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Hydrogen Release from Ammonia Borane University of Pennsylvania ScholarlyCommons Publicly Accessible Penn Dissertations Spring 2010 Hydrogen Release From Ammonia Borane Daniel W. Himmelberger University of Pennsylvania, [email protected] Follow this and additional works at: https://repository.upenn.edu/edissertations Part of the Inorganic Chemistry Commons, Oil, Gas, and Energy Commons, and the Sustainability Commons Recommended Citation Himmelberger, Daniel W., "Hydrogen Release From Ammonia Borane" (2010). Publicly Accessible Penn Dissertations. 158. https://repository.upenn.edu/edissertations/158 This paper is posted at ScholarlyCommons. https://repository.upenn.edu/edissertations/158 For more information, please contact [email protected]. Hydrogen Release From Ammonia Borane Abstract Development of a safe and efficient storage medium for hydrogen is integral to its use as an alternative energy source. The overall goal of the studies described in this dissertation was to investigate the use of a chemical hydride, ammonia borane (AB (19.6 wt% H2)), as a potentially efficient material for drhy ogen storage. The specific goals of this study were both to develop new efficient methods for increasing the rate and extent of H2-release from AB and to elucidate the important mechanistic pathways and intermediates in these reactions. Significant achievements that resulted from this work are that AB H2-release is activated in the presence of either ionic liquids or bases. For example, an AB H2-release reaction carried out at 110 °C in 50 wt% ionic liquid liberated over 2 equivalents H2 in 15 minutes. Reducing ionic liquid loading to 20 wt% at 110 oC yielded a higher materials weight percent (11.4 mat wt%), while still having fast release rates: 2 equivalents in ~2.5 hours. The addition of the strong nitrogen base 1,8-bis(dimethylamino)naphthalene, Proton Sponge™, to ionic liquid solutions of AB increased the AB H2release rate at 85 °C, with over 2 equivalents of H2 achieved within 3 h. Additional Proton Sponge increased the rate of release; however, the mat wt% of H2 decreased since the Proton Sponge added significant weight ot the system. Solid state and solution 11B NMR and DSC studies of reactions in progress allowed the identification of initial and final oductspr in the H2-release reactions and helped elucidate the overall reaction pathway. The initial formation of diammoniate of diborane, the key intermediate in dehydropolymerization of ammonia borane, was promoted by the addition of ionic liquids. Subsequent H2-release resulted in the formation of polyaminoborane then polyborazylene. Proton Sponge increased the release rate of the second equivalent of H2 by a newly proposed anionic polymerization mechanism. The final product was identified yb solid-state 11B NMR and proved to be a sp2-framework of polyborazylene which formed regardless of base additive or amount/type of ionic liquid. Degree Type Dissertation Degree Name Doctor of Philosophy (PhD) Graduate Group Chemistry First Advisor Dr. Larry G. Sneddon Keywords ammonia borane, hydrogen, energy, fuel cell Subject Categories Inorganic Chemistry | Oil, Gas, and Energy | Sustainability This dissertation is available at ScholarlyCommons: https://repository.upenn.edu/edissertations/158 HYDROGEN RELEASE FROM AMMONIA BORANE Daniel W. Himmelberger A DISSERTATION in Chemistry Presented to the Faculties of the University of Pennsylvania in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy 2010 Supervisor of Dissertation _____________________ Professor Larry G. Sneddon, Blanchard Professor of Chemistry Graduate Group Chairperson _____________________ Professor Gary A. Molander, Hirschmann-Makineni Professor of Chemistry Dissertation Committee Professor Christopher B. Murray, Richard Perry University Professor of Chemistry Professor So-Jung Park, Assistant Professor of Chemistry Professor Bradford B. Wayland, Professor of Chemistry, Temple Univeristy ABSTRACT HYDROGEN RELEASE FROM AMMONIA BORANE Daniel W. Himmelberger Supervisor: Professor Larry G. Sneddon Development of a safe and efficient storage medium for hydrogen is integral to its use as an alternative energy source. The overall goal of the studies described in this dissertation was to investigate the use of a chemical hydride, ammonia borane (AB (19.6 wt% H 2)), as a potentially efficient material for hydrogen storage. The specific goals of this study were both to develop new efficient methods for increasing the rate and extent of H 2-release from AB and to elucidate the important mechanistic pathways and intermediates in these reactions. Significant achievements that resulted from this work are that AB H 2-release is activated in the presence of either ionic liquids or bases. For o example, an AB H 2-release