Ionic liquids:
Gespeichert in:
| Weitere Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH-Verl.
2010
|
| Schriftenreihe: | Handbook of green chemistry
6 : Set 2, Green solvents |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXV, 352 S. Ill., graph. Darst. |
| ISBN: | 9783527325924 9783527315741 |
Internformat
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| 300 | |a XXV, 352 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
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Datensatz im Suchindex
| _version_ | 1804142918454214656 |
|---|---|
| adam_text | Contents
Ionic Liquids and
Creen
Chemistry
-
an Extended Preface
XIII
About the Editors
XXI
List of Contributors
XXIII
Part I Green Synthesis
1
Ί
The Green Synthesis of tonic Liquids
3
Maggel Deetlefs and Kenneth R. Seddon
1.1
The Status Quo of Green Ionic Liquid Syntheses
3
1.2
Ionic Liquid Preparations Evaluated for Greenness
4
1.3
Which Principles of Green Chemistry are Relevant to Ionic
Liquid Preparations?
6
1.4
Atom Economy and the
Ë-factor
7
1.4.1
Atom Economy
7
1.4.2
The E-factor
8
1.5
Strengths, Weaknesses, Opportunities, Threats (SWOT) Analyses
8
1.6
Conductive Heating Preparation of l-Alkyl-S-methylimidazolium
Halide Salts
8
1.7
Purification of l-Alkyl-S-methylimidazolium Halide Salts
12
1.7.1
SWOT Analysis: Conductively Heated Preparation of l-Alkyl-3-
Methylimidazolium Halide Salts and Their Subsequent Purification
14
1.8
Ionic Liquid Syntheses Promoted by Microwave Irradiation
15
1.8.1
Microwave-assisted Versus Traditional Ionic Liquid Preparations
18
1.8.2
SWOT Analysis: Microwave-promoted Syntheses of Ionic Liquids
18
1.9
Syntheses of Ionic Liquids Promoted by Ultrasonic Irradiation
20
1.9.1
SWOT Analysis: Ultrasound-promoted Syntheses of Ionic Liquids
22
1.10
Simultaneous Use of Microwave and Ultrasonic Irradiation to
Prepare Ionic Liquids
23
1.10.1
SWOT Analysis: Simultaneous Use of Microwave and Ultrasonic
Irradiation to Prepare Ionic Liquids
24
1.11
Preparation of Ionic Liquids Using
Microreactors
25
1.11.1
SWOT Analysis: Preparation of Ionic liquids Using
Microreactors
27
VI
Contents
1.
12
1.12.1
1
12.2
1
.13
1
.13.1
1
.14
Purification
of Ionic liquids with Non-halide Anions
28
Purification of
Hydrophobie
Versus Hydrophilic Ionic Liquids
28
SWOT Analyses: Purification of
Hydrophobie
and Hydrophilic
Ionic Liquids
29
D
ecolorization of Ionic Liquids
31
SWOT Analysis: Decolorization of Ionic Liquids
31
Conclusion
34
References
36
Part II Green Synthesis Using Ionic Liquids
39
2
Green Organic Synthesis in Ionic Liquids
41
Peter
Wasserscheid
and JoniJoni
2.1
General Aspects
41
2.1.1
The Extremely Low Vapor Pressure of Ionic Liquids
43
2.1.2
Stability of Ionic Liquids in Organic Reactions
44
2.1.3
Liquid—Liquid Biphasic Organic Reactions
46
2.1.3.1
Tunable Solubility Properties
47
2.1.3.2
Product Isolation from Organic Reactions with Ionic liquids
49
2.1
A Reactive or Catalytic Ionic Liquids in Organic Synthesis
51
2.2
Friedel-Crafts Alkylation
54
2.2.1
Introduction and Technical Background
54
2.2.2
Ionic Liquids in Friedel-Crafts Reaction
-
the Unique
Selling Point
55
2.2.3
Liquid—Liquid Biphasic Catalysis
56
2.2.4
Supported Ionic Liquid Phase (SILP) Friedel-Crafts Catalysis
57
References
59
3
Transition Metal Catalysis in Ionic Liquids
65
Peter
Wasserscheid
3.1
Solubility and Immobilization of Transition Metal Complexes
in Ionic Liquids
65
3.2
Ionic Liquid—Catalyst Interaction
67
3.2.1
Activation of Transition Metal Complexes by Lewis Acidic
Ionic Liquids
68
3.2.2
In Situ Carbene Complex Formation
68
3.3
Distillative Product Isolation from Ionic Catalyst Solutions
70
3.4
New Opportunities for Biphasic Catalysis
72
3.5
Green Aspects of Nanoparticle and Nanocluster Catalysis
in Ionic Liquids
75
3.6
Green Aspects of Heterogeneous Catalysis in Ionic liquids
