Hydrogenation and hydrogenolysis in synthetic organic chemistry

Kieboom, A. P. G.; Rantwijk, Fred van

doi:10.1007/978-94-011-7589-0

Cited by 61 publications

(18 citation statements)

References 5 publications

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“…Hydrogenolysis reactions require a site ensemble of two or more metal atoms [10] where little or no hydrogenolytic activity is exhibited by homogeneous catalysts [11]. Ring hydrogenation occurs in preference to hydrogenolysis over Ru and Rh systems while Ni catalysts are known to exhibit appreciable hydrogenolytic behaviour [11,12]. Conventional hydro processing catalysts, such as CoMo/Al 2 O 3 and NiMo/ Al 2 O 3 have been widely used in hydrodeoxygenation applications [5,[13][14][15].…”

Section: Introductionmentioning

confidence: 99%

“…Substituted benzene systems have been used to evaluate the hydrogenolysis versus ring hydrogenation activity of typical hydrotreating catalysts [8,9]. Hydrogenolysis reactions require a site ensemble of two or more metal atoms [10] where little or no hydrogenolytic activity is exhibited by homogeneous catalysts [11]. Ring hydrogenation occurs in preference to hydrogenolysis over Ru and Rh systems while Ni catalysts are known to exhibit appreciable hydrogenolytic behaviour [11,12].…”

Section: Introductionmentioning

confidence: 99%

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Application of the Selective Energy Transfer Model to Account for an Isokinetic Response in the Gas Phase Reductive Cleavage of Hydroxyl, Carbonyl and Carboxyl Groups from Benzene Over Nickel/Silica

Keane

Larsson

2009

Catal Lett

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The gas phase hydrodeoxygenation of a series of aromatic alcohols, aldehydes and acids has been examined over Ni/SiO 2 . Compensation behaviour is established with an isokinetic temperature (518 ± 21 K) that is consistent with with the point of intersection of the Arrhenius lines. This is accounted for using the Selective Energy Transfer model that is based on resonance between the catalytic Ni-H vibration and out-of plane C-H vibrations of the aromatic reactants with a transferral of resonance energy from the catalyst to generate the ''activated complex''. The calculated wave number of this vibration mode is 720 ± 29 cm -1 with an associated anhamonicity of -3.3 ± 0.9 cm -1 . Our analysis suggests that the oxygenated aromatic is weakly adsorbed on the catalyst and surface mobility facilitates reaction with adsorbed hydrogen atoms.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Application of the Selective Energy Transfer Model to Account for an Isokinetic Response in the Gas Phase Reductive Cleavage of Hydroxyl, Carbonyl and Carboxyl Groups from Benzene Over Nickel/Silica

Keane

Larsson

2009

Catal Lett

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“…14.10.2.3.1 Introduction Many excellent monographs [1][2][3][4][5][6][7][8] describe the selective hydrogenation of functional groups from a phenomenological point of view, i.e. describe catalysts, reaction medium and conditions to achieve a specific transformation (Table 2).…”

Section: ->100mentioning

confidence: 99%

“…There are a number of excellent monographs [1][2][3][4][5][6][7][8] providing more detailed information on a broad variety of practical selectivity problems. There are a number of excellent monographs [1][2][3][4][5][6][7][8] providing more detailed information on a broad variety of practical selectivity problems.…”

