''tert''-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH
3)
3COOH. It is one of the most widely used
hydroperoxides in a variety of
oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...
processes, for example 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 viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%â ...
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
''tert''-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as ''t''-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. ''tert''-Butyl alcohol is a colorless solid, which melts near ...
, which can be dehydrated to
isobutene and converted to
MTBE
Methyl ''tertiary''-butyl ether (MTBE), also known as methyl tert-butyl ether and ''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 sol ...
.
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
The United States Department of Transportation (USDOT or DOT) is one of the executive departments of the U.S. federal government. It is headed by the secretary of transportation, who reports directly to the President of the United States a ...
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 U.S.-based National Fire Protection Association. First "tentatively adopted as a guide" in 1960, and revised se ...
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 " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxi ...
, 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