Oxidative degradation of fragrant aldehydes. Autoxidation by molecular oxygen

Marteau, Clémentine; Ruyffelaere, Fanny; Aubry, Jean‐Marie; Penverne, Christophe; Favier, Dominique; Nardello‐Rataj, Véronique

doi:10.1016/j.tet.2013.01.034

Cited by 64 publications

(68 citation statements)

References 28 publications

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“…A PetroOxy test has been widely used for fuel stability studies, 15,16 and its detailed description is provided elsewhere. 16 This test allows for the determination of the IP defined by the time necessary to reach 10% of pressure drop measured in the test cell (ΔP) reflecting oxygen consumption (−d[O 2 ]/dt) and, hence, the oxidation of the fuel as a function of time. Tests were conducted from 383 to 423 K at 7 bar.…”

Section: Introductionmentioning

confidence: 99%

“…Those are characterized by the presence of bisallylic sites that have higher reactivity 24 and, therefore, a higher oxidizability compared to RME. 16,25,26 Table 3 shows an inventory of fuel samples and test conditions used in the two studies of kinetic and oxidation product characterization. The labels designate samples selected for the oxidation product characterization study.…”

Section: Introductionmentioning

confidence: 99%

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Oxidation Stability of Diesel/Biodiesel Fuels Measured by a PetroOxy Device and Characterization of Oxidation Products

et al. 2015

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In the present work, the oxidation stability of diesel, rapeseed (RME), and soybean (SME) fatty acid methyl esters (FAME) and a blend of diesel with 10% (v/v) RME (B10−RME) was studied. Fuel samples were aged in the PetroOxy test device from 383 to 423 K at 7 bar. Experiments were conducted in oxygen excess, and the global kinetic constants were determined. The global kinetic constants for diesel, B10−RME, and RME at 383 K were 7.92 × 10 −6 , 2.78 × 10 −5 , and 8.87 × 10 −5 s −1 , respectively. The oxidation products formed at different stages of the oxidation were monitored by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis−differential thermal analysis (TGA−DTA), and gas chromatography/ mass spectrometry (GC/MS). The impact of the FAME nature and level of blending on the kinetic rate constant and the oxidation products was investigated. Results show that RME oxidation forms C 19 epoxy as the main oxidation product, in addition to a methyl ester FAME derivative and short-chain oxidation products, such as alkane, alkene, aldehydes, ketones, alcohols, and acids with a carbon number up to C 11 . The overall amount of oxidation products increases with a higher degradation time. The DTA profile suggests that higher molecular weight products are formed at an advanced level of oxidation. For all highly oxidized fuels, a similar DTA peak was obtained at a temperature of around 573 K, which may suggest the formation of products having similar molecular weights for both diesel and FAME.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Oxidation Stability of Diesel/Biodiesel Fuels Measured by a PetroOxy Device and Characterization of Oxidation Products

et al. 2015

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“…Hydrolysis of this imine could lead to the formation of acetaldehyde as depicted in the reactions given in Scheme 1. Acetaldehyde product can be further degraded to molecular products (H 2 O, H 2 O 2 , and H(CO)OOH) via a free radical auto-oxidation process as proposed by Marteau et al (2013).…”

Section: Resultsmentioning

confidence: 99%

Selective photoreduction of acetonitrile to acetaldehyde in dilute aqueous solutions

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Stuart

et al. 2014

Toxicological & Environmental Chemistry

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Acetonitrile is a commonly used solvent in both industry and research. The treatment of acetonitrile wastes in dilute aqueous solutions with visible light offers advantages to chemical treatment and ultraviolet (UV) irradiation. This study presents the degradation of acetonitrile via a photoinduced electron transfer reaction in the presence of a photosensitizer (dye) and a sacrificial reductant under visible light. Acetonitrile photodegradation (photoreduction) was investigated utilizing a variety of sacrificial reductants and photosensitizers. Optimal results were observed in the presence of methylene green and tri-isopropanolamine with a decrease of acetonitrile in solution to 86% in 24 hours. The only photoreaction product observed was acetaldehyde and a plausible mechanism for the photochemical degradation of acetonitrile is proposed.

