tert-Butyl hydroperoxide
|
|||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name
2-Methylpropane-2-peroxol[1]
|
|||
| Systematic IUPAC name
tert-Butyl hydroperoxide
|
|||
| Identifiers | |||
75-91-2  |
|||
| Abbreviations | TBHP | ||
| 1098280 | |||
| ChEMBL | ChEMBL348399 |
||
| ChemSpider | 6170 |
||
| EC Number | 200-915-7 | ||
| Jmol 3D model | Interactive image | ||
| MeSH | tert-Butylhydroperoxide | ||
| PubChem | 6410 | ||
| RTECS number | EQ4900000 | ||
| UNII | 955VYL842B  |
||
| UN number | 3109 | ||
|
|||
|
|||
| Properties | |||
| C4H10O2 | |||
| Molar mass | 90.12 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
formation (ΔfH |
−294±5 kJ/mol | ||
|
Std enthalpy of
combustion (ΔcH |
2.710±0.005 MJ/mol | ||
| Vapor pressure | {{{value}}} | ||
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|||
 verify (what is ?) |
|||
| Infobox references | |||
tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.[2] It is normally supplied as a 69–70% aqueous solution.
Application
Industrially, tert-butyl hydroperoxide is used as a radical polymerization initiator.
Synthesis and production
Many synthetic routes are available, including:[3]
- Reaction of hydrogen peroxide with isobutylene or tert-butyl alcohol in the presence of sulfuric acid
- Reaction between tert-butyl alcohol and peroxymonosulfuric acid (however, an explosive intermediate is formed in this reaction)
- Auto-oxidation of isobutylene with oxygen
Safety
tert-butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. [4]
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,[5] however other sources claim lower ratings of 3-2-2 or 1-4-4.[6][7]
See also
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ tert-butyl hydroperoxide at Organic Chemistry Portal
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Sigma Aldrich MSDS
- ↑ "TERT-BUTYL HYDROPEROXIDE" at CAMEO Chemicals NOAA
- ↑ tert-BUTYL HYDROPEROXIDE at Chemicalland21
- ↑ tert-Butyl hydroperoxide at http://environmentalchemistry.com
