14156-10-6Relevant articles and documents
A Mechanistic Study on the Reaction of Non-Heme Diiron(III)-Peroxido Complexes with Benzoyl Chloride
Lerch, Markus,Achazi, Andreas J.,Mollenhauer, Doreen,Becker, Jonathan,Schindler, Siegfried
, p. 4122 - 4132 (2021)
Dinuclear iron peroxido complexes are important intermediates for selective oxidation reactions. A detailed kinetic study of the reaction of benzoyl chloride (BzCl) with a dinuclear iron non-heme cis end-on peroxido complex with the ligand EtHPTB (N,N,N′,
Thermal decomposition of aliphatic peroxy acids
Dutka,Zagorskaya,Dutka, Yu. V.,Savitskaya
, p. 353 - 357 (2011)
The thermal decomposition reactions of aliphatic peroxy acids containing from 8 to 16 carbon atoms in a molecule were studied. It was found that the carbon radical length had no effect on the thermal stability of peroxide groups. The apparent rate constants of thermolysis of peroxydecanoic acid in various solvents and the activation energies of the test reaction were found. The thermal degradation of peroxy acids involved secondary reactions of induced chain degradation in addition to the primary homolysis of the peroxide group. The rate constants of induced chain degradation were found.
Effect of solvents on the rate of epoxidation of α-pinene and Δ3-carene with peroxydecanoic acid
Dutka,Makitra,Dutka,Pal'Chikova,Matsyuk
, p. 298 - 303 (2014)
Reaction of epoxidation of α-pinene and Δ3-carene with peroxydecanoic acid in various organic solvents was studied. Effective activation energies of oxidation of α-pinene and Δ3- carene with peroxydecanoic acid in various media are evaluated. It is shown that reaction medium significantly affects the rate of the process. Correlation dependences connecting the rate of epoxidation with main parameters of solvents are found.
Mass spectrometry characterization of peroxycarboxylic acids as proxies for reactive oxygen species and highly oxygenated molecules in atmospheric aerosols
Steimer, Sarah S.,Kourtchev, Ivan,Kalberer, Markus
, p. 2873 - 2879 (2017)
A significant fraction of atmospheric aerosol particles is composed of organic material with a highly complex but poorly characterized composition. For a better understanding of aerosol effects and processes in the atmosphere, a more detailed knowledge of aerosol components at a molecular level is needed. Peroxy acids might play a significant role in particle toxicity, due to their oxidizing properties, and they were recently found to be involved in particle formation. Because of the lack of appropriate standards, the identification and quantification of peroxy acids is often highly uncertain. Mass spectrometry (MS) is a powerful tool to characterize unidentified compounds in complex mixtures. However, so far there is only little information regarding the ionization and fragmentation behavior of peroxy acids in mass spectrometers. To study their fragmentation patterns, we synthesized 12 peroxy acids with C8 to C10 carbon backbones and mono- or diperoxy acid functionality. The peroxy acids were separated using liquid chromatography, detected via negative mode electrospray ionization high-resolution MS, and their fragmentation patterns (MS/MS spectra) were identified. The MS/MS spectra of the peroxy acids showed fragmentation patterns clearly different from the corresponding acid, with a strong similarity between compounds of different chain length but analogous functional groups. Neutral loss of CH2O2 was observed for all investigated linear peroxy acids but not for carboxylic acids and could therefore serve as a diagnostic ion for peroxy acids. The obtained results are a large step toward unambiguous characterization of peroxy acids in the atmosphere. (Graph Presented).
Effect of Organic Solvents on the Rate of Oxidation of Sulfoxides with Peroxy Acids
Dutka, V. S.,Dutka, Yu. V.,Midyana, G. G.,Pal’chikova, E. Ya.
, p. 329 - 334 (2020/04/27)
Abstract: The reaction of sulfoxides with peroxy acids in various organic media was studied. The reaction mechanism involves the rapid formation of a sulfoxide-–peroxy acid intermediate which decomposes in the second stage to form carboxylic acid and the corresponding sulfone. The second stage is the rate-limiting step. The reaction medium significantly affects the rate of oxidation. The calculated activation parameters of the oxidation process indicate a compensation effect in the investigated reaction. Correlations between the main physicochemical parameters of solvents and the effective rate constants (k) of dimethyl sulfoxide oxidation with peroxy acids were found. Depending on the reaction conditions, the main factors affecting the k values are specific and nonspecific solvation of the reactants and structural factors.
