Diethyl ether peroxide

From Freepedia

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
Image:Diethylether hydroperoxide.png

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.

1 Diethyl ether hydroperoxide
2 Diethyl ether peroxide
3 Tests
4 Degradation
5 References

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.

Image:Diethylether peroxide.png

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.