77
3.7
Green Chemistry Aspects of Hydroformylation Catalysis
in Ionic Liquids
79
3.7.1
Feedstock Solubility
79
3.7.2
Catalyst Solubility and Immobilization
80
Contents
VII
3.7.3
Use of Phosphite ligands in Ionic Liquids
81
3.7.4
Halogen-containing Ionic Liquids Versus Halogen-free
Ionic Liquids in Hydroformylation
81
3.7.5
Hydroformylation in scCC^-Ionic Liquid Multiphasic Systems
82
3.7
Љ
Reducing the Amount of Ionic liquid Necessary
-
the Supported Ionic
Liquid Phase (SILP) Catalyst Technology in Hydroformylation
83
3.8
Conclusion
85
References
85
4
Ionic Liquids in the Manufacture of S-Hydroxymethylfurfural from
Saccharides. An Example of the Conversion of Renewable
Resources to Platform Chemicals
93
Annegret
Stark and
Bernd Ondruschka
4.1
Introduction
93
АЛЛ
Areas of Application for HMF and its Derivatives
95
4.1.1.1
Direct Uses of HMF
95
4.1.1.2
Derivatives of HMF
96
4.1.2
Summary: Application of HMF and Its Derivatives
98
4.2
HMF Manufacture
99
4.2.1
General Aspects of HMF Manufacture
99
4.2.2
Methods of Manufacture of HMF from Fructose
100
4.2.3
Methods of Manufacture of HMF from Sugars Other
Than Fructose
104
4.2
A Deficits in HMF Manufacture
105
4.3
Goals of Study
105
4.4
HMF Manufacture in Ionic liquids
—
Results of Detailed Studies
in the Jena Laboratories
205
4.4.1
Temperature
106
4.4.2
Concentration and Time
106
4.4.3
Effect of Water
108
4.4.4
Effect of Purity
109
4.4.5
Effect of the Choice of Ionic Liquid 111
4.4.6
Other Saccharides
112
4.4.7
Continuous Processing of HMF
114
4.5
Conclusion
127
References
228
5
Cellulose Dissolution and Processing with Ionic Liquids
123
Uwe
Vagt
5.1
General Aspects
223
5.2
Dissolution of Cellulose in Ionic Liquids
227
5.3
Rheological Behavior of Cellulose Solutions in Ionic Liquids
129
5.4
Regeneration of the Cellulose and Recycling of the Ionic Liquid
232
5.5
Cellulosic Fibers
131
5.6
Cellulose Derivatives
134
VIII Contents
5.7
Fractìonatìon
of Biomass with Ionic liquids
134
5.8
Conclusion and Outlook
135
References
135
Part III Ionic Liquids in Green Engineering
137
6
Green Separation Processes with Ionic Liquids
139
Wytze (C. W.) Meindersma,
Ferdy
(S. A
F.)
Onink,
and
André
В.
de Haan
6.1
Introduction
139
6.2
liquid Separations
141
6.2.1
Extraction
141
6.2.1.1
Metal Extraction
141
6.2.1.2
Extraction of Aromatic Hydrocarbons
145
6.2.1.3
Proteins
151
6.2.2
Extractive Distillation
153
6.2.2.1
Conventional Process
153
6.2.2.2
Ionic Liquids in Extractive Distillation
155
6.2.2.3
Conclusions
157
6.3
Environmental Separations
158
6.3.1
Desulfurization and Denitrogenation of Fuels
158
6.3.1.1
Conventional Desulfurization
258
6.3.1.2
Desulfurization with Ionic Liquids
158
6.3.1.3
Oxidative Desulfurization
162
6.3.1.4
Conclusions
163
6.4
Combination of Separations in the Liquid Phase with
Membranes
163
6
A.I Conclusions
164
6.5
Gas Separations
164
6.5.1
Conventional Processes
164
6.5.2
CO2 Separation with Standard Ionic liquids
165
6.5.3
CO2 Separation with Functionalized Ionic Liquids
265
6.5.4
CO2 Separation with Ionic Liquid (Supported) Membranes
266
6.5.5
Olefin—
Paraffin Separations with Ionic Liquids
268
6.5.6
Conclusions
168
6.6
Engineering Aspects
268
6.6.1
Equipment
168
6.6.2
Hydrodynamics
169
6.6.3
Mass Transfer
171
6.6.4
Conclusions
272
6.7
Design of a Separation Process
172
6.7.1
Introduction
172
6.7.2
Application of COSMO-RS
173
6.7.3
Conclusions
274
6.8
Conclusions
175
References
276
Contents
IX
7
Applications of Ionic Liquids in Electrolyte Systems
191
William R. Pitner, Peer
Kirsch, Kentaro
Kawata, and Hirotni Shinohara
7.1
Introduction
191
7.2
Electrolyte Properties of Ionic Liquids
193
7.3
Electrochemical Stability
296
7.4
Dye-sensitized Solar Cells
198
References
200
8
Ionic Liquids as Lubricants
203
Marc Uerdingen
8.1
Introduction
203
8.2
Why Are Ionic Liquids Good Lubricants?
