Vapor phase hydrogen transfer reaction between methacrolein and ethanol over MgO based catalysts

Ueshima, Michio; Shimasaki, Yuuji

doi:10.1007/bf00769165

Cited by 14 publications

(4 citation statements)

References 5 publications

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“…After a complete conversion of myrcene, products 5-7 also begin to be further hydrogenated producing 3, with their reactivity towards hydrogenation decreasing from 5 > 6 > 7. As the concentration of 3 increases, it reacts further to produce a fully hydrogenated product (2). A similar behavior is observed when the reaction is carried out using [IrCl(CO)(PPh 3 ) 2 ] (Vaskas's catalyst).…”

Section: Resultssupporting

confidence: 64%

“…The following compounds were prepared by literature methods [RuCl 2 (CO) 2 6 ] was purchased from Strem Chemicals. Myrcene (Aldrich) was distilled before use.…”

Section: Methodsmentioning

confidence: 99%

“…Hydrogenation of organic substrates is an important step in the preparation of various fine chemicals [1][2][3][4][5][6][7]. Particularly, selective hydrogenation of naturally occurring monoterpenes represents a promising route to produce compounds that could be further functionalized to oxygenated derivatives, which are commercially important in the pharmaceutical, perfume and flavor industries as well as useful synthetic intermediates and chiral building blocks [8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Selective hydrogenation of myrcene catalyzed by complexes of ruthenium, chromium, iridium and rhodium

Speziali

Moura

Robles-Dutenhefner

et al. 2005

Journal of Molecular Catalysis A: Chemical

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Section: Resultssupporting

confidence: 64%

“…The following compounds were prepared by literature methods [RuCl 2 (CO) 2 6 ] was purchased from Strem Chemicals. Myrcene (Aldrich) was distilled before use.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Selective hydrogenation of myrcene catalyzed by complexes of ruthenium, chromium, iridium and rhodium

Speziali

Moura

Robles-Dutenhefner

et al. 2005

Journal of Molecular Catalysis A: Chemical

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“…By modifying the basicity of MgO with other oxides such as silica, titania, boron oxide and potassium oxide, the selectivity to carbonyl reduction can be improved [32,33]. An effective catalyst was prepared by adding SiO 2 and K 2 O to magnesium oxide so that only weak acid and basic properties were present.…”

Section: Basic Compoundsmentioning

confidence: 99%

Meerwein-Ponndorf-Verley Reduction over Heterogeneous Catalysts

Chuah¹,

Jaenicke

Zhu³

et al. 2006

COC

122

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The Meerwein-Ponndorf-Verley (MPV) transfer hydrogenation of aldehydes and ketones to the corresponding alcohols is distinguished by its exceptional chemoselectivity. This reaction is particularly suited for the reduction of unsaturated aldehydes and ketones, compared to catalytic reductions with molecular hydrogen using noble metal catalysts. The MPV reaction has traditionally been carried out using homogeneous catalysts like aluminium or titanium alkoxides. However, over the past two decades, an increasing number of reports on heterogeneous catalysts for the MPV reaction have been published. This interest is stimulated by the advantages of heterogeneous over homogeneous catalysis, particularly for larger-scale applications. The article provides a critical review of the recent literature on heterogeneous catalysts for the MPV reaction. The materials include hydrotalcites, metal oxides such as magnesium oxide, zirconia, silica and alumina, alkoxides of Al, La, Zr and Hf grafted to high surface area mesoporous materials, and zeolites. In particular, zeolite beta has been found to be a highly stereoselective catalyst in the MPV reduction of 4-tertbutylcyclohexanone, giving predominantly cis-4-tert-butylcyclohexanol rather than the thermodynamically stable transalcohol. The activity was improved with the incorporation of other metals such as Ti, Sn and Zr. These materials show good tolerance to moisture, lack of leaching and ease of regeneration, thus making them useful catalysts in MPV reduction. The activity of a catalyst depends on its ligand exchange capability with the reductant with a high ligand exchange rate enabling the use of catalytic amounts.

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A Strategy for the Simultaneous Synthesis of Methallyl Alcohol and Diethyl Acetal with Sn‐β

Wei

Zhu

et al. 2017

ChemSusChem

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A new strategy was developed to simultaneously produce two important chemicals, namely, methallyl alcohol (Mol) and diethyl acetal (Dal) from methacrolein in ethanol solvent at low temperature with the use of Beta zeolites modified by tin (Sn-β catalysts). All the Sn-β catalysts were prepared by the solid-state ion-exchange method, wherein the calcination step was conducted under different gas atmospheres. The catalyst precalcined in Ar (Sn-β-Ar) had a reduced number of extra-framework Sn species and enabled more Sn species to be exchanged into the framework as isolated tetrahedral Sn , enhancing the catalytic activity of the Meerwein-Ponndorf-Verley (MPV) reaction. The sodium-exchanged Sn-β-Ar, with a reduced number of weak Brønsted acid sites, led to an even better selectivity for Mol, owing to the restriction of the side reactions such as acetalization, addition, and etherification. Under optimized catalyst and reaction conditions, the yield of Mol and Dal reached approximately 90 % and 96 %, respectively. The possible reaction pathways, along with a complex network of side products, was proposed after a detailed investigation through the use of different substrates as reactants. The fine-tuning of Sn-β catalysts through different treatments discussed in this work is of great significance toward the understanding and manipulation of complex reactions between α,β-unsaturated aldehydes and primary alcohols.

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Vapor phase hydrogen transfer reaction between methacrolein and ethanol over MgO based catalysts

Cited by 14 publications

References 5 publications

Selective hydrogenation of myrcene catalyzed by complexes of ruthenium, chromium, iridium and rhodium

Selective hydrogenation of myrcene catalyzed by complexes of ruthenium, chromium, iridium and rhodium

Meerwein-Ponndorf-Verley Reduction over Heterogeneous Catalysts

A Strategy for the Simultaneous Synthesis of Methallyl Alcohol and Diethyl Acetal with Sn‐β

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