Hydrogen Storage: Based on Hydrogenation and Dehydrogenation Reactions of Small Molecules

Hydrogen Storage: Based on Hydrogenation and Dehydrogenation Reactions of Small Molecules

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Overview

Hydrogen is believed to be the energy source of the future, enabling zero-emission and efficient production of power. This comprehensive publication presents a broad spectrum of various chemical aspects of hydrogen storage. The authors also address global climate change issues, carbon dioxide sequestration problems and CO2-based hydrogen storage.

Product Details

ISBN-13: 9783110534658
Publisher: De Gruyter
Publication date: 01/14/2019
Sold by: Barnes & Noble
Format: NOOK Book
Pages: 391
File size: 22 MB
Note: This product may take a few minutes to download.
Age Range: 18 Years

About the Author

Dr. Thomas Zell, ADAMA Makhteshim Ltd., Beer Sheva, Israel. Dr. Robert Langer, University of Marburg, Marburg, Germany.

Table of Contents

Preface v

List of contributing authors xiii

1 Introduction: hydrogen storage as solution for a changing energy landscape Thomas Zell Robert Langer 1

1.1 Introduction 1

1.2 Current energy landscape - US statistics 2

1.3 Energy storage systems 5

1.3.1 Large scale centralized energy storage 6

1.3.2 Smaller scale grids and distributed energy storage systems 7

1.4 Energy transportation 9

1.5 H2 storage - production of hydrogen 10

1.6 Efficiencies of hydrogen economy 12

1.7 Hydrogen storage - why hydrogen? 13

1.8 Demands on hydrogen storage systems 15

1.9 Classification of hydrogen storage systems 16

1.10 Physical methods for hydrogen storage 17

1.10.1 Compressing gaseous hydrogen (CGH2) 17

1.10.2 Liquid hydrogen (LH2) 20

1.11 Material based methods for hydrogen storage 20

1.11.1 Hydrogen storage by absorption on solids with large surface area 20

1.12 Chemical methods for hydrogen storage 22

1.12.1 Hydride materials 22

1.12.2 Hydrogenation and dehydrogenation reactions of small molecules 24

References 26

2 CO2-based hydrogen storage: CO2 hydrogenation to formic acid, formaldehyde and methanol 35

2.1 Introduction 35

2.2 Methanol 37

2.2.1 Heterogeneous catalyzed hydrogenation to methanol and reforming 37

2.2.2 Homogeneous catalyzed hydrogenation to methanol and reforming 40

2.3 Formic acid 42

2.3.1 CO2 hydrogenation to formic acid 42

2.3.2 Hydrogen generation from formic acid 44

2.3.3 H2 storage in integrated systems via formic acid/formates 46

2.4 Formaldehyde 47

2.4.1 CO2 Hydrogenation to formaldehyde 48

2.4.2 Hydrogen generation from formaldehyde 50

2.5 Conclusion 51

References 52

3 CO2-based hydrogen storage - formic acid dehydrogenation Thomas Zell Robert Langer 57

3.1 Introduction 57

3.2 The concept of formic acid (FA) as hydrogen storage compound 58

3.3 Selected catalytic processes for the hydrogen generation from FA 62

3.4 Main group compounds as catalysts for FA dehydrogenation 62

3.5 Noble metal catalysts for FA dehydrogenation 65

3.6 Base-metal catalysts for FA dehydrogenation 71

3.7 Heterogeneous catalysts for FA dehydrogenation 79

3.8 Catalytic systems for the reversible storage of H2 in FA 82

3.9 Conclusions and outlook 87

References 88

4 CO2-based hydrogen storage - Hydrogen generation from formaldehyde/water Monica Trincado Hansjörg Grützmacher Martin H. G. Prechtl 95

4.1 Introduction 95

4.2 Production of formaldehyde and related technologies 99

4.2.1 Formaldehyde production and metabolism by biological systems 99

4.2.2 Industrial production of formaldehyde 100

4.2.3 Related technologies for formaldehyde synthesis 101

4.3 Aqueous formaldehyde as hydrogen and energy carrier 105

4.3.1 Base promoted dehydrogenation 105

4.3.2 Metal catalyzed dehydrogenation 107

4.4 Future perspectives 118

References 120

5 CO2-based hydrogen storage - hydrogen liberation from methanol/water mixtures and from anhydrous methanol Monica Trincado Matthias Vogt 125

