Aspects of Homogeneous Catalysis: A Series of Advances

349 Pages·1984·14.004 MB·English

by  Arno Behr (auth.), Renato Ugo (eds.)

ASPECTS OF HOMOGENEOUS
CATALYSIS
Volume 5
ASPECTS OF
HOMOGENEOUS
CATALYSIS
A Series of Advances
EDITED BY
RENATOUGO
ISTlTl;TO 01 CHIMICA GENERALE ED INORGANICA
lINIVERSITA III MILANO
VOLUME 5
D. Reidel Publishing Company
lIo..
"
A MEMBER OF THE KLUWER ACADEMIC PUBLISHERS GROUP
Dordrecht / Boston / Lancaster
The Library of Congress Cataloged the First Issue of this Work as Follows:
Ugo, Renato (ed.)
Aspects of homogeneous catalysis. vol. 1.
1970-
Milano, C. Manfredi.
v. illus. 25 cm. annual.
'A Series of Advances'.
Editor: 1970- R. Ugo.
1. Catalysis-Periodicals. I. Ugo, Renato (ed.).
QD501.A83 541'395 72-623953
ISBN-13: 978-94-009-6365-8 e-ISBN-13: 978-94-009-6363-4
DOl: 10.1007/978-94-009-6363-4
Published by D. Reidel Publishing Company,
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All Rights Reserved
© 1984 by D. Reidel Publishing Company.
Softcover reprint of the hardcover 1st edition 1984
No part of the material protected by this copyright notice may be reproduced or
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Editorial Board
L. Vaska
The Clarckson College of Technology (U.S.A.)
E. W. Stern
Engelhard Industries (U.S.A.)
B. L. Shaw
The University of Leeds (U.K.)
A. Sacco
The University of Bari (Italy)
G. Pregaglia
Montecatini-Edison S.p.A. (Italy)
B. James
The University of British Columbia (Canada)
L. Marko
University of Chemical Industries Academy of Science (Hungary)
M. Volpin
Institute of Organo-Element Compounds Academy of Science (USSR)
A. Misono
University of Tokyo (Japan)
J. Tsuji
Tokyo Institute of Technology (Japan)
J. Garnett
University of New South Wales (Australia)
H. Mimoun
Institut Fran9ais du Petrole (France)
W. Keirn
Institut fur Technische Chemie und Petrolchernie (W. Germany)
P. MaitUs
Sheffield University (England)
J. Roth
Air Products and Chemicals Inc. (U.S.A.)
Contents of Volume 5
Telomerization of Dienes by Homogeneous Transition Metal Catalysts 3
Arno Behr
1. Introduction 5
2. Telomerization of Butadiene 5
3. Telomerization of Isoprene 48
4. Telomerization of Further 1,3-Dienes 58
5. Telomerization of 1,2-Dienes 62
6. Cotelomerizations 65
7. Acknowledgement 66
8. References 67
The Cobalt-Catalyzed Synthesis of Pyridine and Its Derivatives 75
H. B6nnemann and W. Brijoux
1. Introduction 77
2. Survey of the Organocobalt Catalysts 83
3. The Application of the Cobalt-Catalyzed Pyridine Synthesis 105
4. Experimental Details 121
5. Mechanistic Considerations 133
6. Experimental Optimization of the Catalytic Turnover Number 140
7. Synthesis of the Catalysts 147
8. Related Reactions 160
9. Acknowledgement 190
10. Glossary of Abbreviations 190
11. References 191
vii
viii Contents
Homogeneous Catalysis Using Iodide-Promoted Rhodium Catalysts 197
D. J. Drury
1. Introduction 198
2. Rhodium lodocarbonyls 198
3. Catalysis of the Water Gas Shift Reaction 200
4. Alcohol Carbonylation 201
5. Carbonylation of Esters and Ethers 205
6. Reductive Carbonylation of Esters and Ethers 207
7. Hydrocarboxylation of Olefms 208
8. Hydrocarboxylation of Formaldehyde 211
9. Hydrogenolysis Reactions 211
10. Homologation of Carboxylic Acids 213
