Baeyer–Villiger oxidation of cyclohexanone by molecular oxygen with Fe–Sn–O mixed oxides as catalysts

Liang, Zhengyong; Feng, Shuxiao; Zhang, Yadong

doi:10.1002/aoc.3314

Cited by 22 publications

(5 citation statements)

References 28 publications

(37 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Besides bimetal oxides, ternary metal oxides, such as Mg/Sn/W mixed oxides prepared via co-precipitation were found to be capable of providing the highest yield of ε-caprolactone when using a mixture of 50% hydrogen peroxide and acetic acid as co-oxidant [129]. For the same BV oxidation of cyclohexanone, Fe-Sn-O ternary metal oxide catalyst with a tetragonal structure showed a ε-caprolactone yield as high as 98.8%, and without any major decline in catalytic activity even cycled for five times [130]. Reaction conditions: 2-adamantanone 0.1 mmol, catalyst 6 mg, 30% H2O2 2.0 eq., 1,2-dichloroethane 3 mL, 10 h, 75°C.…”

Section: Mo-sno2 Metal Oxide Nanocomposite Catalystsmentioning

confidence: 99%

Sn-based catalysts for Baeyer-Villiger oxidations by using hydrogen peroxide as oxidant

Cui

Shi

2016

Sci. China Mater.

View full text Add to dashboard Cite

Baeyer-Villiger (BV) oxidation is one of the most important transformation reactions in synthetic organic chemistry. Catalytic versions of the BV oxidation are particularly attractive in practical applications, because the catalytic transformation substantially simplifies reaction process while minimizing reactant consumption as well as waste production. Further benefits are expected from replacing peracids, the traditionally used oxidant, by low cost and environmentally friendly hydrogen peroxide (H2O2). This review will first introduce very briefly the features of BV oxidation reactions, and the corresponding oxidants traditionally used. Afterwards, the emphasis will be placed on the specific Sn-based catalysts, their performance comparison for the BV oxidation reaction by using H2O2 as oxidant, and the catalytic mechanisms of most Sn-based catalysts reported so far, including homogeneous Sn-based catalysts (such as Sn-based fluorous biphase system catalysts), heterogeneous Sn-based catalysts (such as Sn-based zeolite catalysts, Sn-based mesoporous composites, Sn-incorporated clay catalysts, Sn-based metal oxide composites and polymer supported Sn catalysts). Finally, the Sn-based catalysts for BV oxidation are outlooked for their potentials and perspectives in enhancing the performance and then accelerating the practical applications of BV oxidations by using H2O2. The developing direction of the Sn-based catalytic BV reaction is also illustrated.

show abstract

Section: Mo-sno2 Metal Oxide Nanocomposite Catalystsmentioning

confidence: 99%

Sn-based catalysts for Baeyer-Villiger oxidations by using hydrogen peroxide as oxidant

Cui

Shi

2016

Sci. China Mater.

View full text Add to dashboard Cite

show abstract

“…Among them, Sn-based materials have been widely studied because of its Lewis acid, which can activate the carbonyl group of cyclohexanone and is more favorable to the cyclohexanone conversion. [14][15][16] In our previous report, it has been demonstrated that Sn-TiO 2 catalyst has good catalytic performance in the oxygen/aldehyde method. [17,18] It was surprised to find that SnÀ Ti submicrosphere catalysts by using hexadecylamine (HDA) as the structure directing agent and polyvinylpyrrolidone (PVP) as the stabilizer and dispersant exhibit better catalytic performance than SnÀ Ti bulk particle due to their short pore channels, which were conducive to mass transfer of substrates.…”

Section: Introductionmentioning

confidence: 96%

“…[6,7] Oxygen, as a green, safe and cheap oxidant, is a very promising substitution for the ε-caprolactone preparation by co-oxidation in the presence of aldehydes. [8][9][10][11][12] Up to now, catalysts used for oxygen/aldehyde oxidation mainly include Fe-based, [8] Cubased, [13] and Sn-based materials, [14] etc. Among them, Sn-based materials have been widely studied because of its Lewis acid, which can activate the carbonyl group of cyclohexanone and is more favorable to the cyclohexanone conversion.…”

Section: Introductionmentioning

confidence: 99%

Sn‐Ti Submicrospheres with Tunable Particle Size for Cyclohexanone Baeyer‐Villiger Oxidation

