Organofluorine Chemistry: Principles and Commercial Applications

651 Pages·1994·18.91 MB·English

by  R. E. Banks

Organofluorlne
Chemistry
Principles and Commercial
Applications
TOPICS IN APPLIED CHEMISTRY
Series Editors: Alan R. Katritzky, FRS
Kenan Professor of Chemistry
University of Florida, Gainesville, Florida
Gebran J. Sabongi
Laboratory Manager, Encapsulation Technology Center, 3M
St. Paul, Minnesota
BIOCATALYSTS FOR INDUSTRY
Edited by Jonathan S. Dordick
CHEMICAL TRIGGERING
Reactions of Potential Utility in Industrial Processes
Gebran J. Sabongi
THE CHEMISTRY AND APPLICATION OF DYES
Edited by David R. Waring and Geoffrey Hallas
HIGH-TECHNOLOGY APPLICATIONS OF ORGANIC COLORANTS
Peter Gregory
INFRARED ABSORBING DYES
Edited by Masaru Matsuoka
LEAD-BASED PAINT HANDBOOK
Jan W. Gooch
ORGANOFLUORINE CHEMISTRY
Principles and Commercial Applications
Edited by R. E. Banks, B. E. Smart, and J. C. Tatlow
POLY(ETHYLENE GLYCOL) CHEMISTRY
Biotechnical and Biomedical Applications
Edited by J. Milton Harris
RADIATION CURING
Science and Technology
Edited by S. Peter Pappas
RESORCINOL
Its Uses and Derivatives
Hans Dressler
STRUCTURAL ADHESIVES
Edited by S. R. Hartshorn
TARGET SITES FOR HERBICIDE ACTION
Edited by Ralph C. Kirkwood
A Continuation Order Plan is available for this series. A continuation order will bring delivery of each
new volume immediately upon publication. Volumes are billed only upon actual shipment. For further
information please contact the publisher.
Organofluorine
Chemistry
Principles and Commercial
Applications
Edited by
R. E. Banks
The University of Manchester Institute
of Science and Technology (UMIST)
Manchester, United Kingdom
B. E. Smart
DuPont Central Research & Development
Wilmington, Delaware
and
J.
C. Tatlow
Editorial Office of the Journal
of Fluorine Chemistry
Birmingham, United Kingdom
Springer Science+ Business Media, LLC
Library of Congress Cata1oging-in-Publication Data
Organofluorine chemistry : principles and commercial applications /
edited by R.E. Banks, B.E. Smart, and J.C. Tatlow.
p. cm. — (Topics 1n applied chemistry)
Includes bibliographical references and Index.
ISBN 978-1-4899-1204-6
1. Organofluorine compounds. I. Banks, R. E. (Ronald Eric),
1932- . II. Smart, B. E. (Bruce E.) III. Tatlow, J. C.
IV. Series.
QD305.H15074 1994
661' .891—dc20 94-26835
CIP
10 98765432
ISBN 978-1-4899-1204-6 ISBN 978-1-4899-1202-2 (eBook)
DOI 10.1007/978-1-4899-1202-2
©1994 Springer Science+Business Media New York
Originally published by Plenum Press, New York in 1994
Softcover reprint of the hardcover 1st edition 1994
All rights reserved
No part of this book may be reproduced, stored in a retrieval system, or transmitted in any
form or by any means, electronic, mechanical, photocopying, microfilming, recording, or
otherwise, without written permission from the Publisher
Contributors
Y. W. Alsmeyer, Fluorochemical Process Technology Center, 3M Company, St. Paul,
Minnesota 55144-1000
Madhu Anand, Air Products and Chemicals, Inc., Allentown, Pennsylvania 18195-
1501
Wolfgang K. Appel, Hauptlaboratorium, Hoechst AG, D-6230 Frankfurt-am-Main
80, Germany
Bruce E. Baker, DuPont Speciality Chemicals, Jackson Laboratory, Chambers Works,
Deepwater, New Jersey 08023
R. E. Banks, Department of Chemistry, The University of Manchester Institute of
