Oxidation of di-n-propyl ether: Characterization of low-temperature products

Belhadj, Nesrine; Benoit, Roland; Dagaut, Philippe; Lailliau, Maxence; Serinyel, Zeynep; Dayma, Guillaume

doi:10.1016/j.proci.2020.06.350

Cited by 24 publications

(25 citation statements)

References 36 publications

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“…25,57 In these experiments, several products of the 2 nd and 3 rd addition of molecular oxygen were detected. More recently, [26][27] products resulting from addition on fuels radicals of up to Their formation was observed here (Table 3). The variation of the integrated C 4 H 9 O 3 + signal obtained by FIA vs. temperature is presented in Figure 2.…”

Section: Resultssupporting

confidence: 61%

“…With the recent development of analytical techniques, e.g., synchrotron-based mass spectrometry, 25,[40][41] ultra-high-pressure liquid chromatography (UHPLC) coupled to Orbitrap®, it becomes possible to better characterize cool flame products. [26][27]42 As part of continuing efforts in this laboratory to better understand the chemical kinetics of fuels combustion, a series of experiments has been carried out recently for the oxidation of several ethers. [26][27] In this paper we extend that work by presenting results of kinetic experiments completed to identify the products of THF cool flame in a JSR.…”

Section: Introductionmentioning

confidence: 99%

“…[26][27]42 As part of continuing efforts in this laboratory to better understand the chemical kinetics of fuels combustion, a series of experiments has been carried out recently for the oxidation of several ethers. [26][27] In this paper we extend that work by presenting results of kinetic experiments completed to identify the products of THF cool flame in a JSR. Among the products detected, we paid particular attention to the detection of ketohydroperoxide isomers since discrepancies between kinetic modeling and measurements have been reported recently 24 .…”

Section: Introductionmentioning

confidence: 99%

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Experimental Characterization of Tetrahydrofuran Low-Temperature Oxidation Products Including Ketohydroperoxides and Highly Oxygenated Molecules

et al. 2020

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HAL is a multi-disciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

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Section: Resultssupporting

confidence: 61%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Experimental Characterization of Tetrahydrofuran Low-Temperature Oxidation Products Including Ketohydroperoxides and Highly Oxygenated Molecules

et al. 2020

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“…This sequence of reactions can proceed again, yielding highly oxygenated products (Z. Belhadj et al, 2020Belhadj et al, , 2021a. Also, QOOH can decompose via QOOH → OH+ cyclic ether, QOOH → OH+ carbonyl + olefin, and QOOH → HO 2 + olefin.…”

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confidence: 99%

On the similarities and differences between the products of oxidation of hydrocarbons under simulated atmospheric conditions and cool flames

et al. 2021

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Abstract. Atmospheric oxidation chemistry and, more specifically, photooxidation show that the long-term oxidation of organic aerosol (OA) progressively erases the initial signature of the chemical compounds and can lead to a relatively uniform character of oxygenated organic aerosol (OOA). This uniformity character observed after a long reaction time seems to contrast with the great diversity of reaction mechanisms observed in the early stages of oxidation. The numerous studies carried out on the oxidation of terpenes, and more particularly on limonene for its diversity of reaction sites (endo- and oxocyclic), allow this evolution to be studied. We have selected, for their diversity of experimental conditions, nine studies of limonene oxidation at room temperature over long reaction times to be compared to the present data set obtained at elevated temperature and short reaction time in order to investigate the similarities in terms of reaction mechanisms and chemical species formed. Here, the oxidation of limonene–oxygen–nitrogen mixtures was studied using a jet-stirred reactor at elevated temperature and atmospheric pressure. Samples of the reacting mixtures were collected and analyzed by high-resolution mass spectrometry (Orbitrap) after direct injection or after separation by reverse-phase ultra-high-pressure liquid chromatography and soft ionization, i.e., (+/-) HESI and (+/-) APCI. Unexpectedly, because of the diversity of experimental conditions in terms of continuous-flow tank reactor, concentration of reactants, temperature, reaction time, mass spectrometry techniques, and analysis conditions, the results indicate that among the 1138 presently detected molecular formulae, many oxygenates found in earlier studies of limonene oxidation by OH and/or ozone are also produced under the present conditions. Among these molecular formulae, highly oxygenated molecules and oligomers were detected in the present work. The results are discussed in terms of reaction pathways involving the initial formation of peroxy radicals (RO2), isomerization reactions yielding keto-hydroperoxides, and other oxygenated intermediates and products up to C25H32O17, products which could derive from RO2 autoxidation via sequential H shift and O2 addition (C10H14O3,5,7,9,11) and products deriving from the oxidation of alkoxy radicals (produced by RO2 self-reaction or reaction with HO2) through multiple H shifts and O2 additions (C10H14O2,4,6,8,10). The oxidation of RO2, with possible occurrence of the Waddington mechanism and of the Korcek mechanism, involving H shifts is also discussed. The present work demonstrates similitude between the oxidation products and oxidation pathways of limonene under simulated atmospheric conditions and in those encountered during the self-ignition of hydrocarbons at elevated temperatures. These results complement those recently reported by Vereecken and Nozière and confirm for limonene the existence of an oxidative chemistry of the alkylperoxy radical beyond 450 K based on the H shift (Nozière and Vereecken, 2019; Vereecken and Nozière, 2020).

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“…To rationally design (bioderived) ethers with improved properties, there have been experimental and computational studies on the combustion kinetics of C2-C8 linear [11][12][13][14][15][16][17][18][19] and branched ethers [20][21][22][23]. These studies give insights into the oxidation chemistry and provide kinetic models for combustion simulations.…”

Section: Main Textmentioning

confidence: 99%

Bioderived ether design for low emission and high reactivity transport fuels

Cho

Kim

Etz

et al. 2021

Preprint

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Bioderived ethers have recently drawn attention as a response to increasing demands on clean alternative fuels. A theory-experiment combined approach was introduced for the five ether molecules representing linear, branched, and cyclic ethers to derive rational design principles for low-emission and high-reactivity ethers. Flow reactor experiments and quantum-mechanical calculations were performed at high (750–1100K) and low temperature (400–700K) regimes to investigate the structural effects on their sooting tendency and reactivity, respectively. At a high-temperature regime, ethers’ high sooting tendency is related to increased C3 and C4 hydrocarbon formation compared to C1 and C2 products from oxidation reactions. On the other hand, the reactivity at the low-temperature regime is determined by the activation energies of reaction steps until ketohydroperoxide formation. These studies found that ethers’ sooting tendency and reactivity are relevant to two structural factors: the carbon type (primary to quaternary) and the relative position of ether oxygen atoms to carbon atoms. These factors were utilized to build a multivariate model to predict the cetane number (CN) and yield sooting index (YSI) of 50 different ethers. The model suggests building blocks with specific carbon types that maximize CN and minimize YSI, leading to the design principles of ethers toward low emissions and high reactivity fuels for transport applications. Ethers with a high CN and low YSI were then proposed using the developed model, and through experimental measurements, it was proved that they are promising biodiesel candidates.

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Oxidation of di-n-propyl ether: Characterization of low-temperature products

Cited by 24 publications

References 36 publications

Experimental Characterization of Tetrahydrofuran Low-Temperature Oxidation Products Including Ketohydroperoxides and Highly Oxygenated Molecules

Experimental Characterization of Tetrahydrofuran Low-Temperature Oxidation Products Including Ketohydroperoxides and Highly Oxygenated Molecules

On the similarities and differences between the products of oxidation of hydrocarbons under simulated atmospheric conditions and cool flames

Bioderived ether design for low emission and high reactivity transport fuels

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