109-13-7

Basic information

• Product Name: tert-Butyl peroxyisobutyrate
• Synonyms: Lupersol 8;Perbutyl IB;Propaneperoxoic acid, 2-methyl-, 1,1-dimethylethyl ester;tert-Butyl 2-methylpropaneperoxoate;Trigonox 41C75;2-Methylperpropionic acid tert-butyl ester;2-Methylpropaneperoxoic acid 1,1-dimethylethyl;2-Methylpropaneperoxoic acid 1,1-dimethylethyl ester
• CAS NO: 109-13-7
• Molecular Formula: C₈H₁₆O₃
• Molecular Weight: 160.21
• EINECS: 203-650-5
• Mol File: 109-13-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 226.12°C (rough estimate)
• Flash Point: 50.6 °C
• Appearance: /
• Density: 1.0227 (rough estimate)
• Vapor Pressure: 1.88mmHg at 25°C
• Refractive Index: 1.4370 (estimate)
• Water Solubility: 3.96g/L at 20℃
• CAS DataBase Reference: tert-Butyl peroxyisobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl peroxyisobutyrate(109-13-7)
• EPA Substance Registry System: tert-Butyl peroxyisobutyrate(109-13-7)

Safety Data

• RIDADR: UN 2142/2562
• HazardClass: 5.2
• PackingGroup: II
• Hazardous Substances Data: 109-13-7(Hazardous Substances Data)

Usage

Uses

Polymerization catalyst.

General Description

tert-Butyl peroxyisobutyrate is particularly sensitive to temperature rises. Above a given "Control Temperature" they decompose violently. tert-Butyl peroxyisobutyrate is generally stored or transported in a solvent slurry. Solvent is usually benzene. Responders must regard hazards of the peroxide as well as the benzene solvent.

Reactivity Profile

TERT-BUTYL PEROXYISOBUTYRATE explodes with great violence when rapidly heated to a critical temperature; pure form is shock sensitive and detonable [Bretherick 1979 p. 602].

Hazard

Flammable, dangerous fire risk. Oxidizing agent.

Flammability and Explosibility

Notclassified

Purification Methods

After diluting 90mL of the material with 120mL of pet ether, the mixture is cooled to 5o and shaken twice with 90mL portions of 5% NaOH solution (also at 5o). The non-aqueous layer, after washing once with cold water, is dried at 0o with a mixture of anhydrous MgSO4 and MgCO3 containing ca 40% MgO. After filtering, this material is passed, twice, through a column of silica gel at 0o (to remove tert-butyl hydroperoxide). The solution is then evaporated at 0o/0.5-1mm to remove the solvent, and the residue is recrystallised several times from pet ether at -60o, then subjected to high vacuum to remove traces of solvent [Milos & Golubovic J Am Chem Soc 80 5994 1958]. Handle with adequate protection due to possible EXPLOSIVE nature.

InChI:InChI=1/C8H16O3/c1-6(2)7(9)10-11-8(3,4)5/h6H,1-5H3

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 79-31-2 isobutyric Acid 
• 103-28-6 benzyl 2-methylpropanoate 
• 556-91-2 aluminum tri-tert-butoxide 
• 103-80-0 phenylacetyl chloride 
• 3944-52-3 2-hydroperoxy-2,4-dimethyl-pentan-3-one 
• 79-30-1 isobutyryl chloride 

Downstream Products

• 15325-61-8 (E)-(3-methylbut-1-en-1-yl)benzene 
• 7565-70-0 Tributyltin isobutyrate 
• 67-64-1 acetone 
• 75-65-0 tert-butyl alcohol 
• 34557-54-5 methane 

Relevant articles and documents

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Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters

Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Cα-branched aliphatic carboxylic acids, which proceeds through the decarboxylation of the peresters and the subsequent formation of alkyl radicals to produce the alkylated adducts with an excellent diastereoselectivity. Theoretical calculations account for the observed reactivity and the outstanding stereocontrol. Importantly, the resultant compounds can be easily converted into ligands for asymmetric and catalytic transformations.

Iron-Catalyzed Dehydrative Alkylation of Propargyl Alcohol with Alkyl Peroxides to Form Substituted 1,3-Enynes

This paper reports a new method for the generation of substituted 1,3-enynes, whose synthesis by other methods could be a challenge. The dehydrative decarboxylative cascade coupling reaction of propargyl alcohol with alkyl peroxides is enabled by an iron catalyst and alkylating reagents. Primary, secondary, and tertiary alkyl groups can be introduced into 1,3-enynes, affording various substituted 1,3-enynes in moderate to good yields. Mechanistic studies suggest the involvement of a radical-polar crossover pathway.

Continuous Method for Producing Acyl Peroxides

The invention relates to a continuous method for producing acyl peroxides. According to said method, an acyl chloride, carboxylic acid anhydride or chloroformate is reacted with an organic hydroperoxide or hydrogen peroxide in at least two mixed reaction zones that are connected in series, the acyl compound, the peroxy compound and an aqueous solution of a base being supplied to the first reaction zone. The first reaction zone comprises a cycle for the two-phase reaction mixture via a heat exchanger in which the reaction mixture is cooled. The method allows the reaction to be carried out reliably and with high space-time yields.