Synthesis of cinnamyl ethyl ether in the hydrogenation of cinnamaldehyde on Au/TiO2 catalysts

Milone, Candida; Trapani, Mariachiara; Galvagno, S.

doi:10.1016/j.apcata.2007.12.010

Cited by 33 publications

(23 citation statements)

References 19 publications

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“…The latter is formed as a result of a side reaction between ethanol and aldehyde (Scheme ). This side product was also observed by Milone et al It is fully eliminated when the hydrogenation is performed using the catalyst totally reduced to the Pd(0) form (Table ). The chemoselectivity of the reaction catalysed by MPd is changed with consecutive cycles (Table ).…”

Section: Resultssupporting

confidence: 72%

Polysiloxane microspheres functionalized with imidazole groups as a palladium catalyst support

Pośpiech

Chojnowski

Mizerska

et al. 2016

Applied Organom Chemis

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Polysiloxane microspheres containing a large number of silanol groups were obtained by an emulsion process of modified polyhydromethylsiloxane. N-substituted imidazole groups were grafted on these microspheres by the silylation of their silanol groups with N-[γ-(dimethylchlorosilyl)propyl]imidazole hydrochloride. The progress of the reaction was monitored using 29 Si and 13 C magic angle spinning (MAS) NMR and its impact on microsphere morphology was studied using scanning electron microscopy (SEM). The usefulness of the imidazole-functionalized microspheres as a support for a metal catalyst was demonstrated by their reaction with PdCl 2 (PhCN) 2 . In this way a new heterogenized catalyst, Pd(II) complex with imidazole ligands supported on polysiloxane microspheres, was generated. This catalyst, MPd, was characterized using 13 C and 29Si MAS NMR, X-ray photoelectron, Fourier transform infrared and far-infrared spectroscopies, X-ray diffraction, SEM-energy-dispersive X-ray spectroscopy and wide-angle X-ray scattering. The catalyst appears in two structures, as Pd(II) complex and Pd(0) nanoclusters. Its catalytic activity was tested using a model reaction, the hydrogenation of cinnamaldehyde, and compared with that of an analogous complex operating in a homogeneous system. MPd showed a high activity in the promotion of hydrogenation of cinnamaldehyde. The activity in the substrate conversion was stable at least in five cycles of this reaction. The main product was hydrocinnamaldehyde which could be obtained with a yield above 70%. A mechanism of the reaction is proposed.

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Section: Resultssupporting

confidence: 72%

Polysiloxane microspheres functionalized with imidazole groups as a palladium catalyst support

Pośpiech

Chojnowski

Mizerska

et al. 2016

Applied Organom Chemis

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“…Yet another route to the etherification product was proposed by Milone et al, who explain the formation of cinnamyl ethyl ether in the reduction of cinnamaldehyde by the hydrogenolysis of the hemiacetal. [17] The possible scenarios for our substrate are outlined in Scheme 3.…”

Section: Effect Of Temperature On Conversion and Selectivitymentioning

confidence: 99%

Selective Hydrogenation of 5‐Ethoxymethylfurfural over Alumina‐Supported Heterogeneous Catalysts

et al. 2009

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Abstract:We report here the synthesis and testing of a set of 48 alumina-supported catalysts for hydrogenation of 5-ethoxymethylfurfural. This catalytic reaction is very important in the context of converting biomass to biofuels. The catalysts are composed of one main metal (gold, copper, iridium, nickel, palladium, platinum, rhodium, ruthenium) and one promoter metal (bismuth, chromium, iron, sodium, tin, tungsten). Using a 16-parallel trickle-flow reactor, we tested all 48 catalyst combinations under a variety of conditions. The results show that both substrate conversion and product selectivity are sensitive towards temperature changes and solvent effects. The best results of > 99% yield to the desired product, 5-ethoxymethylfurfuryl alcohol, are obtained using an iridium/chromium (Ir/Cr) catalyst. The mechanistic implications of different possible reaction pathways in this complex hydrogenation system are discussed.

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“…When gold catalysts are supported on reducible oxides [4][5][6][9][10][11][12][13], it is not possible to determine a clear effect of the gold particles, since reduction temperature affects the catalytic behavior due to strong metal-support interaction (SMSI) effects present in samples when this type of supports are used [14]. On the other hand, size effect of gold nanoparticles in the activity and selectivity of Au-catalyzed hydrogenation of ␣,␤-unsaturated carbonyl compounds is still under debate [15] and it is more complicated than assuming a simple geometric model (gold particle size) or perimeter-interface model [6].…”

Section: Introductionmentioning

confidence: 99%

Hydrogenation of α,β-unsaturated carbonyl compounds over Au and Ir supported on SiO2

Rojas

Díaz

Martínez

et al. 2012

Journal of Molecular Catalysis A: Chemical

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Synthesis of cinnamyl ethyl ether in the hydrogenation of cinnamaldehyde on Au/TiO2 catalysts

Cited by 33 publications

References 19 publications

Polysiloxane microspheres functionalized with imidazole groups as a palladium catalyst support

Polysiloxane microspheres functionalized with imidazole groups as a palladium catalyst support

Selective Hydrogenation of 5‐Ethoxymethylfurfural over Alumina‐Supported Heterogeneous Catalysts

Hydrogenation of α,β-unsaturated carbonyl compounds over Au and Ir supported on SiO2

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