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Di-tert-butyl peroxide

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(Redirected from T-butyl peroxide) Moderately stable organic peroxide
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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.395 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H18O2/c1-7(2,3)9-10-8(4,5)6/h1-6H3Key: LSXWFXONGKSEMY-UHFFFAOYSA-N
  • InChI=1/C8H18O2/c1-7(2,3)9-10-8(4,5)6/h1-6H3Key: LSXWFXONGKSEMY-UHFFFAOYAY
SMILES
  • O(OC(C)(C)C)C(C)(C)C
Properties
Chemical formula C8H18O2
Molar mass 146.230 g·mol
Density 0.796 g/cm
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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.

Safety

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

See also

References

  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

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 
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