Epoxidation of alkenes with hydrogen peroxide catalyzed by ReO4–SiO2·Al2O3 and ReO4–Al2O3

Mandelli, Dalmo; Vliet, Michiel C. A. van; Arnold, Ulrich; Sheldon, Roger A.; Schuchardt, Ulf

doi:10.1016/s1381-1169(00)00521-5

Cited by 45 publications

(27 citation statements)

References 28 publications

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“…36 Although the epoxidation activity of alumina was already known, 37 in our experimental conditions (neutral alumina, 24 wt.% H 2 O 2 in ethyl acetate, reflux temperature) it was much higher. 38 Thus, reasonable epoxide yields were obtained for several alkenes ranging from unreactive terminal alkenes (1-octene: 2.6 g of epoxide per g of alumina) to the highly reactive terpenes (α-pinene oxide: 3.4 g of epoxide per g of alumina).…”

Section: Alumina Catalystsmentioning

confidence: 63%

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Heterogenization of alkene epoxidation catalysts

Buffon¹,

Schuchardt²

2003

J. Braz. Chem. Soc.

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Este trabalho descreve nosso esforço em heterogeneizar catalisadores para epoxidação. Tanto o molibdênio ancorado quanto o engaiolado pelo método de sol-gel mostraram grande seletividade, mas possuem suas atividades fortemente reduzidas. Por outro lado, silicatos de molibdênio foram muito ativos e estáveis até a formação de diols na mistura reacional. Catalisadores heterogeneizados de rênio foram menos ativos, mas permitiram o uso do peróxido de hidrogênio anidro como oxidante. Contudo, o alto custo e a dificuldade de regeneração impedem a aplicação industrial destes catalisadores. Durante estas investigações, descobrimos que a alumina sozinha é ativa para epoxidação com peróxido de hidrogênio anidro, fornecendo boas conversões para epóxidos com alta seletividade. Mais pesquisa é necessária para esclarecer a natureza dos grupos hidroxilas responsáveis pela atividade catalítica, para produzir materiais que permitem a obtenção de epóxidos com alta seletividade em condições industriais.This account describes our efforts to heterogenize epoxidation catalysts. Anchored and sol-gel entrapped molybdenum were shown to be very selective, but had a strongly reduced activity. On the other hand, molybdenum silicates were very active and stable as long as no diols were present in the reaction mixture. Heterogenized rhenium catalysts were less active but allowed the use of anhydrous hydrogen peroxide as oxidant. However, the high cost and difficult regeneration prevents the industrial use of these catalysts. During these investigations, we found that alumina alone is active in the epoxidation with anhydrous hydrogen peroxide, giving good conversions to epoxides with high selectivity. More research is needed in order to clarify the nature of the hydroxyl groups responsible for its catalytic activity and thus to produce an appropriate material which would allow the obtention of epoxides with high selectivity under industrial conditions.

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Section: Alumina Catalystsmentioning

confidence: 63%

“…36 could be used at least in three consecutive runs without any change in the catalytic activity. In each of the three runs, a 65% conversion (TON = 325) was reached after 5 h at 90 o C. The only product, however, was cyclohexanediol.…”

Section: Rhenium Oxide Supported On Aluminamentioning

confidence: 99%

Heterogenization of alkene epoxidation catalysts

Buffon¹,

Schuchardt²

2003

J. Braz. Chem. Soc.

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“…This catalyst is particularly useful in oxidation chemistry and shows high activity for epoxidations, C-H and Si-H oxidations but it can also be applied in other types of catalytic reactions such as olefin metathesis and aldehyde olefinations [24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Rhenium Nanochemistry for Catalyst Preparation

Kessler

Seisenbaeva

2012

Minerals

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Abstract:The review presents synthetic approaches to modern rhenium-based catalysts. Creation of an active center is considered as a process of obtaining a nanoparticle or a molecule, immobilized within a matrix of the substrate. Selective chemical routes to preparation of particles of rhenium alloys, rhenium oxides and the molecules of alkyltrioxorhenium, and their insertion into porous structure of zeolites, ordered mesoporous MCM matrices, anodic mesoporous alumina, and porous transition metal oxides are considered. Structure-property relationships are traced for these catalysts in relation to such processes as alkylation and isomerization, olefin metathesis, selective oxidation of olefins, methanol to formaldehyde conversion, etc.

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“…217 Very high selectivity toward cyclohex-2- Scheme 24. Proposed mechanism for the formation of three main products (47)(48)(49), after the bromonium ion is formed by action of catalytically generated HOBr on styrene.…”

Section: -95%mentioning

confidence: 99%

Synthetic utility of metal catalyzed hydrogen peroxide oxidation of C-H, C-C and C=C bonds in alkanes, arenes and alkenes: Recent advances

Wójtowicz‐Młochowska¹

2016

Arkivoc

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This review presents the current state of the art of homogenic and heterogenic oxygen transfer processes using hydrogen peroxide as oxygen source and compounds and complexes of tranisition metals, Fe, V, Cu, Mn, Rh, Mo, Ti, W, Pd, Os, Zr, Cr, Nb, Co, as the catalysts. Based on the reactions of C-H, C-C and C=C bonds in alkanes, arenes and alkenes various mechanisms of the oxygen-transfer processes are discussed and new methodologies for synthesis of alcohols, phenols, aldehydes, ketones, epoxides and carboxylic acids are indicated.

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Epoxidation of alkenes with hydrogen peroxide catalyzed by ReO4–SiO2·Al2O3 and ReO4–Al2O3

Cited by 45 publications

References 28 publications

Heterogenization of alkene epoxidation catalysts

Heterogenization of alkene epoxidation catalysts

Rhenium Nanochemistry for Catalyst Preparation

Synthetic utility of metal catalyzed hydrogen peroxide oxidation of C-H, C-C and C=C bonds in alkanes, arenes and alkenes: Recent advances

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