tert-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, like the Halcon process.[3] It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide 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.
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
2-Methylpropane-2-peroxol[1] | |||
| Systematic IUPAC name
tert-Butyl hydroperoxide | |||
| Identifiers | |||
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3D model (JSmol) |
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| Abbreviations | TBHP | ||
| 1098280 | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.000.833 
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| EC Number |
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| MeSH | tert-Butylhydroperoxide | ||
PubChem CID |
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| RTECS number |
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| UNII | |||
| UN number | 3109 | ||
CompTox Dashboard (EPA) |
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| Properties | |||
| C4H10O2 | |||
| Molar mass | 90.122 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Density | 0.935 g/mL | ||
| Melting point | −3 °C (27 °F; 270 K) | ||
| Boiling point | 37 °C (99 °F; 310 K) at 2.0 kPa | ||
| miscible | |||
| log P | 1.23 | ||
| Acidity (pKa) | 12.69 | ||
| Basicity (pKb) | 1.31 | ||
Refractive index (nD) |
1.3870 | ||
| Thermochemistry | |||
Std enthalpy of |
−294±5 kJ/mol | ||
Std enthalpy of |
2.710±0.005 MJ/mol | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards |
oxidizer | ||
| GHS labelling: | |||
     
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| Danger | |||
| H226, H242, H302, H311, H314, H317, H331, H341, H411 | |||
| P220, P261, P273, P280, P305+P351+P338, P310 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 43 °C (109 °F; 316 K) | ||
| Safety data sheet (SDS) | [1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
Industrially, tert-butyl hydroperoxide is used to prepare propylene oxide. In the Halcon process, molybdenum-based catalysts are used for this reaction:
The byproduct t-butanol can be dehydrated to isobutene and converted to MTBE.
On a much smaller scale, tert-butyl hydroperoxide is used to produce some fine chemicals by the Sharpless epoxidation.[4]
Many synthetic routes are available,[5] e.g. by the auto-oxidationofisobutane.[3]
tert-butyl hydroperoxide is potentially dangerous, but explosions are rare.[3]
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 rating of 4 for health, 4 for flammability, 4 for reactivity and is a potent oxidant,[6] however other sources claim lower ratings of 3-2-2 or 1-4-4.[7][8]
