Homogeneous catalysis: understanding the art
Saved in:
| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Dordrecht [u.a.]
Kluwer Academic Publ.
2004
|
| Subjects: | |
| Links: | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=012853191&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| Physical Description: | XIII, 407 S. Ill., graph. Darst. |
| ISBN: | 1402019998 1402031769 1402020007 |
Staff View
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| 100 | 1 | |a Leeuwen, Piet W. N. M. van |d 1942- |e Verfasser |0 (DE-588)134176987 |4 aut | |
| 245 | 1 | 0 | |a Homogeneous catalysis |b understanding the art |c by Piet W. N. M. van Leeuwen |
| 264 | 1 | |a Dordrecht [u.a.] |b Kluwer Academic Publ. |c 2004 | |
| 300 | |a XIII, 407 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
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| 650 | 7 | |a Homogene katalyse |2 gtt | |
| 650 | 7 | |a Isomerisatie |2 gtt | |
| 650 | 7 | |a Overgangsmetaalcomplexen |2 gtt | |
| 650 | 7 | |a Polymerisatie |2 gtt | |
| 650 | 4 | |a Catalysis | |
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Record in the Search Index
| DE-BY-TUM_call_number | 0302 CHE 330f 03.2004 A 140 |
|---|---|
| DE-BY-TUM_katkey | 1476694 |
| DE-BY-TUM_location | 03 |
| DE-BY-TUM_media_number | 040030136662 |
| _version_ | 1821933059300130816 |
| adam_text | Table
of
contents
Preface
xi
Acknowledgements
xiii
1.
INTRODUCTION
1
1.1
Catalysis
1
1.2
Homogeneous catalysis
6
1.3
Historical notes on homogeneous catalysis
7
1.4
Characterisation of the catalyst
8
1.5
LlGAND EFFECTS
10
1.5.1
Phosphines and phosphites: electronic effects
10
1.5.2
Phosphines and phosphites: steric effects
12
1.5.3
Linear Free Energy Relationships
14
1.5.4
Phosphines and phosphites: bite angle effects
16
1.6
LlGANDS ACCORDING TO DONOR ATOMS
20
1.6.1
Anionie
and neutral hydrocarbyl groups
20
1.6.2
Alkoxy and imido groups as
anionie
ligands
21
1.6.3
Amines, imines, oxazolines and related ligands
21
1.6.4
Phosphines, phosphites, phosphorus amides, phospholes
and related ligands
23
1.6.5
Carbenes, carbon monoxide
24
1.6.6
Common anions
25
vi
Table of contents
2.
ELEMENTARY STEPS
29
2.1
Creation of a vacant site and co-ordination of the
substrate 29
2.2
insertion versus migration
30
2.3 ß-elimination
and de-insertion
35
2.4
oxidative addition
36
2.5
Reductive elimination
39
2.6
cc-Elimination reactions
41
2.7
Cycloaddition reactions involving a metal
42
2.8
Activation of a substrate toward nucleophilic attack
44
2.8.1
Alkenes
44
2.8.2
Alkynes
45
2.8.3
Carbon monoxide
45
2.8.4
Other substrates
46
2.9
σ
-BOND
metathesis
48
2.10
dlhydrogen activation
48
2.11
Activation by Lewis acids
50
2.11.1
Diels-Alder additions
51
2.11.2
Epoxidation
51
2.11.3
Ester condensation
52
2.12
Carbon-to-phosphorus bond breaking
52
2.13
Carbon-to-sulfur bond breaking
55
2.14
Radical reactions
57
3.
KINETICS
63
3.1
introduction
63
3.2
Two-step reaction scheme
63
3.3
Simplifications of the rate equation and the rate-
determining step
64
3.4
Determining the selectivity
68
3.5
Collection of rate data
71
3.6
Irregularities in catalysis
72
4.
HYDROGENATION
75
4.1
Wilkinson s catalyst
75
4.2
Asymmetric
hydrogénation
77
4.2.1
Introduction
77
4.2.2
Cinnamic acid derivatives
79
4.2.3
Chloride versus weakly coordinating anions; alkylphosphines
versus arylphosphines
86
4.2.4
Incubation times
86
Table of
contents
vii
4.3
OVERVIEW
OF
CHIRAL BIDENTATE LIGANDS
86
4.3.1
DuPHOS
86
4.3.2
BINAP
catalysis
87
4.3.3
Chiral
ferrocene based
ligands
89
4.4
Monodentate
ligands
90
4.5
Non-linear effects
93
4.6
Hydrogen transfer
94
5.
ISOMERISATION
101
5.1
Hydrogen shifts
101
5.2
Asymmetric Isomerisation
103
5.3
Oxygen shifts
105
6.
CARBONYLATION OF
METHANOL
AND METHYL
ACETATE
109
6.1
Acetic acid
109
6.2
Process scheme Monsanto process
114
6.3
Acetic anhydride
116
6.4
Other systems
118
6.4.1
Higher alcohols
118
6.4.2
Phosphine-modified rhodium catalysts
119
6.4.3
Other metals
122
7.