reaction carried out at 110 C in 50 wt% ionic liquid liberated o over 2 equivalents H 2 in 15 minutes. Reducing ionic liquid loading to 20 wt% at 110 C yielded a higher materials weight percent (11.4 mat-wt%), while still having fast release rates: 2 equivalents in ~2.5 hours. The addition of the strong nitrogen base 1,8- bis(dimethylamino)naphthalene, Proton Sponge™, to ionic liquid solutions of AB increased the AB H 2-release rate at 85 °C, with over 2 equivalents of H 2 achieved within 3 h. Additional Proton Sponge increased the rate of release; however, the mat-wt% of H 2 decreased since the Proton Sponge added significant weight to the system. Solid state ii and solution 11 B NMR and DSC studies of reactions in progress allowed the identification of initial and final products in the H 2-release reactions and helped elucidate the overall reaction pathway. The initial formation of diammoniate of diborane, the key intermediate in dehydropolymerization of ammonia borane, was promoted by the addition of ionic liquids. Subsequent H 2-release resulted in the formation of polyaminoborane then polyborazylene. Proton Sponge increased the release rate of the second equivalent of H 2 by a newly proposed anionic polymerization mechanism. The final product was identified by solid-state 11 B NMR and proved to be a sp 2-framework of polyborazylene which formed regardless of base additive or amount/type of ionic liquid. iii Table of Contents Title Page i Abstract ii Table of Contents iv List of Tables ix List of Figures xi List of Equations xvi Chapter 1. The Hydrogen Economy: Benefits, Problems, and Possible Solutions Summary 1 1.1 We Use More than We Make! 2 1.2 Push for a Hydrogen Economy 4 1.2.1 Why Do We Need a Hydrogen Economy? 4 1.2.2 What are the Barriers to a Hydrogen Economy? 5 1.2.2.1 Hydrogen Production 6 1.2.2.2 Hydrogen Delivery 6 1.2.2.3 Hydrogen Storage 7 1.2.3 The Chemical Hydrogen Storage Center of Excellence 9 1.3 What is Ammonia Borane? 11 1.3.1 How to Release Hydrogen from Ammonia Borane? 17 1.3.1.1 Utilizing Hydrolysis to Release Hydrogen. 18 iv 1.3.1.2 The Better Hydrogen Release Method: Thermolysis. 18 1.3.2 Ammonia Borane Solid-State H 2-Release 19 1.3.3 Activated AB H 2-Release from AB 23 1.3.3.1 Mesoporous Scaffolds Aid in Solid-State H 2-Release 23 1.3.3.2 Acid Catalyzed Hydrogen Release Reactions 24 1.3.3.3 Using Transition-Metal Catalysis to Enhance 26 Release Rate and Extent. 1.3.3.3.1 Heterogeneous Transition-Metal Catalysts 26 1.3.3.3.2 Homogeneous Transition-Metal Catalysts 28 1.3.3.3.2.1 Iridium Pincer Catalyst 28 1.3.3.3.2.2 Nickel Carbene Catalyst 31 1.3.3.3.2.3 Titanocene Catalyst 35 1.3.3.3.2.4 Transition-Metal Catalysis in 37 Hydrolysis/Methanolysis 1.3.4 Large Scale Preparations of Ammonia Borane. 38 1.3.5 Recycling the AB Fuel Source. 39 1.3.6 Hybrid Materials Try to Bridge the Gap Between AB and 40 Metal Hydrides. 1.4 Conclusions 42 1.5 References 43 v Chapter 2. Ammonia Borane Hydrogen Release in Ionic Liquids Summary 51 2.1 Introduction 52 2.2 Experimental Section 53 2.2.1 Materials 53 2.2.2 Physical Measurements 53 2.2.2.1 H2-Release Measured On a Toepler Pump 53 2.2.2.2 H2-Release Measured On an Automated Gas Burette 54 2.2.2.3 Procedures for 11 B NMR Studies of Reaction 76 Products 2.3 Results and Discussion 77 2.3.1 Why Use Ionic Liquids? 77 2.3.2 Procedures for AB H 2-release reactions 80 2.3.3 Solid-State vs. Ionic Liquid H 2-Release 81 2.3.4 11 B NMR Characterization of Reaction Products and 93 Pathways 2.3.4.1 11 B NMR of Pyridine Extracts from Reaction 93 Products 2.3.4.2 Solid-State 11 B NMR Studies 96 2.3.4.3 In Situ 11 B NMR Studies in Ionic Liquids 96 2.3.6 Why do Ionic Liquids Accelerate AB H 2-release? What is the 103 Role of DADB? vi 2.3.7 H2-Release Reactions in Tetraglyme 108 2.4 Conclusions 111 2.5 References 112 Chapter 3. Base Promoted Ammonia Borane Hydrogen Release Summary 116 3.1 Introduction 117 3.2 Experimental Section 119 3.2.1 Materials 119 3.2.2 Physical Measurements 119 3.2.3 Procedures for AB H 2-Release Reactions 121 3.2.4 Computational Methods 122 3.3 Results and Discussion 126 3.3.1 H2-Release from AB/PS Solid-State Reactions 126 3.3.2 H2-Release from AB/PS Solution Reactions 132 3.3.2.1 Initial Reactions Measured with the Toepler Pump 132 3.3.2.2 H2-Release Reactions Measured with the Automated Gas Burette 136 3.3.3 11 B NMR Studies of Reaction Pathways and Intermediates 141 3.3.3.1 Solid-State 11 B NMR Studies 141 3.3.3.2 In Situ 11 B NMR Studies of Reaction Progress in 144 Ionic Liquids vii 3.3.4 Proton Sponge Reduces Foaming During AB Thermolysis 146 3.3.5 H2-Release in Other Ionic Liquids and Tetraglyme 147 3.3.6 Why Does Proton Sponge Induce H 2-Release from AB? 151 3.4 Conclusions 158 3.5 References 159 viii List of Tables Chapter 2 Table
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