tert-Butyl hydroperoxide

tert-Butyl hydroperoxide (tBuOOH) is an organic peroxide widely used in a variety of oxidation processes, for example Sharpless epoxidation.[3] It is normally supplied as a 69–70% aqueous solution.

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[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
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
Std enthalpy of
formation (ΔfH⦵298)
 −294±5 kJ/mol
Std enthalpy of
combustion (ΔcH⦵298)
 2.710±0.005 MJ/mol
Hazards
Safety data sheet
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H226, H242, H302, H311, H314, H317, H331, H341, H411
P220, P261, P273, P280, P305+351+338, P310
NFPA 704 (fire diamond)
Flash point 43 °C (109 °F; 316 K)
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 as a radical polymerization initiator. For example, its reaction with propene yields propylene oxide and the byproduct t-butanol which can dehydrate to isobutene and convert to MTBE.

Synthesis and production

Many synthetic routes are available, including:[4]

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. [5]

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]

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See also

References
  1. "IUPAC Complete Draft 2004" (PDF).
  2. Cameo Chemicals, reference for NFPA values.
  3. tert-butyl hydroperoxide at Organic Chemistry Portal
  4. 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.
  5. Sigma Aldrich MSDS
  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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