Supported liquid-phase catalysts containing ruthenium complexes for selective hydrogenation of $alpha;,$beta;-unsaturated aldehyde: importance of interfaces between liquid film, solvent, and support for the control of product selectivity

Fujita, Shin‐ichiro

doi:10.1016/j.jcat.2004.03.037

Cited by 43 publications

(12 citation statements)

References 36 publications

(57 reference statements)

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“…This water favoured the citral adsorption throughout the C=O bond due to its more polarized bond character. In a similar way, with SLPC (supported liquid-phase catalyst) the selectivity towards the unsaturated alcohols can be modified adding water (or another polar solvent) to an organic media [67,68]. The drawback of this type of methodology is that the entire surface should be covered by water in order to maintain the desired selectivity [67].…”

Section: Hydrogenation Selectivitymentioning

confidence: 99%

Catalysts Supported on Carbon Materials for the Selective Hydrogenation of Citral

et al. 2013

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The heterogeneously catalyzed selective-hydrogenation of citral is one of the more feasible ways for obtaining its appreciated unsaturated-alcohols, nerol and geraniol, which are present in over 250 essential oils. Thus, citral has very recently come to be produced petro-chemically in very large quantities, and so partial hydrogenation of citral has become a very economical route for the production of these compounds. However, the selective hydrogenation of citral is not easy, because citral is an α,β-unsaturated aldehyde which possesses three double bonds that can be hydrogenated: an isolated C=C bond and the conjugated C=O and C=C bonds. For this reason, in catalyst selection there are several important issues which affect the product selectivity, for example, the active metal and metal particle size which are factors related to the catalyst preparation method, catalyst precursor, or support surface area, as well as other factors such as porosity, the addition of a second catalytic metal, and, of course, the type of catalyst support. About this last one, carbon materials are very interesting supports for this type of hydrogenation reaction due to their unique chemical and textural properties. This review collects and analyzes the results obtained in the selective hydrogenation of citral catalyzed by carbon material supported metals

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Section: Hydrogenation Selectivitymentioning

confidence: 99%

Catalysts Supported on Carbon Materials for the Selective Hydrogenation of Citral

et al. 2013

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“…The group-9 and group-10 metals, such as Rh, Ir, Ni, Pd, and Pt, are well known to generally hydrogenate the C=C bond more easily than the C=O bond of α,β-unsaturated aldehydes [2]. Despite extensive research [3][4][5], only Ir-, Os-, and Pt-based catalysts have thus far produced unsaturated alcohols [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Development of Nanoporous Ni-Sn Alloy and Application for Chemoselective Hydrogenation of Furfural to Furfuryl Alcohol

Rodiansono

Hara

Ichikuni

et al. 2013

Bull. Chem. React. Eng. Catal.

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A very simple synthetic procedure was developed for the preparation of Ni-Sn alloy catalysts that were utilised for chemoselective hydrogenation of furfural, producing furfuryl alcohol almost exclusively. The mixture of nickel nanoparticles supported on aluminum hydroxide (R-Ni/AlOH) and a solution containing tin was treated under hydrothermal condition, producing the as prepared nickel-tin alloy supported on aluminum hydroxide (Ni-Sn/AlOH). H2 treatment at range of temperature of 673-873 K for 1.5 h to the as prepared Ni-Sn/AlOH produced nanoporous Ni-Sn alloy catalysts. XRD patterns and SEM images revealed that the formation of Ni-Sn alloy of Ni3Sn and Ni3Sn2 phases and the transformation of crystalline gibbsite and bayerite into amorphous alumina were clearly observed after H2 treatment at 873 K. The formation of the Ni-Sn alloy may have played a key role in the enhancement of the chemoselectivity.

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“…This transformation is always known as a challenging reaction because the desired hydrogenation of the C=O bond is, however, thermodynamically and kinetically unfavorable over the C=C bond 3,4 . To improve the selectivity to the C=O hydrogenation, several catalysts have been developed such as organic molecule-modi ed metal nanoparticles [5][6][7] , metal-supported catalysts [8][9][10][11][12] , bimetallic catalysts [13][14][15] and organometallic catalysts 16 . Despite state-of-the-art progress made and cutting-edge catalysis knowledge obtained, these methods of selectivity regulation are largely limited to the tuning of electronic state and structure of catalysts.…”

Section: Introductionmentioning

confidence: 99%

Highly Selective Catalysis at the Liquid–Liquid Interface Microregion

et al. 2021

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Liquid-liquid interfaces in principle have the potential to regulate the selectivity of chemical reactions because of large polar gradients and highly anisotropic microenvironments, but have not yet been well exploited. Here, we present an oil-water interface-based strategy to boost catalytic selectivity, exempli ed by selective hydrogenation of α,β-unsaturated aldehydes. The key to this success is the spatially controlled assembly of tubular catalyst particles at the narrow inner interfacial layer of Pickering emulsion water droplets in oil. The catalyst particles that are assembled at the inner interfacial layer of water droplets exhibit much higher selectivity to C=O hydrogenation than ones located either at the outer interfacial layer, in the interior of droplets or at the conventionally-called Pickering emulsion interface. 92.0−98.0% selectivity to the thermodynamically and kinetically unfavorable C=O hydrogenation over the C=C hydrogenation was achieved unexpectedly. The assembly strategy reported here and the unprecedented effects of interface-induced catalytic selectivity enhancement open up a liquid-liquid interface engineering route to tune reaction outcome.

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Supported liquid-phase catalysts containing ruthenium complexes for selective hydrogenation of $alpha;,$beta;-unsaturated aldehyde: importance of interfaces between liquid film, solvent, and support for the control of product selectivity

Cited by 43 publications

References 36 publications

Catalysts Supported on Carbon Materials for the Selective Hydrogenation of Citral

Catalysts Supported on Carbon Materials for the Selective Hydrogenation of Citral

Development of Nanoporous Ni-Sn Alloy and Application for Chemoselective Hydrogenation of Furfural to Furfuryl Alcohol

Highly Selective Catalysis at the Liquid–Liquid Interface Microregion

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