Table of Contents: 1,4-Butanediol/THF
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TABLE OF CONTENTS
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Introduction
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TECHNOLOGY EVOLUTION
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Overview
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Phase One Acetylene - The Early Years
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Figure 2.1 Acetylene, Butanediol and Buna-S SBR Production
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Phase Two - The New Challengers
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Phase Three - Industry Commoditization through Technology
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Figure 2.2 n-Butane-Based Butanediol Technologies
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Figure 2.3 Non n-Butane-Based Butanediol Technologies
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BUTANEDIOL VALUE CHAIN
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Figure 2.4 The Butanediol Value Chain
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METHODOLOGY AND STUDY OUTLINE
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Commercial Technology
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PROCESSES FOR 1,4-BUTANEDIOL
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Acetylene/Formaldehyde (Reppe Concept)
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Figure 3.1 Synthesis of 1,4-Butanediol from Acetylene and Formaldehyde
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Figure 3.2 Two Step Hydrogenation of 1,4-Butynediol to 1,4-Butanediol
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Mitsubishi Chemical Butadiene Acetoxylation
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Figures 3.3 1,4-Acetoxybutene Production Via Butadiene Acetoxylation
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Lyondell Propylene Oxide Route
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Figure 3.5 Propylene Oxide Isomerization to Allyl Alcohol
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Figure 3.6 4-Hydroxybutyraldehyde Via Allyl Alcohol Hydroformylation
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Darien Propylene Acetoxylation/Hydroformylation
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Figure 3.8 Allyl Alcohol Via Propylene Acetoxylation and Back Cracking
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Davy Process Technology - 1,4-Butanediol Process using Maleic Anhydride
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Figure 3.9 Simplified Worldscale Crude Maleic Anhydride Production from Normal Butane
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Figure 3.10 Davy Process Maleic Anhydride Esterification and Hydrogenation
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Eurodiol (Now BASF) Concept Based on Maleic Anhydride
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Figure 3.12 Schematic View of Eurodiol 1,4-Butanediol and Derivatives Process
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Table 3.1 Eurodiol Butanediol Process (mass balance summary)
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BP/Lurgi Geminox from n-Butane via Maleic Acid
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Figure 3.13 BP Lurgi Geminox Fluid Bed Maleic Acid Production
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PROCESSES FOR TETRAHYDROFURAN
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Dehydration of 1,4-Butanediol
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Figure 3.15 Tetrahydrofuran Via Butanediol Dehydration
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Mitsubishi Chemical Butadiene Acetoxylation
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Figure 3.16 Mitsubish Process: Tetrahydrofuran from 1,4-Diacetoxybutene
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DuPont Transport Bed Concept
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Figure 3.17 DuPont Process: Transport Bed Oxidation of N-Butane to Maleic Acid
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Table 3.3 Design Parameters Used for Maleic Anhydride Reactor
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Figure 3.18 DuPont Process: Conversion of Maleic Acid into Tetrahydrofuran
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Figure 3.19 Fufural Extraction from Pentose-Containing Agricultural Sources
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Pentose/Furfural Approach
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Figure 3.20 Fufural Conversion into Tetrahydrofuran
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Emerging Petrochemical Technology
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BUTADIENE EPOXIDATION
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Process Chemistry
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Process Description
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Figure 4.1 Conceptual Eastman Tetrahydrofuran Process: 3.4 Epoxy-Butene Production from 1,3-Butadiene
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Figure 4.2 Conceptual Eastman Tetrahydrofuran Process: Tetrahydrofuran Production from 3,4 Epoxy-Butane
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LINDE/YUKONG ACETYLENE BASED PROCESS
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Introduction
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Table 4.1 Linde/Yukong Reaction Conditions
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Reppe Chemistry
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Figure 4.3 Conceptual Linde/Yukong Process for Butandiol Acetylene Reaction System
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Butynediol Hydrogenation
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Opportunities
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Figure 4.4 Conceptual Linde/Yukong Process for Butandiol Hydrogenation System
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BASF N-BUTANE TO TETRAHDYROFURAN PROCESS
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Figure 4.5 Conceptual BASF N-Butane to Tetrahydrofuran Process (Front End Only)
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SUMMARY
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Biotransformation Via Succinic Acid
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OVERVIEW
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Current Investigators
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Commentary on Process Chemistry
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PROCESS CONCEPT
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Fermentation
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Succinic Acid Recovery
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Figure 5.1 Electrodialysis in Cationic Mode
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Figure 5.2 Conceptual Biotransformation Process for ButanSection Figure Caption
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Figure 5.3 Conceptual Biotransformation Process for Butanediol Via Succinic Acid - Work Up Step
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Conversion to Butanediol
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Figure 5.4 Conceptual Biotransformation Process for Butanediol Via Succinic Acid - Hydrogenation Step
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FURTHER POTENTIAL IMPROVEMENTS
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Fermentation
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Succinic Acid Neutralization
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SUMMARY
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Process Economics
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OVERVIEW
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Table 6.1 Feedstocks and Product Prices
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Table 6.2 Utilities and Manpower Charges
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TECHNO-ECONOMICS FOR COMMERCIAL BUTANEDIOL PROCESSES
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Acetylene/Formaldehyde (Reppe Concept)
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Figure 6.1 Integrated Reppe Butanediol Process
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Table 6.3 Cost of Production Estimate for: 1,4-Butanediol
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Table 6.4 Cost of Production Estimate for: 1,4-Butanediol
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Table 6.5 Cost of Production Estimate for: 1,4-Butanediol
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Table 6.6 Cost of Production Estimate for: 1,4-Butanediol
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Table 6.7 Cost of Production Estimate for: 1,4-Butanediol
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Table 6.8 Cost of Production Estimate for: 1,4-Butanediol
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Table 6.9 Cost of Production Summary for 1,4-Butanediol
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Figure 6.2 Cost of Production Summary for 1,4-Butanediol
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Mitsubishi Chemical Butadiene Acetoxylation
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Lyondell Propylene Oxide Route
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Darien Propylene Acetoxylation/Hydroformylation Route
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Table 6.10 Cost of Production Estimate for: 1,4-Butanediol
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Table 6.11 Cost of Production Estimate for: 1,4-Butanediol
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