CONTENTS. Chapter 1 Industrial Catalysts. Chapter 2 The First Catalysts

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1 CONTENTS Chapter 1 Industrial Catalysts 1.1 Introduction What is a Catalyst? Activity Selectivity and Yield Stability Strength Catalyst Production Precipitation Impregnation Other Production Methods Catalyst Testing Physical Tests Chemical Composition Activity Testing Catalyst Operation Reactor Design Catalytic Reactors Catalyst Operating Conditions 1.6 Conclusion References 22 Chapter 2 The First Catalysts 2.1 Sulfuric Acid The Lead Chamber Process Chemistry of the Lead Chamber Process 26 xi

2 xii Contents The Continuing Use of the Lead Chamber Process Raw Material for Sulfuric Acid Production Contact Process Development Modern Sulfuric Acid Processes Catalyst Preparation Sulfuric Acid Plant Design Cesium-Promoted Catalysts Sulfuric Acid Plant Operation Improved Catalyst Shapes The Deacon Process The Process Operation Catalyst Preparation Development Claus Sulfur Recovery Process The Claus Process Claus Plant Operation Claus Process Catalysts Catalyst Operation Ammonia Synthesis Sir William Crookes Development of the Ammonia Synthesis Process Commercial Application of Ammonia Synthesis Catalysts The Haber Bosch Synthesis Reactor Conclusions Coal Hydrogenation The Bergius Process Commercial Development by I. G. Farben Cooperation between I. G. Farben and Standard Oil Commercial Developments by ICI International Cooperation Coal Hydrogenation Processes The I. G. Farben Process The ICI Process Catalysts for Coal Hydrogenation Creosote and Other Feeds The Fischer-Tropsch Process Postwar Development of the Synthol Process by Sasol The Importance of Gas-to-Liquids as Gasoline Prices Increase 68 References 69

3 Contents xiii Chapter 3 Hydrogenation Catalysts 3.1 The Development of Hydrogenation Catalysts Sabatier and Senderens The First Industrial Application of Nickel Catalysts Ipatieff and High-Pressure Hydrogenation of Liquids Colloidal Platinum and Palladium Catalysts by Paal Platinum and Palladium Black Catalysts by Willstatter Adams Platinum Oxide Raney Nickel Catalysts Nickel Oxide/Kieselguhr Catalysts Nickel Oxide-Alumina Catalysts Copper Chromite Catalysts Copper Oxide/Zinc Oxide Catalysts Hydrogenation of Fats and Oils Process Development Oil Hydrogenation Fat Hardening Catalysts Catalyst Selectivity Feed Pretreatment Catalyst Operation Catalyst Poisons Fatty Acid Hydrogenation The Production of Fatty Alcohols Natural Fatty Alcohols Catalyst Operation Reaction of Fatty Alcohols Some Industrial Hydrogenation Processes Nitrobenzene Reduction Benzene Hydrogenation Removal of Aromatics Hydrogenation of Phenol Selective Hydrogenation of Acetylenes and Dienes Acetylene Hydrogenation Process Design Early Acetylene Hydrogenation Catalysts Sulfided Cobalt Molybdate Sulfided Nickel Oxide Fused Iron Oxide Palladium Catalyst Guard Beds 106

4 xiv Contents Modern Acetylene Hydrogenation Catalysts Acetylene Hydrogenation Catalyst Preparation Acetylene Hydrogenation Catalyst Operation Tail-End Acetylene Hydrogenation Tail-End Methyl Acetylene/Propadiene Hydrogenation Front-End Acetylene Hydrogenation Selective Hydrogenation of Pyrolysis Gasoline Catalyst Types Catalyst Operation 114 References 115 Chapter 4 Oxidation Catalysts 4.1 Nitric Acid The Ammonia Oxidation Process Catalyst Operation Platinum Recovery Formaldehyde Silver Catalyst Operation Mixed Oxide Catalyst Operation Andrussov Synthesis of Hydrogen Cyanide Hopcalite Catalysts For Carbon Monoxide Oxidation Phthalic Anhydride Naphthalene Oxidation Orthoxylene Oxidation Maleic Anhydride Benzene Feedstock n-butene Feedstock n-butane Feedstock n-butane Oxidation in a Circulating Fluidized Bed Ethylene Oxide Catalyst Operation and Reaction Mechanism Applications of Ethylene Oxide A Redox Oxidation Mechanism: Mars and Van Krevelen Acrolein and Acrylonitrile 156

