Structure via PubChem · Public domain (PubChem)
epichlorohydrin
Sign in to saveAlso 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 papers- Epichlorohydrin.IARC monographs on the evaluation of carcinogenic risks to humans · 1999
- Epichlorohydrin.IARC monographs on the evaluation of the carcinogenic risk of chemicals to man · 1976
- Epichlorohydrin.Report on carcinogens : carcinogen profiles · 2011
- Epichlorohydrin.Report on carcinogens : carcinogen profiles · 2004
- Epichlorohydrin.Veterinary and human toxicology · 1979
via PubMed
Wikidata facts
- Mass
- 92.00289246
Show 16 more facts
- melting point
- -57
- chemical formula
- C₃H₅ClO
- boiling point
- 116.11
- Commons category
- Epichlorohydrin
- NIOSH Pocket Guide ID
- 0254
- density
- 1.18
- immediately dangerous to life or health
- 283.5
- vapor pressure
- 13
- flash point
- 93
- lower flammable limit
- 3.8
- upper flammable limit
- 21
- ionization energy
- 10.20
- time-weighted average exposure limit
- 19
- ceiling exposure limit
- 0
- canonical SMILES
- C1C(O1)CCl
- solubility
- 7
via Wikidata · CC0
~4 min read
Article
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