109-13-7 Usage
Description
tert-Butyl peroxyisobutyrate is an organic peroxide compound that is highly sensitive to temperature increases. It decomposes violently when exposed to temperatures above a specific "Control Temperature." Due to its sensitivity, it is typically stored or transported in a solvent slurry, with benzene being the common solvent used. The hazards associated with the peroxide and the benzene solvent must be carefully considered by responders.
Uses
Used in Polymerization Industry:
tert-Butyl peroxyisobutyrate is used as a polymerization catalyst for its ability to initiate and control the polymerization process. Its sensitivity to temperature allows for precise control over the reaction, making it a valuable component in the production of various polymers.
Used in Chemical Synthesis:
In the chemical synthesis industry, tert-Butyl peroxyisobutyrate is used as a reagent for the synthesis of various organic compounds. Its decomposition properties can be harnessed to drive specific chemical reactions, contributing to the production of desired products.
Used in Propellant Industry:
tert-Butyl peroxyisobutyrate is used as an ingredient in the formulation of propellants, particularly in the production of solid rocket propellants. Its decomposition characteristics make it suitable for use in propellant systems that require precise control over the combustion process.
Used in Benzene Solvent:
As a component of the solvent slurry, tert-Butyl peroxyisobutyrate is used in conjunction with benzene to facilitate its storage and transportation. The benzene solvent helps to stabilize the peroxide and provides a medium for its safe handling and distribution.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 109-13-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 109-13:
(5*1)+(4*0)+(3*9)+(2*1)+(1*3)=37
37 % 10 = 7
So 109-13-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O3/c1-6(2)7(9)10-11-8(3,4)5/h6H,1-5H3
109-13-7Relevant articles and documents
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Milas,Golubovic
, p. 5994,5995 (1958)
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Stereoselective Alkylation of Chiral Titanium(IV) Enolates with tert-Butyl Peresters
Pérez-Palau, Marina,Sanosa, Nil,Romea, Pedro,Urpí, Fèlix,López, Rosa,Gómez-Bengoa, Enrique,Font-Bardia, Mercè
supporting information, p. 8852 - 8856 (2021/11/17)
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
Ye, Changqing,Qian, Bo,Li, Yajun,Su, Min,Li, Daliang,Bao, Hongli
supporting information, p. 3202 - 3205 (2018/06/11)
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
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Page/Page column 5, (2010/03/02)
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.
