Jump to content

Diethyl ether peroxide

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by ZooFari (talk | contribs) at 01:05, 6 February 2011 (removed Category:Organic peroxides; added Category:Organic hydroperoxides using HotCat). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

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 - 64 °C 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. nitroglycerin
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.

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 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 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 Äther, Angewandte Chemie 49(5):106 (1936) (German)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Diethyl_ether_peroxide&oldid=412258530"