Ionic liquids in synthesis:
Saved in:
| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2003
|
| Edition: | 1. reprint. |
| Series: | Green chemistry
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XVI, 364 S. Ill., graph. Darst. |
| ISBN: | 3527305157 |
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| adam_text | Titel: Ionic liquids in synthesis
Autor: Wasserscheid, Peter
Jahr: 2003
Contents
Preface XI
Contributors XV
1 Introduction 1
2 Synthesis and Purification of Ionic Liquids 7
2.1 Synthesis oflonic Liquids 7
2.1.1 Introduction 7
2.1.2 Quaternization Reactions 9
2.1.3 Anion-exchange Reactions 12
2.1.3.1 Lewis Acid-based Ionic Liquids 12
2.1.3.2 Anion Metathesis 14
2.1.4 Purification of Ionic Liquids 17
2.1.5 Conclusions 19
2.2 Quality Aspects and Other Questions Related
to Commercial Ionic Liquid Production 21
2.2.1 Introduction 21
2.2.2 Quality Aspects of Commercial Ionic Liquid Production 22
2.2.2.1 Color 23
2.2.2.2 Organic Starting Materials and other Volatiles 24
2.2.2.3 Halide Impurities 25
2.2.2.4 Protic Impurities 26
2.2.2.5 Other Ionic Impurities from Incomplete Metathesis Reactions
2.2.2.6 Water 27
2.2.3 Upgrading of Commercial Ionic Liquids 27
2.2.4 Scaling-up of Ionic Liquid Synthesis 28
2.2.5 HSE data 29
2.2.6 Future Price of Ionic Liquids 30
2.2.7 Intellectual Property Aspects Regarding Ionic Liquids 31
2.3 Synthesis of Task-specific Ionic Liquids 33
Contents
3 Physicochemical Properties of Ionic Liquids 41
3.1 Melting Points and Phase Diagrams 41
3.1.1 Introduction 41
3.1.2 Determination of Liquidus Ranges 43
3.1.2.1 Melting points 43
3.1.2.2 Upper limit decomposition temperature 44
3.1.3 Effect of Ion Sizes on Salt Melting Points 45
3.1.3.1 Anion size 46
3.1.3.2 Mixtures of anions 47
3.1.3.3 Cation size 48
3.1.3.4 Cation symmetry 49
3.1.4.1 Imidazolium salts 50
3.1.4.2 Imidazolium substituent alkyl chain length 50
3.1.4.3 Branching 52
3.1.5 Summary 53
3.2 Viscosity and Density of Ionic Liquids 56
3.2.1 Viscosity of Ionic Liquids 56
3.2.1.1 Viscosity measurement methods 56
3.2.1.2 Ionic liquid viscosities 59
3.2.2 Density of Ionic Liquids 65
3.2.2.1 Density measurement 66
3.2.2.2 Ionic liquid densities 66
3.3 Solubility and Solvation in Ionic Liquids 68
3.3.1 Introduction 68
3.3.2 Metal Salt Solubility 70
3.3.2.1 Halometalate salts 70
3.3.2.2 Metal complexes 70
3.3.3 Extraction and Separations 72
3.3.3.1 Anionic extractants 73
3.3.3.2 Organic extractants 73
3.3.4 Organic Compounds 75
3.3.5 Conclusions 79
3.4 Gas Solubilities in Ionic Liquids 81
3.4.1 Introduction 81
3.4.2 Experimental Techniques 83
3.4.2.1 Gas solubilities and related thermodynamic properties
3.4.2.2 Stoichiometric technique 84
3.4.2.3 Gravimetric technique 85
3.4.2.4 Gas chromatography 85
3.4.3 Gas Solubilities 86
3.4.3.1 Water vapor 86
3.4.3.2 Other gases 88
3.4.4 Applications 89
3.4.4.1 Reactions involving gases 89
3.4.4.2 Gas separations 90
Contents | VII
3.4.4.3 Extraction of solutes from ionic liquids with
compressed gases or supercritical fluids 92
3.4.5 Summary 91
3.5 Polarity 94
3.5.1 Chromatographic Measurements 94
3.5.2 Absorption Spectra 96
3.5.3 Fluorescence Spectra 99
3.5.4 Refractive Index 99
3.5.5 Organic Reactions 100
3.5.5.1 Alkylation of sodium 2-naphthoxide 100
3.5.5.2 Diels-Alder reactions 100
3.5.5.3 Photochemical reactions 101
3.5.6 General Conclusions 102
3.6 Electrochemical Properties of Ionic Liquids 103
3.6.1 Electrochemical Potential Windows 104
3.6.2 Ionic Conductivity 209
3.6.3 Transport Properties 118
4 Molecular Structure and Dynamics 127
4.1 Order in the Liquid State and Structure 127
4.1.1 Neutron Diffraction 127
4.1.2 Formation of Deuteriated Samples 128
4.1.3 Neutron Sources 129
4.1.3.1 Pulsed (spallation) neutron sources 129
4.1.3.2 Reactor sources 129
4.1.4 Neutron Cells for Liquid Samples 130
4.1.5 Examples 131
4.1.5.1 Binary mixtures 131
4.1.5.2 Simple salts 133
4.1.6 X-ray Diffraction 134
4.1.6.1 Cells for liquid samples 135
4.1.6.2 Examples 235
