Diethyl ether peroxide

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Diethyl ether hydroperoxide
Diethyl ether peroxide.svg
Identifiers
CAS number 18321-53-4 YesY
ChemSpider 19985446 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H10O3
Molar mass 106.12 g/mol
Density 1.005 g/cm3
Boiling point 62 to 64 °C (144 to 147 °F; 335 to 337 K) at 18.7 hPa (reduced pressure)
Hazards
Main hazards Explosive
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerin Special hazards (white): no codeNFPA 704 four-colored diamond
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.

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, 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.

Formation of diethyl ether peroxide

Tests[edit]

Diethyl ether peroxides can be detected with a potassium iodide (KI) solution in acetic acid or potassium iodide / starch paper. A positive test results in the formation of iodine (I2) that causes a yellow or brown color of the ether phase or a dark bluish spot on the paper strip.[1]

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)
  1. ^ "Peroxide Forming Solvents". Sigma-Aldrich. Retrieved 2014-07-09.