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tert-Butyl hydroperoxide

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tert-Butyl hydroperoxide
Skeletal formula of tert-butyl hydroperoxide
Ball-and-stick model of the tert-butyl hydroperoxide molecule
Names
Preferred IUPAC name 2-Methylpropane-2-peroxol
Systematic IUPAC name tert-Butyl hydroperoxide
Identifiers
CAS Number
3D model (JSmol)
Abbreviations TBHP
Beilstein Reference 1098280
ChEMBL
ChemSpider
ECHA InfoCard 100.000.833 Edit this at Wikidata
EC Number
  • 200-915-7
MeSH tert-Butylhydroperoxide
PubChem CID
RTECS number
  • EQ4900000
UNII
UN number 3109
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3Key: CIHOLLKRGTVIJN-UHFFFAOYSA-N
SMILES
  • CC(C)(C)OO
Properties
Chemical formula C4H10O2
Molar mass 90.122 g·mol
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
Solubility in water miscible
log P 1.23
Acidity (pKa) 12.69
Basicity (pKb) 1.31
Refractive index (nD) 1.3870
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		−294±5 kJ/mol
Std enthalpy of
combustion (ΔcH298) 		2.710±0.005 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards oxidizer
GHS labelling:
Pictograms GHS02: Flammable GHS03: Oxidizing GHS05: Corrosive GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
Signal word Danger
Hazard statements H226, H242, H302, H311, H314, H317, H331, H341, H411
Precautionary statements P220, P261, P273, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazard OX: Oxidizer. E.g. potassium perchlorate
4 4 4OX
Flash point 43 °C (109 °F; 316 K)
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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.

Application

Industrially, tert-butyl hydroperoxide is used to prepare propylene oxide. In the Halcon process, molybdenum-based catalysts are used for this reaction:

(CH3)3COOH + CH2=CHCH3 → (CH3)3COH + CH2OCHCH3

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.

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 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, however other sources claim lower ratings of 3-2-2 or 1-4-4.

See also

References

  1. "IUPAC Complete Draft 2004" (PDF).
  2. Cameo Chemicals, reference for NFPA values.
  3. ^ Roger A. Sheldon (1983). "Synthesis and uses of alkyl hydroperoxides and dialkyl peroxides". In Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. pp. 161–200. doi:10.1002/9780470771730.ch6. ISBN 978-0-471-10218-2.
  4. tert-butyl hydroperoxide at Organic Chemistry Portal
  5. Jose Sanchez; Terry N. Myers (2000). "Peroxides and Peroxide Compounds, Organic Peroxides". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley-VCH Verlag GmbH & Co. doi:10.1002/0471238961.1518070119011403.a01. ISBN 978-0-471-48494-3.
  6. "TERT-BUTYL HYDROPEROXIDE" at CAMEO Chemicals NOAA
  7. tert-BUTYL HYDROPEROXIDE at Chemicalland21
  8. tert-Butyl hydroperoxide at http://environmentalchemistry.com
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