Chemistry:Di-tert-butyl peroxide

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Short description: DTBP: organic compound consisting of a peroxide group bonded to two tert-butyl groups


Di-tert-butyl peroxide
Chemical structure of di-tert-butyl peroxide
Ball-and-stick model
Names
Preferred IUPAC name
2-(tert-Butylperoxy)-2-methylpropane
Identifiers
3D model (JSmol)
ChemSpider
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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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]

Reactions

The peroxide bond undergoes homolysis at temperatures above 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 + CH•3
2 CH•3 → C2H6

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 the nose, eyes, and skin. It is also flammable, so it should be handled with care.

See also

References

  1. ↑ RajanBabu, T. V.; Simpkins, Nigel S. (2005). "1,1-Di-tert-butyl Peroxide". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd066.pub2. ISBN 0471936235. 
  2. ↑ Pritchard, H. O.; Clothier, P. Q. E. (1986). "Anaerobic operation of an internal combustion engine". J. Chem. Soc. Chem. Commun. 1986 (20): 1529–1530. doi:10.1039/C39860001529. 

External links

  • Faraj, Mahmoud K., "Preparation of dialkyl peroxides", US patent 5288919, published 1994-02-22
  • Liotta, Frank J., Jr.; Mahmoud K. Faraj & Daniel B. Pourreau et al., "Integrated process for the production of ditertiary butyl peroxide", US patent 5312998, published 1994-05-17
  • Pourreau, Daniel B.; Haven S., Jr. Kesling & Frank J., Jr. Liotta et al., "Preparation of dialkyl peroxides", US patent 5371298, published 1994-12-06



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