| IUPAC name
| Other names
|Molar mass||44.05 g/mol|
|Density|| 0.882 g/cm3 (at 10 °C)|
|Melting point||−111.3 °C (−168.3 °F; 161.8 K)|
|Boiling point||10.7 °C (51.3 °F; 283.8 K)|
|Solubility|| Miscible with carbon tetrachloride, ethers|
Soluble in acetone, benzene, diethyl ether, ethanol
|Vapor pressure||1.46 atm (20°C)|
Std enthalpy of
|Safety data sheet||Praxair|
|Flash point||−20 °C|
|Lethal dose or concentration (LD, LC):|
LC50 (Median concentration)
| 836 ppm (mouse, 4 hr)|
4000 ppm (rat, 4 hr)
800 ppm (rat, 4 hr)
819 ppm (guinea pig, 4 hr)
1460 ppm (rat, 4 hr)
835 ppm (mouse, 4 hr)
960 ppm (dog, 4 hr)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Ethylene oxide, properly called oxirane by IUPAC, is the organic compound with the formula C2H4O. It is the simplest epoxide and cyclic ether. Ethylene oxide is isomeric with acetaldehyde and vinyl alcohol.
Ethylene oxide is highly flammable and will burn in open air.
- C2H4O + 5/2 O2 → 2 CO2 + 2 H2O
Ethylene oxide is a colorless gas at room temperature, but liquid below 10°C, with a sweet ether-like smell (some sources say bruised-apple like). It is miscible with water, carbon tetrachloride and other organic solvents.
Ethylene oxide is sold by various chemical suppliers, either pure or in solution, but due to its strong carcinogenicity it's sale is restricted to companies.
The preparation of ethylene oxide is not easy, but can be done if the procedure is followed carefully.
- 2 OH–CH2CH2–Cl + Ca(OH)2 → 2 (CH2CH2)O + CaCl2 + 2 H2O
The resulting ethylene oxide is purified through rectification and condensed.
Another route is to absorb dry hydrogen chloride gas into warm ethylene glycol, in the presence of anhydrous zinc chloride and distill the resulting 2-chloroethanol. Some water will also distill and must be removed. Plenty of 1,2-dichloroethane will be produced as a side product.
1,2-Diiodoethane will react with silver oxide to yield ethylene oxide at high temperatures.
Ethylene glycol is a very useful reagent, but its use is limited due to its toxicity. Wear proper protection when working with the compound.
- Make polyethylene glycol
- Make very pure ethylene glycol
- Preparation of ethanolamines
- Phenethyl alcohol synthesis
- Make ethylene carbonate
Ethylene oxide is extremely flammable, very toxic and a potent carcinogen. It's sweet smell can induce the false sense of safety.
Ethylene oxide should be stored in gas cylinders, in dark well ventilated areas.
Ethylene oxide can be safely burned outside. Hydrolysis will lead to ethylene glycol which is non-volatile and safer to handle.
- Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 562
- Zahalka, Hayder A.; Sasson, Yoel; Synthesis; nb. 9; (1986); p. 763 - 765