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Hydrogenation Methods Paul N. Rylander Engelhard Corporation Edison, New Jersey
1985
ACADEMIC PRESS (Harcourf Brace Jovanovich. Publishers)
London Orlando San Diego New York Toronto Montreal Sydney Tokyo
This book is a guide to provide general information concerning its subject matter; it is not a procedural manual. Synthesis of chemicals is a rapidly changing field. The reader should consult current procedural manuals for state-of-the-art instructions and applicable government safety regulations. The Publisher and the authors do not accept responsibility for any misuse of this book, including its use as a procedural manual or as a source of specific instructions.
COPYRIGHT © 1985 BY ACADEMIC PRESS INC. (LONDON) LTD. ALL RIGHTS RESERVED. NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WRITING FROM THE PUBLISHER.
ACADEMIC PRESS INC. (LONDON) LTD. 24-28 Oval Road LONDON NWl 7DX
United States Edition published by ACADEMIC PRESS, INC. Orlando, Florida 32887
BRITISH LIBRARY CATALOGUING IN PUBLICATION DATA Rylander, Paul N. Hydrogenation methods. (Best synthetic methods) 1. Hydrogenation 2. Chemistry, Organic I. Title II. Series 547'.23 QD281.H8
LIBRARY OF CONGRESS CATALOGING IN PUBLICATION DATA Rylander, Paul NeIs, Date Hydrogenation methods. (Best synthetic methods) Includes index. 1. Hydrogenation. QD281.H8R93 1985 ISBN 0-12-605365-0 (alk. paper)
PRINTED IN THE UNITED STATES OF AMERICA 85 86 87 88
9 8 7 6 5 4 3 2 1
Contents
Foreword
vii
Preface
ix
Detailed Contents
xi
Chapter 1.
Catalysts, Reactors, and Reaction Parameters
1
Chapter 2.
Hydrogenation of Olefins
29
Chapter 3.
Hydrogenation of Acetylenes
53
Chapter 4.
Hydrogenation of Aldehydes and Ketones
66
Chapter 5.
Hydrogenation of Acids, Anhydrides, and Esters
78
Chapter 6.
Reductive Alkylation
82
Chapter 7.
Hydrogenation of Nitriles and Oximes
94
Chapter 8.
Hydrogenation of Nitro Compounds
104
Chapter 9.
Hydrogenation of Carbocyclic Aromatic Compounds
117
Chapter 10.
Hydrogenation of Anilines, Phenols, and Derivatives
123
Chapter 11.
Hydrogenation and Hydrogenolysis of Heterocycles
133
Chapter 12.
Catalytic Dehydrohalogenation
148
Chapter 13.
Miscellaneous Hydrogenolyses
157
Index of Compounds and Methods
185
Foreword
There is a vast and often bewildering array of synthetic methods and reagents available to organic chemists today. Many chemists have their own favoured methods, old and new, for standard transformations, and these can vary considerably from one laboratory to another. New and unfamiliar methods may well allow a particular synthetic step to be done more readily and in higher yield, but there is always some energy barrier associated with their use for the first time. Furthermore, the very wealth of possibilities creates an information retrieval problem: How can we choose between all the alternatives, and what are their real advantages and limitations? Where can we find the precise experimental details, so often taken for granted by the experts? There is therefore a constant demand for books on synthetic methods, especially the more practical ones like "Organic Syntheses," "Organic Reactions/' and "Reagents for Organic Synthesis," which are found in most chemistry laboratories. We are c