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]

Di-tert-butyl peroxide

Chemical structure of di-tert-butyl peroxide
Names
Preferred IUPAC name 2-(tert-Butylperoxy)-2-methylpropane
Identifiers
CAS Number	110-05-4 Y
3D model (JSmol)	Interactive image
ChemSpider	7742 Y
ECHA InfoCard	100.003.395
PubChem CID	8033
UNII	M7ZJ88F4R1 Y
CompTox Dashboard (EPA)	DTXSID2024955
InChI InChI=1S/C8H18O2/c1-7(2,3)9-10-8(4,5)6/h1-6H3 Y Key: LSXWFXONGKSEMY-UHFFFAOYSA-N Y InChI=1/C8H18O2/c1-7(2,3)9-10-8(4,5)6/h1-6H3 Key: LSXWFXONGKSEMY-UHFFFAOYAY
SMILES O(OC(C)(C)C)C(C)(C)C
Properties
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). Y verify (what is YN ?) Infobox references

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
• Bis(trimethylsilyl) peroxide