''tert''-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH
3)
3COOH. It is one of the most widely used
hydroperoxides
Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group (). Hydroperoxide also refers to the hydroperoxide anion () and its salts, and the neutra ...
in a variety of
oxidation
Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
processes, like the
Halcon process.
It is normally supplied as a 69–70% aqueous solution. Compared to
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 ...
and organic peracids, ''tert''-butyl hydroperoxide is less reactive and more soluble in organic solvents. Overall, it is renowned for the convenient handling properties of its solutions. Its solutions in organic solvents are highly stable.
Application
Industrially, ''tert''-butyl hydroperoxide is used to prepare propylene oxide. In the Halcon process, molybdenum-based catalysts are used for this reaction:
:(CH
3)
3COOH + CH
2=CHCH
3 → (CH
3)
3COH + CH
2OCHCH
3
The byproduct
t-butanol can be dehydrated to
isobutene
Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.
Productio ...
and converted to
MTBE
Methyl ''tert''-butyl ether (MTBE), also known as ''tert''-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly soluble in water. Primarily used as ...
.
On a much smaller scale, ''tert''-butyl hydroperoxide is used to produce some fine chemicals by the
Sharpless epoxidation.
Synthesis and production
Many synthetic routes are available,
e.g. by the
auto-oxidation of
isobutane.
[
]
Safety
''tert''-butyl hydroperoxide is potentially dangerous, but explosions are rare.[
A solution of ''tert''-butyl hydroperoxide and water with a concentration of greater than 90% is forbidden to be shipped according to US Department of Transportation Hazardous Materials Table 49 CFR 172.101.
In some sources it also has an ]NFPA 704
"NFPA 704: Standard System for the Identification of the Hazards of Materials for Emergency Response" is a standard maintained by the United States, U.S.-based National Fire Protection Association. First "tentatively adopted as a guide" in 1960, ...
rating of 4 for health, 4 for flammability, 4 for reactivity and is a potent oxidant
An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or "Electron acceptor, accepts"/"receives" an electron from a (called the , , or ''electr ...
, however other sources claim lower ratings of 3-2-2 or 1-4-4.tert-Butyl hydroperoxide
at http://environmentalchemistry.com
See also
* Di-tert-butyl peroxide
References
{{DEFAULTSORT:Butyl hydroperoxide, tert-
Hydroperoxides
Reagents for organic chemistry
Tert-butyl compounds
Oxidizing agents