Diethyl ether peroxide
| Diethyl ether hydroperoxide | |
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| Identifiers | |
| CAS number | 18321-53-4 |
| ChemSpider | 19985446  |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C4H10O3 |
| Molar mass | 106.12 g/mol |
| Density | 1.005 g/cm³ |
| Boiling point |
62 - 64 °C at 18.7 hPa (reduced pressure) |
| Hazards | |
| Main hazards | Explosive |
| NFPA 704 |
 4
2
4
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.
Contents |
Diethyl ether hydroperoxide [edit]
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 [edit]
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.[who?] The dangerous properties of ether peroxides are the reason that diethyl ether and other peroxide forming ethers like tetrahydrofuran (THF) or ethylene glycol dimethyl ether (1,2-dimethoxyethane) are avoided in industrial processes.
Tests [edit]
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 [edit]
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 [edit]
- A. Rieche, R. Meister, Modellversuche zur Autoxidation der Äther, Angewandte Chemie 49(5):106 (1936) (German)
