EPICHLORHYDRIN
EPICHLOROHYDRIN; 2-(Chloromethyl)oxirane; Epichlorhydrin; 1-Chloro-2,3-epoxypropane; Glycidyl chloride;106-89-8; 2-(chloromethyl)oxirane; InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2; BRLQWZUYTZBJKN-UHFFFAOYSA-N; C1C(O1)CCl; ech; ECH
CAS NUMBER: 106-89-8
EC NUMBER:203-439-8
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.
Applications
Glycerol and epoxy resins synthesis.
Epichlorohydrin is mainly converted to bisphenol A diglycidyl ether, a building block in the manufacture of epoxy resins. It is also a precursor to monomers for other resins and polymers. Another usage is the conversion to synthetic glycerol:
CH2CHOCH2Cl + 2 H2O › HOCH2CH(OH)CH2(OH) + HCl
However, the rapid increase in biodiesel production, where glycerol is a waste product, has led to a glut of glycerol on the market, rendering this process uneconomic for the mass market. Synthetic glycerol is now used only in sensitive pharmaceutical, technical and personal care applications where quality standards are very high
Epichlorohydrin is a versatile precursor in the synthesis of many organic compounds. For example, it is converted to glycidyl nitrate, an energetic binder used in explosive and propellant compositions. The epichlorohydrin is reacted with an alkali nitrate, such as sodium nitrate, producing glycidyl nitrate and alkali chloride. It is used as a solvent for cellulose, resins, and paints, and it has found use as an insect fumigant. Polymers made from epichlorohydrin, e.g., polyamide-epichlorohydrin resins, are used in paper reinforcement and in the food industry to manufacture tea bags, coffee filters, and sausage/salami casings as well as with water purification. An important biochemical application of epichlorohydrin is its use as crosslinking agent for the production of Sephadex size-exclusion chromatographic resins from dextrans.