
Catalytic Hydrogenation over Platinum Metals
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Catalytic Hydrogenation over Platinum Metals focuses on catalytic hydrogenation as an effective process in attaining controlled transformations of organic compounds. Composed of contributions of various authors, the book first provides information on catalysts, equipment, and conditions. Catalyst stability and reuse; types of catalyst; platinum metals; and synergism are covered. The text proceeds with discussions on hydrogenation reactors. Topics include atmospheric pressure reactors; low pressure reactors; microreactors; and high pressure reactors. The book also covers hydrogenation of carbon-carbon unsaturation. Catalytic metal; modified catalyst systems; stereochemistry; diacetylenes; and hydrogenolysis are discussed. The text also looks at the hydrogenation of aromatics, nitrogen and carbonyl compounds, and hydrogenolysis. Numerical representations and analysis, diagrams, and reactions of compounds when exposed to different laboratory conditions are considered. The selection is a great source of data for readers interested in studying the process of catalytic hydrogenation.
Table of Contents
Preface
Part I Catalysts, Equipment, and Conditions
1 Platinum Metal Catalysts
I. Platinum Metals
II. Types of Catalyst
III. Synergism
IV. Catalyst Stability
V. Safety
VI. Catalyst Reuse
VII. Induction Periods
VIII. Reproducibility of Catalysts
IX. Inhibitors and Poisons
X. Promoters
XI. Preparation of Catalysts
References
2 Hydrogenation Reactors
I. Atmospheric Pressure Reactors
II. Low Pressure Reactors
III. Microreactors
IV. High Pressure Reactors
References
3 Reaction Conditions
I. Temperature
II. Amount of Catalyst
III. Pressure
IV. Agitation
V. Mode of Addition
VI. Solvents
References
Part II Hydrogenation of Carbon-Carbon Unsaturation
4 Acetylenes
I. Catalytic Metal
II. Modified Catalyst Systems
III. Stereochemistry
IV. Diacetylenes
V. Vinylacetylenes
VI. Hydrogenolysis
References
5 Olefins
I. Catalysts
II. Effect of Solvent
III. Effect of Olefin Structure
IV. Double-Bond Migration
V. Stereochemistry
VI. Olefin Saturation in Polyfunctional Molecules
References
Part III Hydrogenation of Nitrogen Compounds
6 Imines
I. Acidic Media
II. Neutral or Basic Media
III. Effect of Structure
References
7 Azines
I. Solvents
II. Preparation of Azo Compounds
References
8 Hydrazones
I. Hydrogenolysis
II. Disproportionation
III. Hydrazines by Reductive Alkylation
References
9 Oximes
I. Catalysts
II. Substrate
III. Solvent
IV. Products of Partial Reduction
V. Oximino Ketones
VI. Products of Interaction with Other Functions
VII. Stereochemistry
References
10 Nitroso Compounds
I. Hydroxylamine
II. N-Nitrosoamines
III. C-Nitroso Compounds
References
11 Nitro Compounds
I. Catalysts
II. Solvents
III. Reduction of the Aromatic Nitro Group to the Amine
IV. Reduction of Aliphatic Nitro Groups to the Amine
V. Difunctional Compounds
VI. Rearrangements
VII. Loss of Nitrogen by Hydrogenolysis
VIII. Products of Partial Reduction
References
12 Nitriles
I. Coupling Reactions: Secondary and Tertiary Amines
II. Products of Reductive Hydrolysis
III. Nitriles with Other Functional Groups
References
Part IV Carbonyl Compounds
13 Hydrogenation of Acids, Esters, and Anhydrides
I. Acids
II. Esters
III. Anhydrides
References
14 Hydrogenation of Aldehydes
I. Saturated Aliphatic Aldehydes
II. Aromatic Aldehydes
III. Unsaturated Aldehydes
References
15 Hydrogenation of Ketones
I. Aliphatic Ketones
II. Aromatic Ketones
III. Stereochemistry
References
16 Reductive Alkylation-Preparation of Amines
I. Substrates
II. Catalysts
III. Stereochemistry
IV. Incipient Amine and Carbonyl Compounds
References
17 Reductive Alkylation-Alkylidene Derivatives
Text
References
Part V Hydrogenation of Aromatics
18 Carbocyclic Aromatics
I. Comparison of Catalysts
II. Partial Reduction of Aromatic Rings
III. Strained Rings
IV. Selective Hydrogenation
V. Reduction of Benzyl Compounds
VI. Fused Rings
VII. Stereochemistry
References
19 Phenols and Phenyl Ethers
I. Platinum Metals
II. Effect of Catalyst and Temperature on Stereochemistry
III. Hydrogenolysis without Ring Reduction
IV. Partial Ring Reduction
V. Ring Saturation without Hydrogenolysis
VI. Ring Reduction with Hydrogenolysis
References
20 Anilines
I. Reduction to the Saturated Amine
II. Secondary Amines
III. Hydrogenolysis
IV. Hydrolysis
References
21 Furans
I. Hydrogenation of the Furan Nucleus
II. Hydrogenolysis of Furans
References
22 Nitrogen Heterocyclic Compounds
I. Pyrroles
II. Indoles
III. Pyridines
IV. Quinolines and Isoquinolines
V. Imidazoles
VI. Pyridazines
VII. Pyrazines
VIII. Pyrimidines
References
Part VI Hydrogenolysis
23 Hydrogenation of Acid Chlorides—Rosenmund Reduction
I. Catalyst Regulators
II. Side-Reactions
III. Procedure
IV. Selective Hydrogenation
References
24 Catalytic Dehalogenation
I. Catalysts
II. Dehalogenation in Basic Media
III. Choice of Base
IV. Halogen Compounds with Other Functions
V. Selective Hydrogenation of Polyhalo Compounds
VI. Rearrangements
VII. Coupling Reactions
VIII. Dehalogenation with Hydrazine
References
25 Miscellaneous Hydrogenolyses
I. Allylic Oxygen
II. Allylic Nitrogen
III. Vinyl Functions
IV. Debenzylation
V. Hydrogenolysis of the Carbon-Carbon Bond
VI. Hydrogenolysis of the Carbon-Oxygen Bond
VII. Hydrogenolysis of the Carbon-Nitrogen Bond
VIII. Hydrogenolysis of the Nitrogen-Oxygen Bond
IX. Hydrogenolysis of the Oxygen-Oxygen Bond
X. Hydrogenolysis of the Nitrogen-Nitrogen Bond
References
Author Index
Subject Index
Product details
- No. of pages: 564
- Language: English
- Copyright: © Academic Press 1967
- Published: January 1, 1967
- Imprint: Academic Press
- eBook ISBN: 9780323145862
About the Author
Paul Rylander
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