Heterogeneous Catalysis and Fine Chemicals III: Proceedings of the 3rd International Symposium, Poitiers, April 5-8, 1993

739 Pages·1993·31.43 MB·English

by  M. Guisnet

Studies in Surface Science and Catalysis 78
HETEROGENEOUS CATALYSIS AND FINE CHEMICALS 111
This Page Intentionally Left Blank
Studies in Surface Science and Catalysis
Advisory Editors: B. Delmon and J.T. Yates
VOI. 7a
HETEROGENEOUS
CATALYSIS AND FINE
CHEMICALS 111
Proceedingso f the 3rd International Symposium, Poitiers, April 5-8,1993
Editors
M. Guisnet, J. Barbier, J. Barrault, C. Bouchoule, D. Duprez, G. Perot and
C. Montassier
Laboratoire de Catalyse en Chimie Organique (URA CNRS 3501,F aculte des
Sciences, Universite de Poitiers, 40Avenue du Recteur Pineau, 86022
Poitiers, France
-
ELSEVIER Amsterdam -London New York -Tokyo 1993
ELSEVIER SCIENCE PUBLISHERS B.V.
Sara Burgerhartstraat 25
P.O. Box211.1000AE Amsterdam,The Netherlands
Library of Congress Cataloging-in-Publication Data
Heterogeneous catalysis and fine chemicals I11 proceedings of the
3rd international symposium. POltierS. April 5-8. 1993 / editors. M.
...
Guisnet Let al.1 (Laboratoire de catalyse en chinle organique.
Faculte des sciences. UniVerSite de Poitiers).
p. cn. -- (Studies in surface science and catalysis , 78)
Includes Inoexes.
ISBN 0-444-89063-7 (acid-free1
1. Heterogeneous catalysis--Congresses. I. Guisnet. M.
I!. Universite de Poitiers. Laboratoire de catalyse en chlmle
organique. ::I. Series
Oi505.H4632 '993
541,3'95--dc23 93-26769
CIP
ISBN 0-444-89063-7
0 1993 Elsevier Science Publishers B.V. All rights reserved
No part of this publication may be reproduced, stored in a retrieval system or transmitted in any
form or by any means, electronic, mechanical, photocopying, recording or otherwise, without
the prior written permission of the publisher, Elsevier Science Publishers B.V., Copyright &
Permissions Department, P.O. Box 521,1000 AM Amsterdam, The Netherlands.
Special regulations for readers in the U.S.A. - This publication has been registered with the
Copyright Clearance Center Inc. (CCC), Salem, Massachusetts. Information can be obtained from
the CCC about conditions under which photocopies of parts of this publication may be made in
the U.S.A. All other copyright questions, including photocopying outside of the U.S.A., should be
referred tothe copyright owner, Elsevier Science Publishers B.V., unless otherwise specified.
No responsibility is assumed by the publisher for any injury and/or damage to persons or
property as a matter of products liability, negligence or otherwise, or from any use or operation
of any methods, products, instructions or ideas contained in the material herein.
This book is printed on acid-free paper.
Printed in the Netherlands
V
CONTENTS
Foreword xiii
Preface xv
Scientific Committee xvi
Organizing Committee xv i
Financial Support xvii
PLENARY LECTURES
Trends and Opportunities with modern hydrogenation catalysts
I. Dodgson 1
Catalytic oxidations with hydrogen peroxide : new and selective catalysts
M.G. Clerici 21
Basic Catalysts and Fine Chemicals
H. Hattori 35
Solvent effects in Heterogeneous Catalysis : Application to the synthesis
of Fine Chemicals
L. Gilbert and C. Mercier 51
RESEARCH PAPERS
1. HYDROGENATION AND RELATED REACTIONS
Phenyl vs. carbomethoxy group effect on selectivity during hydrogenation
and exchange of a,b-unsaturated esters over modified and unmodified
deuterated Raney nickel
G.V. Smith, R. Song, J.M. Delich and M. Bartok 67
The role of the support in selective hydrogenations promoted by Cu/AI,O,
N. Ravasio, M. Antenori and M. Gargano 75
Liquid-phase hydrogenation of acrolein to ally1 alcohol on supported cobalt
catalysts
Y. Nitta. T. Kato and T. lmanaka 83
