PEP Review ON-PURPOSE BUTADIENE PRODUCTION By Richard Nielsen with a Contribution by Russell Heinen (June 2011)

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1 PEP Review ON-PURPOSE BUTADIENE PRODUCTION By Richard Nielsen with a Contribution by Russell Heinen (June 2011) ABSTRACT 1,3-Butadiene is currently almost entirely produced as a by-product of ethylene steam cracking of naphtha or gas oil feedstocks. Some butadiene is recovered from olefinic refinery gases, mainly from the fluid catalytic cracker. Butadiene is recovered in the ethylene cracker in the crude C 4 fraction. The production of butadiene is dependent upon the feedstock cracked, operating rate and severity of cracking. In high severity naphtha cracking, the C 4 fraction is about 9 wt% of the cracked products and contains wt% butadiene. The small amount produced by cracking light feedstocks is not economically recoverable and these units usually do not have butadiene extraction equipment. A switch to lighter feedstocks has reduced the amount of butadiene available from ethylene cracking and presented a foreseeable market demand for on-purpose butadiene. In 2012, at least two butadiene plants are expected to start up in India with 11 more projects scheduled to start-up in the next five years. As our primary objective, we extensively reviewed proven or potential technologies for producing 1,3-butadiene, whether commercial or in the research or development stage, with emphasis on developments since Today, there is interest in producing butadiene from renewable resources such as ethanol, which was a major feedstock before the development and commercialization of petroleum-based processes, mainly during World War II. Since catalysis is a very major contributor to the successful production of butadiene, the catalyst literature is reviewed. The two main processes, the Houdry Catadiene process and the Texas Petrochemical Corporation Oxo-D process, are described and discussed in greater detail. These two processes have demonstrated the most commercial success historically. Process economics for producing 100,000 mt/year of 1,3-butadiene from n-butane via these two processes, combined with extractive distillation purification, are updated based on PEP Reports 35A1 and 35B plus PEP Review SRI Consulting PEP Review

2 A private report by the Process Economics Program Review No ON-PURPOSE BUTADIENE PRODUCTION by Richard Nielsen with a Contribution by Russell Heinen June 2011 Menlo Park, California 94025

3 SRIC agrees to assign professionally qualified personnel to the preparation of the Process Economics Program s reports and will perform the work in conformance with generally accepted professional standards. No other warranties expressed or implied are made. Because the reports are of an advisory nature, neither SRIC nor its employees will assume any liability for the special or consequential damages arising from the Client s use of the results contained in the reports. The Client agrees to indemnify, defend, and hold SRIC, its officers, and employees harmless from any liability to any third party resulting directly or indirectly from the Client s use of the reports or other deliverables produced by SRIC pursuant to this agreement. For detailed marketing data and information, the reader is referred to one of the SRI Consulting programs specializing in marketing research. THE CHEMICAL ECONOMICS HANDBOOK Program covers most major chemicals and chemical products produced in the United States and the WORLD PETROCHEMICALS PROGRAM covers major hydrocarbons and their derivatives on a worldwide basis. In addition the SRIC DIRECTORY OF CHEMICAL PRODUCERS services provide detailed lists of chemical producers by company, product, and plant for the United States, Western Europe, Canada, and East Asia, South America and Mexico.

4 CONTENTS INTRODUCTION... 1 CONCLUSIONS... 4 SUMMARY... 4 INDUSTRY STATUS... 7 Demand... 7 Supply... 9 Prices Specifications TECHNOLOGY REVIEW Chemistry Reaction Equilibrium Kinetics Crude Butadiene Commercial Processes Dehydrogenation to Butadiene Houdry (Catadiene) Dow Shell Phillips Butane Dehydrogenation Phillips Butene Dehydrogenation Dehydrogenation to n-butenes Snamprogetti-Yarsintez Snamprogetti (Research) Linde-BASF Uhde STAR UOP Oleflex Selective Hydrogen Combustion Uhde (Research) Sunoco, Inc. (R&M) (Research) Oxidative Dehydrogenation SRI Consulting iii PEP Review

5 CONTENTS (Continued) PetroTex Oxo-D Phillips O-X-D SK Energy (Developmental) Mitsubishi (Developmental) BP (Developmental) Nippon Zeon (Developmental) Saipem, S.p.A. (Research) Oxidative-Halo-Dehydrogenation Renewable Feedstock-Based Ethanol Butanol (Developmental) Starch Methanol from Biomass (Developmental) Acetylene-Based Four-Step (Aldol) Process Reppe Process Other Developmental Processes Membrane Processes Monolith Catalyst Process Rapid Pressure Swing Reaction Process Process Patents Discussion Comparison of Non-Oxidative Dehydrogenation Processes CATALYSIS LITERATURE REVIEW Bismuth Molybdenum Catalysts Ferrite Catalysts Pyrophosphate Catalysts Vanadium Catalysts Precious Metal Catalysts Other Catalysts SRI Consulting iv PEP Review

