Baeyer–Villiger Oxidation of Cyclic Ketones by Using Tin–Silica Pillared Catalysts
The Baeyer–Villiger oxidation is an important transformation of ketones into esters and particularly for cyclic ketones to lactones. We report here preparation and catalytic activity of layered Sn–silicate catalysts and mesoporous ordered silica catalysts in this reaction. Sn was introduced by using...
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Published in | ChemCatChem Vol. 9; no. 15; pp. 3063 - 3072 |
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Abstract | The Baeyer–Villiger oxidation is an important transformation of ketones into esters and particularly for cyclic ketones to lactones. We report here preparation and catalytic activity of layered Sn–silicate catalysts and mesoporous ordered silica catalysts in this reaction. Sn was introduced by using so‐called tin–silica pillaring or by impregnation with a mixture of tetraethylorthosilicate and tin(IV) alkoxide. The prepared catalysts were characterized by XRD, N2 physisorption, SEM, UV/Vis, and inductively coupled plasma optical emission spectroscopy (ICP‐OES) techniques and the catalysts were studied in the Baeyer–Villiger oxidation of cyclopentanone, norcamphor, and 2‐adamantanone with aqueous hydrogen peroxide. Norcamphor and 2‐adamantanone were oxidized easily with selectivity up to 99 %. Sn‐MS and IPC‐1‐SnPI materials exhibited the highest conversions (e.g., norcamphor: Sn‐MS 37 %, IPC‐1‐SnPI 36 % after 8 h vs. Sn‐MCM‐41 22 %). On the other hand, oxidation of cyclopentanone suffered from product hydrolysis to the corresponding 4‐hydroxybutanoic acid.
Tin–silica pillaring of a layered zeolite enables the preparation of a tin‐containing catalyst, which combines the advantages of crystalline zeolites and mesoporous molecular sieves. The tin–silica pillared zeolites catalyze the Baeyer–Villiger oxidation of cyclic ketones with aqueous hydrogen peroxide. |
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AbstractList | The Baeyer-Villiger oxidation is an important transformation of ketones into esters and particularly for cyclic ketones to lactones. We report here preparation and catalytic activity of layered Sn-silicate catalysts and mesoporous ordered silica catalysts in this reaction. Sn was introduced by using so-called tin-silica pillaring or by impregnation with a mixture of tetraethylorthosilicate and tin(IV) alkoxide. The prepared catalysts were characterized by XRD, N2 physisorption, SEM, UV/Vis, and inductively coupled plasma optical emission spectroscopy (ICP-OES) techniques and the catalysts were studied in the Baeyer-Villiger oxidation of cyclopentanone, norcamphor, and 2-adamantanone with aqueous hydrogen peroxide. Norcamphor and 2-adamantanone were oxidized easily with selectivity up to 99%. Sn-MS and IPC-1-SnPI materials exhibited the highest conversions (e.g., norcamphor: Sn-MS 37%, IPC-1-SnPI 36% after 8h vs. Sn-MCM-41 22%). On the other hand, oxidation of cyclopentanone suffered from product hydrolysis to the corresponding 4-hydroxybutanoic acid. The Baeyer–Villiger oxidation is an important transformation of ketones into esters and particularly for cyclic ketones to lactones. We report here preparation and catalytic activity of layered Sn–silicate catalysts and mesoporous ordered silica catalysts in this reaction. Sn was introduced by using so‐called tin–silica pillaring or by impregnation with a mixture of tetraethylorthosilicate and tin(IV) alkoxide. The prepared catalysts were characterized by XRD, N2 physisorption, SEM, UV/Vis, and inductively coupled plasma optical emission spectroscopy (ICP‐OES) techniques and the catalysts were studied in the Baeyer–Villiger oxidation of cyclopentanone, norcamphor, and 2‐adamantanone with aqueous hydrogen peroxide. Norcamphor and 2‐adamantanone were oxidized easily with selectivity up to 99 %. Sn‐MS and IPC‐1‐SnPI materials exhibited the highest conversions (e.g., norcamphor: Sn‐MS 37 %, IPC‐1‐SnPI 36 % after 8 h vs. Sn‐MCM‐41 22 %). On the other hand, oxidation of cyclopentanone suffered from product hydrolysis to the corresponding 4‐hydroxybutanoic acid. Tin–silica pillaring of a layered zeolite enables the preparation of a tin‐containing catalyst, which combines the advantages of crystalline zeolites and mesoporous molecular sieves. The tin–silica pillared zeolites catalyze the Baeyer–Villiger oxidation of cyclic ketones with aqueous hydrogen peroxide. Abstract The Baeyer–Villiger oxidation is an important transformation of ketones into esters and particularly for cyclic ketones to lactones. We report here preparation and catalytic activity of layered Sn–silicate catalysts and mesoporous ordered silica catalysts in this reaction. Sn was introduced by using so‐called tin–silica pillaring or by impregnation with a mixture of tetraethylorthosilicate and tin(IV) alkoxide. The prepared catalysts were characterized by XRD, N 2 physisorption, SEM, UV/Vis, and inductively coupled plasma optical emission spectroscopy (ICP‐OES) techniques and the catalysts were studied in the Baeyer–Villiger oxidation of cyclopentanone, norcamphor, and 2‐adamantanone with aqueous hydrogen peroxide. Norcamphor and 2‐adamantanone were oxidized easily with selectivity up to 99 %. Sn‐MS and IPC‐1‐SnPI materials exhibited the highest conversions (e.g., norcamphor: Sn‐MS 37 %, IPC‐1‐SnPI 36 % after 8 h vs. Sn‐MCM‐41 22 %). On the other hand, oxidation of cyclopentanone suffered from product hydrolysis to the corresponding 4‐hydroxybutanoic acid. |
Author | Carretero, Marta Arroyo Přech, Jan Čejka, Jiří |
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Snippet | The Baeyer–Villiger oxidation is an important transformation of ketones into esters and particularly for cyclic ketones to lactones. We report here preparation... Abstract The Baeyer–Villiger oxidation is an important transformation of ketones into esters and particularly for cyclic ketones to lactones. We report here... The Baeyer-Villiger oxidation is an important transformation of ketones into esters and particularly for cyclic ketones to lactones. We report here preparation... |
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SubjectTerms | Catalysts Catalytic activity Emission analysis Esters heterogeneous catalysis Hydrogen peroxide Hydrolysis Inductively coupled plasma Ketones Lactones layered zeolite Optical emission spectroscopy Oxidation Plasma Selectivity Silicon dioxide Spectroscopic analysis Tin tin–silicate |
Title | Baeyer–Villiger Oxidation of Cyclic Ketones by Using Tin–Silica Pillared Catalysts |
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