''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 containing the hydroperoxide functional group (ROOH). If the R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. O ...
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 d ...
processes, for example the
Halcon process In chemistry, the Halcon process refers to technology for the production of propylene oxide by oxidation of propylene with tert-butyl hydroperoxide. The reaction requires metal catalysts, which typically contain molybdenum:
:(CH3)3COOH + CH2=C ...
.
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%†...
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
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 ''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
The Sharpless epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols. The oxidizing agent is ''tert''-butyl hydroperoxide. The method relies on a catalyst formed fro ...
.
Synthesis and production
Many synthetic routes are available,
e.g. by the
auto-oxidation
Autoxidation (sometimes auto-oxidation) refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organi ...
of
isobutane
Isobutane, also known as ''i''-butane, 2-methylpropane or methylpropane, is a chemical compound with molecular formula HC(CH3)3. It is an isomer of butane. Isobutane is a colourless, odourless gas.
It is the simplest alkane with a tertiary carbon a ...
.
[
]
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 and ...
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 sev ...
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
Di-''tert''-butyl peroxide or DTBP is an organic compound consisting of a peroxide group bonded to two tert-butyl groups. It is one of the most stable organic peroxides, due to the ''tert''-butyl groups being bulky. It is a colorless liquid.
...
References
{{DEFAULTSORT:Butyl hydroperoxide, tert-
Hydroperoxides
Reagents for organic chemistry
Tert-butyl compounds
Oxidizing agents