5587-14-4

Basic information

• Product Name: tert-butyl 2-methylbutan-2-yl peroxide
• Synonyms: 2-(tert-Butylperoxy)-2-methylbutane; peroxide, 1,1-dimethylethyl 1,1-dimethylpropyl; tert-Butyl 2-methylbutan-2-yl peroxide
• CAS NO: 5587-14-4
• Molecular Formula: C₉H₂₀O₂
• Molecular Weight: 160.2539
• Mol File: 5587-14-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 155.107°C at 760 mmHg
• Flash Point: 36.038°C
• Density: 0.844g/cm³
• Vapor Pressure: 3.961mmHg at 25°C
• Refractive Index: 1.411
• CAS DataBase Reference: tert-butyl 2-methylbutan-2-yl peroxide(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-methylbutan-2-yl peroxide(5587-14-4)
• EPA Substance Registry System: tert-butyl 2-methylbutan-2-yl peroxide(5587-14-4)

Safety Data

• Hazardous Substances Data: 5587-14-4(Hazardous Substances Data)

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 75-85-4 tert-Amyl alcohol 
• 513-35-9 2-methyl-but-2-ene 
• 507-36-8 2-bromo-2-methylbutane 
• 98336-49-3 2,2,2-trichloro-acetimidic acid tert-pentyl ester 

Downstream Products

• 75-85-4 tert-Amyl alcohol 
• 1889-67-4 dicumene 
• 67-64-1 acetone 
• 75-65-0 tert-butyl alcohol 

Relevant articles and documents

Preparation of di-t-alkyl peroxides and t-alkyl hydroperoxides from n-alkyl ethers

A process for production of a t-alkyl peroxide compound includes the steps of: a) reacting an n-alkyl t-alkyl ether with a reactant mixture comprising an acid catalyst and a compound of the formula RO2H??(I) ?where R is H or t-alkyl, provided that if R is t-alkyl the t-alkyl peroxide compound product is a di-t-alkyl peroxide, and b) isolating a reaction product comprising said t-alkyl peroxide compound from the mixture resulting from step a). The process can be used to prepare t-butyl hydroperoxide or di-t-butyl peroxide from methyl t-butyl ether. Sulfuric acid may be used as the acid catalyst.

Substituent Effects in the Decomposition of t-Alkyl t-Butyl Peroxides

The decomposition rates and products of various t-alkyl t-butyl peroxides were examined in cumene at several temperatures.The decomposition of these peroxides took place homolytically, depending on the structure of the t-alkoxyl moieties (RC(CH3)2-O), and was retarded in the order: R = (CH3)3CCH2 > (CH3)2CH > CH3CH2CH2 > PhCH2 > CH3CH2 > ClCH2 > CH3.The rate constants for the electron-donating alkyl substituents at 150 deg C are correlated very well to a Taft equation (log kd = -10.93Σ?*-6.61 (correlation coefficient of 0.9501)), which is fairly different from the equation log kd = -0.131Σ?*-3.422 for electron-withdrawing polar substituents.From this correlation and a product analysis, the nature of the polar character at the transition state of the decomposition is discussed.