COBALT CATALYSED HYDROFORMYLATION
125
7.1
Introduction
125
7.2
Thermodynamics
126
7.3
Cobalt catalysed processes
126
7.4
Cobalt catalysed processes for higher alkenes
128
7.5 kuhlmann
cobalt hydroformylation process
130
7.6
рноѕрнпче
modified cobalt catalysts: the shell process
131
7.7
Cobalt carbonyl phosphine complexes
і
32
7.7.1
Carbonyl species
132
7.7.2
Phosphine derivatives
135
8.
RHODIUM CATALYSED HYDROFORMYLATION
139
8.1
Introduction
139
8.2
Triphenylphosphine as the ligand 1
41
8.2.1
The mechanism
141
8.2.2
Ligand effects and kinetics
144
8.2.3
Regioselectivity
147
8.2.4
Process description, rhodium-tpp
149
8.2.5
Two-phase process, tppts:
Ruhrchemie/Rhône-Poulenc
150
8.2.6
One-phase catalysis, two-phase separation
152
viii Table of
contents
8.3
DlPHOSPHINES AS LIGANDS
153
8.3.1
Xantphos ligands:
tuneable bite angles
155
8.4
Phosphites as ligands
161
8.4.1
Electronic
effects
161
8.4.2
Phosphites: steric effects
162
8.5
DlPHOSPHITES
163
8.6
Asymmetric Hydroformylation
166
8.6.1
Rhodium catalysts: diphosphites
166
8.6.2
Rhodium catalysts: phosphine-phosphite ligands
168
9.
ALKENE OLIGOMERISATION
175
9.1
Introduction
175
9.2
Shell-Higher-Olefins-Process
176
9.2.1
Oligomerisation
176
9.2.2
Separation
180
9.2.3
Purification, isomerisation, and metathesis
180
9.2.4
New catalysts
181
9.3
Ethenetrimerjsation
184
9.4
OTHER
ALICENE
OLIGOMERISATION REACTIONS
187
10.
PROPENE
POLYMERISATION
191
10.1
Introduction to polymer chemistry
191
10.1.1
Introduction to
Ziegler Natta
polymerisation
193
10.1.2
History of homogeneous catalysts
196
10.2
Mechanistic investigations
199
10.2.1
Chain-end control: syndiotactic polymers
199
10.2.2
Chain-end control: isotactic polymers
201
10.3
ANALYSIS BY I3C NMR SPECTROSCOPY
202
10.3.1
Introduction
202
10.3.2
Chain-end control
204
10.3.3
Site control mechanism
204
10.4
THE DEVELOPMENT OF METALLOCENE CATALYSTS
206
10.4.1
Site control: isotactic polymers
206
10.4.2
Site control: syndiotactic polymers
209
10.4.3
Double stereoselection: chain-end and site control
211
10.5
agost1c interactions
212
10.6
the effect of dihydrogen
214
10.7
further work using
propene
and other alkenes
215
10.8
non-metallocene etm catalysts
220
10.9
Late transition metal catalysts
222
Table of contents
ix
11.
HYDROCYANATION OF ALKENES
229
11.1
THE ADIPONITRILE PROCESS
229
11.2
LlGAND EFFECTS
233
12.
PALLADIUM CATALYSED CARBONYLATIONS OF
ALKENES
239
12.1
Introduction
239
12.2
Polyketone
239
12.2.1
Background and history
239
12.2.2
Elementary steps: initiation
241
12.2.3
Elementary steps: migration reactions
244
12.2.4
Elementary steps: chain termination, chain transfer
250
12.2.5
Elementary steps: ester formation as chain termination
252
12.3
LlGAND EFFECTS ON CHAIN LENGTH
256
12.3.1
Polymers
256
12.3.2
Ligand effects on chain length: Propanoate
258
12.3.3
Ligand effects on chain length:
Oligomers
261
12.4
Ethene/propene/CO terpolymers
262
12.5
Stereoselective
styrene
/СО
copolymers
263
13.
PALLADIUM CATALYSED CROSS-COUPLING REACTIONS
271
13.1
Introduction
271
13.2
allylic alkylation
273
13.3
Heck reaction
281
13.4
Cross-coupling reaction
286
13.5 heteroatom-carbon
bond formation
290
13.6
Suzuki reaction
294
14.
EPOXID
ATION
299
14.1
Ethene and
Propene oxide
299
14.2
Asymmetric EPOxiDATiON
301
14.2.1
Introduction
301
14.2.2
Katsuki-Sharpless asymmetric epoxidation
301
14.2.3
The Jacobsen asymmetric epoxidation
305
14.3
Asymmetric hydroxylation of alkenes with osmium
tetroxide 308
14.3.1
Stoichiometric reactions
308
14.3.2
Catalytic reactions
312
14.4
Jacobsen asymmetric ring-opening of epoxides
314
14.5
Epoxidations with dioxygen
316
x
Table of contents
15.