5.1 Introduction 125

5.2 Production of methanol 127

5.2.1 Industrial bulk production 127

5.2.2 Experimental approaches toward the formation of methanol 128

5.3 Aqueous methanol as hydrogen and energy carrier 135

5.3.1 Biological systems 136

5.3.2 Hydrogen production from aqueous methanol in artificial systems 138

5.4 Outlook 165

5.4.1 Hydrogen as sustainable energy carrier and methanol as hydrogen storage material 165

5.4.2 Dehydrogenation of methanol 166

References 168

6 Hydrogenation of carbonyl compounds of relevance to hydrogen storage in alcohols Andrés Suárez 183

6.1 Introduction 183

6.2 Hydrogenation of ketones 185

6.2.1 General considerations 185

6.2.2 Ruthenium and osmium catalysts 186

6.2.3 Iridium catalysts 191

6.2.4 Non-noble metal catalysts 193

6.3 Hydrogenation of esters 195

6.3.1 General considerations 195

6.3.2 Ruthenium and osmium catalysts 197

6.3.3 Iridium catalysts 206

6.3.4 Non-noble metal catalysts 207

6.4 Hydrogenation of amides 211

6.4.1 General considerations 211

6.4.2 Ruthenium catalysts 212

6.4.3 Non-noble metal catalysts 216

6.5 Hydrogenation of carboxylic acids 219

6.5.1 General considerations 219

6.5.2 Noble metal catalysts 220

6.5.3 Non-noble metal catalysts 222

6.6 Conclusions and outlook 223

References 223

7 Dehydrogenation of alcohols and polyols from a hydrogen production perspective Jesús Campos 231

7.1 Introduction 231

7.2 General perspective on acceptorless alcohol dehydrogenation reactions 234

7.3 Ethanol dehydrogenation 245

7.4 Glycerol dehydrogenation 254

7.5 Sugars and sugar alcohol dehydrogenation 258

7.6 Conclusion 262

References 263

8 Hydrogenation of nitriles and imines for hydrogen storage Moran Feller 271

8.1 Introduction 271

8.2 Catalytic hydrogenation of nitriles 273

8.2.1 Nitrile hydrogenation - selectivity issues and homogeneous Ru-based catalysts 273

8.2.2 Homogeneous earth-abundant metals-based catalysts 278

8.2.3 Heterogeneous metals-based catalysts 281

8.3 Imine hydrogenation 284

8.4 Conclusions 285

References 286

9 Transition metal-catalyzed dehydrogenation of amines Daniel L. J. Broere 295

9.1 Introduction 295

9.2 Catalytic dehydrogenation of amines 297

9.2.1 Primary amines to imines and secondary amines 297

9.2.2 Selective catalytic dehydrogenation of primary amines to nitriles 303

9.2.3 Catalytic dehydrogenation of N-heterocycles 306

9.3 Conclusions 318

References 319

10 Homogeneously catalyzed hydrogenation and dehydrogenation reactions - From a mechanistic point of view Zhuofeng Ke Yinwu Li Cheng Hou Yan Liu 327

10.1 Introduction 328

10.2 Non-cooperation mechanisms 330

10.2.1 Oxidative addition/reductive elimination mechanism 330

10.2.2 σ-Bond metathesis mechanism 332

10.3 LB-TM cooperation mechanisms 333

10.3.1 n-Type LB-TM cooperation mechanism 334

10.3.2 n-Type LB-TM cooperation mechanism: (de)aromatization/tautomerization 338

10.3.3 σ-Type LB-TM cooperation mechanism 339

10.3.4 Ligand-innocent non-LB-TM cooperation mechanism 340

10.4 LA-TM cooperation mechanism 340

10.4.1 ρ-Type LA-TM cooperation mechanisms 342

10.4.2 σ-Type LA-TM cooperation mechanism 344

10.4.3 π*-Type LA-TM cooperation mechanism 345

10.4.4 Ligand-innocent non-MLC mechanism in LA-TM systems 345

10.4.5 Hydrogenation/dehydrogenation mechanism in LA-TM systems 346

10.5 LA-LB cooperation (FLP) mechanism 348

10.5.1 H2 activation mechanisms in LA-LB cooperation systems 348

10.5.2 Hydrogenation/dehydrogenation reaction mechanisms in LA-LB cooperation systems 350

10.6 Ambiphilic mechanism 351

10.6.1 H2 activation mechanism in ambiphilic systems 353

10.6.2 Hydrogenation mechanism via ambiphilic cooperation 354

10.7 TM-TM cooperation mechanism 354

10.7.1 Homolytic mechanism via TM-TM cooperation 355

10.7.2 Heterolytic mechanism via TM-TM cooperation 356

10.7.3 Oxidative addition mechanism 356

10.7.4 Hydrogenation/dehydrogenation mechanism in TM-TM systems 357

10.8 Key factors governing the mechanistic preferences 360

10.8.1 The role of the metal and the ligand in MLC 360

10.8.2 Proton shuttle 362

10.9 Concluding remarks 363

References 364

Index 369

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