Mechanism of ozonation reactions. III. Ethers

Erickson, Ronald E.; Hansen, Robert T.; Harkins, James

doi:10.1021/ja01026a038

Cited by 34 publications

(16 citation statements)

References 2 publications

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“…The authors mentioned the formation of alcohols, aldehydes, ketones and esters with production of hydrogen peroxide and molecular oxygen. Erickson et al (1968) identified tert-butyl acetate, tert-butyl formate and tert-butyl alcohol as ETBE ozonation byproducts. According to Bailey and Lerdal (1978), two types of initial attack of ozone on ethers take place and lead to the formation of hydrotrioxide intermediates (identified by Stary et al, 1976).…”

Section: And the Year 2000 By A Quadrupling Of The American Consumptmentioning

confidence: 99%

“…Studies on the ozonation of ethers were conducted mainly in organic solvents between -80°C and room temperature (Price and Tumolo, 1964;Erickson et al, 1968;Bailey and Lerdal, 1978). The authors mentioned the formation of alcohols, aldehydes, ketones and esters with production of hydrogen peroxide and molecular oxygen.…”

Section: And the Year 2000 By A Quadrupling Of The American Consumptmentioning

confidence: 99%

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Oxidation of Methyl tert-Butyl Ether (MTBE) and Ethyl tert-Butyl Ether (ETBE) by Ozone and Combined Ozone/Hydrogen Peroxide

Leitner¹,

Papailhou²,

Croué³

et al. 1994

Ozone: Science & Engineering

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The aim of this work was to study the reaction of ozone and combined ozone/hydrogen peroxide on oxygenated additives such as methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE) in dilute aqueous solution using controlled experimental conditions. Experiments conducted in a semi-continuous reactor with MTBE and ETBE in combination (initial concentration: 2 mmol/L of each) showed that ETBE was better eliminated than MTBE with both ozone and combined 0j/H 2 0 2 . Batch experiments led to the determination of the ratio of the kinetic constants for the reaction of OH°-radical with MTBE and ETBE [KH°/nit/Kt<"mu = 1-7). Tert-butyl formate and tert-butyl acetate were identified as the ozonation byproducts of MTBE and ETBE, respectively, while tert-butyl alcohol was found to be produced during the ozonation of both compounds.

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Section: And the Year 2000 By A Quadrupling Of The American Consumptmentioning

confidence: 99%

Section: And the Year 2000 By A Quadrupling Of The American Consumptmentioning

confidence: 99%

Oxidation of Methyl tert-Butyl Ether (MTBE) and Ethyl tert-Butyl Ether (ETBE) by Ozone and Combined Ozone/Hydrogen Peroxide

Leitner¹,

Papailhou²,

Croué³

et al. 1994

Ozone: Science & Engineering

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“…Antiperiplanar lone pairs will elongate the C-H bond as well as stabilize the incipient dioxonium ion. The 1,3-diplolar insertion mechanism (Scheme 3b) has been postulated for the ozonation of ethers (10)(11)(12), aldehydes (13,14), and hydrocarbons (15,16). Ozone attack on oxygen (Scheme 3c) is similar to that proposed for the ozonation of certain amines (18), and ethers (12).…”

Section: Substituent Effectsmentioning

confidence: 99%

The mechanism of oxidation of acetals by ozone. I. Stoichiometry, order of the reaction, solvent effects, and substituent effects

Taillefer¹,

Thomas²,

Nadeau³

et al. 1980

Can. J. Chem.

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A systematic investigation of the reaction between ozone and acetals to form acetal hydrotrioxides A has been undertaken. The stoichiometry of the reaction has been shown to be 1:l in each reactant and the order of the reaction was also one in each reactant. Substituent effects measured in a variety of systems and under several conditions of temperature and solvent were found to be small (p = -1.10 to -1.58). Solvent polarity was also found to have little effect on the rate of the reaction. Mechanistically, these facts are interpreted in terms of a 1.3-dipolar insertion of ozone into the C-H bond of the acetal function.ROLAND J. TAILLEFER, SHIRLEY E. THOMAS, YVES NADEAU, S. FLISZAR et HERVE HENRY. Can. J. Chem. 58, 1138Chem. 58, (1980. Une etude systematique de la rtaction de I'ozone avec les acetals pour former les acktals hydrotrioxides A a t t t entreprise. On a trouve que la stoechiomttrie et I'ordre de la reaction etaient de un dans chacun des reactifs. L'effet des substituents sur la vitesse de reaction, mesure dans plusieurs systimes et sous difftrentes conditions de temperatures et de solvants est faible (p = -1.108 -1.58) de mime que I'effet de la polarit6 des solvants. Ces faits sont interpretis en invoquant un mecanisme d'addition 1,3-dipolaire de I'ozone dans le lien C-H de la fonction acetale.

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“…Ozon zeigt bei tiefer Temperatur Einschiebungsreaktionen in CH-Bindungen. Ffir DiisopropylMher (= RH) und Isopropanol wurde die Bildung von bei -80 ~ noch stabilen Trioxiden mit drei aneinandergeknfipften O-Atomen vermutet [29][30][31][32]: Das unterschiedliche mechanistische Verhalten mit der Konzentration ist nur mit Typ F12 vereinbar, der zweite Schritt k6nnte mindestens zwei Schritte unterschiedlicher Ordnung aufweisen. Dies wfirde auch die Konzentrationsabhfingigkeit der W/irmet6nung erklgren.…”

Section: Ozonisation Yon Diisopropyl~ither Und Isopropanolunclassified

“…3). Diese Befunde deuten auf die Bildung eines analogen Trioxids in viel schlechterer Ausbeute, was auch aufgrund der Ergebnisse mit anderen Untersuchungsmethoden vermutet wurde [30][31][32][33]. Der zweite Peak entspricht nahezu einer Reaktion erster Ordnung.…”

Section: Ro + Ro2 (Ro)20 (18)unclassified

Reaktionsanalyse durch nichtisotherme Kalorimetrie: Lösungsreaktionen von Peroxiden, Ozoniden und Trioxiden

Koch

1974

Journal of Thermal Analysis

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Homogeneous solution reactions (half-life-time for 1 M solutions r20 ~ 3> ,~ 10-~ sec,[AH] > 0.5 kcal/mole) have been investigated by non-isothermal differential calorimetry. By application of a new diagnostic procedure developed by use of an analogue computer, it can be decided whether the reactions of the substances tested are formal one-step processes, or what types of reaction-mechanisms must be considered. For the decompositions of some peroxide compounds the basic mechanism types, activation energies and action constants or entropies of the starting processes were determined. The cyclic furan ozonides have similar stabilities to that of the trioxide of di-isopropyl ether. On the other hand, triphenyl phosphite ozonide is considerably more unstable and can transfer oxygen to various acceptors below its decomposition temperature.

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Mechanism of ozonation reactions. III. Ethers

Cited by 34 publications

References 2 publications

Oxidation of Methyl tert-Butyl Ether (MTBE) and Ethyl tert-Butyl Ether (ETBE) by Ozone and Combined Ozone/Hydrogen Peroxide

Oxidation of Methyl tert-Butyl Ether (MTBE) and Ethyl tert-Butyl Ether (ETBE) by Ozone and Combined Ozone/Hydrogen Peroxide

The mechanism of oxidation of acetals by ozone. I. Stoichiometry, order of the reaction, solvent effects, and substituent effects

Reaktionsanalyse durch nichtisotherme Kalorimetrie: Lösungsreaktionen von Peroxiden, Ozoniden und Trioxiden

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