204
8.2.1
Wear and Friction Behavior
204
8.2.2
Pressure Behavior
210
8.2.3
Thermal Stability
210
8.2.4
Viscosity Index and Pour Point
213
8.2.5
Corrosion
215
8.2.6
Electric Conductivity
215
8.2.7
Ionic Greases
216
8.3
Applications, Conclusion and Future Challenges
217
References
218
9
New Working Pairs for Absorption Chillers
221
Matthias
Seiler
and Peter Schwab
9.1
Introduction
221
9.2
Absorption Chillers
222
9.3
Requirements and Challenges
223
9.3.1
Thermodynamics, Heat and Mass Transfer
224
9.3.2
Crystallization Behavior
224
9.3.3
Corrosion Behavior
225
9.3.4
Viscosity
225
9.3.5
Thermal Stability
225
9.4
State of the Art and Selected Results
226
9.5
Abbreviations
228
References
228
Part IV Ionic Liquids and the Environment
233
10
Design of I n herently Safer Ionic Liquids: Toxicology
and
Biodegradation 235
Marianne Matzke, Jürgen
Arning, Johannes
Ranke, Bernd Jastorff,
and Stefan
Stolte
10.1
Introduction
235
10.1.1
The
Т
-SAR
Approach and the Test Kit Concept
236
10.1.2
Strategy for the Design of Sustainable Ionic Liquids
238
X
Contents
10.2
(Eco^oxicity of Ionic Liquids
239
10.2.1
Influence of the Side Chain
243
10.2.2
Influence of the Head Group
254
10.2.3
Influence of the
Anion
255
10.2.4
Toxicity
of Ionic Liquids as a Function of the Surrounding Medium
257
10-2.5
Combination Effects
259
10.2.6
(Quantitative) Structure-Activity Relationships and Modes
of Toxic Action
261
10.2.7
Conclusion
263
10.3
Biodegradability of Ionic Liquids
265
10.3.1
Introduction
265
10.3.2
Testing of Biodegradability
266
10.3.3
Results from
Biodegradation
Experiments
268
10.3.3.1
Biodegradability of Ionic liquid Anions
269
10.3.3.2
Biodegradability of Imidazolium Compounds
283
10.3.3.3
Pyridinium and 4-(Dimethylamino)pyridinium Compounds
284
10.3.3.4
Biodegradability of Other Head Groups
285
10.3.4
Misleading Interpretation of
Biodegradation Data 286
10.3.5
Metabolic Pathways of Ionic Liquid Cations
288
10.3.6
Abiotic Degradation
290
10.3.7
Outlook
290
10.4
Conclusion
290
10.4.1
Toxicity
and (Eco)toxicity of Ionic Liquids
291
10.4.2
Biodegradability of Ionic Liquids
293
10.4.3
The Goal Conflict in Designing Sustainable Ionic Liquids
293
10.4.4
Final Remarks
294
References
295
ΊΊ
Eco-efficiency Analysis of an Industrially Implemented Ionic
Liquid-based Process
-
the BASF BASIL Process
299
Peter
Sáling,
Matthias Maase, and
Uwe
Vagţ
11.1
The Eco-efficiency Analysis Tool
299
11.1.1
General Aspects
299
11.2
The Methodological Approach
299
11.2.1
Introduction
300
11.2.2
What is Eco-efficiency Analysis
? 302
11.2.3
Preparation of a Specific life-cycle Analysis for All Investigated
Products and Processes
303
11.3
The Design of the Eco-efficiency Study of BASIL
303
11.4
Selected Single Results
304
11.4.1
Energy Consumption
304
11.4.2
Global Warming Potential (GWP)
306
11.4.3
Water Emissions
307
11.4.4
The Ecological Fingerprint
307
11.4.5
Cost Calculation
308
Contents
XI
11.5
The Creation of the Eco-efficiency Portfolio
309
11.6
Scenario Analysis
311
11.7
Conclusion
312
11.8
Outlook
313
References
314
12
Perspectives of Ionic Liquids as Environmentally Benign Substitutes
for Molecular Solvents
315
Denise
Ott, Dana Krausen, and Annegret Stark
12.1
Introduction
315
12.2 Evaluation
and Optimization of R&D Processes: Developing
a Methodology
317
12.2.1
Solvent Selection Tools
317
12.2.2
LCA Methodology
318
12.2.3
The ECO Method
319