Section: Introductionmentioning

confidence: 99%

Selective Hydrogenation of Functionalized Hydrocarbons

Blaser¹,

Schnyder²,

Steiner³

et al. 2008

Handbook of Heterogeneous Catalysis

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The sections in this article are Introduction Significance of Catalytic Methods in Organic Synthesis Guidelines for the Selection of a Catalytic Hydrogenation System Introduction General Approaches to Tuning Catalytic Processes A Selectivity in Catalytic Hydrogenation: a Challenge for Organic Chemists B Concepts and Tools Useful for Catalytic Hydrogenation General Strategy and Experiment Planning Catalyst Selection A Metal Selection B Catalyst Support C Catalyst Particle Size and Morphology D Porosity of the Support and Location of the Metal E Metal Dispersion and Metal Crystallite Size F Other Factors Selection of the Reaction Medium A Solvent B Acids and Bases C Catalyst Modifiers Reaction Conditions A Temperature B Hydrogen Pressure C Substrate Concentration D Catalyst Loading and Substrate to Catalyst Ratio E Degree of Conversion Chemoselectivity in Catalytic Hydrogenation Selective Hydrogenation of Functionalized Aromatic Nitro Compounds Introduction Mechanism of Nitroarene Reductions Practical Aspects A Catalysts B Reaction Medium and Conditions C Safety and Health Aspects a Hazards Related to Hydrogen b Hazards Related to the Catalyst c Hazards Due to the Hydrogenation Reaction d Hazards Due to the High Decomposition Energy of Aromatic Nitro Compounds and some Intermediates e Toxicity D Hydrogenation Equipment Selective Hydrogenation of Halogenated Nitroarenes A Introduction B Catalysts a Modified Catalysts b In Situ Modification New Catalyst Systems for the Hydrogenation of a Nitro Group in the Presence of Reducible Functional Groups A Lead‐Modified Platinum Catalysts: the “Lindlar Approach” B H 3 PO 2 ‐Modified Pt Catalysts in the Presence of Vanadium Promoters Hydroxylamine Accumulation Selective Semihydrogenation of Alkynes Introduction Chemical and Physical Background for Selectivity in Alkyne Hydrogenation Tools to Achieve Selectivity for Alkene Formation A Metal Selection B Chemical Composition of the Support C Metal Location D Metal Dispersion and Crystallite Size E Catalyst Modifiers F Solvent G Temperature H Hydrogen Pressure I Substrate Concentration J Catalyst/Substrate Ratio K Agitation L Degree of Conversion Selective Catalytic Debenzylation Introduction Catalysts Used for Selective Debenzylation Influence of Reaction Conditions A Hydrogen Source and Pressure B Solvent, Modifiers and Promoters Selective Removal of Benzyl Groups A Selective Removal of O ‐Benzyl Groups in the Presence of other O ‐Benzyl Groups B Selective Removal of O ‐Benzyl Groups in the Presence of N ‐Benzyl Groups C Selective Removal of O ‐Benzyl Groups in the Presence of other Reducible Functions D Selective Removal of N ‐Benzyl Groups in the Presence of other N ‐Benzyl Groups E Selective Removal of N ‐Benzyl Groups in the Presence of other Reducible Functions F New Protecting Groups Mechanism of Debenzylation and Mode of Action of Modifiers Stereoselective Reactions Diastereoselective Hydrogenation Enantioselective Hydrogenation Chemoselective Hydrogenation of Nitriles Primary Amine Formation Chemoselective Hydrogenation of Unsaturated Nitriles

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“…Similarly, Bonilla et al 17 described that the existence of cobalt and nickel obviously improved the sensitivity for Pb determination by HG-AAS. Brown et al [18][19][20][21] showed that the reaction between sodium borohydride and the ions of Fe, Co and Ni produced metal borides, the so-called Brown catalyst, 22 which provided a higher catalytic activity for hydrogenation reactions. [23][24][25] This suggests a mechanism for the improvement of Cd and Hg hydrides formation by metal borides.…”

mentioning

confidence: 99%

Simultaneous Determination of Trace Cadmium and Mercury in Chinese Herbal Medicine by Non-dispersive Atomic Fluorescence Spectrometry Using Intermittent Flow Vapor Generator

2003

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A method was proposed for the simultaneous determination of trace cadmium and mercury by vapor generation nondispersive atomic fluorescence spectrometry using an intermittent flow system. The effects of the parameters on the performance were studied systematically. The parameters such as acid concentration of the reaction medium, flow rate of the carrier gas and shield gas, the observation height and the atomizer temperature, etc. which affected the sensitivity, were optimized. Ascorbic acid, cobalt ion and thiourea were used as enhancement reagents or masking agents to enhance the generation efficiency of the volatile species of Cd and Hg. The mechanisms of their effects on vapor generation were investigated. In the presence of thiourea and ascorbic acid, the influences of some coexisting elements on the determination of cadmium and mercury were investigated. The detection limits (3σ) were 0.010 µg l -1 for Cd and 0.019 µg l -1 for Hg, respectively. The relative standard deviations for Cd and Hg at 1.00 µg l -1 were 2.6% and 0.97% (n = 11), respectively. The proposed method has been satisfactorily applied to the determination of trace cadmium and mercury in Chinese herbal medicine.

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Hydrogenation and hydrogenolysis in synthetic organic chemistry

Cited by 61 publications

References 5 publications

Application of the Selective Energy Transfer Model to Account for an Isokinetic Response in the Gas Phase Reductive Cleavage of Hydroxyl, Carbonyl and Carboxyl Groups from Benzene Over Nickel/Silica

Application of the Selective Energy Transfer Model to Account for an Isokinetic Response in the Gas Phase Reductive Cleavage of Hydroxyl, Carbonyl and Carboxyl Groups from Benzene Over Nickel/Silica

Selective Hydrogenation of Functionalized Hydrocarbons

Simultaneous Determination of Trace Cadmium and Mercury in Chinese Herbal Medicine by Non-dispersive Atomic Fluorescence Spectrometry Using Intermittent Flow Vapor Generator

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