Di-tert-butyl peroxide
{{Short description|Moderately stable organic peroxide}}
{{DISPLAYTITLE:Di-tert-butyl peroxide}}
{{chembox
| Watchedfields = changed
| Name=Di-tert-butyl peroxide
| verifiedrevid = 455130886
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Di-tert-butyl peroxide.svg
| ImageSize = 180
| ImageName = Chemical structure of di-tert-butyl peroxide
| ImageFile1 = Di-tert-butyl-peroxide-3D-balls.png
| ImageSize1 = 180
| ImageAlt1 = Ball-and-stick model
| PIN = 2-(tert-Butylperoxy)-2-methylpropane
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7742
| PubChem = 8033
| InChI = 1/C8H18O2/c1-7(2,3)9-10-8(4,5)6/h1-6H3
| InChIKey = LSXWFXONGKSEMY-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H18O2/c1-7(2,3)9-10-8(4,5)6/h1-6H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LSXWFXONGKSEMY-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 110-05-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M7ZJ88F4R1
| SMILES = O(OC(C)(C)C)C(C)(C)C
}}
|Section2={{Chembox Properties
| C = 8 | H = 18 | O = 2
| Density = 0.796 g/cm3
| MeltingPtC = -40
| BoilingPtC = 109 to 111
}}
}}
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.{{cite encyclopedia|first1=T. V. |last1=RajanBabu |first2=Nigel S. |last2=Simpkins |title=1,1-Di-tert-butyl Peroxide |entry=1,1-Di-tert-butyl Peroxide |encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis |date=2005 |doi=10.1002/047084289X.rd066.pub2|isbn=0471936235 }}
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 + {{chem|CH|3|•}}
:2 {{chem|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.{{cite journal | first1 = H. O. |last1=Pritchard |first2=P. Q. E. |last2=Clothier | title = Anaerobic operation of an internal combustion engine | journal = J. Chem. Soc. Chem. Commun. | year = 1986 | volume = 1986 | pages = 1529–1530 | doi = 10.1039/C39860001529 | issue = 20}}
Safety
DTBP is an irritant to the nose, eyes, and skin. It is also flammable, and can explode unpredictably at high (≈150 °C) temperatures.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|doi-access=free}}
See also
References
{{reflist}}
External links
- {{cite patent|inventor-last=Faraj|inventor-first=Mahmoud K.|pridate=1993-05-13|pubdate=1994-02-22|title=Preparation of dialkyl peroxides|country=US|number=5288919}}
- {{cite patent|inventor1-last=Liotta|inventor1-first=Frank J., Jr.|inventor2-last=Faraj|inventor2-first=Mahmoud K.|inventor3-last=Pourreau|inventor3-first=Daniel B.|inventor4-last=Kesling|inventor4-first=Haven S., Jr.|pridate=1993-06-10|pubdate=1994-05-17|title=Integrated process for the production of ditertiary butyl peroxide|country=US|number=5312998}}
- {{cite patent|inventor1-last=Pourreau|inventor1-first=Daniel B.|inventor2-last=Kesling|inventor2-first=Haven S., Jr.|inventor3-last=Liotta|inventor3-first=Frank J., Jr.|inventor4-last=McFarland|inventor4-first=Jeffrey M.|pridate=1993-12-22|pubdate=1994-12-06|title=Preparation of dialkyl peroxides|country=US|number=5371298}}