tert-Butyl hydroperoxide
From Wikipedia, the free encyclopedia
| tert-Butyl hydroperoxide | |
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tert-Butyl hydroperoxide[citation needed] |
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2-Methylpropane-2-peroxol[citation needed] |
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| Identifiers | |
| Abbreviations | TBHP |
| CAS number | 75-91-2  |
| PubChem | 6410 |
| ChemSpider | 6170 |
| UNII | 955VYL842B  |
| EC number | 200-915-7 |
| UN number | 3109 |
| MeSH | tert-Butylhydroperoxide |
| ChEMBL | CHEMBL348399 |
| RTECS number | EQ4900000 |
| Beilstein Reference | 1098280 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H10O2 |
| Molar mass | 90.12 g mol−1 |
| Exact mass | 90.068079564 g mol−1 |
| Appearance | Colourless liquid |
| Density | 935 mg cm−3 |
| Melting point |
−3 °C, 270 K, 27 °F |
| Boiling point |
37 °C, 310 K, 99 °F (at 2.0 kPa) |
| Solubility in water | miscible |
| log P | 1.23 |
| Acidity (pKa) | 12.69 |
| Basicity (pKb) | 1.31 |
| Refractive index (nD) | 1.3870 |
| Hazards | |
| MSDS | msds.chem.ox.ac.uk |
| GHS pictograms |    |
| GHS signal word | DANGER |
| GHS hazard statements | H226, H242, H302, H311, H314, H331 |
| GHS precautionary statements | P220, P261, P280, P305+351+338, P310, P410 |
| EU classification |  O  C |
| R-phrases | R7, R10, R20/21/22, R34, R43 R52/53 |
| S-phrases | S3/7, S14, S16, S17, S24, S36/37/39, S45, S61 |
| NFPA 704 |
 2
3
2
OX
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| Flash point | 43 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.[1] It is normally supplied as a 69-70% aqueous solution.
Contents |
[edit] Application
Industrially, tert-butyl hydroperoxide is used as a starter of radical polymerization.
[edit] Synthesis and Production
Many synthetic routes are available[2]
- Reaction of hydrogen peroxide with isobutylene or tert-butanol in the presence of sulfuric acid
- Reaction between tert-butanol and peroxymonosulfuric acid (however, an explosive intermediate is formed in this reaction)
- Auto-oxidation of isobutylene with oxygen
[edit] See also
[edit] References
- ^ tert-butyl hydroperoxide at Organic Chemistry Portal
- ^ Peroxides and Peroxide Compounds, Organic Peroxides; Kirk‑Othmer Encyclopedia of Chemical Technology, Jose Sanchez and Terry N. Myers, Wiley-VCH Verlag GmbH & Co