Selective hydrogenation of aromatic aldehydes using precious metal
catalysts on new high surface-area TiO, supports
M. Bankmann, R. Brand, A. Freund and T. Tacke 91
vi
Kinetic comparison of enantioselective hydrogenations
A. Tungler, T. Tarnai, A. Deak, S. Kemhy, A. Gybry, T. Math6
and J. Petr6 99
Enantioselective metal complex catalysts immobilized on inorganic supports
via carbamate links
B. Pugin and M. Muller 107
Stereoselective thymol hydrogenation : comparative study of
charcoal-supported, platinum, rhodium and iridium catalysts
M. Besson, L. Bullivant, N. Nicolaus-Dechamp and P. Gallezot 115
The selective hydrogenation of 6-chloro-2(1H )-hydroxyquinoxaline-4-oxides
to 6-chloro-2(1H )-quinoxalinone
R.E. Malz Jr., M.P. Reynolds and C.J. Fagouri 123
Study of the hydrogenation of methyl benzoate to benzaldehyde on various
metal oxides
A. Aboulayt, A. Chambellan, M. Marzin, J. Saussey, F. Mauge,
J.C. Lavalley, C. Mercier and R. Jacquot 131
Enantioselective hydrogenation of a-ketoacids using platinum catalysts
modified with cinchona alkaloids
H.U. Blaser and H.P. Jalett 139
Surface organometallic chemistry on metals ; selective hydrogenation of
citral on silica supported rhodium modified by tetra-n-butyl germanium, tin
and lead
B. Didillon, J.P. Candy, F. Le Peletier, O.A. Ferretti and J.M. Basset 147
Hydrogenation of citral in the liquid phase over new bimetallic Ni-M
catalysts
supported on graphite
J. Court, J. Jablonski and S. Hamar-Thibault 155
Hydrogenation of cinnamaldehyde and citral over Ru supported catalysts
S. Galvagno, C. Milone, G. Neri, A. Donato, R. Pietropaolo 163
Selective hydrogenation of cawone on Pt and Pt-Au catalysts
G. Del Angel, R. Melendrez, V. Bertin, J.M. Dominguez, P. Marecot
and J. Barbier 171
Selective catalytic hydrogenation of bifunctional compounds over
amorphous nickel alloys
B. Tbrbk, A. Molnar, K. Borszeky, E. Toth-KBdar and I. Bakonyi 179
vii
Stereoselective hydrogenation of D-fructose to D-rnannitol on skeletal
and supported copper containing catalysts
M. Hegedus, S. Gobolos and J.L. Margitfalvi 187
-
Furfural Hydrogen reactions, manipulation of activity and selectivity of
the catalyst
T.B.L.W. Marinelli, V. Ponec, C.G. Raab and J.A. Lercher 195
Selective hydrogenation of a, b unsaturated compounds in the
presence of cobalt catalysts
J. Barrault, M. Blanchard, A. Derouault, M. Ksibi and M.I. Zaki 203
Selective hydrogenation of crotonaldehyde over Pt derived catalysts
C.G. Raab, M. Englisch, T.B.L.W. Marinelli and J.A. Lercher 21 1
Crotonaldehyde hydrogenation over Pt-TiO, catalysts : variations of
activity and selectivity with the partial pressure of crotonaldehyde
R. Makouangou-Mandilou, R. Touroude and A. Dauscher 219
Selective hydrogenation of fatty acid ethyl esters on sepiolite-supported
Ni and Ni-Cu catalysts
F.M. Bautista, J.M. Campelo, A. Garcia, R. Guardeiio, D. Luna,
J.M. Marinas and M.C. Ordoiiez 227
Selective hydrotreatment of rapeseed oil on nickel-cerium mixed oxides
modified by Al additive
A. Alouche, R. Hubaut, J.P. Bonnelle, Ph. Davies and D. Lamberi 235
Kinetics of the liquid-phase stereoselective hydrogenation of
44ertbutylphenol over rhodium catalyst
D.Yu. Murzin. A.I. Allachverdiev and N.V. Kul’kova 243
Liquid phase catalytic hydrogenation of benzophenone : Role of metal
support interaction, bimetallic catalysts, solvents and additives
P.S. Kumbhar and the late R.A. Rajadhyaksha 251
Solvent effects in selective hydrogenation : Catalytic hydrogenation of
Acetamido-4 hydroxy-2 butyrophenone
F. Grass, J.M. Grosselin and C. Mercier 259
Factors influencing activity and selectivity of palladium catalysts
J. Petro, T. Mallat, A. Tungler, T. Mathe and E. Polyanszky 267
Selective hydrogenation of maleic anhydride by modified copper
