Diethyl ether peroxide
Encyclopedia : D : DI : DIE : Diethyl ether peroxide
| Diethyl ether hydroperoxide | |
|---|---|
| Formula | C4H10O3 |
| Molecular mass | 106.12 g/mol |
| Boiling point | 62 - 64 °C at 18.7 hPa (reduced pressure) |
| Density | 1.005 g/cm3 |
| CAS number | 18321-53-4 |
| SMILES | CCOC(OO)C |
 | |
Diethyl ether peroxides are a class of organic peroxides that slowly form in diethyl ether upon storage under air, light, or in the presence of metal by autoxidation.
Diethyl ether hydroperoxide
Diethyl ether hydroperoxide (CH3-CH2-O-CH(OOH)-CH3) is a colorless liquid of low viscosity with a pleasant smell. Upon heating it weakly deflagrates, resulting in a fog of acetic acid and water. Diethyl ether hydroperoxide decomposes in the presence of sodium hydroxide and Fe2+ containing salts.
Diethyl ether peroxide
Diethyl ether peroxide, also known as ethylidene peroxide, (-CH(CH3)OO-)n is a polymerization product of diethyl ether hydroperoxide. It is a colorless oily liquid that is an extremely brisant and friction sensitive explosive material. Amounts of less than 5 milligrams can damage chemical apparatuses. The dangerous properties of ether peroxides are the reason that diethyl ether and other peroxide forming ethers like tetrahydrofuran (THF) or ethylenglycoldimethylether (1,2-dimethoxyethane) are avoided in industrial processes.
Tests
Diethyl ether peroxides can be detected with potassium iodide (KI) solution or potassium iodide / starch paper. A positive test results in the formation of iodine (I2) that causes a pink color of the ether phase or a dark bluish spot on the paper strip.
Degradation
Ether peroxides can be destroyed by disproportionation to acetaldehyde with Fe2+ or Mn2+ ions or with triphenylphosphine (PPh3). The resulting aldehyde has to be removed to prevent a rapid back-formation of peroxides.
References
- A. Rieche, R. Meister, Modellversuche zur Autoxidation der Äther, Angewandte Chemie 49(5):106 (1936) (German)
External links
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
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