11. Heterogenisation of the Rhll Catalyst 213
12. Conclusions 214
13. References 214
Recent Developments in the Homogeneous Catalysis of the Water-Gas Shift Reaction 217
Richard M Laine and Robert B. Wilson. Jr.
1. Introduction 217
2. Background 219
3. Chemistry of the WGSR Catalytic Cycles 220
4. Catalysis of the WGSR under Basic Conditions 227
5. Catalysis of the WGSR under Acidic or Neutral Conditions 233
6. References 238
Homologation of Alcohols, Acids and Their Derivatives by CO + H2 241
Giuseppe Braca and Glauco Sbrana
1. Introduction 242
2. Homologation of Alcohols 243
3. Carbonylation and Homologation of Ethers 279
4. Homologation of Aldehydes 284
5. Homologation of Carboxylic Acids 287
6. Homologation of Carboxylic Acid Esters 291
7. Homologation Reactions with Heterogeneous Catalysts 296
8. Homologation Reactions with CO and H20 296
9. Reaction Mechanism 298
Contents ix
10. Concluding Remarks 323
11. Addendum 324
12. Glossary of Abbreviations 331
13. References 331
Index 339
ASPECTS OF HOMOGENEOUS
CATALYSIS
Volume 5
Telomerization of Dienes by
Homogeneous Transition Metal Catalysts
ARNO BEHR
institut jUr Technische Chemie und Petrolchemie der
Rheinisch-Westftiltschen Technischen Hochschule Aachen,
Womnger Weg 1, D-51 00 Aachen, F.R.G.
1. Introduction 5
2. Telomerization of Butadiene 5
2.1. MECHANISTIC ASPECTS 5
2.1.1. Palladium Compounds 6
2.1.2. Nickel Compounds 12
2.1.3. Rhodium Compounds 14
2.1.4. Platinum and Further Group VIII Metals 15
2.2. TELOMERIZATION WITH O-H-NUCLEOPHILES 16
2.2.1. Alcohols 17
2.2.2. Phenols 20
2.2.3. Silanols 21
2.2.4. Carboxylic Acids 21
2.2.5. Hydroxycarboxylic Esters 23
2.2.6. Boric Acids 23
2.2.7. Water 24
2.3. TELOMERIZATION WITH N-H-NUCLEOPHILES 25
2.3.1. Amines 25
2.3.2. Ammonia and Ammonium Salts 30
2.4. TELOMERIZATION WITH C-H-NUCLEOPHILES 30
2.4.1. Carbonyl Compounds 31
2.4.2. Nitroalkanes 33
2.4.3. Nitriles 34
2.4.4. Sulfones 34
2.5. TELOMERIZATION WITH Si-H-NUCLEOPHILES 35
2.6. SULFINIC ACIDS AND SULFUR DIOXIDE 36
3
R. Ugo (ed.), Aspects of Homogeneous Catalysis, Vol. 5,3-73.
© 1984 by D. Reidel Publishing ComlNlnv.
4 Telomerization of dienes
2.7. TELOMERIZATION WITH TWO-CENTRE NUCLEOPHILES 38
2.7.1. Diols 39
2.7.2. Diamines 39
2.7.3. Aminoa1cohols 39
2.7.4. Oximes 40
2.7.5. Hydrazones 40
2.7.6. Imines 41
2.7.7. Acylamino Ketones 41
2.7.8. Acyloins 42
2.7.9. Organodisilanes 42
2.8. TELOMERIZATION WITH C=X DOUBLE BOND NUCLEOPHILES 43
2.8.l. Aldehydes 43
2.8.2. Ketones 44
2.8.3. Carbon Dioxide 45
2.8.4. Schiff Bases 46
2.8.5. Isocyanates 46
2.9. TELOMERIZATION WITH ORGANOMAGNESIUM COMPOUNDS 46
2.l0. CARBOXY-TELOMERIZATION 47
2.10.1. Alcohols 47
2.l 0.2. Acids 48
2.10.3. Amines and Ammonia 48
2.l1. UTIUZA TION OF THE BUTADIENE TELOMERS 48
3. Telomerization of Isoprene 48
3.1. TELOMERIZA TION WITH OH-NUCLEOPHILES 51
3.1.1. Alcohols 51
3.1.2. Carboxylic Acids 52
3.1.3. Water 53
3.2. TELOMERIZA TION WITH NH-NUCLEOPHILES S4
3.3. TELOMERIZATION WITH CH-, SiH- AND SiSi-NUCLEOPHILES 56
3.4. TELOMERIZATION WITH C=X DOUBLE BOND NUCLEOPHILES S7
3.5. CARBOXY -TELOMERIZA TION S7
3.6. UTILIZA TION OF THE ISOPRENE TELOMERS S8
4. Telomerization of Further 1,3·Dienes 58
4.1. 1, 3-PENT ADIENE S9
4.2. 2,3-DIMETHYL-l ,3-BUT ADIENE 61