Di-tert-butyl peroxide

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by 老坛陈醋 (talk | contribs) at 02:15, 3 July 2020. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Di-tert-butyl peroxide
Chemical structure of di-tert-butyl peroxide
Ball-and-stick model
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 ?)

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 >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

References

  1. ^ 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
  2. ^ 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.); Faraj, Mahmoud K. & Pourreau, Daniel B. et al., "Integrated process for the production of ditertiary butyl peroxide", issued 17 May 1994 
  • US 5371298, Pourreau, Daniel B.; Kesling, Haven S. (Jr.) & Liotta, Frank J. (Jr.) et al., "Preparation of dialkyl peroxides", issued 6 December 1994 
Retrieved from "https://en.wikipedia.org/w/index.php?title=Di-tert-butyl_peroxide&oldid=965728891"