Improved procedure for the preparation of diethyl ketone triperoxide and kinetics of its thermal decomposition reaction in solution

Eyler, Gladys N.; Cañizo, Adriana I.; Álvarez, Élida; Cafferata, Lázaro F. R.

doi:10.1016/s0040-4039(00)60767-0

Cited by 32 publications

(24 citation statements)

References 3 publications

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“…DEKTP and PDP were prepared following the methods described in the literature (Eyler et al, 1993;Eyler et al, 2002) Caution: peroxides must be handled with care because they can be detonated by shock.…”

Section: Methodsmentioning

confidence: 99%

Effect of ionic liquid on the thermal decomposition of cyclic organic peroxides

Barreto

Rodríguez

Morales

et al. 2019

Arabian Journal of Chemistry

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The thermolysis of cyclic diethylketone triperoxide (3,3,6,6,9,2,4,5,7, DEKTP) and cyclic pinacolone diperoxide (3,6-diterbutyl-3,6-dimethyl-1,2,4,5-tetraoxacyclohexane , PDP) were studied in neat N,N-dimetyhlformamide (DMF) and in binary mixtures DMF/Ionic Liquid (1-butyl-3-methylimidazolium tetrafluoroborate, [BMIM + ][BF 4 -]). The activation parameters for the decomposition of both peroxides in DMF, correspond to a process of homolytic cleavage of one O-O bond, generating a biradical in the initial step of radical mechanism. The rate constant values (k d ) are higher for reactions performed in mixtures. A gradual increase of [BMIM + ][BF 4 -]in the reaction media generate higher k d for both peroxides (i. e. k d, DEKTP in DMF/[BMIM + ][BF 4 -] 4.0 mol L -1 is 3.3 times greater than the k d obtained for the mixture with a concentration 1.0 mol L -1 , under the same experimental conditions). The increase in decomposition rate can be associated to a more solvated and stabilized transition state when the ionic liquid is part of the reaction medium.

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Section: Methodsmentioning

confidence: 99%

Effect of ionic liquid on the thermal decomposition of cyclic organic peroxides

Barreto

Rodríguez

Morales

et al. 2019

Arabian Journal of Chemistry

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“…DEKTP was prepared in a one-step reaction using diethylketone and hydrogen peroxide following the method described by Eyler et al 20 In a clean roundbottom flask, 4.6 mL (59 mmol) of hydrogen peroxide (H 2 O 2 30% v/v), 7.3 mL of sulfuric acid (H 2 SO 4 70% v/v), and 5.6 mL (50 mmol) of diethylketone were added. The solution was stirred for 3 h, and the temperature of the reaction was kept at À10 C. The reaction mixture was extracted using petroleum ether and washed with an aqueous solution of ammonium sulfate ((NH 4 ) 2 SO 4 ).…”

Section: Synthesis Of Dektpmentioning

confidence: 99%

Synthesis of polystyrene oligomers by nitroxide‐mediated radical polymerization using diethylketone triperoxide as a multifunctional radical initiator

Anda

Santos

Morales

2011

J of Applied Polymer Sci

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Styrene oligomers (M n , 2500-3000 g/mol) with low polydispersity index and containing peroxidic groups within their structure were synthesized using a novel trifunctional cyclic radical initiator, diethylketone triperoxide (DEKTP), through nitroxide-mediated radical polymerization (NMRP), using OH-TEMPO. During the synthesis of the polystyrene (PS) oligomers, camphorsulfonic acid (CSA) was used to inhibit the thermal autoinitiation of styrene at the evaluated temperatures (T ¼ 120-130 C). The polymerization rate, which can be related to the slope of the plot of monomer conversion with reaction time, was monitored as a function of OH-TEMPO, DEKTP, and CSA concentrations. The experimental results showed that all the synthesized polymers presented narrow molecular weight distributions, and the monomer conversion and the molecular weight of the polymers increased as a function of reaction time.

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“…38 Differentiation between 1,2,4,2,4,5,7, conveniently and rapidly accessed. The temperature-independent spectra of 1h-10h indicate that the hexaoxonane ring is either rigid or highly flexible.…”

Section: Synthesis Of Tetraoxanes and Hexaoxonanesmentioning

confidence: 99%

“…In some cases, the procedure developed for the preparation of tetraoxanes produces instead a mixture of tetraoxanes and hexaoxonanes [2] or only hexaoxonanes [3]. Therefore, it is important to distinguish between these oligomers.…”

mentioning

confidence: 99%

Differentiation between 1,2,4,5‐tetraoxanes and 1,2,4,5,7,8‐hexaoxonanes using ¹H and ¹³C NMR analyses

Dong

Vennerstrom

2001

Journal of Heterocyclic Chem

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The proton and carbon resonance spectra of ten pairs of 1,2,4,5-tetraoxanes and 1,2,4,5,7,8-hexaoxonanes derived from acyclic and cyclic ketones have been recorded. A reliable method for distinguishing between 1,2,4,5-tetraoxanes and 1,2,4,5,7,8-hexaoxonanes by inspection of their chemical shifts, signal number, signal shape, and dynamic features has been developed. This method provides a rapid structural assignment of 1,2,4,5-tetraoxanes and 1,2,4,5,7,8-hexaoxonanes without using vapor pressure osmometry, isotope labeling or low temperature NMR techniques.

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Improved procedure for the preparation of diethyl ketone triperoxide and kinetics of its thermal decomposition reaction in solution

Cited by 32 publications

References 3 publications

Effect of ionic liquid on the thermal decomposition of cyclic organic peroxides

Effect of ionic liquid on the thermal decomposition of cyclic organic peroxides

Synthesis of polystyrene oligomers by nitroxide‐mediated radical polymerization using diethylketone triperoxide as a multifunctional radical initiator

Differentiation between 1,2,4,5‐tetraoxanes and 1,2,4,5,7,8‐hexaoxonanes using ¹H and ¹³C NMR analyses

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Improved procedure for the preparation of diethyl ketone triperoxide and kinetics of its thermal decomposition reaction in solution

Cited by 32 publications

References 3 publications

Effect of ionic liquid on the thermal decomposition of cyclic organic peroxides

Effect of ionic liquid on the thermal decomposition of cyclic organic peroxides

Synthesis of polystyrene oligomers by nitroxide‐mediated radical polymerization using diethylketone triperoxide as a multifunctional radical initiator

Differentiation between 1,2,4,5‐tetraoxanes and 1,2,4,5,7,8‐hexaoxonanes using 1H and 13C NMR analyses

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Differentiation between 1,2,4,5‐tetraoxanes and 1,2,4,5,7,8‐hexaoxonanes using ¹H and ¹³C NMR analyses