellant compositions.^[3] The epichlorohydrin is reacted with an alkali nitrate, such as sodium nitrate, producing glycidyl nitrate and alkali chloride.

Epichlorohydrin is flammable, toxic and carcinogenic.^[2]

References

1. ^ Merck Index, 12th Edition, 3648.
2. ^ ^{a b} EPA consumer factsheet
3. ^ Gould, R.F. Advanced Propellant Chemistry, ACS Chemistry Series 54, 1966

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