Catalyst Separation

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CATALYST SEPAR
RR AND RECYCLING
P R TION, RECOVE
Catalysis by Metal Complexes
Vo lume 30
Editors:
Brian James,
University of British Columbia, Vancouver, Canada
Piet W. N. M. van Leeuwen,
University of Amsterdam, The Netherlands
Advisory Board:
Albert S.C. Chan,
The Hong Kong Polytechnic University, Hong Kong
Robert Crabtee,
Yale University, U.S.A.
David Cole-Hamilton,
University of St Andrews, Scotland
István Horváth,
Eotvos Lorand University, Hungary
Kyoko Nozaki,
University of To kyo, Japan
Robert Waymouth,
Stanford University, U.S.A.
The titles published in this series are listed at the end of this volume.
CATALYST SEPAR
A
RR
AND RECYCLING
Chemistry and Process Design
Edited by
DAVID J. COLE-HAMILTON
EaStCHEM, School of Chemistry, University of St. Andrews, S t. Andrews,
Fife, Scotland
and
ROBERT P. TOOZE
Sasol Technology (UK) Ltd., St. Andrews,
Fife, Scotland
P R TION, RECOVE
A C.I.P. Catalogue record for this book is available from the Library of Congress.
ISBN-10 1-4020-4086-5 (HB)
ISBN-13 978-1-4020-4086-3 (HB)
ISBN-10 1-4020-4087-3 (e-book)
ISBN-13 978-1-4020-4087-0 (e-book)
Published by Springer,
P.O. Box 17, 3300 AA Dordrecht, The Netherlands.
www.springer.com
w
Printed on acid-free paper
All Rights Reserved
© 2006 Springer
No part of this work 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, with the exception
of any material supplied specifically for the purpose of being entered
and executed on a computer system, for exclusive use by the purchaser of the work.
Printed in the Netherlands.
TABLE OF CONTENTS
CHAPTER 1 HOMOGENEOUS CATALYSIS – ADVANTAGES AND
PROBLEMS ....................................................................................... 1
1.1 Catalysis............................................................................................................ 1
1.2 Catalyst Stability ............................................................................................. 4
1.2.1 THERMALLY INDUCED DECOMPOSITION.............................................. 4
1.2.2 CHEMICALLY INDUCED DECOMPOSITION ............................................ 5
1.2.3 PHYSICAL LOSS FROM THE PROCESS ..................................................... 6
1.3
Layout of the Book .......................................................................................... 6
1.4
References ........................................................................................................ 8
CHAPTER 2 CLASSICAL HOMOGENEOUS CATALYST SEPARATION
TECHNOLOGY ............................................................................... 9
2.1.1 Coverage of Chapter ........................................................................................ 9
2.2 General Process Considerations...................................................................... 9
2.3 Everything is a Reactor.................................................................................. 10
2.4 Overview of Separation Technologies .......................................................... 10
2.4.1 TRADITIONAL COBALT WITH CATALYST DECOMPOSITION.......... 10
2.4.2 UNION CARBIDE-DAVY GAS RECYCLE PROCESS .............................. 11
2.4.3 LIQUID RECYCLE ........................................................................................ 12
2.4.4 BIPHASIC SYSTEMS; WATER-ORGANIC................................................ 14
2.4.5 INDUCED PHASE SEPARATION ............................................................... 14
2.4.6 NON-AQUEOUS PHASE SEPARATION .................................................... 15
2.4.6.1 NAPS Using a Non-Polar Catalyst .................................................................
16
2.4.6.2 NAPS Using a Polar Catalyst .........................................................................
17
2.4.6.3 Ligand Structure and Solubility Properties ....................................................
17
2.5 Hypothetical processes - How Might the Product be Separated from the
Catalyst? ......................................................................................................... 18
2.5.1 PROPENE HYDROFORMYLATION........................................................... 19
2.5.2 1-OCTENE HYDROFORMYLATION ......................................................... 20
2.5.3 ALLYL ALCOHOL........................................................................................ 20
2.5.4 METHOXYVINYLNAPHTHALENE ........................................................... 21
2.5.5 SEPARATION TECHNOLOGY FOR LESS STABLE CATALYSTS ........ 22
2.5.5.1 Mitsubishi TPPO/TPP Separation ...................................................................
22
2.5.5.2 Organic Polymer for Catalyst Stabilization.....................................................
22
2.6 Real-World Complications ............................................................................22
2.6.1 ORGANOPHOSPHORUS LIGAND DEGRADATIONS ..............................23
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