Second order interactions in unsaturated nitriles hydrogenation

Dallons, Jl.; Jannes, G.; Delmon, Bernard

doi:10.1016/0920-5861(89)80030-6

Cited by 12 publications

(11 citation statements)

References 7 publications

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“…Nevertheless it is in agreement with the study by Delmon and co-workers [9] who found the non-conjugated allyl cyanide reacted faster than crotononitrile.…”

Section: Scheme 2 Order Of Reactivity Of Isolated C=c Bondssupporting

confidence: 82%

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Comparison of C═C Bond Hydrogenation in C-4 Unsaturated Nitriles over Pt/Alumina

Ali

Monaghan

Jackson

2016

Ind. Eng. Chem. Res.

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Abstract.The hydrogenation of allyl cyanide (but-1-ene-4-nitrile, AC), trans-and cis-crotononitrile (Eand Z-but-2-ene nitrile, TCN and CCN), and methacrylonitrile (2-cyano-1-propene, MCN) were studied, both singly and competitively, over a Pt/alumina catalyst in the liquid phase.Each unsaturated nitrile only underwent C=C bond hydrogenation: no evidence was found for the formation of the saturated or unsaturated amine. The non-conjugated allyl cyanide was found to be the most reactive unsaturated nitrile. Activation energies for the hydrogenation of the C=C bond in AC and MCN were determined giving values of 64±7 kJ.mol -1 for AC and 37±4 kJ.mol -1 for MCN. The reaction was zero order for both nitriles. Competitive hydrogenations revealed that not only does allyl cyanide react preferentially over the other isomers but that it also inhibits the hydrogenation of the other isomers. When all four nitriles were simultaneously hydrogenated, inhibition effects were easily seen suggesting that in terms of strength of bonding to the surface an order of AC > CCN > TCN ~ MN can be generated.

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“…Nevertheless it is in agreement with the study by Delmon and co-workers [9] who found the non-conjugated allyl cyanide reacted faster than crotononitrile.…”

Section: Scheme 2 Order Of Reactivity Of Isolated C=c Bondssupporting

confidence: 82%

“…The site was postulated to be a hydroxyl [7] and these may be replaced by the isopropoxy ion from the IPA solvent. A study over Raney Nickel of the hydrogenation of allyl cyanide and crotononitrile [9] at ~308 K in the liquid phase also found no evidence for the formation of the amine and attributed this to the low temperature.…”

Section: Discussionmentioning

confidence: 99%

Comparison of C═C Bond Hydrogenation in C-4 Unsaturated Nitriles over Pt/Alumina

Ali

Monaghan

Jackson

2016

Ind. Eng. Chem. Res.

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“…The increase of the rate of CQC bond hydrogenation using the polar solvents was observed therein. [25][26][27] One of the possible explanations is that the polar solvents favour adsorption of double bond containing compounds on the catalyst surface, because of their lower affinity for this molecule. 25,26 However, it has been mentioned that several factors can be responsible for the effect of solvent on the activity and selectivity, e.g.…”

Section: Hydrogenation Of 2-methyl-3-butyn-2-olmentioning

confidence: 99%

ZnO based nanowires grown by chemical vapour deposition for selective hydrogenation of acetylene alcohols

Protasova

Rebrov

Choy

et al. 2011

Catal. Sci. Technol.

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“…Molecules with olefinic and nitrile groups in conjugation or in close proximity are even more difficult to reduce selectively. 233,234 Kukula et al reported that Ni-B and Cr-promoted Ni-B favor the hydrogenation of the olefinic bond, whereas Co-B and Cr-promoted Co-B favor the formation of the unsaturated amine. 235 The Cr-promoted Co-B treated with NaOH hydrogenated cinnamonitrile, 1-cyclohexenyl-acetonitrile, and trans-3-pentenenitrile to the corresponding primary unsaturated amines with mediumto-high selectivities without the aid of ammonia at high conversion levels.…”

Section: Raneymentioning

confidence: 99%

Synthesis and catalysis of chemically reduced metal–metalloid amorphous alloys

et al. 2012

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Amorphous alloys structurally deviate from crystalline materials in that they possess unique short-range ordered and long-range disordered atomic arrangement. They are important catalytic materials due to their unique chemical and structural properties including broadly adjustable composition, structural homogeneity, and high concentration of coordinatively unsaturated sites. As chemically reduced metal-metalloid amorphous alloys exhibit excellent catalytic performance in applications such as efficient chemical production, energy conversion, and environmental remediation, there is an intense surge in interest in using them as catalytic materials. This critical review summarizes the progress in the study of the metal-metalloid amorphous alloy catalysts, mainly in recent decades, with special focus on their synthetic strategies and catalytic applications in petrochemical, fine chemical, energy, and environmental relevant reactions. The review is intended to be a valuable resource to researchers interested in these exciting catalytic materials. We concluded the review with some perspectives on the challenges and opportunities about the future developments of metal-metalloid amorphous alloy catalysts.

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Second order interactions in unsaturated nitriles hydrogenation

Cited by 12 publications

References 7 publications

Comparison of C═C Bond Hydrogenation in C-4 Unsaturated Nitriles over Pt/Alumina

Comparison of C═C Bond Hydrogenation in C-4 Unsaturated Nitriles over Pt/Alumina

ZnO based nanowires grown by chemical vapour deposition for selective hydrogenation of acetylene alcohols

Synthesis and catalysis of chemically reduced metal–metalloid amorphous alloys

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