Catalysis of Organic Reactions

417 Pages·2020·103.867 MB·English

by  John R. Kosak (editor), Thomas A. Johnson (editor)

Catalysis of
Organic Reactions
CHEMICAL INDUSTRIES
A Series ofReference Books and Textbooks
Consulting Editor
HEINZ HEINEMANN
Heinz Heinemann, Inc.,
Berkeley, California
Volume 1: Fluid Catalytic Cracking with Zeolite Catalysts,
Paul B. Venuto and E. Thomas Habib, Jr.
Volume 2: Ethylene: Keystone to the Petrochemical Industry,
Ludwig Knie/, Olaf Winter, and Karl Stork
Volume 3: The Chemistry and Technology of Petroleum,
James G. Speight
Volume 4: The Desulfurization of Heavy Oils and Residua,
James G. Speight
Volume 5: Catalysis of Organic Reactions,
edited by William R. Moser
Volume 6: Acetylene-Based Chemicals from Coal and Other Natural
Resources, Robert J. Tedeschi
Volume 7: Chemically Resistant Masonry,
Walter Lee Sheppard, Jr.
Volume 8: Compressors and Expanders: Selection and Application
for the Process Industry, Heinz P. Bloch, Joseph A.
Cameron, Frank M. Danowski, Jr., Ralph James, Jr.,
Judson S. Swearingen, and Marilyn E. Weightman
Volume 9: Metering Pumps: Selection and Application,
James P. Poynton
Volume JO: Hydrocarbons from Methanol,
Clarence D. Chang
Volume 11 : Foam Flotation: Theory and Applications,
Ann N. Clarke and David J. Wilson
Volume 12: The Chemistry and Technology of Coal,
James G. Speight
Volume 13: Pneumatic and Hydraulic Conveying of Solids,
0. A. Williams
Volume 14: Catalyst Manufacture: Laboratory and Commercial
Preparations, Alvin B. Stiles
Volume 15: Characterization of Heterogeneous Catalysts,
edited by Francis Delannay
Volume 16: BASIC Programs for Chemical Engineering Design,
James H. Weber
Volume 17: Catalyst Poisoning,
L. Louis Hegedus and Robert W. McCabe
Volume 18: Catalysis of Organic Reactions,
edited by John R. Kosak
Volume 19: Adsorption Technology: A Step-by-Step Approach
to Process Evaluation and Application, edited by
Frank L. Slejko
Volume 20: Deactivation and Poisoning of Catalysts,
edited by Jacques Oudar and Henry Wise
Volume 21: Catalysis and Surface Science: Developments in
Chemicals from Methanol, Hydrotreating of
Hydrocarbons, Catalyst Preparation, Monomers
and Polymers, Photocatalysts and Photovoltaics,
edited by Heinz Heinemann and Gabor A. Somorjai
Volume 22: Catalysis of Organic Reactions,
edited by Robert L. Augustine
Additional Volumes in Preparation