4.1.7 Extended X-ray Absorption Fine-structure Spectroscopy 139
4.1.7.1 Experimental 140
4.1.7.2 Examples 142
4.1.8 X-ray Reflectivity 145
4.1.8.1 Experimental set-up 146
4.1.8.2 Examples 146
4.1.9 Direct Recoil Spectrometry (DRS) 147
4.1.9.1 Experimental set-up 148
4.1.9.2 Examples 149
4.1.10 Conclusions 149
4.2 Quantum Mechanical Methods for Structure Elucidation 252
4.2.1 Introduction 152
4.2.3 Ion-pair Models and Possible Corrections 153
VIII Contents
4.2.4 Ab Initio Structures of Ionic Liquids 154
4.2.5 DFT Structure of l-Methyl-3-nonylimidazolium
Hexafluorophosphate 255
4.2.6 Additional Information Obtained from Semi-empirical
and Ab Initio Calculations 156
4.3 Molecular Dynamics Simulation Studies 157
4.3.1 Performing Simulations 157
4.3.2 What can we Learn? 159
4.4 Translational Diffusion 162
4.4.1 Main Aspects and Terms of Translational Diffusion 162
4.4.2 Use of Translational Diffusion Coefficients 164
4.4.3 Experimental Methods 165
4.4.4 Results for Ionic Liquids 166
4.5 Molecular Reorientational Dynamics 168
4.5.1 Introduction 168
4.5.2 Experimental Methods 168
4.5.3 Theoretical Background 269
4.5.4 Results for Ionic Liquids 272
5 Organic Synthesis 274
5.1 Stoichiometric Organic Reactions and Acid-Catalyzed Reactions
in Ionic Liquids 174
5.1.1 Stoichiometric Organic Reactions 275
5.1.1.1 Molten salts as reagents 275
5.1.1.2 Reactions in chloroaluminate{III) and related ionic liquids 277
5.1.1.3 Reactions in neutral ionic liquids 181
5.1.2 Acid-Catalyzed Reactions 192
5.1.2.1 Electrophilic substitutions and additions 191
5.1.2.2 Friedel-Crafts alkylation reactions 196
5.1.2.3 Friedel-Crafts acylation reactions 203
5.1.2.4 Cracking and isomerization reactions 208
5.2 Transition Metal Catalysis in Ionic Liquids 213
5.2.1 Why use Ionic Liquids as Solvents for Transition Metal Catalysis? 217
5.2.1.1 Their nonvolatile natures 227
5.2.1.2 New opportunities for biphasic catalysis 218
5.2.1.3 Activation of a transition metal catalyst in ionic liquids 220
5.2.2 The Role of the Ionic Liquid 220
5.2.2.1 The ionic liquid as innocent solvent 221
5.2.2.2 Ionic liquid as solvent and co-catalyst 221
5.2.2.3 Ionic liquid as solvent and ligand/ligand precursor 222
5.2.2.4 Ionic liquid as solvent and transition metal catalyst 225
5.2.3 Methods of Analysis of Transition Metal Catalysts in Ionic Liquids 226
5.2.4 Selected Examples of the Application of Ionic Liquids
in Transition Metal Catalysis 229
5.2.4.1 Hydrogenation 229
5.2.4.2 Oxidation reactions 232
5.2.4.3 Hydroformylation 234
5.2.4.4 Heck, Suzuki, Stille, and Negishi coupling reactions 241
5.2.4.5 Dimerization and oligomerization reactions 244
5.2.5 Concluding Remarks 252
5.3 Ionic Liquids in Multiphasic Reactions 258
5.3.1 Multiphasic Reactions: General Features, Scope, and Limitations 258
5.3.2 Multiphasic Catalysis: Limitations and Challenges 259
5.3.3 Why Ionic Liquids in Multiphasic Catalysis? 261
5.3.4 Different Technical Solutions to Catalyst Separation through
the Use of Ionic Liquids 263
5.3.5 Immobilization of Catalysts in Ionic Liquids 266
5.3.6 Scaling up Ionic Liquid Technology from
Laboratory to Continuous Pilot Plant Operation 270
5.3.6.1 Dimerization of alkenes catalyzed by Ni complexes 271
5.3.6.2 Alkylation reactions 275
5.3.6.3 Industrial use of ionic liquids 277
5.3.7 Concluding Remarks and Outlook 278
5.4 Multiphasic Catalysis with Ionic Liquids in Combination
with Compressed C02 281
5.4.1 Introduction 281
5.4.2 Catalytic Reaction with Subsequent Product Extraction 282
5.4.3 Catalytic Reaction with Simultaneous Product Extraction 282
5.4.4 Catalytic Conversion of C02 in an Ionic Liquid/scC02
Biphasic Mixture 283
5.4.5 Continuous Reactions in an Ionic Liquid/Compressed C02 System 283
5.4.6 Concluding Remarks and Outlook 287
6 Inorganic Synthesis 289
6.1 Directed Inorganic and Organometallic Synthesis 289
6.1.1 Coordination Compounds 289
6.1.2 Organometallic Compounds 290
6.1.3 Other Reactions 292
6.1.4 Outlook 293
6.2 Making of Inorganic Materials by Electrochemical Methods 294
