Diethyl ether peroxide

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Diethyl ether hydroperoxide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4H10O3/c1-3-6-4(2)7-5/h4-5H,3H2,1-2H3 checkY
    Key: CXWWPQGYBJCHJL-UHFFFAOYSA-N checkY
  • InChI=1/C4H10O3/c1-3-6-4(2)7-5/h4-5H,3H2,1-2H3
    Key: CXWWPQGYBJCHJL-UHFFFAOYAS
  • CCOC(OO)C
  • CC(OCC)OO
Properties
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
Occupational safety and health (OHS/OSH):
Main hazards
 Explosive
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. propaneInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
4
4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

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

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.[2]

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

  1. ^ A. Rieche, R. Meister (1936). "Modellversuche zur Autoxidation der Äther". Angewandte Chemie (in German). 49 (5): 106.
  2. ^ "Peroxide Forming Solvents". Sigma-Aldrich. Retrieved 2014-07-09.
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