Hydrogenation of cinnamaldehyde catalysed by homogeneous and heterogenized rhodium(I) and ruthenium(II) complexes

Broučková, Zuzana; Czaková, Marie; Čapka, M.

doi:10.1016/0304-5102(85)80030-4

Cited by 19 publications

(6 citation statements)

References 15 publications

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“…The selective hydrogenation of the CO double bond to the corresponding alcohol is thus a way to obtain particular substituted alcohols. Various ruthenium complexes have been proved to show high activities toward the selective hydrogenation of CO versus CC double bonds in model reactions with homogeneous as well as heterogeneous catalysts. ,,− …”

Section: Resultsmentioning

confidence: 99%

Poly(Alumosiloxanes) as Matrixes for the Immobilization of Catalytically Active Ruthenium(II) Complexes¹

et al. 1998

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The trimethoxysilyl-(T)-functionalized ruthenium(II) complexes cis-Cl(H)Ru(CO)(P∼O) 3 [2a(T 0 ) 3 , 2b(T 0 ) 3 , and 2c(T 0 ) 3 ] (T ) T-type silicon atom, three oxygen neighbors, P∼O ) P-coordinated ether-phosphines with different spacer lengths) were sol-gel processed with different silicon-containing precursors {tetraethoxysilanesilicon atom, four oxygen neighbors], methyltrimethoxysilane [MeSi(OMe) 3 , T 0 , T ) T-type silicon atom, three oxygen neighbors], or dimethyldiethoxysilane [Me 2 Si(OEt) 2 , D 0 , D ) D-type silicon atom, two oxygen neighbors]} and aluminum 2-propanolate [Al(OiPr) 3 ]. All components are simultaneously polycondensed to result in the poly(alumosiloxane)-bound ruthenium complexes [2(a,b,c)From 31 P and 13 C CP/MAS NMR as well as IR spectroscopy it can be concluded that the complex fragment cis-Cl(H)Ru(CO)(P∼O) 3 is preserved during the immobilization. The aluminum is incorporated as tetrahedrally coordinated AlO 4 units while 6-fold-coordinated AlO 6 groups are built in as interstitials. Stoichiometric formulas and structural models of the carrier matrixes are derived from 27 Al and 29 Si solid-state NMR spectroscopy, including 27 Al{ 1 H} REDOR and 1 H-27 Al CP/MAS NMR techniques, as well as energy-dispersive X-ray spectroscopy (EDX). The dynamic behavior of the various catalysts is investigated by 2D WISE spectroscopy and 31 P CP/MAS NMR line widths. The immobilized complexes act as hydrogenation catalysts of n-butenal and are easy to separate from the reaction mixture by simple centrifugation.

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Section: Resultsmentioning

confidence: 99%

Poly(Alumosiloxanes) as Matrixes for the Immobilization of Catalytically Active Ruthenium(II) Complexes¹

et al. 1998

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“…The selective hydrogenation of the CO double bond to the corresponding alcohol is thus a way to obtain particular substituted alcohols. Various ruthenium complexes have been proved to show high activities toward the selective hydrogenation of CO vs CC double bonds in model reactions with homogeneous as well as heterogeneous catalysts. − …”

Section: Resultsmentioning

confidence: 99%

“…Various ruthenium complexes have been proved to show high activities toward the selective hydrogenation of CdO vs CdC double bonds in model reactions with homogeneous as well as heterogeneous catalysts. [34][35][36][37] (25) Corriu, R. J. P.; Moreau, J. J. E.; Thepot, P.; Wong Chi Man, M. J.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Poly(alumosiloxane)-Bound (Ether−phosphine)ruthenium(II) Complexes¹^,²

