The main differences in reactivity of mono- and diunsaturated fatty acid esters during aerobic oxidation

Cherepanova, A.D.; Сапунов, В. Н.

doi:10.1007/s11696-020-01108-2

Cited by 5 publications

(3 citation statements)

References 60 publications

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“…In an earlier communication (Cherepanova and Sapunov, 2020), the compositions of products of aerobic oxidation of FAME of vegetable oils were analyzed. Three main components consumption pathways were also identified as (I) formation of peroxide-compounds with different structure (hydroperoxides, endoperoxides, oligo-and polyperoxides [Frankel, 1980;Gardner, 1989;Mogilevich and Pliss, 1990;Spickett and Forman, 2015]), (II) formation of compounds with epoxides rings and (III) "aerobic" BV reaction (Brink et al, 2004;Imada et al, 2005;Jeong et al, 2011;Nabae et al, 2013) resulting from the formation of compounds with additional ester-groups in reaction mixture.…”

Section: Resultsmentioning

confidence: 99%

“…It was observed that during the aerobic oxidation of FAME with different fatty acid compositions, the BV reaction proceeded rapidly (Cherepanova and Sapunov, 2020). Intensive consumption of epoxide and peroxide compounds was accompanied by significant increase in ester value (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…To this end, FAME of sunflower oil were oxidized by atmospheric oxygen at 110 °C and 20 mL·s −1 airflow rate to maximum yield of epoxide compounds (≈ 25 wt. % in case of this raw material) (Cherepanova and Sapunov, 2020). Based on crucial industry criteria of LCST, mass fraction of volatile components, and the depth of color, as seen in Table 3, the plasticizer obtained in this investigation showed inferior characteristics in comparison with Etalon, the industry standard.…”

Section: Resultsmentioning

confidence: 99%

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A New Green Method for the Production Polyvinylchloride Plasticizers from Fatty Acid Methyl Esters of Vegetable Oils

Cherepanova

Savel’ev

Alieva

et al. 2020

J Americ Oil Chem Soc

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The current work has shown the potentials for the aerobic oxidation of fatty acid methyl ester (FAME) of vegetable oils in the production of polyvinylchloride (PVC) plasticizers with the exclusion of other reagents. The reaction mixtures contain epoxidized derivatives of FAME, and esters, with the quantity of the ester groups being higher than in the initial raw material. It was established that the increase in the additional ester groups resulting from the "aerobic" Baeyer-Villiger (BV) reaction has a significantly positive influence on the plasticizing ability of the oxidized FAME mixtures for PVC when compared to the formation of epoxide compounds. The development of the technology for the production of PVC plasticizers proposed in this investigation provides an opportunity for resolving some of the environmental issues normally associated with the use of phthalate-based plasticizers.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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A New Green Method for the Production Polyvinylchloride Plasticizers from Fatty Acid Methyl Esters of Vegetable Oils

Cherepanova

Savel’ev

Alieva

et al. 2020

J Americ Oil Chem Soc

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The specific features of the liquid-phase oxidation of saturated esters. Kinetics, reactivity and mechanisms of formation of destruction products

Perkel

Voronina

2020

Russ Chem Bull

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Data on kinetics, reactivity, and mechanisms of formation of destruction products of the liquid-phase oxidation of saturated esters by molecular oxygen have been systematized and discussed. The ester group has both an activating and deactivating eff ects on the reactivity of the СН bonds of the alkoxyl (α´-, β´-, γ´-, and δ´-) and acyl (α-, β-, and γ-) groups. The activating eff ect in esters is weaker than in alcohols, ketones, and ethers and extends to the αand α´-CH bonds. The reactivity of the β-, β´-, and γ´-СН bonds is signifi cantly lower than that of the secondary СН bonds of hydrocarbons. Oxidation of the β-СН bonds of the acyl moieties of esters leads to НОО • radical, α,β-epoxy-, α,β-dihydroxy-, and α,β-unsaturated esters, but not to hydroperoxides. Upon the oxidation of esters, the highly active α-carboxyalkylperoxy-, α-acyloxyperoxy-, and НОО • -radicals are formed. The recombination reactions involving these radicals occur both with and without chain termination. The specifi city of the decomposition of ester hydroperoxides are due to intra-and intermolecular interactions of the hydroperoxide groups with the ester groups. Labile peroxide intermediates (α-hydroxyperoxyesters, peroxyesters, and peroxylactones) are formed through the corresponding tetrahedral intermediates and decay predominantly by the non-radical pathway. The recombination of the peroxyl radicals and the decay of labile peroxides result in the parallel accumulation of per oxide and non-peroxide products during the oxidation of esters.

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Analysis of the kinetic regularities of diffusion-controlled aerobic oxidation of FAMEs

Cherepanova

Сапунов

2021

Chem. Pap.

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The main differences in reactivity of mono- and diunsaturated fatty acid esters during aerobic oxidation

Cited by 5 publications

References 60 publications

A New Green Method for the Production Polyvinylchloride Plasticizers from Fatty Acid Methyl Esters of Vegetable Oils

A New Green Method for the Production Polyvinylchloride Plasticizers from Fatty Acid Methyl Esters of Vegetable Oils

The specific features of the liquid-phase oxidation of saturated esters. Kinetics, reactivity and mechanisms of formation of destruction products

Analysis of the kinetic regularities of diffusion-controlled aerobic oxidation of FAMEs

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