6 CONTENTS (Continued) CATADIENE PROCESS Process Description Process Discussion Feed Composition Reactors Downstream Emissions TPC OXO-D PROCESS Process Description Process Discussion Feedstock Reactor Downstream Product Emissions NMP EXTRACTIVE DISTILLATION UNIT Process Description Extractive Distillation Degassing Section Butadiene Purification Section Solvent Recovery Section PROCESS ECONOMICS Capital Costs Case Case PRODUCTION COSTS Case Case Cost Comparison SRI Consulting v PEP Review

7 CONTENTS (Concluded) CITED REFERENCES Literature Patents SRI Consulting Process Economics Program Publications Process Flow Diagrams SRI Consulting vi PEP Review

8 FIGURES 1 Typical Steam Cracker C 4 Flow to Produce Crude Butadiene Typical Extractive Distillation Butadiene Recovery from Crude C 4 s and Purification Global Consumption Growth from Allocated by End-Use U.S. Gulf Coast Butadiene and Butane Price History Reaction Network for Non-Oxidative Dehydrogenation of n-butane Equilibrium Conversion of Light Alkanes at 1 Atmosphere Oxidative Dehydrogenation of n-butane Reaction Scheme Simplified Houdry Process Lummus Catadiene Process Schematic Phillips Two-Stage Butane Dehydrogenation Process Snamprogetti Fluid Bed Process Phillips Star Process UOP Oleflex Process UOP Oleflex Catalyst Regeneration PetroTex (TPC) Oxo-D Simplified Process Phillips O-X-D Simplified Flowsheet Plant Cash Costs On-Purpose Butadiene Plant Cash Margins Houdry Catadiene Process Process Flow Diagram TPC Oxo-D Process Process Flow Diagram BASF NMP Extractive Distillation Process Process Flow Diagram SRI Consulting vii PEP Review

9 TABLES 1 Typical Crude Refinery C 4 Stream Butadiene Content from Steam Cracking Various Feedstocks Comparison of Oxidative and Non-Oxidative Dehydrogenation Dual Bed Technology Improves Conversion of n-butene Isomers Regional Forecast Consumption Growth Rates of 1,3-Butadiene, Distribution of Butadiene Capacity Expansion of Butadiene Capacity from 2009 to Example of a 1,3-Butadiene Product Specification Typical Specifications of Butadiene Conversion of n-butene Isomers Depends upon the Catalyst Reaction Equilibrium of n-butane, Butenes and Butadiene Chemical Reactions for the Oxidative Dehydrogenation of n-butane to Butene and Butadiene Rates of Formation Equations Example Crude Butadiene Stream Analysis Normal Boiling Points of C 3 and C 4 Hydrocarbons Binary Azeotropes of 1,3-Butadiene and of Other C 4 Hydrocarbons Typical Raw C 4 Refinery Fraction Composition Butene Dehydrogenation Catalyst Performance Dual Bed Technology Improves Conversion of n-butene Isomers Characterization of an Early MoBiFeSi Composite Catalyst Process Patents Separation/Purification Patents Houdry Process versus Phillips Two-Stage Process Comparison of Oxidative and Non-Oxidative Dehydrogenation Comparison of Non-Oxidative Dehydrogenation Processes Comparison of Oxidative Dehydrogenation Processes Summary of n-butene Processes SRI Consulting viii PEP Review

10 TABLES (Concluded) 28 Non-Oxidative Dehydrogenation Catalysts Oxidative Dehydrogenation Catalysts Patents on Production of Butenes Oxydehydrogenation Catalyst Patents Dehydrogenation/Other Catalyst Patents Total Feedstock Composition Chrome-Alumina Catalyst Typical Properties Reactor Effluent Composition Fresh C 4 Feedstock Composition Oxo-D Process Maximum Fresh Feed Impurities Oxo-D Process Crude Butadiene Composition PEP Cost Sub-Indices ,3-Butadiene, Case 1 Total Capital Investment ,3-Butadiene, Case 2 Total Capital Investment ,3-Butadiene, Case 1 Production Costs ,3-Butadiene, Case 2 Production Costs SRI Consulting ix PEP Review

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