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]
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| ChemSpider | |
| ECHA InfoCard | 100.003.395 |
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CompTox Dashboard (EPA) |
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| 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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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
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References
- 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
- 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
External links
- 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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