Perdecanoic acid as a safe and stable medium-chain peracid for Baeyer-Villiger oxidation of cyclic ketones to lactones
Sitko, Magdalena,Szelwicka, Anna,Wojewódka, Andrzej,Skwarek, Andrzej,Tadasiewicz, Dariusz,Schimmelpfennig, Lech,Dziuba, Krzysztof,Morawiec-Witczak, Magdalena,Chrobok, Anna
, p. 30012 - 30018 (2019/10/02)
Stability studies dedicated to high-energy compounds for a series of linear peracids (C6-C12), including sensitivity to mechanical impulse (shock and friction), as well as electrical (spark) and thermal sensitivity (temperature and heat of decomposition), were presented in this work for the first time. Studies revealed that all peracids were insensitive to shock, while in the case of the other sensitivity tests sharp differences between results for C8 and C10 peracids were observed. Taking into account the relatively high initial temperature of decomposition (above 64 °C) perdecanoic acid was selected as a safe alternative to commonly used hazardous short-chain peracids. Next, a new method for the Baeyer-Villiger oxidation was presented. Oxidation of 2-adamantanone was chosen as a model reaction. Peroctanoic, perdecanoic and perdodecanoic acids were tested as oxidants. Peroctanoic acid was the most reactive but taking into account both safety and kinetic issues, perdecanoic acid was selected for the further studies. The influence of reaction conditions on reaction rate was investigated. Optimized reaction conditions were suggested (two-fold molar excess of peracid with respect to the ketone, toluene as a solvent, 35 °C). This exploratory study offers promise with regard to the development of safer alternatives to peracetic acid in industrial oxidation.
Method For Producing Acyloxy Benzoic Acids
-
, (2013/08/28)
The invention relates to a method for producing acyloxy benzoic acids of the formula (I), in which R1 is a linear or branched saturated alkyl group with 6 to 30 carbon atoms, a linear or branched mono- or polyunsaturated alkenyl group with 6 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms. The acyloxy benzoic acids of the formula (I) are produced from para-hydroxy benzoic acid and a corresponding carboxylic acid halide in the presence of an alkali hydroxide.
Liquid chromatographic simultaneous determination of peroxycarboxylic acids using postcolumn derivatization
Effkemann,Pinkernell,Neumueller,Schwan,Engelhardt,Karst
, p. 3857 - 3862 (2007/10/03)
The first liquid chromatographic method with postcolumn derivatization for the simultaneous determination of peroxycarboxylic acids is described. Aliphatic peracids with chain lengths from C2 to C12 are separated by HPLC on a reversed-phase C18 column with acetonitrile/water gradient elution. For improved peak shape, tetrahydrofuran and acetic acid are added to the aqueous eluent. After chromatographic separation, the peroxycarboxylic acids react with 2,2′-azino-bis(3-ethylbenzothiazoline)-6-sulfonate, a popular substrate for the enzyme peroxidase. Iodide traces are added as catalyst. The oxidation product, a green radical cation, is determined using a UV/ visible detector in four characteristic regions of the visible and near-infrared spectrum in the range 405-815 nm. The advantages of the new method are detection limits in the low micromolar range, negligible matrix interferences, high reproducibility, and the possibility for simultaneous determination of several peroxycarboxylic acids.
Decomposition of Peroxydecanoic Acid using BCHPC under Argon Atmosphere
Sorba, Janine,Lefort, Daniel,Fossey, Jacques,Grisel, Frederic,Sanderson, William R.
, p. 1565 - 1569 (2007/10/02)
Using BCHPC as a source of alkoxycarbonyloxyl radical at moderate temperature in benzene or cyclohexane and in the absence of O2 (under argon), the peroxydecanoic acid RCO3H is transformed into nonan-1-ol ROH in good yield.A mechanism, implying the acylperoxyl radical RCO3. as an intermediate, is proposed.
NOUVEAUX DECONTAMINANTS. DESTRUCTION CHIMIQUE TOTALE, RAPIDE ET DOUCE D'INSECTICIDES ET DE TOXIQUES DE GUERRE PAR LES PERACIDES
Lion, C.,Charvy, C.,Hedayatullah, Mir,Bauer, P.,Sentenac-Roumanou, H.,et al.
, p. 127 - 133 (2007/10/02)
Peroxyacids RCOOOH (R = n C7H15 to n C13H27) are very good decontamination reagents.Paraoxon (O,O-diethyl O-p nitrophenyl phosphate), VX and HD (2,2'-dichlorodiethylsulfide) react for example, with perdodecanoic acid, completely in a few seconds.The reaction rate is enhanced by micellar catalysis.