5 Contents xv Manufacture of Mixed Oxide Catalysts for Acrolein and Acrylonitrile The Acrylonitrile Process Reaction Mechanism Partial Oxidation of Propane Acrylic Acid Oxidation of Isobutene Oxidative Dehydrogenation of n-butenes to Butadiene 162 References 163 Chapter 5 Catalytic Cracking Catalysts 5.1 Introduction Process Development Fixed Beds Moving and Fluidized Beds Catalyst Regeneration and Carbon Monoxide Combustion Catalyst Regeneration Carbon Monoxide Combustion Promoter Equilibrium Catalyst Reaction Mechanism of Catalytic Cracking Reactions Catalyst Development Natural Clay Catalysts Synthetic Silica Alumina Catalysts Preparation of Synthetic Catalysts Zeolite Catalysts Commercial Zeolites Production of Zeolites Formation of Active Sites by Ion Exchange Use of Zeolites in Catalytic Cracking The Catalyst Matrix Octane Catalysts (Catalysts to Increase Octane Rating) Hydrothermal Dealumination of Y-Zeolites Chemical Dealumination of Y-Zeolites Increasing Octane Number Shape Selective Cracking Residue Cracking Catalysts Residual Feeds 198

6 xvi Contents Residue Catalyst Formulation Coke Formation Residue Catalyst Additives Nickel Additives Vanadium Additives Sulfur Oxides Transfer Additives Bottoms Cracking Additive Reformulated Gasoline 206 References 209 Chapter 6 Refinery Catalysts 6.1 The Development of Catalytic Refinery Processes Polymer Gasoline Alkylation Liquid Acid Processes The Mechanism of Alkylation with an Acid Catalyst Liquid Acid Operating Conditions Processes Using Solid-State Acid Catalysts Hydrotreating What Is Hydrotreating? Hydrotreating Processes Catalyst Production and Operation Catalyst Handling Activating the Catalyst Catalyst Operation Catalyst Regeneration Hydrocracking Hydrocracking Processes Single-Stage Processes Two-Stage Processes Once-Through Process Hydrocracking Catalysts Acid Supports Hydrogenation Catalysts Catalyst Preparation Catalyst Activity Catalyst Reactivation 237

7 Contents xvii 6.6 Catalytic Reforming Naphtha Reforming Reactions Reformer Operation Coke Formation Reforming Catalysts Bimetallic Catalysts Catalyst Preparation Catalyst Regeneration Carbon Burn Oxychlorination Platinum Re-Dispersal Catalyst Reduction Catalyst Life Octane Boosting Selectoforming M-Forming Aromatics Production Aromatics Process Cyclar Process M2-Forming Process Catalytic Dewaxing Isomerization Isomerization Catalysts Reaction Mechanism 257 References 258 Chapter 7 Petrochemical Catalysts 7.1 The Development of Petrochemicals Isopropyl Alcohol Acetone Bisphenol-A Cumene Vinyl Chloride The Oxychlorination Reaction Oxychlorination Catalyst Catalyst Operation Synthetic Rubber From Butadiene and Styrene 273

8 xviii Contents Butadiene from Butane Butadiene from Butenes Oxidative Dehydrogenation Propylene from Propane Styrene Ethylbenzene Production Styrene Production after Styrene Plant Operation Ethylbenzene Dehydrogenation (Styrene) Catalysts Synthetic Fibers Nylon Production of Nylon Intermediates Adipic Acid Hexamethylenediamine Nylon Polymer Nylon Caprolactam Cyclohexanone Cyclohexanone Oxime Snia-Viscosa Process Conversion of Cyclohexanone Oxime to Caprolactam Caprolactam from Butadiene Polyesters Paraxylene Terephthalic Acid Alternative Routes for Terephthalic Acid Production Use of Polyesters Hydroformylation and Carbonylation Cobalt Carbonyl Catalysts Phosphine Modified Catalysts Low-Pressure Hydroformylation Commercial Operation Acetic Acid Acetaldehyde Metathesis of Olefins Process Development The Shell Higher-Olefins Process 305 References 306

