Highly selective mono-epoxidation of dicyclopentadiene with aqueous H2O2 over heterogeneous peroxo-phosphotungstic catalysts

Shen, Yun; Lu, Xinhuan; Cai, Wei; Ma, Xuetao; Peng, Cong; He, Jie; Zhou, Dan; Xia, Qinghua

doi:10.1016/j.mcat.2016.12.012

Cited by 18 publications

(12 citation statements)

References 46 publications

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“…In a very similar approach the same group used a polystyrene-bound peroxophosphotungstic acid as a catalyst for the epoxidation of various dienes with H 2 O 2 [ 131 ]. The best results were obtained with dicyclopentadiene where the monoepoxide was obtained in nearly quantitative yield.…”

Section: Synthetic Applications In Heterogeneous Systemsmentioning

confidence: 99%

Organic Synthesis Using Environmentally Benign Acid Catalysis

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2019

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Recent advances in the application of environmentally benign acid catalysts in organic synthesis are reviewed. The work includes three main parts; (i) description of environmentally benign acid catalysts, (ii) synthesis with heterogeneous and (iii) homogeneous catalysts. The first part provides a brief overview of acid catalysts, both solid acids (metal oxides, zeolites, clays, ion-exchange resins, metal-organic framework based catalysts) and those that are soluble in green solvents (water, alcohols) and at the same time could be regenerated after reactions (metal triflates, heteropoly acids, acidic organocatalysts etc.). The synthesis sections review a broad array of the most common and practical reactions such as Friedel-Crafts and related reactions (acylation, alkylations, hydroxyalkylations, halogenations, nitrations etc.), multicomponent reactions, rearrangements and ring transformations (cyclizations, ring opening). Both the heterogeneous and homogeneous catalytic synthesis parts include an overview of asymmetric acid catalysis with chiral Lewis and Brønsted acids. Although a broad array of catalytic processes are discussed, emphasis is placed on applications with commercially available catalysts as well as those of sustainable nature; thus individual examples are critically reviewed regarding their contribution to sustainable synthesis.

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Section: Synthetic Applications In Heterogeneous Systemsmentioning

confidence: 99%

Organic Synthesis Using Environmentally Benign Acid Catalysis

Kokel

Schäfer

Török

2019

COS

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“…Due to these evident advantages, PW 4 has received significant attention as an active component for construction of heterogeneous epoxidation catalysts (Neumann and Miller, 1995;Neumann and Cohen, 1997;Hoegaerts et al, 2000;Sakamoto and Pac, 2000;Sels et al, 2000;Kovalchuk et al, 2007;Sofia et al, 2009;Maksimchuk et al, 2010;Leng et al, 2011;Doherty et al, 2012;Swalus et al, 2013;Nojima et al, 2015;Peng et al, 2016;Masteri-Farahani and Modarres, 2017;Shen et al, 2017;You et al, 2018). Silica modified by various cationic functional groups was widely used as support for immobilization of PW 4 (Neumann and Miller, 1995;Neumann and Cohen, 1997;Hoegaerts et al, 2000;Sakamoto and Pac, 2000;Kovalchuk et al, 2007;Sofia et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

“…Some of the SiO 2 -supported catalysts were prone to leaching and/or had a poor recyclability Kovalchuk et al, 2007) (sometimes information about reusability was not provided Neumann and Miller, 1995;Sakamoto and Pac, 2000). Several catalysts based on ion-exchange organic polymers and PW 4 have been developed Doherty et al, 2012;Swalus et al, 2013;Peng et al, 2016;Shen et al, 2017;You et al, 2018). In general, catalysts PW 4 /polymer showed high selectivity for epoxides and most of them could be recycled without a decrease in attainable conversion and selectivity Swalus et al, 2013;Peng et al, 2016;Shen et al, 2017;You et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

“…Several catalysts based on ion-exchange organic polymers and PW 4 have been developed Doherty et al, 2012;Swalus et al, 2013;Peng et al, 2016;Shen et al, 2017;You et al, 2018). In general, catalysts PW 4 /polymer showed high selectivity for epoxides and most of them could be recycled without a decrease in attainable conversion and selectivity Swalus et al, 2013;Peng et al, 2016;Shen et al, 2017;You et al, 2018). However, their stability in terms of activity (retention of the reaction rate during the recycling) was not often addressed Peng et al, 2016;Shen et al, 2017;You et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

“…In general, catalysts PW 4 /polymer showed high selectivity for epoxides and most of them could be recycled without a decrease in attainable conversion and selectivity Swalus et al, 2013;Peng et al, 2016;Shen et al, 2017;You et al, 2018). However, their stability in terms of activity (retention of the reaction rate during the recycling) was not often addressed Peng et al, 2016;Shen et al, 2017;You et al, 2018). PW 4 and PW 12 incorporated into the cages of the metal-organic framework MIL-101(Cr) demonstrated fairly good catalytic activity, selectivity, and recyclability .…”

Section: Introductionmentioning

confidence: 99%

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Carbon Nanotubes Modified by Venturello Complex as Highly Efficient Catalysts for Alkene and Thioethers Oxidation With Hydrogen Peroxide

et al. 2019

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In this work, we elaborated heterogeneous catalysts on the basis of the Venturello complex [PO 4 {WO(O 2 ) 2 } 4 ] 3− (PW 4 ) and nitrogen-free or nitrogen-doped carbon nanotubes (CNTs or N-CNTs) for epoxidation of alkenes and sulfoxidation of thioethers with aqueous hydrogen peroxide. Catalysts PW 4 /CNTs and PW 4 /N-CNTs (1.8 at. % N) containing 5-15 wt. % of PW 4 and differing in acidity have been prepared and characterized by elemental analysis, N 2 adsorption, IR spectroscopy, HR-TEM, and HAADF-STEM. Studies by STEM in HAADF mode revealed a quasi-molecular dispersion of PW 4 on the surface of CNTs. The addition of acid during the immobilization is not obligatory to ensure site isolation and strong binding of PW 4 on the surface of CNTs, but it allows one to increase the PW 4 loading and affects both catalytic activity and product selectivity. Catalytic performance of the supported PW 4 catalysts was evaluated in H 2 O 2 -based oxidation of two model substrates, cyclooctene and methyl phenyl sulfide, under mild conditions (25-50 • C). The best results in terms of activity and selectivity were obtained using PW 4 immobilized on N-free CNTs in acetonitrile or dimethyl carbonate as solvents. Catalysts PW 4 /CNTs can be applied for selective oxidation of a wide range of alkenes and thioethers provided a balance between activity and selectivity of the catalyst is tuned by a careful control of the amount of acid added during the immobilization of PW 4 . Selectivity, conversion, and turnover frequencies achieved in epoxidations over PW 4 /CNTs catalysts are close to those reported in the literature for homogeneous systems based on PW 4 . IR spectroscopy confirmed the retention of the Venturello structure after use in the catalytic reactions. The elaborated catalysts are stable to metal leaching, show a truly heterogeneous nature of the catalysis, can be easily recovered by filtration, regenerated by washing and evacuation, and then reused several times without loss of the catalytic performance.

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