Diethyl Ether Peroxide

Diethyl ether hydroperoxide
FormulaC4H10O3
Molecular mass106.12 g/mol
Boiling point62 - 64 C at 18.7 hPa (reduced pressure)
Density1.005 g/cm3
CAS number18321-53-4
SMILESCCOC(OO)C
Chemical structure of diethyl ether hydroperoxide.png
Diethyl ether peroxides are a class of 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. Formation of diethyl ether peroxide

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 ther, Angewandte Chemie 49(5):106 (1936) (German)

 

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