12.23.1
The Key Objectives
320
12.2.3.2
The Evaluation and Optimization Procedure
321
12.3
Assessment of Ionic Liquid Synthesis
—
Case Studies
322
12.3.1
Synthesis of Ionic Liquids: Extract from the Optimization
Procedure
324
12.3.2
Validation of EFas an Indicator for Several Impact Categories
of the LCA Methodology
326
12.3.3
Comparison of the Life Cycle Environmental Impacts
of the Manufacture of Ionic Liquids with Molecular Solvents
327
12
A Assessment of the Application of Ionic Liquids in Contrast
to Molecular Solvents
329
12
A.I Case Study: Diels-Alder Reaction
329
12.4.1.1
Evaluation of the Solvent Performance
330
12.4.1.2
Evaluation of the Energy Factor EF
330
12.4.1.3
Evaluation of the Environmental and Human Health Factor
EHF
-
Examples
332
12.4Л.4
Evaluation of the Cost Factor CF
332
12.4.1.5
Alternative Ionic Liquid Choices
334
12.4.1.6
Decision Support
334
12.5
Conclusions
335
References
336
index
341
|
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| id | DE-604.BV036437559 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T22:39:24Z |
| institution | BVB |
| isbn | 9783527325924 9783527315741 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-020309982 |
| oclc_num | 705472296 |
| open_access_boolean | |
| owner | DE-1028 DE-83 DE-91G DE-BY-TUM DE-355 DE-BY-UBR |
| owner_facet | DE-1028 DE-83 DE-91G DE-BY-TUM DE-355 DE-BY-UBR |
| physical | XXV, 352 S. Ill., graph. Darst. |
| publishDate | 2010 |
| publishDateSearch | 2010 |
| publishDateSort | 2010 |
| publisher | Wiley-VCH-Verl. |
| record_format | marc |
| series | Handbook of green chemistry |
| series2 | Handbook of green chemistry |
| spelling | Ionic liquids ed. by Peter Wasserscheid ... Weinheim Wiley-VCH-Verl. 2010 XXV, 352 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Handbook of green chemistry 6 : Set 2, Green solvents Ionische Flüssigkeit (DE-588)7548899-1 gnd rswk-swf Grüne Chemie (DE-588)7563215-9 gnd rswk-swf Lösungsmittel (DE-588)4036160-3 gnd rswk-swf Ionische Flüssigkeit (DE-588)7548899-1 s Lösungsmittel (DE-588)4036160-3 s Grüne Chemie (DE-588)7563215-9 s DE-604 Wasserscheid, Peter 1970- (DE-588)12089257X edt Handbook of green chemistry 6 : Set 2, Green solvents (DE-604)BV035406315 6 Digitalisierung UB Regensburg - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020309982&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Ionic liquids Handbook of green chemistry Ionische Flüssigkeit (DE-588)7548899-1 gnd Grüne Chemie (DE-588)7563215-9 gnd Lösungsmittel (DE-588)4036160-3 gnd |
| subject_GND | (DE-588)7548899-1 (DE-588)7563215-9 (DE-588)4036160-3 |
| title | Ionic liquids |
| title_auth | Ionic liquids |
| title_exact_search | Ionic liquids |
| title_full | Ionic liquids ed. by Peter Wasserscheid ... |
| title_fullStr | Ionic liquids ed. by Peter Wasserscheid ... |
| title_full_unstemmed | Ionic liquids ed. by Peter Wasserscheid ... |
| title_short | Ionic liquids |
| title_sort | ionic liquids |
| topic | Ionische Flüssigkeit (DE-588)7548899-1 gnd Grüne Chemie (DE-588)7563215-9 gnd Lösungsmittel (DE-588)4036160-3 gnd |
| topic_facet | Ionische Flüssigkeit Grüne Chemie Lösungsmittel |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020309982&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| volume_link | (DE-604)BV035406315 |
| work_keys_str_mv | AT wasserscheidpeter ionicliquids |