chromite catalysts
G.L. Castiglioni, M. Gazzano, G. Stefani and A. Vaccari 275
viii
Selective hydrogenation of dinitriles to arninotriles on Raney catalysts
S.B. Ziernecki 283
Hydrogenation of dinitriles into diarnines. Influence of the nature of dinitrile
on activity and selectivity of the reaction
P. Marion, M. Joucla, C. Taisne and J. Jenck 29 1
Selective hydrogenation of 3-butenonitrile and 2-butenonitrile on palladium
exchanged titanium pillared montrnorillonite
A. Lamesch, H. del Castillo, P. Vandetwegen, L. Daza, G. Jannes
and P. Grange 299
One step synthesis of dissyrnetrical arnines R,NR' from nitriles in the
presence of copper catalysts
J. Barrault, S. Brunet, N. Essayern, A. Piccirelli, C. Guirnon and
J.P. Garnet 305
A process for coproduction of mono- and diarninoalkylated glycols
K.S. Hayes and T.A. Johnson 31 3
New process for isophoronediarnine synthesis
J.P. Gillet, J. Kervennal and M. Pralus 32 1
Catalytic synthesis of 2-rnethylpyrazine over Zn-Cr-O/Pd. A simplified
kinetic scheme
L. Forni and R. Miglio 329
Properties of sol-gel derived Ru/Cu/SiO, catalysts and role of water in
the selective hydrogenation of benzene to cyclohexene with the catalysts
F. Mizukami, S.4 Niwa, S. Ohkawa and A. Katayarna 337
The partial hydrogenation of benzene and of toluene over ruthenium
catalysts - The effect of salt addition on the selectivity to
(methyl)-cyclohexenes
M. Soede, E.J.A.X. van de Sandt, M. Makkee and J.J.F. Scholten 345
Shape-selectivity of Pt on carbon fibers catalysts
S. Kogan, M.V. Landau, M. Herskowitz and J.E. Koresh 353
On the XPS-surface characterization of activated carbons resp.
Pd/C catalysts and a correlation to the catalytic activity
R. Burrneister, B. Despeyroux, K. Deller, K. Seibold and P. Albers 361
Thiophene synthesis by dehydrogenation of?etrahydrothiophene on
chromium catalysts
A. Cornrnarieu, E. Arretz, D. Duprez and C. Guirnon 369
ix
II. OXIDATION
Partial oxidation of water-insoluble alcohols over Bi-promoted Pt on alumina.
Electrochemical characterization of the catalyst in its working state
T. Mallat, 2. Bodnar and A. Baiker 377
Selective oxidation reactions over vanadium silicate molecular sieves
P.R. Hari Prasad Rao, K. Ramesh Reddy, A.V. Ramaswamy
and P. Ratnasamy 385
Selective oxidation of organic compounds over the large pore
Beta-Ti zeolite
M.A. Camblor, A. Corma, A. Martinez, J. Perez-Pariente and J. Primo 393
Selective photocatalytic oxidation of hydrocarbon compounds over zeolites
0. Beaune, A. Finiels, P. Geneste, P. Graffin, A. Guida, J.L. Olive
and A. Saeedan 40 1
Photocatalytic oxygenation of hydrocarbons on TiO,/iron-porphyrin-hybrid
catalysts
E. Polo, R. Amadelli, V. Carassiti and A. Maldotti 409
Selective oxidation of alkenes on a zeolite supported iron phthalocyanine
catalyst
A. Zsigmond, F. Notheisz, M. Bartok and J.E. Backvall 41 7
Some physical correlations with the catalytic activity of Mo(VI)-grafted
carboxylated resins used as epoxidation catalysts
E. Tempesti, E. Ranucci, C.L. Bianchi, V. Ragaini, L. Giuffre,
G. Airoldi and C. Mazzocchia 425
Photocatalyzed oxidation of 1,4-pentanedioI on UV-illuminated suspensions
of ZrTiO, powders
J.A. Navio, M. Garcia Gomez, M.A. Pradera-Adrian and
J. Fuentes-Mota 43 1
Selective electrocatalytic oxidation of sucrose on smooth and upd-lead
modified platinum electrodes in alkaline medium
P. Parpot, K.B. Kokoh, B. Beden, E.M. Belgsir, J.-M. Leger and
C. Lamy 439
Selective oxidation of substituted aromatics using different peroxides
C. Marchal, A. Tuel and Y. Ben Taarit 447
Catalytic hydroxylation of phenol by hydrogen peroxide. Kinetic study and
comparison between solid acids and titanosilicates
M. Allian, A. Germain, T. Cseri and F. Figueras 455