Catalytic Activity of H3PW12O40/Aliquat 336 in Epoxidation of (Z,E,E)-1,5,9-Cyclododecatriene to (E)-1,2-Epoxy-(Z,E)-5,9-Cyclododecadiene

Wołosiak, Agnieszka; Lewandowski, Grzegorz; Milchert, Eugeniusz

doi:10.1021/ie1021738

Cited by 3 publications

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“…Examples of such compounds are ethylene oxide, propylene oxide, 1,2epoxylimonene, and 1,2-epoxy-5,9-cyclododecadiene (ECDD). The last of these compounds, the obtaining of which was the aim of the research in this article, has found, inter alia, applications for the production of cyclododecanone, which is the raw material used for the production of laurolactam and dodecanedioic acid [1][2][3]. ECDD is currently finding newer applications, e.g., as a fragrance compound for the production of perfumes with the scent of musk, as well as a raw material for the production of other fragrances, e.g., 4,8-cyclododecadienone (the ingredient in perfumes with a woody-musky scent) [4,5].…”

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confidence: 99%

W-SBA-15 as an Effective Catalyst for the Epoxidation of 1,5,9-Cyclododecatriene

et al. 2022

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The results of a study on the epoxidation of 1,5,9-cyclododecatriene (CDT) on a W-SBA-15 catalyst using the batch and half-periodic methods are presented. During this study, the activity of the W-SBA-15 catalyst was compared to that of the Ti-SBA-15 catalyst, and the W-SBA-15 catalyst was found to be about 20 times more active than the Ti-SBA-15 catalyst. The highest CDT conversion so far, amounting to 86 mol%, was obtained after carrying out the 4 h epoxidation process. Conducting the studied process using the semi-batch method did not result in the significant improvement in value functions describing this process (CDT conversion and selectivity of CDT transformation to ECDD), but the fastest H2O2 dosing rate (246 µL/h) allowed us to obtain 9 mol% higher CDT conversion in comparison to the batch method.

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Section: Introductionmentioning

confidence: 99%

W-SBA-15 as an Effective Catalyst for the Epoxidation of 1,5,9-Cyclododecatriene

et al. 2022

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Approach for the Preparation of Various Classes of Peroxides Based on the Reaction of Triketones with H₂O₂: First Examples of Ozonide Rearrangements

Yaremenko

Terent’ev

Vil

et al. 2014

Chemistry A European J

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The reaction of β,δ-triketones with an ethereal solution of H2O2 catalyzed by heteropoly acids in the presence of a polar aprotic co-solvent proceeds via three pathways to form three classes of peroxides: tricyclic monoperoxides, bridged tetraoxanes, and a pair of stereoisomeric ozonides. The reaction is unusual in that produces bridged tetraoxanes and ozonides with one of the three carbonyl groups remaining intact. In the synthesis of bridged tetraoxanes, the peroxide ring is formed by the reaction of hydrogen peroxide with two carbonyl groups at the β positions. The synthesis of ozonides from ketones and hydrogen peroxide is a unique process in which the ozonide ring is formed with the participation of two carbonyl groups at the δ positions. Rearrangements of ozonides were found for the first time after more than one century of their active investigation. Ozonides are interconverted with each other and rearranged into tricyclic monoperoxides, whereas ozonides and tricyclic monoperoxides are transformed into bridged tetraoxanes. The individual reaction products were isolated by column chromatography and characterized by NMR spectroscopy, mass spectrometry, and elemental analysis. One representative of each class of peroxides was characterized by X-ray diffraction.

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Epoxidation of 1,5,9-Cyclododecatriene with Hydrogen Peroxide over Ti-MCM-41 Catalyst

et al. 2021

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This work presents the results of our research on the epoxidation of 1,5,9-cyclododecatriene (CDT) with hydrogen peroxide over the Ti-MCM-41 catalyst. The influence of the following parameters on the course of the process was investigated: temperature, CDT:H2O2 molar ratio, solvent composition and its type, and catalyst content. The highest selectivity of CDT transformation to 1,2-epoxy-5,9-cyclododecadiene (ECDD)—approximately 100 mol%, the highest yet reported—was obtained at the CDT conversion of 13 mol% and with the following parameter values: a catalyst content of 5 wt%; a molar ratio of CDT:H2O2 = 2; isopropyl alcohol (i-PrOH) as the solvent, with a composition of 80 wt% in the reaction mixture; a temperature of 80 °C; and a reaction time of 240 min. The highest conversion of CDT (37 mol%) was obtained at the ECDD selectivity of 56 mol% and using the following process parameters: a catalyst content of 5 wt%; a molar ratio of CDT:H2O2 = 0.5; i-PrOH used as the solvent, with solvent composition of 80 wt%; a temperature of 80 °C; and a reaction time of 60 min. It should be emphasized that the CDT conversion obtained in the current study is higher (by 9 mol%) than that described in the literature on heterogeneous catalysts.

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Catalytic Activity of H₃PW₁₂O₄₀/Aliquat 336 in Epoxidation of (Z,E,E)-1,5,9-Cyclododecatriene to (E)-1,2-Epoxy-(Z,E)-5,9-Cyclododecadiene

Cited by 3 publications

References 26 publications

W-SBA-15 as an Effective Catalyst for the Epoxidation of 1,5,9-Cyclododecatriene

W-SBA-15 as an Effective Catalyst for the Epoxidation of 1,5,9-Cyclododecatriene

Approach for the Preparation of Various Classes of Peroxides Based on the Reaction of Triketones with H₂O₂: First Examples of Ozonide Rearrangements

Epoxidation of 1,5,9-Cyclododecatriene with Hydrogen Peroxide over Ti-MCM-41 Catalyst

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Catalytic Activity of H3PW12O40/Aliquat 336 in Epoxidation of (Z,E,E)-1,5,9-Cyclododecatriene to (E)-1,2-Epoxy-(Z,E)-5,9-Cyclododecadiene

Cited by 3 publications

References 26 publications

W-SBA-15 as an Effective Catalyst for the Epoxidation of 1,5,9-Cyclododecatriene

W-SBA-15 as an Effective Catalyst for the Epoxidation of 1,5,9-Cyclododecatriene

Approach for the Preparation of Various Classes of Peroxides Based on the Reaction of Triketones with H2O2: First Examples of Ozonide Rearrangements

Epoxidation of 1,5,9-Cyclododecatriene with Hydrogen Peroxide over Ti-MCM-41 Catalyst

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Catalytic Activity of H₃PW₁₂O₄₀/Aliquat 336 in Epoxidation of (Z,E,E)-1,5,9-Cyclododecatriene to (E)-1,2-Epoxy-(Z,E)-5,9-Cyclododecadiene

Approach for the Preparation of Various Classes of Peroxides Based on the Reaction of Triketones with H₂O₂: First Examples of Ozonide Rearrangements