Abstract Process Economics Program Report 21F NEW GENERATION OXO ALCOHOLS (October 2012)

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1 Abstract Process Economics Program Report 21F NEW GENERATION OXO ALCOHOLS (October 2012) This report follows a series of Process Economics Program reports on the topic of oxo alcohols. The last report on the subject was PEP 21E, Oxo Alcohols, published in September This report covers the BASF design concept for hydroformylation of raffinate II C 4 olefin feedstock for the production of n-valeraldehyde. The intermediate n-valeraldehyde is used for the production of 2-propylheptanol by BASF aldol condensation and hydrogenation (based on patents of Mitsubishi and Hoechst). The intermediate n-valeraldehyde is also used for the by-product production of amyl alcohol. The main focus of this report is evaluating the technoeconomics of the following three process routes: (1) the production of n-valeraldehyde at a base case capacity of 260 million lb/yr; (2) the production of 2-propylheptanol, at a base case capacity of 188 million lb/yr; (3) the byproduct production of amyl alcohol via direct hydrogenation of n-valeraldehyde, at a base case capacity of 59 million lb/yr. We determine the total capital investment and product value for a plant constructed in the US Gulf Coast region IHS PEP Report 21F

2 A private report by the Process Economics Program Report No. 21F NEW GENERATION OXO ALCOHOLS by Dipti Dave October 2012 Santa Clara, California 95054

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4 CONTENTS 1 INTRODUCTION BACKGROUND PROCESS PRODUCT PROPERTIES MARKET GROWTH REPORT OVERVIEW SUMMARY WORLD CAPACITY WORLD PLASTICIZER ALCOHOL PRODUCERS EXISTING COMMERICAL PRODUCTION Supply United States Supply Western European Recently Planned Capacity Additions Supply China TECHNOLOGY AND LICENSORS Manufacturing Processes n-valeraldehydes Propylheptanol Amyl Alcohol N-VALERALDEHYDE PRODUCTION BASF CONCEPT Catalyst System Reaction Conditions By-Products/Impurities RECENT DEVELOPMENT ON CATALYZED HYDROFORMYLATION PROCESS ECONOMICS Fixed-Capital Costs n-valeraldehyde Production Costs n-valeraldehyde Conclusion n-valeraldehyde Fixed-Capital Costs 2-Propylheptanol Production Costs 2-Propylheptanol Fixed-Capital Costs Amyl Alcohol Production Costs Amyl Alcohol IHS iii PEP Report 21F

5 CONTENTS (Continued) 3 INDUSTRY STATUS PRODUCTS MARKET GROWTH WORLD CAPACITY WORLD PLASTICIZER ALCOHOL PRODUCERS Supply United States Supply Western European Recently Planned Capacity Additions Supply China TECHNOLOGY AND LICENSORS Manufacturing Processes n-valeraldehydes Propylheptanol Amyl Alcohol TECHNOLOGY REVIEW BACKGROUND HYDROFORMYLATION Homogeneous Catalysis HYDROFORMYLATION AND CATALYSIS Catalytic Cycle Catalyst and Ligand Degradation N-VALERALDEHYDE Catalyst System Reaction Conditions By-Products/Impurities RECENT DEVELOPMENT ON CATALYZED HYDROFORMYLATION Finland Study Japan Study China Study BASF DOW ALDOL CONDENSATION Aldol Condensation Reactions IHS iv PEP Report 21F

6 CONTENTS (Continued) BASF Aldol Condensation Davy Aldolization-Dehydration Process N-VALERALDEHYDE FROM C 4 OLEFINS BY BASF HYDROFORMYLATION PROCESS DESCRIPTION Chemistry MAIN REACTIONS Process Chemistry Hydroformylation BASIS FOR DESIGN AND EVALUATION Design References PROCESS DESCRIPTION Section 100 Feed Distillation with Equilibrium Reaction and Isomerization plus Hydrogenation Section 200 Hydroformylation with Pressure Separation and Recovery Distillation Stream Flows PROCESS DISCUSSION Section 100 Feed Distillation with Equilibrium Reaction and Isomerization plus Hydrogenation Section 200 Hydroformylation with Pressure Separation and Recovery Distillation Offsite Storage Environmental COST ESTIMATES Fixed-Capital Costs Production Costs CONCLUSION PRODUCTION OF 2-PROPYLHEPTANOL FROM N-VALERALDEHYDE ALDOL CONDENSATION Chemistry for Aldol Condensation Hydrogenation Chemistry for Hydrogenation PROCESS DESCRIPTION IHS v PEP Report 21F

7 CONTENTS (Continued) Section Propyl-2-Heptenal Production Section Propylheptanol Production PROCESS DISCUSSION Raw Material Source Catalysts Reactors Heat-Exchanger Sizing Product Recovery Materials of Construction Equipment Listing and Utilities Consumption COST ESTIMATES Fixed-Capital Costs Production Costs PRODUCTION OF AMYL ALCOHOL FROM N-VALERALDEHYDE HYDROGENATION Chemistry for Hydrogenation PROCESS DESCRIPTION Section 100 Amyl Alcohol Production PROCESS DISCUSSION Raw Material Source Catalysts Reactors Heat-Exchanger Sizing Product Recovery Materials of Construction Equipment Listing and Utilities Consumption COST ESTIMATES Fixed-Capital Costs Production Costs APPENDIX A PATENT SUMMARY TABLES... A-1 APPENDIX B DESIGN AND COST BASES... B-1 APPENDIX C CITED REFERENCES... C IHS vi PEP Report 21F