Science and Technology, Manchester M60 lQD, England
BemdA. Bloch, RLMTC, Hoechst Celanese Corporation, Summit, New Jersey 07901
Ian J. Brass, Air Products PLC, Walton-on-Thames, Surrey KT12 4RZ, England
David Cartwright, Zeneca Agrochemicals, Jeallott's Hill Research Station, Brack
nell, Berkshire RG 12 6EY, England
W. V. Childs, Fluorochemical Process Technology Center, 3M Company, St. Paul,
Minnesota 55144-1000
Richard A. Du Boisson, PeR Inc., Gainesville, Florida 32602
Philip Neil Edwards, Zeneca Pharmaceuticals, Aldedey Park, Macclesfield, Cheshire
SKI04TG, England
Arthur J. Elliott, Halocarbon Products Corporation, North Augusta, South Carolina
29841-0369
A. Engel, Bayer AG, Research and Development-Dyes and Pigments, D-51368
Leverkusen 1, Germany
v
vi Contributors
Andrew E. Feiring, DuPont Central Research & Development Department, Experi
mental Station, Wilmington, Delaware 19880-0328
Peter Field, PGF Associates Ltd., Buxton, Derbyshire SK17 6EW, England
R. M. Flynn, Fluorochemical Process Technology Center, 3M Company, St. Paul,
Minnesota 55144-1000
S. W. Green, Rhone-Poulenc Chemicals Ltd., Avonmouth, Bristol BS11 9HP, England;
present address: 69 South Road, Kingswood, Bristol BS 15 2JF, England
Donald F. Halpern, Ohmeda, P.P.D., Murray Hill, New Jersey 07076; present address:
44 Murray Hill Square, Murray Hill, New Jersey 07974.
K. J. Herd, Bayer AG, Research and Development-Dyes and Pigments, D-51368
Leverkusen 1, Germany
J. P. Hobbs, Air Products and Chemicals, Inc., Allentown, Pennsylvania 18195-1501
Takeshi Inoi, Technical Division, Chisso Corporation, Tokyo, Japan; present address:
8-8-6 Sugita, Isogo-ku, Yokohama-shi, Kanagawa-ken 236, Japan
tNobuo Ishikawa, F & F Research Center, Shizushin Building, Minato-ku, Tokyo
107, Japan
Bernard Langlois, Laboratoire de Chimie Organique III, Universite Claude Bernard
Lyon I, 69622 Villeurbanne Cedex, France
Andre Lantz, Atochem, Centre de Recherche Rhone-Alpes, 69310 Pierre-Benite,
France
Anestis L. Logothetis, DuPont Elastomers, Experimental Station, Wilmington, Dela
ware 19880-0328
Kenneth C. Lowe, Mammalian Physiology Unit, Life Science Department, Univer
sity of Nottingham, University Park, Nottingham NG7 2RD, England
Ganpat Mani, Allied-Signal Inc., Fluorine Products Division, Morristown, New
Jersey 07962-1139
Guiseppe Marchionni, AusimontIMontefluos, MontedisonIMontefluos Group,
20021 Bollate, Milano, Italy
Harubisa Miyake, Research Center, Asahi Glass Co. Ltd., Kanagawa-ku, Yokohama
221, Japan
tDeceased.
Contributors vii
J. S. MoilIiet, Zeneca Agrochemicals, Huddersfield HD2 IFF, England; present
address: BNFL Fluorochemicals, Springfields, Salwick, Preston PR4 OXJ, England
G. G. I. Moore, Fluorochemical Process Technology Center, 3M Company, St. Paul,
Minnesota 55144-1000
Yohnosuke Ohsaka, Daikin Industries, Ltd., Chemical Division, 1-1 Nishi Hitotsuya,
Settsu-shi, Osaka 566, Japan; present address: 1-16-5 Shirakawa, !baraki, Osaka,
Japan
Ralph J. De Pasquale, AusimontiMontefluos, MontedisonIMontefluos Group, 20021
Bollate, Milano, Italy; present adddress: 5500 Atlantic View, St. Augustine, Florida
32084
Richard L. Powell, ICI Klea, Runcorn Technical Centre, Runcorn, Cheshire WA7
4QD, England
Nandakumar S. Rao, DuPont Speciality Chemicals, Jackson Laboratory, Chambers
Works, Deepwater, New Jersey 08023
v.
