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Di-tert-butyl peroxide

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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]

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
ECHA InfoCard 100.003.395 Edit this at Wikidata
UNII
  • InChI=1S/C8H18O2/c1-7(2,3)9-10-8(4,5)6/h1-6H3 checkY
    Key: LSXWFXONGKSEMY-UHFFFAOYSA-N checkY
  • InChI=1/C8H18O2/c1-7(2,3)9-10-8(4,5)6/h1-6H3
    Key: LSXWFXONGKSEMY-UHFFFAOYAY
  • O(OC(C)(C)C)C(C)(C)C
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).
checkY verify (what is checkY☒N ?)

Reactions

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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]

Safety

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DTBP is an irritant to the nose, eyes, and skin. It is also flammable, and can explode unpredictably at high (≈150 °C) temperatures.[3]

See also

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References

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  1. ^ RajanBabu, T. V.; Simpkins, Nigel S. (2005). "1,1-Di-tert-butyl Peroxide". 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.
  3. ^ Sime, Rodney J. (13 June 1988). "Di-tert-butyl peroxide" (letter to the editor), in Chemical & Engineering News, p. 4. doi:10.1021/cen-v066n024.p004
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  • US 5288919, Faraj, Mahmoud K., "Preparation of dialkyl peroxides", published 1994-02-22 
  • US 5312998, Liotta, Frank J., Jr.; Faraj, Mahmoud K. & Pourreau, Daniel B. et al., "Integrated process for the production of ditertiary butyl peroxide", published 1994-05-17 
  • US 5371298, Pourreau, Daniel B.; Kesling, Haven S., Jr. & Liotta, Frank J., Jr. et al., "Preparation of dialkyl peroxides", published 1994-12-06 
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