3006-82-4

Usage

Chemical Properties

t-Butyl peroxy-2-ethylhexanoate is a colorless liquid. It has a half-life in benzene of 10.0 h at 162°F (72°C). It is used as a medium temperature initiator for the polymerization of vinyl monomers and the curing of styrene-unsaturated polyester resins. It is regarded as an intermediate fire hazard; however, it has low impact sensitivity .

General Description

This peroxide is particularly sensitive to temperature rises and contamination. Above a given "Control Temperature" they decompose violently. tert-Butyl peroxy-2-ethylhexanoate is generally stored or transported with inert solids to mitigate the explosion hazard.

Reactivity Profile

TERT-BUTYL PEROXY-2-ETHYL- HEXANOATE explodes with great violence when rapidly heated to a critical temperature; pure form is shock sensitive and detonable [Bretherick 1979 p. 602]. Decomposes violently or explosively at temperatures 0-10°C owing to self- accelerating exothermic decomposition; Several explosions were due to shock, heat or friction; amines and certain metals can cause accelerated decomposition [Bretherick 1979 p. 156]. Danger of explosion when dry

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H24O3/c1-6-8-9-10(7-2)11(13)14-15-12(3,4)5/h10H,6-9H2,1-5H3

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 149-57-5 2-Ethylhexanoic acid 
• 760-67-8 2-ethylhexanoic acid chloride 

Downstream Products

• 67-64-1 acetone 
• 75-65-0 tert-butyl alcohol 
• 1394826-51-7 (3-ethylhept-1-yn-1-yl)benzene 
• 6278-74-6 2-(3-heptyl)benzothiazole 

Relevant academic research and scientific papers

Method for synthesizing alkyl peroxycarboxylate by using titanium silicalite molecular sieve composite catalyst

The invention relates to a method for synthesizing alkyl peroxycarboxylate by using a titanium silicalite molecular sieve composite catalyst, and belongs to the technical field of peroxide production. The method overcomes the defects in the prior art, and adopts the titanium silicalite molecular sieve and aluminosilicate molecular sieve composite catalyst to synthesize the alkyl peroxycarboxylate. In the chemical reaction process that tert-butyl hydroperoxide or tert-amyl hydroperoxide reacts with carboxylic acid to generate tert-butyl peroxycarboxylate or tert-amyl peroxycarboxylate, reaction water is generated. The reaction water needs to be removed from the reaction mixture in time. Azeotropic distillation and molecular distillation dehydration are generally adopted. However, these process operations require a high temperature, and are not conducive to the stabilization and safety of alkyl peroxycarboxylate. The catalyst disclosed by the invention contains the aluminosilicate molecular sieve, so that water generated by reaction can be adsorbed in time, and the synthesis reaction can be smoothly completed.

Method for producing alkyl peroxycarboxylate based on titanium silicalite molecular sieve composite catalyst

The invention relates to a method for synthesizing alkyl peroxycarboxylate based on a titanium silicalite molecular sieve composite catalyst, and belongs to the technical field of peroxide production. According to the method, the defects in the prior art are overcome, and alkyl peroxycarboxylate is synthesized by adopting a titanium silicalite molecular sieve and a metal oxide composite catalyst. In the chemical reaction process that tert-butyl hydroperoxide or tert-amyl hydroperoxide reacts with carboxylic acid to generate tert-butyl peroxycarboxylate or tert-amyl peroxycarboxylate, reaction water is generated. The reaction water is to be removed from the reaction mixture in time. Azeotropic distillation and molecular distillation dehydration are generally adopted. However, these process operations require higher temperatures, which are not conducive to the stabilization and safety of alkyl peroxycarboxylate. The catalyst disclosed by the invention contains metal oxide, so that water generated by reaction can be adsorbed in time, and the synthesis reaction can be smoothly completed.

Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters

Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.

Iron-Catalyzed Vinylic C?H Alkylation with Alkyl Peroxides

A variety of alkyl peresters and alkyl diacyl peroxides, which are readily accessible from carboxylic acids, are utilized as general primary, secondary, and tertiary alkylating reagents for iron-catalyzed vinylic C?H alkylation of vinyl arenes, dienes, and 1,3-enynes. This transformation affords olefinic products in up to 98 % yield with high E/Z values. A broad range of functionalities, including carboxyl, boronic acid, methoxy, ester, amino, and halides, are tolerated. This protocol provides a facile approach to some olefins that are difficult to access, and hence, offers an alternative to existing systems. The synthetic utility of this method is demonstrated by late-stage functionalization of selected natural-product derivatives.

Iron-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides

An iron-catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C?C triple bonds and diverse α-alkylated ketones were synthesized. Mechanism studies revealed that this reaction involves highly reactive alkyl free radicals. A unique equilibrium between lauric acid and water catalyzed by the iron(III) catalyst was observed.

Iron-catalyzed C-H alkylation of heterocyclic C-H bonds

An efficient, iron-catalyzed C-H alkylation of benzothiazoles by using alkyl diacyl peroxides and alkyl tertbutyl peresters which are readily accessible from carboxylic acids to synthesize 2-alkylbenzothiazoles is developed. This reaction is environmentally benign and compatible with a broad range of functional groups. Various primary, secondary, and tertiary alkyl groups can be efficiently incorporated into diverse benzothiazoles. The effectiveness of this method is illustrated by late-stage functionalization of biologically active heterocycles.

Method for producing acyl peroxides

The invention relates to a method for producing acyl peroxides. According to said method, an acyl compound is reacted with an organic hydroperoxide and a base, the pH of the two-phase mixture so obtained is adjusted to 6 to 13, the obtained organic phase is extracted with an aqueous solution of a base and the aqueous extract is recirculated to the reaction step. The method according to the invention allows the recirculation of unreacted hydroperoxide to the reaction step.

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.

METHOD FOR THE PRODUCTION OF ORGANIC PEROXIDES BY MEANS OF A MICROREACTION TECHNIQUE

The invention provides a process for efficient and reliable preparation of organic peroxides, preferably dialkyl peroxides, peroxycarboxylic acids, peroxycarboxylic esters, diacyl peroxides, peroxycarbonate esters, peroxydicarbonates, ketone peroxides and perketals with the aid of at least one static micromixer and an apparatus for performing the process.