N. M. Rao, DuPont Central Research & Development, Experimental Station,
Wilmington, Delaware 19880-0262
George A. Shia, Allied-Signal Inc., Fluorine Products Division, Buffalo Research
Laboratory, Buffalo, New York 14210
Dario Sianesi, AusimontiMontefluos, MontedisonIMontefluos Group, 20021 Bollate,
Milano, Italy
R. N. F. Simpson, RMne-Poulenc Chemicals Ltd., Avonmouth, Bristol BSll 9Hp,
England; present address: Fluoro Systems Ltd., Abbots Leigh, Bristol BS8 3Rp,
England
D. S. L. Slinn, RMne-Poulenc Chemicals Ltd., Avonmouth, Bristol BSll 9Hp,
England; present address: Fluoro Systems Ltd., Abbots Leigh, Bristol BS8 3RP,
England
Bruce E. Smart, DuPont Central Research & Development, Experimental Station,
Wilmington, Delaware 19880-0328
J. C. Smeltzer, Fluorochemical Process Technology Center, 3M Company, St. Paul,
Minnesota 55144-1000
J. Hugo Steven, ICI Klea, Runcorn Technical Centre, Runcorn, Cheshire WA7 4QD,
England
Michael StObbe, Hauptlaboratorium, Hoechst AG, D-6230 Frankfurt-am-Main 80,
Germany
viii Contributors
J. C. Tatlow, Editorial Office of the Journal of Fluorine Chemistry, 30 Grassmoor
Road, Kings Norton, Birmingham B38 8Bp, England
Claude Wakselman, CNRS-CERCOA, 94320 Thiais, France
A. J. Woytek, Air Products and Chemicals Inc., Industrial Gas Division, Allentown,
Pennsylvania 18105
Masaaki Yamabe, Research Center, Asahi Glass Co. Ltd., Kanagawa-ku, Yokohama
221, Japan
Preface
During the past fifteen years commercial interest in compounds containing carbon
fluorine bonds has burgeoned beyond all expectations, mainly owing to business
opportunities arising from work on biologically active fluoroorganics-particularly
agrochemicals, the relentless search for new markets for fluoropolymers and fluoro
carbon fluids, developments in the field of medical diagnostics, and the drive to find
replacements for ozone-depleting CFCs and Halon fire-extinguishing agents. Judging
the situation to warrant the publication of a comprehensive collection of up-to-date
reviews dealing with commercial organofluorine compounds within a single volume
of manageable size (and hence reasonable cost), we were delighted to be invited by
Plenum Publishing Corporation to produce a suitable book.
In order to provide an authentic and wide-ranging account of current commercial
applications of fluoroorganic materials, it clearly was necessary to assemble a sizeable
team of knowledgeable contributing authors selected almost entirely from industry.
Through their efforts we have been able to produce an almost complete coverage of
the modem organofluorochemicals business in a manner designed to attract a reader
ship ranging from experts in the field, through chemists and technologists currently
unaware of the extent of industrial involvement with fluoroorganics, to students of
applied chemistry. Promised chapters dedicated to perfluoroolefin oxides and 18F
labeling of radiopharmaceuticals failed to materialize. This is somewhat unfortunate
in view of our aim to achieve comprehensive coverage of the subject. However, not
only do other chapters touch on these topics, but an excellent 149-page review,
Fluorine-I8 Labeling of Radiopharmaceuticals (National Academy Press, Washing
ton DC, 1990) by Michael R. Kilbourn is available gratis from The Board on Chemical
Sciences and Technology, National Research Council, 2101 Constitution Avenue NW,
Washington, D.C. 20418, U.S.A. Finally we must emphasize that the production of
this book has been a team effort and our sincere thanks go to all those who have
contributed: librarians, typists, the staff at Plenum, co-workers and colleagues of
authors, and-preeminently-the collaborating authors themselves. Sadly, one of our
authors, Professor Nobuo Ishikawa, died in 1991, and we respectfully dedicate this
book to his memory.
Employment of such a large number of contributing authors, coupled with the
busy lives they lead and the need to have manuscripts cleared for publication by the
ix