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“…4 Although the oxidation of aliphatic aldehyde into carboxylic acids proceeds by O 2 even without a catalyst, 5,6 several methods have been developed for the preparation of α,β-unsaturated carboxylic acids from their aldehyde derivatives, requiring severe and complex reaction conditions. 7 Recently, N-heterocyclic carbene (NHC)-catalyzed O 2 oxidation reactions of α,β-unsaturated aldehyde were developed by several groups, yet more than equimolar amounts of base were essential for good reaction yields.…”

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confidence: 99%

“…17 Nevertheless, an electrondeficient additive enhanced selectivity for the product in this catalysis. A possible catalyst generated in the reaction mixture was [Fe 3 O(O 2 CCF 3 ) 6 (H 2 O) 3 ] (3). 18 The catalytic oxidation of 1a by 3, however, afforded 2a with only 47% selectivity, indicating that 3 is not an active catalyst (Scheme 1b).…”

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confidence: 99%

Iron-catalyzed Selective Oxidation of α,β-Unsaturated Aldehydes to α,β-Unsaturated Carboxylic Acids by Molecular Oxygen

et al. 2016

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Selective oxidation of α,β-unsaturated aldehydes to α,β-unsaturated carboxylic acids was performed using O 2 as the oxidant in the presence of a simple iron catalyst. The addition of an alkali metal carboxylate as a cocatalyst enhanced the selectivity for the desired product. Redox tuning of the iron catalyst via association with the alkali metal led to a controlled radical generation during the catalytic O 2 oxidation.Molecular oxygen (O 2 ) is a readily available, inexpensive oxidant and is regarded as a promising natural resource for oxygen-containing chemical products.1,2 Conventional chemical processes including oxidations often use stoichiometric amounts of hazardous oxidants, leading to the formation of equimolar amounts of a by-product as waste. Although oxidation by O 2 would proceed with 100% atom efficiency under ideal conditions and thus generate no waste, such dioxygenase-type reactions have been reported less frequently than monooxygenaseand oxidase-type oxidation reactions, in which only one O atom of O 2 incorporates into substrate and O 2 is consumed by reoxidation of catalyst, respectively.3 In particular, the synthesis of value-added chemical products should be replaced by dioxygenase-type reactions to reduce waste generated during multistep reactions.α,β-Unsaturated carboxylic acids are among the most valuable intermediates and precursors for chemical production and pharmaceuticals. 4 Although the oxidation of aliphatic aldehyde into carboxylic acids proceeds by O 2 even without a catalyst, 5,6 several methods have been developed for the preparation of α,β-unsaturated carboxylic acids from their aldehyde derivatives, requiring severe and complex reaction conditions.7 Recently, N-heterocyclic carbene (NHC)-catalyzed O 2 oxidation reactions of α,β-unsaturated aldehyde were developed by several groups, yet more than equimolar amounts of base were essential for good reaction yields.8 From the standpoint of green-sustainable chemistry, catalytic oxidation using O 2 without large amounts of base is promising even if an organocatalyst could be employed.9 Nobile et al. reported a Fe catalyst bearing 2-(acetoacetoxy)ethyl methacrylate ligandcatalyzed O 2 oxidation of trans-2-hexenal; however, substrates were limited and a halogenated solvent was required.10 Mukaiyama et al. proposed the effectiveness of β-diketonate ligand to activate metal-catalyzed oxidation.11 More useful methods and systems to activate a base-metal complex must be developed to realize practical O 2 oxidation for the production of valuable fine chemicals.It is widely accepted that non-redox metal ions have considerable effect on the redox state of redox-active metal, promoting electron-transfer reactions 12 as well as catalytic reactions. 13 An appropriate combination of redox-active and non-redox-active base metals might act as simpler catalysts exhibiting enhanced activity in oxidation reactions. Herein, we report the preparation of α,β-unsaturated carboxylic acids from α,β-unsaturated aldehydes using a combination of O 2 and a...

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Oxidative degradation of fragrant aldehydes. Autoxidation by molecular oxygen

Cited by 64 publications

References 28 publications

Oxidation Stability of Diesel/Biodiesel Fuels Measured by a PetroOxy Device and Characterization of Oxidation Products

Oxidation Stability of Diesel/Biodiesel Fuels Measured by a PetroOxy Device and Characterization of Oxidation Products

Selective photoreduction of acetonitrile to acetaldehyde in dilute aqueous solutions

Iron-catalyzed Selective Oxidation of α,β-Unsaturated Aldehydes to α,β-Unsaturated Carboxylic Acids by Molecular Oxygen

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