tert-Butyl hydroperoxide

tert-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is a hydroperoxide, in fact one of the most widely used in a variety of oxidation processes, for example 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, 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.

tert-Butyl hydroperoxide
Names
Preferred IUPAC name
2-Methylpropane-2-peroxol[1]
Systematic IUPAC name
tert-Butyl hydroperoxide
Identifiers
3D model (JSmol)
Abbreviations TBHP
1098280
ChEMBL
ChemSpider
ECHA InfoCard 100.000.833
EC Number
  • 200-915-7
MeSH tert-Butylhydroperoxide
RTECS number
  • EQ4900000
UNII
UN number 3109
  • InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3 Y
    Key: CIHOLLKRGTVIJN-UHFFFAOYSA-N Y
  • CC(C)(C)OO
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
1.3870
Thermochemistry
−294±5 kJ/mol
2.710±0.005 MJ/mol
Hazards
GHS labelling:
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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, which can be dehydrated to isobutene and convert to MTBE.

On a much smaller scale, tert-butyl hydroperoxide is used to produce some fine chemicals by the Sharpless epoxidation.[4]

Synthesis and production

Many synthetic routes are available,[5] e.g. by the auto-oxidation of isobutane.[3]

Safety

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]

See also

References
  1. "IUPAC Complete Draft 2004" (PDF).
  2. Cameo Chemicals, reference for NFPA values.
  3. Roger A. Sheldon (1983). Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771730.ch6.
  4. tert-butyl hydroperoxide at Organic Chemistry Portal
  5. Jose Sanchez; Terry N. Myers. "Peroxides and Peroxide Compounds, Organic Peroxides". Kirk‑Othmer Encyclopedia of Chemical Technology. Wiley-VCH Verlag GmbH & Co. doi:10.1002/0471238961.1518070119011403.a01.
  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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