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

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. The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Image File history File links No higher resolution available. ... The general structure of an organic peroxide. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... Autoxidation is any oxidation that occurs in open air or in presence of oxygen and/or UV radiation and forms peroxides and hydroperoxides. ...

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. The related Category:Units of viscosity has been nominated for deletion, merging, or renaming. ... A log in a fire place. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... This article describes water from a scientific and technical perspective. ... Sodium hydroxide (NaOH), also known as lye or caustic soda, is a caustic metallic base. ... General Name, Symbol, Number iron, Fe, 26 Chemical series transition metals Group, Period, Block 8, 4, d Appearance lustrous metallic with a grayish tinge Standard atomic weight 55. ... A magnified crystal of a salt (halite/sodium chloride) Salt covering the floor of Bad Water in Death Valley, CA, the lowest point in the US. A salt, in chemistry, is any ionic compound composed of cations (positively charged ions) and anions (negative ions) so that the product is neutral...

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. This is the article about the process. ... Brisance is a measure of the rapidity with which an explosive develops its maximum pressure. ... Friction is the force that opposes the relative motion or tendency toward such motion of two surfaces in contact. ... Preparing C-4 explosive This article is concerned solely with chemical explosives. ... The milligram (symbol mg) is an SI unit of mass. ... Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... For other uses of THF, see THF (disambiguation) Tetrahydrofuran is a heterocyclic organic compound. ... Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a clear, colorless, aprotic, and liquid ether that is used as a solvent. ...

Image File history File links No higher resolution available. ...

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. Potassium iodide is a white crystalline salt with chemical formula KI, used in photography and radiation treatment. ... Potassium iodide is a white crystalline salt with chemical formula KI, used in photography and radiation treatment. ... Starch (CAS# 9005-25-8) is a complex carbohydrate which is soluble in water; it is used by plants as a way to store excess glucose. ... General Name, Symbol, Number iodine, I, 53 Chemical series halogens Group, Period, Block 17, 5, p Appearance violet-dark gray, lustrous Standard atomic weight 126. ...

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. Disproportionation is a concept in chemistry and is a redox reaction where a reactant is both oxidised and reduced in the same chemical reaction. ... R-phrases , , S-phrases , , , Flash point −39 °C Autoignition temperature 185 °C RTECS number AB1925000 Supplementary data page Structure and properties n, εr, etc. ... General Name, Symbol, Number manganese, Mn, 25 Chemical series transition metals Group, Period, Block 7, 4, d Appearance silvery metallic Atomic mass 54. ... “Multivalent” redirects here. ... Triphenylphosphine (in Europe: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 - often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. ... An aldehyde. ...

References

• A. Rieche, R. Meister, Modellversuche zur Autoxidation der Äther, Angewandte Chemie 49(5):106 (1936) (German)

External links

• Links to external chemical sources