9 Contents xix Chapter 8 Olefin Polymerization Catalysts 8.1 Low-Pressure Polyethylene Polyethylene Process Development The Development of Polypropylene Catalysts Ziegler Natta Catalysts Early Polyolefin Catalysts Ziegler s Brown Titanium Trichloride Natta s Violet Titanium Trichloride Second-Generation Propylene Polymerization Catalysts Supported Polyethylene Catalysts Supported Polypropylene Catalysts Third-Generation Catalysts Fourth-Generation Catalysts Phillips Polyethylene Catalysts Catalyst Production Catalyst Reduction Catalyst Operation Catalyst Modifiers Titanium Alumina and Zirconia Fluorides Use of Co-catalysts Organo-chromium Catalysts Other Catalysts Polymerization Processes Slurry Processes Solution Processes Gas Phase Process Metallocene/Single-Site Catalysts Early Development Early Development Industrial Operation Catalyst Activators Molecular Weight Control New Catalyst Developments The Molecular Structure of Polyolefins Formation of Polymer Chains 341

10 xx Contents Polymer Chain Termination Molecular Weight 344 References 345 Chapter 9 Synthesis Gas 9.1 Ammonia Synthesis Gas Process Developments Increased Ammonia Production by Steam Reforming Modern Ammonia Plants Feedstock Purification Activated Carbon Hydrodesulfurization Chlorine Removal Sulfur Absorption Operation with Zinc Oxide Preparation of Zinc Oxide Desulfurization of Other Gases Steam Reforming Reformer Design Reforming Catalysts Reformer Operation Secondary Reforming Carbon Monoxide Removal High Temperature Carbon Monoxide Conversion High Temperature Conversion Catalysts Operating Conditions Low Temperature Carbon Monoxide Conversion Operation Catalyst Methanation Operation Catalyst Other Methanation Processes Other Applications of Steam Reforming Methanol Synthesis Gas OXO Synthesis Gas Hydrogen Production Reducing Gas 391

11 Contents xxi Town Gas Production Substitute Natural Gas Autothermal Reforming 393 References 395 Chapter 10 Ammonia and Methanol Synthesis 10.1 Ammonia Synthesis Process Development from Haber-Bosch Process Claude Process Casale Process United States of America Mont Cenis/Uhde Process United Kingdom Ammonia Synthesis Catalysts Catalyst Production Pre-reduced Catalysts Loading Catalyst to Converter Catalyst Discharge from the Converter Catalyst Reduction Reduction of Oxidized Catalyst Reduction of Pre-reduced Catalyst Mechanism of Catalyst Reduction The Ammonia Synthesis Process The Ammonia Synthesis Loop Converter Design New Catalyst Developments Magnetite Catalyst Containing Cobalt Ruthenium Catalyst Catalyst Preparation Full-scale Operation with Ruthenium Catalyst Methanol Synthesis High-pressure Synthesis Zinc Oxide-Chromium Oxide Catalysts High-Pressure Operation Low-pressure Synthesis Copper Oxide Catalysts Copper Catalyst Production 426

12 xxii Contents Precipitates Forming During Production Operation with Copper Catalysts Reaction Mechanism with Copper Catalysts Selectivity Low-pressure Methanol Reactor Types Catalyst Reduction Novel Catalysts 434 References 435 Chapter 11 Environmental Catalysts 11.1 Stationary Sources Selective Catalytic Reduction Selective Catalytic Reduction Catalysts Catalyst Composition Catalyst Operation Reaction Mechanism Removal of Sulfur Dioxide as Sulfuric Acid Gas Turbine Exhausts Low Temperature Vanadium Pentoxide Catalysts Catalytic Combustion Processes Nitric Acid Plant Exhaust Gas Ion-exchanged ZSM-5 Zeolites Mobile Sources Automobile Emission Control Automobile Emission Control Catalysts Bead Catalysts Monolith Catalysts Washcoat Composition Platinum Group Metal Catalysts Catalyst Poisons Platinum Metal Group Availability Catalyst Operation Nitrogen Oxide Removal in Lean-Burn Engines Diesel Engines Volatile Organic Compounds VOC Removal Processes VOC Oxidation Catalysts 468 Reference 469 Index 471

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