8 CONTENTS (Concluded) APPENDIX D PATENT REFERENCES BY COMPANY... D-1 APPENDIX E PROCESS FLOW DIAGRAMS... E IHS vii PEP Report 21F

9 FIGURES 2.1 World Consumption of Oxo Chemicals Ligand Structure World Consumption of Oxo Chemicals Chemicals from Heterogeneous Catalytic (and Noncatalytic) Processing of Crude Oil Chemicals and Classes of Chemicals That Are Manufactured by Homogeneous Catalytic Processes Basic Catalytic Cycle for the Hydroformylation of Propylene with Rh/PPh 3 - Based Catalyst Basic Catalytic Cycle for the Degradation of PPh 3 Ligand and Catalyst Ligand Structure Asymmetric Hydroformylation BASF Process Scheme for n-valeraldehyde Conversion of C 4 Raffinate as a Function of Time Calixarene Bisphosphite Ligand Aldol Condensation and Hydrogenation Process Flow Diagram Aldolization-Dehydration Process Production of n-valeraldehyde from Raffinate II C 4 Olefins Process Flow Diagram... E Ligand Structure n-valeraldehyde Trimer Production of 2-Propylheptanol from n-valeraldehyde Process Flow Diagram... E Production of Amyl Alcohol from n-valeraldehyde Process Flow Diagram... E IHS viii PEP Report 21F

10 TABLES 1.1 Physical Properties of n-valeraldehyde Physical Properties of 2-Propylheptanol Physical Properties of Amyl Alcohol World Capacity for Plasticizer Alcohols World Consumption of Plasticizer Alcohols Major World Producers of Plasticizer Alcohols US Producers of n-valeraldehyde Western European Producers of n-valeraldehyde Announced Western European Capacity Additions for n-valeraldehyde Chinese Producer of Plasticizer Alcohol Relation between Base Capacity and Product Value n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Total Capital Investment n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Capital Investment by Section n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Production Costs n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Utilities Summary n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Major Equipment Production of 2-Propylheptanol from n-valeraldehyde Total Capital Investment Production of 2-Propylheptanol from n-valeraldehyde Capital Investment by Section Production of 2-Propylheptanol from n-valeraldehyde Production Costs Production of Amyl Alcohol from n-valeraldehyde Total Capital Investment Production of Amyl Alcohol from n-valeraldehyde Production Costs World Capacity for Plasticizer Alcohols World Consumption of Plasticizer Alcohols Major World Producers of Plasticizer Alcohols US Producers of n-valeraldehyde IHS ix PEP Report 21F

11 TABLES (Continued) 3.5 Western European Producers of n-valeraldehyde Announced Western European Capacity Additions for n-valeraldehyde Chinese Producer of Plasticizer Alcohol Process Parameters for Several Hydroformylation Processes Sequential Conversion of an Olefin Library to an Aldehyde Library Effect of BISBIS/Rh Molar Ratio Effect of Reaction Temperature Effect of Pressure Effect of Catalyst Concentration Effect of [1-Butene]/[Rh] Molar Ratio Effect of Recycling of Rhodium Catalyst Raffinate II Stream Composition C 4 Raffinate Stream Composition Reaction Equipment Items with Name and Section Number Butane and Butene Forming Reactions Hydroformylation Reactions Process Sections n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Design Basis and Assumptions n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Stream Flows Process Waste Streams Relation between Base Capacity and Product Value n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Total Capital Investment n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Capital Investment by Section n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Production Costs n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Utilities Summary n-valeraldehyde from C 4 Olefins by BASF Hydroformylation Major Equipment Production of 2-Propylheptanol from n-valeraldehyde Design Bases IHS x PEP Report 21F

12 TABLES (Concluded) 6.2 Production of 2-Propylheptanol from n-valeraldehyde Stream Flows Production of 2-Propylheptanol from n-valeraldehyde Major Equipment Production of 2-Propylheptanol from n-valeraldehyde Utilities Summary Production of 2-Propylheptanol from n-valeraldehyde Total Capital Investment Production of 2-Propylheptanol from n-valeraldehyde Capital Investment by Section Production of 2-Propylheptanol from n-valeraldehyde Production Costs Production of Amyl Alcohol from n-valeraldehyde Design Bases Production of Amyl Alcohol from n-valeraldehyde Stream Flows Production of Amyl Alcohol from n-valeraldehyde Major Equipment Production of Amyl Alcohol from n-valeraldehyde Utilities Summary Production of Amyl Alcohol from n-valeraldehyde Total Capital Investment Production of Amyl Alcohol from n-valeraldehyde Capital Investment by Section Production of Amyl Alcohol from n-valeraldehyde Production Costs IHS xi PEP Report 21F