epichlorohydrin
Also known as 2-(chloromethyl)oxirane, 1-chloro-2,3-epoxypropane, 2-chloropropylene oxide, gamma-chloropropylene oxide, (RS)-3-Chloro-1,2-epoxypropane, Epoxychloropropane
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 electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.
Chemical data
- Formula
- C3H5ClO
- Molecular weight
- 92.52 g/mol
- IUPAC name
- 2-(chloromethyl)oxirane
- SMILES
- C1C(O1)CCl
- InChIKey
- BRLQWZUYTZBJKN-UHFFFAOYSA-N
- XLogP
- 0.5
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,904 papersArticle
9 sectionsContents
- Production
- Glycerol routes
- Other routes
- Applications
- Glycerol and epoxy resins synthesis
- Minor and niche applications
- Safety
- Regulation in the United States
- 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 electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.
==Production== Epichlorohydrin is traditionally manufactured from allyl chloride in two steps, beginning with the addition of hypochlorous acid, which affords a mixture of two isomeric alcohols: class=skin-invert-image|320px