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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Bibliographic Details
Published inChemCatChem Vol. 9; no. 15; pp. 3063 - 3072
Main Authors Přech, Jan, Carretero, Marta Arroyo, Čejka, Jiří
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 09.08.2017
Subjects
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
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Summary: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.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201700162