(S)-(+)-Epichlorohydrin Chemical Properties

Melting point:

−57 °C(lit.)

Boiling point:

92-93 °C360 mm Hg(lit.)

alpha 

34 º (589nm, c=1, MeOH)

Density 

1.183 g/mL at 25 °C(lit.)

vapor density 

3.2 (vs air)

vapor pressure 

13.8 mm Hg ( 21.1 °C)

refractive index 

n20/D 1.438(lit.)

Flash point:

93 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Methanol (Slightly)

form 

Liquid

color 

Clear colorless to very pale yellow

explosive limit

21%

optical activity

[α]20/D +35°, c = 1 in methanol

Water Solubility 

insoluble

BRN 

1420784

Dielectric constant

22.9（20℃）

CAS DataBase Reference

67843-74-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

45-10-23/24/25-34-43

Safety Statements 

53-45

RIDADR 

UN 2023 6.1/PG 2

WGK Germany 

3

RTECS 

TX4900000

Autoignition Temperature

1421 °F

HazardClass 

6.1

PackingGroup 

II

HS Code 

29038900

MSDS

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(S)-(+)-Epichlorohydrin Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Chemical Properties

Epichlorhydrin is a colourless liquid with odour, b.p. 115°C.

Uses

(S)-(+)-Epichlorohydrin is utilized for the synthesis of macquarimicins and hydroxyisoxazolidines and (+)-cis-sylvaticin, which is a potential antitumor agent. It is used to synthesize inhibitors of fatty acid oxidation as potential metabolic modulators. It acts as a solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels, lacquers and cement for celluloid. It is also used as a stabilizer and also useful as a bifunctional alkylating agent with the potential to form DNA cross-links.

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

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