Epoxidation of alkenes by dioxirane intermediates generated in the reaction of potassium caroate with ketones

Curci, Ruggero; Fiorentino, Michele; Troisi, Luigino; Edwards, John O.; Pater, Ruth H.

doi:10.1021/jo01311a040

Cited by 224 publications

(84 citation statements)

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“…Epoxidation of methyl oleate and methyl ricinoleate were reported by Sonnet affording the corresponding epoxides in excellent yield (Sonnet and Foglia, 1996). Both of these reactions were accomplished under biphasic conditions employing 2-butanone as the solvent as reported by Curci et al (1980).…”

Section: Dioxiranesmentioning

confidence: 97%

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

et al. 2017

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SUMMARY:The highly strained ring in epoxides makes these compounds very versatile intermediates. Epoxidized vegetable oils are gaining a lot of attention as renewable and environmentally friendly feedstock with various industrial applications such as plasticizers, lubricant base oils, surfactants, etc. Numerous papers have been published on the development of the epoxidation methods and the number is still growing. This review reports the synthetic approaches and applications of epoxidized vegetable oils. KEYWORDS: Epoxidation; Renewable feedstock; Unsaturated fatty acids; Vegetable Oils RESUMEN:Modificación del doble enlace olefínico en ácidos grasos insaturados y en derivados de aceites vegetales via epoxidación: Revisión. La alta tensión del anillo en los epóxidos hace que estos compuestos intermediarios sean muy versátiles. Los aceites vegetales epoxidados están ganando mucha atención como materia prima renovable y respetuosa con el medio ambiente con diversas aplicaciones industriales, tales como plastificantes, aceites base para lubricantes, tensioactivos, etc. Por esta razón, se han publicado numerosos trabajos sobre el desarrollo de métodos de epoxidación y el número todavía es creciente. Esta revisión aporta información sobre enfoques sintéticos y aplicaciones de aceites vegetales epoxidados.

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Section: Dioxiranesmentioning

confidence: 97%

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

et al. 2017

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“…Although the preparation of 2 via epoxidation of tri-O-benzyl-D D-glucal 1 with DMDO solution was already described, 4 we were interested in the epoxidation of this and other glycals using in situ formed DMDO. Indeed, in the early report of Curci et al, 11 the epoxidation of hydrophobic alkenes was carried out using in situ generated DMDO solutions under phase-transfer catalysis conditions. An example of a methodologically simpler procedure employing Oxone Ò /acetone system in biphasic conditions (CH 2 Cl 2 -aqueous NaHCO 3 ) was reported for the epoxidation of allenes.…”

mentioning

confidence: 99%

Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO

Cheshev

Marra

Dondoni

2006

Carbohydrate Research

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“…When the pH value is greater than 8.0, the peroxomonosulfate exists as a dianion, increasing its nucleophilicity and thus leading to decomposition. [20] This nonproductive path way can be suppressed by the slow addition of OXONE as well as careful control of pH. The decrease in conversion at lower pH is caused by a loss of reactivity of OXONE (OXONE preservation).…”

Section: Epoxidation With Dioxiranementioning

confidence: 99%

“…[18,19] Dioxiranes are generated from potassium peroxomonosulfate (OXONE) using ketones, such as cetone, [20] 2-butanone, [21] or cyclohexanone [22] as catalysts. Dioxiranes can be used either generated in situ or as isolated species.…”

Section: Introductionmentioning

confidence: 99%

Epoxidation of partially norbornylized linseed oil

Chen

Soucek

Simonsick

et al. 2002

Macromol. Chem. Phys.

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Epoxidation of linseed oil was performed with peracetic acid formed in situ by the reaction of hydrogen peroxide and acetic acid in the presence of Amberlite 120H as catalyst, and toluene as solvent. Some variables were evaluated as temperature and the molar ratio and solution of aqueous hydrogen peroxide (30 and 50 wt%) for obtaining a maximum of yield and conversion of epoxidized oil. The characterization of conversion of double bonds (DB) to epoxy ring, the relative percentage of epoxidation and selectivity, were performed by 1 H-NMR and FTIR-HART. The conditions rendered a maximum epoxidation of 93.4%, a conversion or double bonds of 97% and a selectivity of 96.3% were obtained at 80°C, employing a molar ratio 1:1.5 of double bonds (DB) to H 2 O 2 (50 wt%), 1:0.5 of DB to acetic acid, and 25 wt% of catalyst, in only 50 min and with a good reproducibility (±1.1%).

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Epoxidation of alkenes by dioxirane intermediates generated in the reaction of potassium caroate with ketones

Cited by 224 publications

References 0 publications

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

Direct epoxidation of d-glucal and d-galactal derivatives with in situ generated DMDO

Epoxidation of partially norbornylized linseed oil

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