Chemical Properties
Colorless to light yellow liqui
Uses
S-enantiomer of Epichlorohydrin, (S)-Epichlorohydrin), an important industrial chemical, is a bifunctional alkylating agent with the potential to form DNA cross-links. It is used as a solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels and lacquers, cement for Celluloid. Also, it is used as stabilizer.
Definition
ChEBI: (S)-epichlorohydrin is an epichlorohydrin. It is functionally related to a (R)-1,2-epoxypropane. It is an enantiomer of a (R)-epichlorohydrin.
Synthesis
The general procedure for the synthesis of (S)-(+)-epichlorohydrin from 1-chloro-2,3-epoxypropane is as follows: first, 463 kg of racemic epichlorohydrin was mixed with 19.2 kg of the catalyst [(1-RR)-(dibenzoyl-LLA)] made from Example 1 of the Preparation and the mixture was cooled to 5 °C. Subsequently, 49.5 kg of water was slowly added and the reaction continued at 20°C for 7 hours. Upon completion of the reaction, the reaction mixture was subjected to reduced-pressure thin-film evaporation at less than 30 °C to afford 190 kg of (S)-epichlorohydrin with an optical purity of 99.8% ee and a yield of 82%. The above reaction process was repeated by adding new racemic epichlorohydrin and water to the evaporated residue to again obtain (S)-epichlorohydrin with an optical purity of more than 99.0%ee.
References
[1] Patent: WO2008/153280, 2008, A1. Location in patent: Page/Page column 41
[2] Patent: WO2008/153280, 2008, A1. Location in patent: Page/Page column 28
[3] Tetrahedron Asymmetry, 2003, vol. 14, # 22, p. 3633 - 3638
[4] Journal of the American Chemical Society, 1995, vol. 117, # 21, p. 5897 - 5898
[5] Journal of the American Chemical Society, 1999, vol. 121, # 17, p. 4147 - 4154
