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
CAS Number
3D model (JSmol)
Abbreviations TBHP
Beilstein Reference
 1098280
ChEMBL
ChemSpider
ECHA InfoCard 100.000.833
EC Number
  • 200-915-7
MeSH tert-Butylhydroperoxide
PubChem CID
RTECS number
  • EQ4900000
UNII
UN number 3109
CompTox Dashboard (EPA)
Properties
Chemical formula
 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
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 (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
GHS precautionary statements
 P220, P261, P273, P280, P305+351+338, P310
NFPA 704 (fire diamond)
4
4
4
OX
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]

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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