Selective hydrogenation of cinnamaldehyde to cinnamyl alcohol using an Ir/C catalyst: Influence of reaction conditions

Jackson, S. David; Hargreaves, J. S. J.; Lennon, David; Breen, John; Burch, Robbie; Gomez-Lopez, Javier; Griffin, Ken; Hayes, Martin J.

doi:10.1039/9781847550347-00045

Cited by 25 publications

(34 citation statements)

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“…For the liquid phase hydrogenation over a variety of catalysts, CALC was formed while ST and EB were not detected. [10][11][12][13][14] It is well known that the Ni metal predominantly catalyzes the hydrogenation of C=C bond rather than C=O bond when both double bonds are present in the reactant. 7 As a result, the CALC selectivity was quite small (< 1 mol%) in this study.…”

Section: Cald Hydrogenationmentioning

confidence: 99%

“…Pd/carbon nanofiber, 5 Pt-Ni/CNT, 6 Ru/carbon nanofiber, 7 Ru/beta zeolite, 8 and Pd/CNT. 9 On the other hand, selective formation of cinnamyl alchol (CALC) was attained over Pt-MCM-48, 10 Ru/MCM-41 and Ru/Y, 11 Ir/ C, 12 Pt/SiO 2 , 13 and Au/g-Al 2 O 3 . 14 As shown in Scheme I, the reaction pathways over these catalysts involved only hydrogenation on the C=C and C=O double bond.…”

Section: Introductionmentioning

confidence: 95%

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Vapour Phase Hydrogenation of Cinnamaldehyde over Nano Ni and Ni/SiMCM‐41 Catalysts

Jao

Liu

Yang

et al. 2009

J Chinese Chemical Soc

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Ni nanoparticles (Ni(1) and Ni(2)) and Ni loaded SiMCM-41 (15Ni/SiMCM-41) were prepared and characterized with XRD, TEM, N 2 adsorption, CO chemisorption, and H 2 -TPR. The Ni specific surface area followed the order of 15Ni/SiMCM-41 > Ni(1) >> Ni(2), whereas the Ni particle size exhibited the opposite trend. These catalysts were utilized for vapour phase hydrogenation of cinnamaldehyde at 1 atm and 200°C in a fixed-bed, down flow reactor. The main products include hydrocinnamaldehyde, styrene, ethylbenzene, and 2-phenyl-1-propanol. The catalytic activity decreased in the same order as that of Ni specific surface areas. The SiMCM-41 support possessed very large surface area, leading to enhanced dispersion and specific surface area of Ni nanoparticles. As a result, the 15Ni/SiMCM-41 catalyst exhibited the highest activity. Based on the investigation of reaction pathways, it is important to emphasize that both hydrogenation and hydroelimination of formaldehyde (hydrodeformylation) occur in the vapour phase reaction.Keywords: Hydrogenation; Hydrodeformylation; Ni nanoparticles; Ni/SiMCM-41;Cinnamaldehyde. INTRODUCTIONThe Ni metal and Ni containing materials as hydrogenation catalysts have drawn much attention in both academic research and industrial application due to their chemical properties and low costs. Metal nanoparticles exhibit special properties of surface area, crystal size and shape, electron density, and ionization energies. Consequently, these materials exhibit better catalytic results in many reactions.

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Section: Cald Hydrogenationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 95%

Vapour Phase Hydrogenation of Cinnamaldehyde over Nano Ni and Ni/SiMCM‐41 Catalysts

Jao

Liu

Yang

et al. 2009

J Chinese Chemical Soc

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“…Cinnamaldehyde (CMA), one of these unsaturated aldehydes, is important in industry and its selective hydrogenation products are widely used in the perfume industry. Supported platinum [5][6][7][8], iridium [9], ruthenium [10], cobalt [11,12], copper [13], gold [14,15], and metal boride [16,17] catalysts have been investigated for their selectivity to cinnamyl alcohol (CMO) in the hydrogenation of CMA. Supported ruthenium [18] and palladium [19][20][21][22] catalysts have been used in the selective hydrogenation of CMA to HCMA.…”

Section: Introductionmentioning

confidence: 99%

Selective Hydrogenation of Cinnamaldehyde to Hydrocinnamaldehyde over SiO2 Supported Nickel Phosphide Catalysts

2008

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A series of SiO 2 supported transition metal (Fe, Co, Ni, Mo and W) phosphide catalysts were synthesized and tested for the selective hydrogenation of cinnamaldehyde (CMA). Among these tested catalysts, Ni 12 P 5 /SiO 2 and Ni 2 P/SiO 2 prepared with initial Ni/P ratios of 2/1.3 and 1/1 exhibited high activity and selectivity for the conversion of CMA to hydrocinnamaldehyde (HCMA). The two nickel phosphide catalysts showed selectivity to HCMA up to 90% at a conversion of 90%. The properties of the nickel phosphide catalysts were characterized by BET surface area determinations, X-ray powder diffraction (XRD) analysis, and transmission electron microscopy (TEM). The influences of reaction temperature, hydrogen pressure, Ni/P ratio, and reduction temperature were studied in detail. For comparison, Pd/SiO 2 catalyst was also used in this reaction, and the possible reasons for the different catalytic performances of the two kinds of catalysts are presented.

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“…Various approaches have been tested in an attempt to improve the ______________________ selectivity of the reaction to produce cinnamyl alcohol [1]. These include the type of hydrogenation active metal as well that of the support, particle size effects, the application of selectivity promoters, the application of biphasic catalysts [2] and the effect of reaction conditions [3].…”

Section: Introductionmentioning

confidence: 99%

A kinetic study of the liquid-phase hydrogenation of phenylpropanal over alumina-supported Ir catalysts

Hammoudeh

Mahmoud

2007

React Kinet Catal Lett

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Selective hydrogenation of cinnamaldehyde to cinnamyl alcohol using an Ir/C catalyst: Influence of reaction conditions

Cited by 25 publications

References 0 publications

Vapour Phase Hydrogenation of Cinnamaldehyde over Nano Ni and Ni/SiMCM‐41 Catalysts

Vapour Phase Hydrogenation of Cinnamaldehyde over Nano Ni and Ni/SiMCM‐41 Catalysts

Selective Hydrogenation of Cinnamaldehyde to Hydrocinnamaldehyde over SiO2 Supported Nickel Phosphide Catalysts

A kinetic study of the liquid-phase hydrogenation of phenylpropanal over alumina-supported Ir catalysts

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