Epichlorohydrin

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(±)-Epichlorohydrin[1]
Epichlorohydrin
Ball-and-stick model of the epichlorohydrin molecule
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 disclaimer and references

Epichlorohydrin is 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 the price of glycerine has fallen. Indeed, at least three companies have announced plans to convert glycerine to epichlorohydrin. "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]

[edit] 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