Zhou

Sun

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

Sn-Ti submicrospheres with tunable particle size were successfully synthesized by adjusting the water amount over Polyvinylpyrrolidone(PVP)-assisted sol-gel method in this paper, and the effect of the submicrosphere size on the catalytic performance in the B-V oxidation of cyclohexanone by molecular oxygen was also investigated. Their physical and chemical properties were character-rized by Scanning electron microscope (SEM), X-ray diffraction (XRD), N 2 sorption, Pyridineadsorbed IR(Py-IR), Uvioletvisible diffuse reflection spectroscopy(UV-vis), X-ray photoelectron spectra (XPS), Transmission electron microscope and Energy dispersive X-ray detector(TEM-EDX) techniques. The characterization results showed that the Sn-Ti crystal phase would be affected by the initial water amount resulting in the variation for the incorporation of tin species into the tetrahedral TiO 2 . The regular Sn-Ti submicrospheres with particle size about 210 � 5 nm and typical Lewis acidities for MTS-W-4.0 sample can be obtained when water amount was as high as 4.0 mL, and it exhibited higher catalytic performance than other catalysts where its εcaprolactone yield was 97.8 %. Compared to the decline range of 13.6 % with the submicrospheres particle size as about 450 nm, the drop of ε-caprolactone yield was only 3.9 % and the yield of ε-caprolactone can be kept at 93.9 % over MTS-W-4.0 sample after repeated use for 5 times.

show abstract

“…[19][20][21] Catalysts based on tin were introduced by Corma et al as a novel way of addressing the selectivity problem where the ketone substrate is oxidized by activating the carbonyl group instead of activating hydrogen peroxide using Sn/zeolite heterogeneous catalyst. 22 Since then, several heterogeneous catalysts of tin-based zeolites, 23,24 silica, [25][26][27] metal oxides, 28,29 and polymer supported, 30,31 have been studied for the BV oxidation. In contrast, the utilization of tin complexes in a homogeneous catalytic BV oxidation is limited to few examples.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and structural characterization of diorganotin(IV) complexes with a tridentate N‐heterocyclic podand ligand and investigation of their catalytic activity in Baeyer–Villiger oxidation of cyclic ketones to lactones

Basu Baul,

Khatiwara,

Addepalli

et al. 2023

Applied Organom Chemis

View full text Add to dashboard Cite

Diorganotin(IV) complexes of composition [Me2SnL] (1), [n‐Bu2SnL] (2), and [Bz2SnL] (3) were synthesized by reacting the N2,N6‐di(pyridin‐2‐yl)pyridine‐2,6‐dicarboxamide pro‐ligand (H2L, where H2 denotes the two acidic protons) with Me2SnO, n‐Bu2SnO, and Bz2SnO, respectively, in refluxing toluene. The amide ligand leads to highly stable diorganotin(IV) complexes via the dianionic tridentate donor set (Npy, N−, N−) with pendent pyridine arms, and the coordination domain is completed by the respective two alkyl ligands. Solution‐state structures of the compounds 1–3 were studied by 1H, 13C, and 119Sn nuclear magnetic resonance (NMR) spectroscopy, revealing that the complexes adopt a five‐coordinate structure in non‐coordinating solvent. Additionally, homogenity and purity of the bulk materials of 1–3 were judged using the high‐resolution mass spectrometry in acetonitrile solution. The molecular and crystal structures of 1·0.5C6H6, 2, and 3 in the solid phase were established by single‐crystal X‐ray diffraction analysis. For all three compounds, the core defined by the rigid tridentate pyridine dicarboxamide ligand and the Sn‐coordinating C atoms adopts nearly C2v symmetry and thus matches none of the most popular geometries for five‐coordinated species, namely square‐pyramidal or trigonal‐bipyramidal coordination. Thermogravimetric analysis (TGA) was performed to probe the thermal stabilities of 1–3. The results serve as a basis for designing highly efficient diorganotin(IV) mimics for catalytic applications. Catalytic studies of ε‐caprolactone formation via Baeyer–Villiger oxidation of cyclohexanone with aqueous H2O2 were performed under microwave (MW) irradiation. The consequences of several reaction parameters like catalyst quantity, time, temperature, and solvent were studied.

show abstract

Baeyer–Villiger oxidation of cyclohexanone by molecular oxygen with Fe–Sn–O mixed oxides as catalysts

Cited by 22 publications

References 28 publications

Sn-based catalysts for Baeyer-Villiger oxidations by using hydrogen peroxide as oxidant

Sn-based catalysts for Baeyer-Villiger oxidations by using hydrogen peroxide as oxidant

Sn‐Ti Submicrospheres with Tunable Particle Size for Cyclohexanone Baeyer‐Villiger Oxidation

Synthesis and structural characterization of diorganotin(IV) complexes with a tridentate N‐heterocyclic podand ligand and investigation of their catalytic activity in Baeyer–Villiger oxidation of cyclic ketones to lactones

Contact Info

Product

Resources

About