OXIDATION WITH DIOXYGEN
319
15.1
Introduction
319
15.2
The
Wacker
reaction
320
15.3 Wacker
type reactions
324
15.4
TEREPHTHALIC ACID
327
15.5
PPO
332
16.
ALKENE METATHESIS
337
16.1
introduction
337
16.2
The mechanism
339
16.3
Reaction Overview
343
16.4
Well-characterised tungsten and molybdenum
catalysts
344
16.5
Ruthenium catalysts
346
16.6
Stereochemistry
349
16.7
Catalyst decomposition
350
16.8
Alkynes
352
16.9
Industrial applications
354
17.
ENANTIOSELECTIVECYCLOPROP
ANATION 359
17.1
Introduction
359
17.2
Copper catalysts
360
17.3
Rhodium catalysts
364
17.3.1
Introduction
364
17.3.2
Examples of rhodium catalysts
367
18.
HYDROSILYLATION
371
18.1
introduction
371
18.2
Platinum catalysts
373
18.3
Asymmetric palladium catalysts
378
1
8.4
Rhodium catalysts for asymmetric
ketone
reduction
380
19.
C
-Н
FUNCTIONALISATION
387
19.1
Introduction
387
19.2
Electron-rich metals
389
1
9.3
Hydrogen transfer reactions of alkanes
394
19.4
borylation of alkanes
395
19.5
The
Murai
reaction
396
19.6
Catalytic
σ
-BOND
metathesis
397
19.7
ELECTROPHILIC CATALYSTS
397
SUBJECT INDEX
403
|
| any_adam_object | 1 |
| author | Leeuwen, Piet W. N. M. van 1942- |
| author_GND | (DE-588)134176987 |
| author_facet | Leeuwen, Piet W. N. M. van 1942- |
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| dewey-ones | 541 - Physical chemistry |
| dewey-raw | 541/.395 |
| dewey-search | 541/.395 |
| dewey-sort | 3541 3395 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Physik |
| format | Book |
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| id | DE-604.BV019390451 |
| illustrated | Illustrated |
| indexdate | 2024-12-20T11:59:38Z |
| institution | BVB |
| isbn | 1402019998 1402031769 1402020007 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-012853191 |
| oclc_num | 54966334 |
| open_access_boolean | |
| owner | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM DE-11 DE-355 DE-BY-UBR |
| owner_facet | DE-91G DE-BY-TUM DE-703 DE-19 DE-BY-UBM DE-11 DE-355 DE-BY-UBR |
| physical | XIII, 407 S. Ill., graph. Darst. |
| publishDate | 2004 |
| publishDateSearch | 2004 |
| publishDateSort | 2004 |
| publisher | Kluwer Academic Publ. |
| record_format | marc |
| spellingShingle | Leeuwen, Piet W. N. M. van 1942- Homogeneous catalysis understanding the art Homogene katalyse gtt Isomerisatie gtt Overgangsmetaalcomplexen gtt Polymerisatie gtt Catalysis Metallorganische Verbindungen (DE-588)4038906-6 gnd Homogene Katalyse (DE-588)4160579-2 gnd Übergangsmetallkomplexe (DE-588)4131837-7 gnd |
| subject_GND | (DE-588)4038906-6 (DE-588)4160579-2 (DE-588)4131837-7 |
| title | Homogeneous catalysis understanding the art |
| title_auth | Homogeneous catalysis understanding the art |
| title_exact_search | Homogeneous catalysis understanding the art |
| title_full | Homogeneous catalysis understanding the art by Piet W. N. M. van Leeuwen |
| title_fullStr | Homogeneous catalysis understanding the art by Piet W. N. M. van Leeuwen |
| title_full_unstemmed | Homogeneous catalysis understanding the art by Piet W. N. M. van Leeuwen |
| title_short | Homogeneous catalysis |
| title_sort | homogeneous catalysis understanding the art |
| title_sub | understanding the art |
| topic | Homogene katalyse gtt Isomerisatie gtt Overgangsmetaalcomplexen gtt Polymerisatie gtt Catalysis Metallorganische Verbindungen (DE-588)4038906-6 gnd Homogene Katalyse (DE-588)4160579-2 gnd Übergangsmetallkomplexe (DE-588)4131837-7 gnd |
| topic_facet | Homogene katalyse Isomerisatie Overgangsmetaalcomplexen Polymerisatie Catalysis Metallorganische Verbindungen Homogene Katalyse Übergangsmetallkomplexe |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=012853191&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT leeuwenpietwnmvan homogeneouscatalysisunderstandingtheart |
Table of contents
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Branch Library Chemistry
| Call Number: |
0302 CHE 330f 03.2004 A 140
Floor plan |
|---|---|
| Copy 1 | Available for loan On Shelf |