The active sites in the heterogeneous Baeyer-Villiger oxidation of cyclopentanone by hydrotalcite catalysts

Ueno, Shinji; Ebitani, Kohki; Ookubo, Akira; Kaneda, Kiyotomi

doi:10.1016/s0169-4332(97)00334-6

Cited by 47 publications

(34 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…125 The base property of hydrotalcites can be precisely tuned by changing the Mg/Al ratio and the content of interlayer anion species, e.g., CO 3 2À , Cl À , and SO 4 2À (Chart 3, type D). The amount of base sites of the hydrotalcites was measured by the zeta-potential method and calorimetric heat of benzoic acid adsorption.…”

Section: ð27-3þmentioning

confidence: 99%

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Kaneda¹,

Ebitani²,

Mizugaki³

et al. 2006

Bulletin of the Chemical Society of Japan

Self Cite

142

View full text Add to dashboard Cite

This account reviews a novel approach to designing high-performance heterogeneous metal catalysts using hydroxyapatites, montmorillonites, and hydrotalcites as macroligands of active metal species for aerobic alcohol oxidations, carbon-carbon bond formations, and one-pot syntheses. The catalytic systems using the above heterogeneous catalysts offer significant benefits in achieving environmentally friendly organic syntheses aiming towards Green and Sustainable Chemistry. Furthermore, the present preparation method for the immobilization of metal species is strikingly simple and allows a strong protocol for creating various nanostructured and functionalized heterogeneous catalysts.Green and Sustainable Chemistry (GSC) is a revolutionary philosophy that aims to bring about a sustainable society by improvement of the safety and environmental aspects of chemical processes and reduction of the risks of chemical products to people and the environment.1 The emphasis is on eliminating waste at the source-primary pollution prevention-rather than finding incremental end-of-pipe solutions. This concept aims to solve the societal problems of the last century associated with the mass production and consumption of materials, and plays a prime role in providing a venous function in society, encouraging reuse and circulation of resources.One of the powerful solutions in the move toward GSC is the replacement of traditional synthetic methods using harmful stoichiometric reagents that produce vast amounts of waste with cleaner and simple catalytic alternatives with high atom efficiency 1a and low E-factors. 1b Catalytic chemistry, therefore, is of ever-increasing importance because catalysis is a key element in material transformations at atomic and molecular levels, which are an essential realm of chemistry and chemical processes.Our approach to GSC is to develop a highly functionalized heterogeneous metal catalyst based on the unique characteristics of natural layered inorganic materials such as hydroxyapatite, montmorillonite, and hydrotalcite, by using them as macroligands for metal species.2 We consider the above inorganic materials to be advanced nano-scaled catalyst supports allowing for the control of the location of catalytically active metal species, which can be found, for example, on the surface, among the layers, or in the interlayer space. Furthermore, these materials are capable of creating catalytically active metal species responsible for targeted organic transformations involving monomers, chain-like species or giant clusters. The creation of well-defined active metal sites on a solid surface, as characterized by X-ray absorption spectroscopy, not only opens up an avenue to materials that boost catalytic performance, but also aids in the understanding of the molecular basis of heterogeneous catalysis. Another advantage of these catalysts is the possibility of a one-pot synthesis based on a cooperative action by several immobilized active species on the solid surface as multifunctional catalysts. The target react...

show abstract

Section: ð27-3þmentioning

confidence: 99%

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Kaneda¹,

Ebitani²,

Mizugaki³

et al. 2006

Bulletin of the Chemical Society of Japan

Self Cite

142

View full text Add to dashboard Cite

show abstract

“…Thus, Fe-Sn-1:1-850-5 is a suitable catalyst. 4,5). This indicates that the size, shape and the electron cloud distribution have a significant impact on lactone yield.…”

Section: Catalytic Activities Of Fe-sn-o Mixed Oxidesmentioning

confidence: 94%

“…The Baeyer–Villiger (B‐V) oxidation reaction, originating from the 1890s, provides a method for converting ketones to the corresponding lactones or esters, which are important intermediates in the chemical and drug industries [1‐7] . However, traditional oxidants used in B‐V oxidation are generally peroxonitrates which might erode the reaction equipment and pollute the environment [6,8‐10] .…”

Section: Introductionmentioning

confidence: 99%

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

Liang

Feng

Zhang

2015

Applied Organom Chemis

View full text Add to dashboard Cite

Fe-Sn-O mixed oxides were synthesized and used as catalysts for Baeyer-Villiger oxidation of cyclohexanone, which showed both high catalytic activity and selectivity. X-ray powder diffraction and scanning electron microscopy suggested that the Fe-Sn-O catalysts had a tetragonal structure with a grain size of 29.3 nm. An ε-caprolactone yield as high as 98.8% was obtained in a small-scale experiment (5 mmol of cyclohexanone). In a scale-up test (20 mmol of cyclohexanone), the cyclohexanone conversion and ε-caprolactone yield were 96.7 and 96.5%, respectively. In addition, the catalysts can be reused five times without any major decline in catalytic activity.

show abstract

“…These derivatives can also deactivate the ribonucleotide reductase in tumor cells inhibiting their growth and have been employed for melanoma treatment and applied in AIDS therapy [1][2][3][4][5][6][7]. The oxidation of cyclic and linear ketones to their respective lactones and esters, using oxidants such as organic peroxides or peroxyoxides, alkyl hydroperoxides or hydrogen peroxide, are very important industrial intermediates finding application in polymers, pharmaceuticals and herbicides production and as solvents [8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Study of Selectivity of Metal Phosphates and Phosphonates in Baeyer–Villiger Oxidations

2010

View full text Add to dashboard Cite

Layered materials including metal phosphates and phosphonates have been widely investigated in several fields acting as good selective catalysts in a great number of oxidative reactions. Zirconium phosphate amorphous [Zr(HPO 4 ) 2 ÁH 2 O; ZrPA], sodium exchanged zirconium phosphate amorphous [Zr(NaPO 4 ) 2 ; NaZrPA], potassium exchanged zirconium phosphate amorphous [Zr(KPO 4 ) 2 ; KZrPA], zirconium phenylphosphonate amorphous [Zr(O 3 PC 6 H 5 ) 2 ; ZrPPA], zirconium carboxyethylphosphonate [Zr(O 3 PCH 2 CH 2 COOH) 2 ; ZrCEP] and aluminium carboxyethylphosphonate [Al 3 (OH) 3 (O 3 PCH 2 CH 2 CO 2 ) 2 Á 3H 2 O; AlCEP] were prepared, characterized and evaluated as selective catalysts in the Baeyer-Villiger oxidation of cyclopentanone, p-methoxybenzaldehyde and 2,4,6-trimethylbenzaldehyde by hydrogen peroxide, in acetic acid. The selectivity of d-valerolactone, p-methoxyphenol and 2,4,6-trimethylphenol have been found to be strongly related with the properties and structure of each catalyst.

show abstract

The active sites in the heterogeneous Baeyer-Villiger oxidation of cyclopentanone by hydrotalcite catalysts

Cited by 47 publications

References 23 publications

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

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

Study of Selectivity of Metal Phosphates and Phosphonates in Baeyer–Villiger Oxidations

Contact Info

Product

Resources

About