Selective hydrogen peroxide oxidation of sulfides to sulfoxides or sulfones with MWW-type titanosilicate zeolite catalyst under organic solvent-free conditions

Kon, Yoshihiro; Yokoi, Toshiyuki; Yoshioka, Masato; Tanaka, Shinji; Uesaka, Yumiko; Mochizuki, Takehisa; Satō, Kazuhiko; Tatsumi, Takashi

doi:10.1016/j.tet.2014.07.091

Cited by 44 publications

(22 citation statements)

References 78 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The lower diffusion restrictions, the higher sulphoxide selectivity was observed. The assumption of the diffusion driven selectivity is also in accordance with the data reported by Corma et al 23 and Kon et al 25 on MPS oxidation. The TS-1-PITi stands again out of the trend (S = 85%).…”

Section: Page 10 Of 33 Catalysis Science and Technologysupporting

confidence: 90%

Selective oxidation of bulky organic sulphides over layered titanosilicate catalysts

Přech

Morris

Čejka

2016

Catal. Sci. Technol.

View full text Add to dashboard Cite

Section: Page 10 Of 33 Catalysis Science and Technologysupporting

confidence: 90%

Selective oxidation of bulky organic sulphides over layered titanosilicate catalysts

Přech

Morris

Čejka

2016

Catal. Sci. Technol.

View full text Add to dashboard Cite

“…All catalysts reach complete conversion within 6 h, with Nb‐SiO 2 and Ti‐SiO 2 converting all thioanisole within 30 min of reaction (Figure ). Nb‐SiO 2 and Ti‐SiO 2 also have similarly high selectivities towards the sulfoxide intermediate, with maximum values of about 80 % observed at short reaction times (Table ), consistent with prior reports by others for similar catalysts –. In contrast, Zr‐SiO 2 notably facilitates almost exclusive formation of the methyl phenyl sulfone overoxidation product; few reports exist in the literature for silica‐supported zirconium(IV) catalysts for sulfoxidation, but similarly poor (<20 %) sulfoxide selectivities have been noted by others under similar conditions in acetonitrile .…”

Section: Resultsmentioning

confidence: 99%

Rate and Selectivity Control in Thioether and Alkene Oxidation with H₂O₂ over Phosphonate‐Modified Niobium(V)–Silica Catalysts

Thornburg

Notestein

2017

ChemCatChem

View full text Add to dashboard Cite

Supported metal oxide catalysts are versatile materials for liquid‐phase oxidations, including alkene epoxidation and thioether sulfoxidation with H2O2. Periodic trends in H2O2 activation was recently demonstrated for alkene epoxidation, highlighting Nb‐SiO2 as a more active and selective catalyst than Ti‐SiO2. Three representative catalysts are studied consisting of NbV, TiIV, and ZrIV on silica, each made through a molecular precursor approach that yields highly dispersed oxide sites, for thioanisole oxidation by H2O2. Initial rates trend Nb>Ti≫Zr, as for epoxidation, and Nb outperforms Ti for a number of other thioethers. In contrast, selectivity to sulfoxide vs. sulfone trends Ti>Nb≫Zr at all conversions. Modifying the Nb‐SiO2 catalyst with phenylphosphonic acid does not completely remove sulfoxidation reactivity, as it did for photooxidation and epoxidation, and results in an unusual material active for sulfoxidation but neither epoxidation nor overoxidation to the sulfone.

show abstract

“…H2O2 Oxidation of Sulfides Sulfoxides and sulfones are useful intermediates for various pharmaceuticals such as antifungal medications 16) . Numerous methods are available for the oxidation of sulfides using aqueous H2O2 as an oxidant 17) .…”

Section: Recyclable Titanosilicate Zeolite Catalyst Formentioning

confidence: 99%

Metal-catalyzed Hydrogen Peroxide Oxidation for Synthesis of Value-added Chemicals

Kon

2017

J. Jpn. Petrol. Inst.

Self Cite

View full text Add to dashboard Cite

Hydrogen peroxide is an ideal oxidant for industrial processes that produce useful chemicals such as propylene oxide, oxime and catechol because this environmentally benign oxidant has excellent oxygen atom efficiency and low cost. However, hydrogen peroxide is a weak oxidant with low selectivity, so application of hydrogen peroxide oxidation technology to the synthesis of complex organic compounds containing various functional groups remains challenging. We have found that various methods of hydrogen peroxide oxidation of olefins can be used to synthesize a wide range of fine chemicals. Here we report our recent investigations of a practical synthetic method that uses common metals and reusable catalysts to expand our previous catalytic system using tungstenbased catalysts using three components. For example, our new method employs high-speed styrene oxide synthesis using an iron picolinate catalyst, bulky sulfide oxidation employing a reusable titanosilicate zeolite catalyst, and high-conversion synthesis of nitroxide radical polymer. The desired compounds are formed in over 90 % selectivity despite their complex structures, under safe reaction conditions and with the high efficiency of hydrogen peroxide.

show abstract

Selective hydrogen peroxide oxidation of sulfides to sulfoxides or sulfones with MWW-type titanosilicate zeolite catalyst under organic solvent-free conditions

Cited by 44 publications

References 78 publications

Selective oxidation of bulky organic sulphides over layered titanosilicate catalysts

Selective oxidation of bulky organic sulphides over layered titanosilicate catalysts

Rate and Selectivity Control in Thioether and Alkene Oxidation with H₂O₂ over Phosphonate‐Modified Niobium(V)–Silica Catalysts

Metal-catalyzed Hydrogen Peroxide Oxidation for Synthesis of Value-added Chemicals

Contact Info

Product

Resources

About

Selective hydrogen peroxide oxidation of sulfides to sulfoxides or sulfones with MWW-type titanosilicate zeolite catalyst under organic solvent-free conditions

Cited by 44 publications

References 78 publications

Selective oxidation of bulky organic sulphides over layered titanosilicate catalysts

Selective oxidation of bulky organic sulphides over layered titanosilicate catalysts

Rate and Selectivity Control in Thioether and Alkene Oxidation with H2O2 over Phosphonate‐Modified Niobium(V)–Silica Catalysts

Metal-catalyzed Hydrogen Peroxide Oxidation for Synthesis of Value-added Chemicals

Contact Info

Product

Resources

About

Rate and Selectivity Control in Thioether and Alkene Oxidation with H₂O₂ over Phosphonate‐Modified Niobium(V)–Silica Catalysts