Diethyl ether hydroperoxide is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula C₂H₅OCH(OOH)CH₃. It is a colorless liquid. Diethyl ether hydroperoxide and its condensation products are responsible for the explosive

organic peroxide In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group (). If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. The O−O bond of peroxides easily b ...

s that slowly form upon exposure of

diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...

to ambient air and temperature conditions.

Synthesis and reactions

Diethyl ether hydroperoxide can be formed by the

photooxygenation A photooxygenation is a light-induced oxidation reaction in which molecular oxygen is incorporated into the product(s). Initial research interest in photooxygenation reactions arose from Oscar Raab's observations in 1900 that the combination of li ...

of diethyl ether. This is a radical process, driven by UV excitation of molecular oxygen into a more reactive form. Its formation is usually undesirable due to the associated risk of explosion. For this reason commercial samples of diethyl ether will usually contain

antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...

s such as BHT and be contained in a material able to block UV rays, such as amber glass. : Ether-autoxidation

It can be intentionally prepared in high yield by the acid-catalyzed addition of

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...

ethyl vinyl ether Ethyl vinyl ether is an organic compound with the chemical formula CH3CH2OCH=CH2. It is the simplest enol ether that is liquid at room temperature. It is used as a synthetic building block and a monomer. Preparation and reactions Ethyl vinyl e ...

: :C₂H₅OCH=CH₂ + H₂O₂ → C₂H₅OCH(OOH)CH₃ Related hydroperoxides can be produced similarly. Diethyl ether hydroperoxide, upon heating in water, decomposes to

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic compound, organic chemical compound with the chemical formula, formula , sometimes abbreviated as . It is a colorless liquid or gas, boiling near room temperature. It is one of the most ...

: :C₂H₅OCH(OOH)CH₃ → CH₃CHO + C₂H₅OH + H₂O₂ Diethyl ether hydroperoxide forms polymers known as diethyl ether peroxide, or ethylidene peroxide: The peroxide is a colorless oil that is an extremely

brisant Brisance (; ) is the shattering capability of a high explosive, determined mainly by its detonation pressure. Application Brisance is of practical importance in explosives engineering for determining the effectiveness of an explosion in blastin ...

and

friction Friction is the force resisting the relative motion of solid surfaces, fluid layers, and material elements sliding against each other. Types of friction include dry, fluid, lubricated, skin, and internal -- an incomplete list. The study of t ...

sensitive

explosive material An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An exp ...

, however the polymeric materials are solid making them more dangerous as evaporation of the volatile diethyl ether can leave thin films of pure explosive.

Tests

Diethyl ether peroxides can be detected with a

potassium iodide Potassium iodide is a chemical compound, medication, and dietary supplement. It is a medication used for treating hyperthyroidism, in radiation emergencies, and for protecting the thyroid gland when certain types of radiopharmaceuticals are u ...

(KI) solution in acetic acid or

starch Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human diet ...

paper. A positive test results in the formation of

iodine Iodine is a chemical element; it has symbol I and atomic number 53. The heaviest of the stable halogens, it exists at standard conditions as a semi-lustrous, non-metallic solid that melts to form a deep violet liquid at , and boils to a vi ...

(I₂) that causes a yellow or brown color of the ether phase or a dark bluish spot on the paper strip.

References

{{Reflist Organic peroxides Ethers Liquid explosives Organic peroxide explosives Ethoxy compounds