6.2.1 Electrodeposition of Metals and Semiconductors 294
6.2.1.1 General considerations 294
6.2.1.2 Electrochemical equipment 295
6.2.1.3 Electrodeposition of less noble elements 297
6.2.1.4 Electrodeposition of metals that can also be obtained from water 300
6.2.1.5 Electrodeposition of semiconductors 303
6.2.2 Nanoscale Processes at the Electrode/Ionic Liquid Interface 305
6.2.2.1 General considerations 305
6.2.2.2 The scanning tunneling microscope 305
6.2.2.3 Results 306
6.2.3 Summary 316
X Contents
7 Polymer Synthesis in Ionic Liquids 319
7.1 Introduction 319
7.2 Acid-catalyzed Cationic Polymerization and Oligomerization 320
7.3 Free Radical Polymerization 324
7.4 Transition Metal-catalyzed Polymerization 326
7.4.1 Ziegler-Natta Polymerization of Ethylene 326
7.4.2 Late Transition Metal-catalyzed Polymerization of Ethylene 327
7.4.3 Metathesis Polymerization 328
7.4.4 Living Radical Polymerization 329
7.5 Preparation of Conductive Polymers 331
7.6 Conclusions 332
8 Biocatalytic Reactions in Ionic Liquids 336
8.1 Introduction 336
8.2 Biocatalytic Reactions and their Special Needs 336
8.3 Examples of Biocatalytic Reactions in Ionic Liquids 339
8.3.1 Whole-cell Systems and Enzymes other than Lipases in Ionic Liquids 339
8.3.2 Lipases in Ionic Liquids 342
8.4 Conclusions and Outlook 345
9 Outlook 348
Index 356
|
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| indexdate | 2024-07-09T19:18:31Z |
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| spelling | Ionic liquids in synthesis P. Wasserscheid ... (ed.) 1. reprint. Weinheim Wiley-VCH 2003 XVI, 364 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Green chemistry Composés inorganiques - Synthèse Composés organiques - Synthèse Solutions ioniques Inorganic compounds Synthesis Ionic solutions Organic compounds Synthesis Chemische Synthese (DE-588)4133806-6 gnd rswk-swf Elektrolytlösung (DE-588)4133913-7 gnd rswk-swf Ionische Flüssigkeit (DE-588)7548899-1 gnd rswk-swf Lösungsmittel (DE-588)4036160-3 gnd rswk-swf Chemische Synthese (DE-588)4133806-6 s Lösungsmittel (DE-588)4036160-3 s Elektrolytlösung (DE-588)4133913-7 s DE-604 Ionische Flüssigkeit (DE-588)7548899-1 s 1\p DE-604 Wasserscheid, Peter 1970- Sonstige (DE-588)12089257X oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010530146&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Ionic liquids in synthesis Composés inorganiques - Synthèse Composés organiques - Synthèse Solutions ioniques Inorganic compounds Synthesis Ionic solutions Organic compounds Synthesis Chemische Synthese (DE-588)4133806-6 gnd Elektrolytlösung (DE-588)4133913-7 gnd Ionische Flüssigkeit (DE-588)7548899-1 gnd Lösungsmittel (DE-588)4036160-3 gnd |
| subject_GND | (DE-588)4133806-6 (DE-588)4133913-7 (DE-588)7548899-1 (DE-588)4036160-3 |
| title | Ionic liquids in synthesis |
| title_auth | Ionic liquids in synthesis |
| title_exact_search | Ionic liquids in synthesis |
| title_full | Ionic liquids in synthesis P. Wasserscheid ... (ed.) |
| title_fullStr | Ionic liquids in synthesis P. Wasserscheid ... (ed.) |
| title_full_unstemmed | Ionic liquids in synthesis P. Wasserscheid ... (ed.) |
| title_short | Ionic liquids in synthesis |
| title_sort | ionic liquids in synthesis |
| topic | Composés inorganiques - Synthèse Composés organiques - Synthèse Solutions ioniques Inorganic compounds Synthesis Ionic solutions Organic compounds Synthesis Chemische Synthese (DE-588)4133806-6 gnd Elektrolytlösung (DE-588)4133913-7 gnd Ionische Flüssigkeit (DE-588)7548899-1 gnd Lösungsmittel (DE-588)4036160-3 gnd |
| topic_facet | Composés inorganiques - Synthèse Composés organiques - Synthèse Solutions ioniques Inorganic compounds Synthesis Ionic solutions Organic compounds Synthesis Chemische Synthese Elektrolytlösung Ionische Flüssigkeit Lösungsmittel |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010530146&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT wasserscheidpeter ionicliquidsinsynthesis |