Di-tert-butyl peroxide
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Preferred IUPAC name 2-(tert-Butylperoxy)-2-methylpropane | |
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ECHA InfoCard | 100.003.395 ![]() |
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Chemical formula | 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). ![]() ![]() ![]() Infobox references |
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]
Safety
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
- tert-Butyl hydroperoxide
References
- ^ 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.
- ^ 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.
- ^ 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
External links
- 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