et al. 1997

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The trimethoxysilyl-(T)-functionalized ruthenium(II) complex cis-Cl(H)Ru(CO)(P∼O) 3 [2(T 0 ) 3 ] (P∼O: Pcoordinated ether-phosphine) is sol-gel processed with tetraethoxysilane (TEOS, Q 0 ) and aluminum 2-propanolate [Al(OiPr) 3 ]. All components are simultaneously polycondensed to result in the poly(alumosiloxane)-bound ruthenium complexes A and B with various amounts of aluminum. From 31 P and 13 C CP MAS NMR as well as IR spectroscopy it can be concluded that the complex fragment cis-Cl(H)Ru(CO)(P∼O) 3 is preserved during the immobilization. Polymers A and B show a remarkable number of Si-O-Al bonds in the 29 Si solid state NMR spectra. The aluminum is incorporated as tetrahedrally coordinated AlO 4 units with a formal negative charge. The 6-fold coordinated AlO 6 groups containing water and hydroxide groups as ligands are sited as interstitials and act as their counterions. Stoichiometric formulas of A and B derived by 27 Al and 29 Si solid state NMR spectroscopy and energy dispersive X-ray spectroscopy (EDX) suggest that the amount of aluminum can be adjusted by the applied stoichiometry. The two materials A and B act as hydrogenation catalysts of transcrotylaldehyde and are easy to separate from the reaction mixture by simple centrifugation.

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“…Recently, a large number of homogeneous catalysts such as metal hydrides, aluminium isopropoxide, and others have been developed for selective hydrogenation of cinnamaldehyde to cinnamic alcohol [9,10]; however, efficient separation and recovery of these advanced catalysts from reaction vessel are still a challenge, which prevents their widespread applications [11]. To this end, the development of heterogeneous catalysts on various supports provides a promising solution because of its environment-friendly property, ability to selectively hydrogenate, and simple method to recover [5,9].…”

Section: Introductionmentioning

confidence: 99%

Effect of Carbon Supported Pt Catalysts on Selective Hydrogenation of Cinnamaldehyde

Han

Liu

Wang

et al. 2016

Journal of Chemistry

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Selective hydrogenation of cinnamaldehyde (CAL) to cinnamyl alcohol (COL) is of both fundamental and industrial interest. It is of great significance to evaluate the possible differences between different supports arising from metal dispersion and electronic effects, in terms of activity and selectivity. Herein, Pt catalysts on different carbon supports including carbon nanotubes (CNTs) and reduced graphene oxides (RGO) were developed by a simple wet impregnation method. The resultant catalysts were well characterized by XRD, Raman, N2physisorption, TEM, and XPS analysis. Applied in the hydrogenation of cinnamaldehyde, 3.5 wt% Pt/CNT shows much higher selectivity towards cinnamyl alcohol (62%) than 3.5 wt% Pt/RGO@SiO2(48%). The enhanced activity can be ascribed to the high graphitization degree of CNTs and high density of dispersed Pt electron cloud.

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Hydrogenation of cinnamaldehyde catalysed by homogeneous and heterogenized rhodium(I) and ruthenium(II) complexes

Cited by 19 publications

References 15 publications

Poly(Alumosiloxanes) as Matrixes for the Immobilization of Catalytically Active Ruthenium(II) Complexes¹

Poly(Alumosiloxanes) as Matrixes for the Immobilization of Catalytically Active Ruthenium(II) Complexes¹

Synthesis and Characterization of Poly(alumosiloxane)-Bound (Ether−phosphine)ruthenium(II) Complexes¹^,²

Effect of Carbon Supported Pt Catalysts on Selective Hydrogenation of Cinnamaldehyde

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Hydrogenation of cinnamaldehyde catalysed by homogeneous and heterogenized rhodium(I) and ruthenium(II) complexes

Cited by 19 publications

References 15 publications

Poly(Alumosiloxanes) as Matrixes for the Immobilization of Catalytically Active Ruthenium(II) Complexes1

Poly(Alumosiloxanes) as Matrixes for the Immobilization of Catalytically Active Ruthenium(II) Complexes1

Synthesis and Characterization of Poly(alumosiloxane)-Bound (Ether−phosphine)ruthenium(II) Complexes1,2

Effect of Carbon Supported Pt Catalysts on Selective Hydrogenation of Cinnamaldehyde

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Poly(Alumosiloxanes) as Matrixes for the Immobilization of Catalytically Active Ruthenium(II) Complexes¹

Poly(Alumosiloxanes) as Matrixes for the Immobilization of Catalytically Active Ruthenium(II) Complexes¹

Synthesis and Characterization of Poly(alumosiloxane)-Bound (Ether−phosphine)ruthenium(II) Complexes¹^,²