Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis / Edition 1

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Overview

The most comprehensive reference in the field, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis provides synthetic chemists and chemical engineers in fine chemicals and pharmaceuticals with detailed experimental guidelines for heterogeneous catalytic hydrogenation. Organized by functional groups for ready reference and featuring detailed examples of hundreds of reactions, this handbook covers hydrogenations of alkenes, alkynes, aldehydes and ketones, nitriles, imines, nitro and nitroso compounds, carboxylic acids and esters, and aromatic and heterocyclic compounds. In addition, coverage includes the preparation of amines by reductive alkylation and the hydrogenolysis of a variety of compounds. Examples of hydrogenation of functional groups and reaction pathways are illustrated with numerous equations and schemes.

Practitioners will appreciate the plenitude of experimental details given for most of the reactions selected, including amounts of reagents and catalysts, reaction temperatures, hydrogen pressures, and reaction times. They will also find helpful the more than one hundred tables included throughout the book detailing the effects of key factors governing rate and selectivity, such as compound structure, the nature of catalysts and supports, and the nature of solvents. Researchers will benefit from the introductory chapters covering an array of hydrogenation catalysts, including nickel, cobalt, copper, iron, platinum group metals, rhenium, and other oxide and sulfide catalysts, as well as reactors and reaction conditions.

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Editorial Reviews

From the Publisher
"Chemists will find this a useful guide and it should be in all organic chemistry libraries." (Organic Process Research & Development Journal)

"...this book is easy to use to find information quickly...it adds to a useful armoury for dealing with most queries...it is therefore good value..." (Platinum Metals Review, Vol. 46, No. 2, April 2002)

"this book is easy to use to find information quickly" (Platinum Metals Review, April 2002)

"...a welcome and valuable day-to-day manual..." (Synthesis, No.9, 2002)

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Product Details

  • ISBN-13: 9780471396987
  • Publisher: Wiley
  • Publication date: 4/17/2001
  • Edition number: 1
  • Pages: 720
  • Product dimensions: 6.34 (w) x 9.47 (h) x 1.66 (d)

Meet the Author

SHIGEO NISHIMURA, DSc, is Professor Emeritus at the Tokyo University of Agriculture and Technology. He is a member of the Chemical Society of Japan and the Catalysis Society of Japan.

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Read an Excerpt


Catalytic hydrogenation is undoubtedly the most useful and widely applicable method for the reduction of chemical substances, and has found numerous applications in organic synthesis in research laboratories and industrial processes. Almost all catalytic hydrogenations have been accomplished using heterogeneous catalysts since the earliest stages. Homogeneous catalysts have been further developed and have extended the scope of catalytic hydrogenation, in particular, for highly selective transformations. However, heterogeneous catalysts today continue to have many advantages over homogeneous catalysts, such as in the stability of catalyst, ease of separation of product from catalyst, a wide range of applicable reaction conditions, and high catalytic ability for the hydrogenation of hard-to-reduce functional groups such as aromatic nuclei and sterically hindered unsaturations and for the hydrogenolyses of carbon–carbon bonds. Also, many examples are included here where highly selective hydrogenations have been achieved over heterogeneous catalysts, typically in collaborationwith effective additives, acids and bases, and solvents.

Examples of the hydrogenation of various functional groups and reaction pathways are illustrated in numerous equations and schemes in order to help the reader easily understand the reactions. In general, the reactions labeled as equations are described with experimental details to enable the user to choose a pertinent catalyst in a proper ratio to the substrate, a suitable solvent, and suitable reaction conditions for hydrogenation to be completed within a reasonable time. The reactions labeled as schemes will be helpful for better understanding reaction pathways as well as the selectivity of catalysts, although the difference between equations and schemes is not strict. Simple reactions are sometimes described in equations without experimental details. Comparable data are included in more than 100 tables, and will help the user understand the effects of various factors on the rate and/or selectivity, including the structure of compounds, the nature of catalysts and supports, and the nature of solvents and additives. A considerable number of experimental results not yet published by the author and co-workers can be found in this Handbook.

This book is intended primarily to provide experimental guidelines for organic syntheses. However, in fundamental hydrogenations, mechanistic aspects (to a limited extent) are also included. The hydrogenations of industrial importance have been described with adequate experimental and mechanistic details.

The references quoted here are by no means comprehensive. In general, those that seem to be related to basic or selective hydrogenations have been selected.

I am grateful to the authors of many excellent books to which I have referred during preparation of this book. These books are listed at the end of chapters under "General Bibliography."

I wish to express my thanks to the libraries and staff of The Institute of Physical and Chemical Research, Wako, Saitama and of Tokyo University of Pharmacy and Life Science, Hachioji, Tokyo. I acknowledge John Wiley and Sons, Inc. and their editorial staff for their cordial guidance and assistance in publishing this book. I thank Professor Emeritus Michio Shiota of Ochanomizu University and Professor Yuzuru Takagi of Nihon University for their helpful discussions. Special thanks are due to my three children who provided me with a new model personal computer with a TFT-LC display for preparing the manuscript and to my wife Yasuko, who had continuously encouraged and supported me in preparing and publishing this book until her death on November 28, 1999.

SHIGEO NISHIMURA

Hachioji, Tokyo

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Table of Contents

Preface.

Hydrogenation Catalysts.

Reactors and Reaction Conditions.

Hydrogenation of Alkenes.

Hydrogenation of Alkynes.

Hydrogenation of Aldehydes and Ketones.

Preparation of Amines by Reductive Alkylation.

Hydrogenation of Nitriles.

Hydrogenation of Imines, Oximes, and Related Compounds.

Hydrogenation of Nitro, Nitroso, and Related Compounds.

Hydrogenation of Carboxylic Acids, Esters, and Related Compounds.

Hydrogenation of Aromatic Compounds.

Hydrogenation of Heterocyclic Aromatic Compounds.

Hydrogenolysis.

General Bibliography.

Author Index.

Subject Index.

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