Di-tert-butyl peroxide

Di-tert-butyl peroxide or DTBP is an organic compound consisting of a peroxide group bonded to two tert-butyl groups. It is one of the most stable organic peroxides, due to the tert-butyl groups being bulky. It is a colorless liquid.[1]

Di-tert-butyl peroxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.395
UNII
Properties
C8H18O2
Molar mass 146.230 g·mol−1
Density 0.796 g/cm3
Melting point −40 °C (−40 °F; 233 K)
Boiling point 109 to 111 °C (228 to 232 °F; 382 to 384 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reactions

The peroxide bond undergoes homolysis at temperatures >100 °C. For this reason di-tert-butyl peroxide is commonly used as a radical initiator in organic synthesis and polymer chemistry. The decomposition reaction proceeds via the generation of methyl radicals.

(CH3)3COOC(CH3)3 → 2 (CH3)3CO.
(CH3)3CO.(CH3)2CO + CH3.
2 CH3. → CH3-CH3

DTBP can in principle be used in engines where oxygen is limited, since the molecule supplies both the oxidizer and the fuel.[2]

Toxicity

DTBP is an irritant to noses, and eyes and skin. It is also flammable, so it should be handled with care.

See also

References

  1. T. V. RajanBabu, Nigel S. Simpkins, T. V. RajanBabu "1,1-Di-tert-butyl Peroxide" in e-EROS Encyclopedia of Reagents for Organic Synthesis 2005.doi:10.1002/047084289X.rd066.pub2
  2. H. O. Pritchard and P. Q. E. Clothier (1986), "Anaerobic operation of an internal combustion engine", J. Chem. Soc. Chem. Commun., 1986 (20): 1529–1530, doi:10.1039/C39860001529
  • US 5288919, Faraj, Mahmoud K., "Preparation of dialkyl peroxides", issued 22 February 1994
  • US 5312998, Liotta, Frank J. (Jr.); Mahmoud K. Faraj & Daniel B. Pourreau et al., "Integrated process for the production of ditertiary butyl peroxide", issued 17 May 1994
  • US 5371298, Pourreau, Daniel B.; Haven S. (Jr.) Kesling & Frank J. (Jr.) Liotta et al., "Preparation of dialkyl peroxides", issued 6 December 1994
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