Catalysis of
Organic Reactions
edited by
Robert L. Augustine
Department of Chemistry
Seton Hall University
South Orange, New Jersey
MARCEL DEKKER, INC. New York • Basel
Library of Congress Cataloging in Publication Data
Main entry under title:
Catalysis of organic reactions.
(Chemical industries ; 22)
Papers from the Tenth Conference on the Catalysis
of Organic Reactions, held May 7-9, 1984, at
Williamsburg, VA.
Includes index.
I. Chemistry, Organic-Synthesis-Congresses.
2. Catalysis-Congresses. I. Augustine, Robert L.,
[date). II. Conference on the Catalysis of
Organic Reactions (I 0th : 1984 : Williamsburg, VA.)
III. Series: Chemical industries ; v. 22.
QD262.C35 1985 547.1'395 85-10242
ISBN 0-8247-7263-6
COPYRIGHT© 1985 by MARCEL DEKKER, INC. ALL RIGHTS RESERVED.
Neither this book nor any part may be reproduced or transmitted in any form
or by any means, electronic or mechanical, including photocopying, microfilm-
ing, and recording, or by any information storage and retrieval system, without
permission in writing from the publisher.
MARCEL DEKKER, INC.
270 Madison Avenue, New York, New York 10016
Current printing (last digit):
IO 9 8 7 6 5 4 3 2 I
PRINTED IN THE UNITED STATES OF AMERICA
Preface
About twenty years ago a group of individuals who were involved on a
day to day basis with the application of catalytic processes to organic
synthesis came together to establish a forum for the discussion of the
practical aspects of catalysis in organic chemistry. The result was a
conference held in June, 1966 on Catalytic Hydrogenation and Analogous
Pressure Reactions,! sponsored by the New York Academy of Sciences and
co-chaired by Joseph M. O'Connor of CIBA(presently CIBA-Geigy), Morris
Friefelder of Abbot, and Melvin A. Rebensdorf of Upjohn. This conference
was very successful and two years later in June, 1968, the Second
Conference on Catalytic Hydrogenation and Analogous Pressure Reactions2
was held, chaired by Joseph O'Connor and again sponsored by the New York
Academy of Sciences. The Third Conference3 (June, 1970), chaired by
Melvin A. Rebensdorf and the Fourth Conference4 (September, 1972),
chaired by Paul N. Rylander of Engelhard, were also sponsored by the New
York Academy of Sciences despite the Academy's general policy of not
sponsoring series of conferences in the same area, a fact which attests to
the value of these conferences.
At this stage, however, continuing Academy support for further
conferences was not forthcoming so a small group of active participants in
these previous meetings worked to independently sponsor the next
iii
iv Preface
conference. This group called itself The Organic Reactions Catalysis
Society and in the discussions leading to the formulation of a general policy
for future meetings it became clear that the titles used for the first four
conferences did not accurately describe the groups' changing interests.
Thus, the Fifth Conference on Catalysis in Organic Synthesis5, co-chaired
by Paul Rylander and Harold Greenfield of Uniroyal Chemical was held in
Boston in April, 1975. A result of these conferences was the merging of the
interests of the organic chemists with those of the catalytic chemists.
Further evidence of this development came in 1975 with the affiliation of
the Organic Reactions Catalysis Society (ORCS) with the North American
Catalysis Society. The Sixth Conference on Catalysis in Organic Synthesis6,
chaired by Gerard V. Smith of Southern Illinois University was held in Boston
in May, 1976 in order to have the ORCS biennial conferences held in those
years in which the biennial North American Catalysis Society National
Meetings were not held.
The Seventh Conference on Catalysis in Organic Synthesis?, chaired by
William H. Jones of Merck Sharp and Dohme, was held in Chicago in June,
1978. Throughout this time the interests of the Society were expanding to
include chemical processes and catalyst development. The Eighth
Conference, chaired by William R. Moser of Worcester Polytechnic Institute
and held in New Orleans in June, 1980, reflected this with a change in the
conference title to Catalysis of Organic Reactions.8 The Ninth Conference
on Catalysis of Organic Reactions,9 chaired by John R. Kosak of du Pont,
was held in Charleston, SC in April, 1982. And that brings us to the present,
the Tenth Conference on Catalysis in Organic Reactions held on May, 7-9,
1984, in Williamsburg, VA, which is the topic of this volume.
It is obvious that the Organic Reactions Catalysis Society could not
have reached this milestone without the enthusiastic support of a lot of
people. Particular thanks must go to our "Founding Fathers" who worked so
hard in the 1960's to get the first conferences established: Dale Blackburn
of Smith Kline and French, Jack Campbell of Lilly, Morris Friefelder of
Abbott, William Jones of Merck Sharp and Dohme, Joseph O'Connor of CIBA
(now CIBA Geigy), William Pearlman of Parke-Davis (now Warner Lambert),
Melvin Rebensdorf of Upjohn, Paul Rylander of Engelhard, William Selby of
G.D. Searle, and David Wagner of Hoffman-LaRoche. Thanks must also go
Preface
V
to the New York Academy of Sciences for its support during the formative
years of the Society and to all of the Officers and Directors who have
served over the years to develop the Society into what it is today.
We cannot forget that without participants and speakers there would
be no conferences and I would particularly like to thank our present speakers
for taking the time out of their busy schedules to present aspects of their
work and for being so cooperative in providing manuscripts of their talks so
readily as to facilitate the publication of these proceedings.
The financial support of this conference from the following
corporations is gratefully acknowledged: Air Products and Chemicals,
Allied Corporation, Chemical Data Systems, Degussa, E.I. du Pont de
Nemours and Company, General Electric Company, W.R. Grace and
Company, Hoffman-LaRoche, Merck Sharp and Dohme, The Procter and
Gamble Company, Sandoz, G.D. Searle, Shell Development Company, Smith
Kline and French, Standard Oil Company (SOHIO), Uniroyal Chemical, and
Warner Lambert Company.
The excellent job done by Jean DeRosa in preparing all of the
manuscripts in this volume for publication is greatly appreciated.
References
I. Catalytic Hydrogenation and Analogous Pressure Reactions (J.M.
O'Connor, ed.) Ann. N.Y. Acad. Sci., 145, Art. I, 1-206 (1967).
2. Second Conference .2!!. Catalytic Hydrogenation and Analogous
Pressure Reactions (J.M. O'Connor, ed.), Ann. N.Y. Acad. Sci., 158,
Art. 2, 439-588 (1969).
3. Third Conference .2!!. Catalytic Hydrogenation and Analogous Pressure
Reactions (M.A. Rebensdorf, ed.), Ann. N.Y. Acad. Sci., 172, Art 9, 151-
276 (1970).
4. Fourth Conference on Catalytic Hydrogenation and Analogous
Pressure Reactions (P.N. Rylander, ed.), Ann. N.Y. Acad. Sci., 214
(1973).
5. Catalysis in Organic Synthesis, 1976 (P.N. Rylander and H. Greenfield,
eds.), Academic Press, New York, 1976.
6. Catalysis in Organic Synthesis, 1977 (G.V. Smith, ed.), Academic Press,
New York, 1977.