Caprolactam June 2015 Report Contents

Caprolactam
Table of Contents
A Report by NexantThinking™
Process Evaluation/Research Planning (PERP) Program
PERP Report 2015-1 – Published June 2015
www.nexantthinking.com

Section Page

1 Executive Summary ............................................................................................................... 1

1.1 INTRODUCTION ....................................................................................................... 1
1.2 COMMERCIAL TECHNOLOGIES ............................................................................ 2
1.3 DEVELOPING TECHNOLOGIES ............................................................................. 3
1.4 PROCESS ECONOMICS.......................................................................................... 4
1.5 GLOBAL MARKET ANALYSIS ................................................................................. 7
1.6 STRATEGIC OUTLOOK FOR CAPROLACTAM ...................................................... 10
2 Introduction ............................................................................................................................. 11
2.1 OVERVIEW ............................................................................................................... 11
2.2 PRODUCTION TECHNOLOGY ................................................................................ 13
2.2.1 Conventional Caprolactam Production ......................................................... 13
2.2.2 Developing Technologies ............................................................................. 14
2.3 BUSINESS DEVELOPMENTS ................................................................................. 15
2.4 TECHNOLOGY LICENSING STATUS AND MAJOR PRODUCERS ....................... 15
2.5 STRATEGIC AND BUSINESS CONSIDERATIONS ................................................ 16
2.6 PHYSICAL AND THERMODYNAMIC PROPERTIES .............................................. 16
2.7 SPECIFICATIONS .................................................................................................... 17
2.8 HEALTH HAZARDS .................................................................................................. 17
2.9 STORAGE AND TRANSPORTATION ...................................................................... 17
3 Commercial Technologies ...................................................................................................... 18
3.1 CAPROLACTAM FROM AROMATIC FEEDSTOCKS .............................................. 18
3.1.1 Background .................................................................................................. 18
3.1.2 Process Technology ..................................................................................... 26
3.2 CAPROLACTAM FROM BUTADIENE ...................................................................... 53
3.2.1 Background .................................................................................................. 53
3.2.2 DuPont/DSM Altam Process ........................................................................ 55

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3.3 CAPROLACTAM FROM ADIPONITRILE ................................................................. 61

3.3.1 Background .................................................................................................. 61
3.3.2 BASF/DuPont Co-Production of HMDA and Caprolactam........................... 61
4 Developing Technologies ....................................................................................................... 73
4.1 RECENT DEVELOPMENTS IN CONVENTIONAL CAPROLACTAM
MANUFACTURING ................................................................................................... 73
4.1.1 Sumitomo Chemical ..................................................................................... 73
4.1.2 BASF ............................................................................................................ 75
4.1.3 Fibrant (DSM) ............................................................................................... 76
4.2 BIO-CAPROLACTAM FROM ADIPIC ACID ............................................................. 77
4.2.1 Background .................................................................................................. 77
4.2.2 Rennovia Adipic Acid Amination via Glucaric Acid ...................................... 77
4.2.3 Genomatica GENO™ Direct Fermentation to Nylon Intermediates ............. 83
4.2.4 BioAmber ...................................................................................................... 91
4.2.5 Joule Unlimited ............................................................................................. 92
4.3 BIO-CAPROLACTAM FROM L-LYSINE ................................................................... 92
4.3.1 Background .................................................................................................. 92
4.3.2 Fibrant (DSM) Caprolactam Production Technology ................................... 93
4.3.3 Amyris Biotechnologies (Draths) Caprolactam Production Technology ...... 95
5 Economics .............................................................................................................................. 100
5.1 COSTING BASIS ...................................................................................................... 100
5.1.1 Investment Basis .......................................................................................... 100
5.1.2 Pricing Basis ................................................................................................. 100
5.1.3 Cost of Production Basis .............................................................................. 102
5.2 PROCESS COMPETITIVENESS ............................................................................. 102
5.2.1 Aromatics-Based Processes ........................................................................ 102
5.2.2 Butadiene/Adiponitrile Based Processes ..................................................... 119
5.2.3 Glucose Based Processes ........................................................................... 125
5.3 REGIONAL COMPETITIVENESS ............................................................................ 127
5.3.1 Cyclohexane Oxidation with Raschig Process ............................................. 127
5.3.2 Cyclohexane Oxidation with NO Reduction Process ................................... 132
5.3.3 Cyclohexane Oxidation with DSM HPO Process ......................................... 136
5.3.4 Honeywell Phenol Process .......................................................................... 140
5.3.5 EniChem Cyclohexane Ammoxidation with Sumitomo Rearrangement ...... 144
5.3.6 Toray Cyclohexane Photonitrozation Process ............................................. 148
5.3.7 SNIA Toluene Process ................................................................................. 152
5.3.8 DuPont/DSM Altam Process ........................................................................ 156
5.3.9 BASF/DuPont adiponitrile Process with HMDA Co-product ........................ 160
5.3.10 Rennovia Process via Glucaric and Adipic Acid .......................................... 164

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5.4 SENSITIVITY STUDY ............................................................................................... 168

5.4.1 Overview ...................................................................................................... 168
5.4.2 Cyclohexane Oxidation with Raschig Process ............................................. 169
5.4.3 Cyclohexane NO Reduction Process ........................................................... 169
5.4.4 Cyclohexane DSM HPO Process ................................................................. 170
5.4.5 Honeywell Phenol Process .......................................................................... 170
5.4.6 EniChem Cyclohexane Ammoxidation with Sumitomo Rearrangement ...... 171
5.4.7 Toray Cyclohexane Photonitrozation Process ............................................. 172
5.4.8 SNIA Toluene Process ................................................................................. 172
5.4.9 DuPont/DSM Altam Process ........................................................................ 173
5.4.10 BASF/DuPont Adiponitrile Process with HMDA Co-product ........................ 173
5.4.11 Rennovia Process ........................................................................................ 174
6 Regional Market Analysis ....................................................................................................... 175
6.1 GLOBAL .................................................................................................................... 175
6.1.1 Consumption ................................................................................................ 175
6.1.2 Supply .......................................................................................................... 176
6.1.3 Supply, Demand, and Trade ........................................................................ 177
6.2 NORTH AMERICA .................................................................................................... 178
6.2.1 Consumption ................................................................................................ 178
6.2.2 Supply .......................................................................................................... 178
6.2.3 Supply, Demand, and Trade ........................................................................ 179
6.3 WESTERN EUROPE ................................................................................................ 180
6.3.1 Consumption ................................................................................................ 180
6.3.2 Supply .......................................................................................................... 180
6.3.3 Supply, Demand, and Trade ........................................................................ 180
6.4 ASIA PACIFIC ........................................................................................................... 182
6.4.1 Consumption ................................................................................................ 182
6.4.2 Supply .......................................................................................................... 182
6.4.3 Supply, Demand, and Trade ........................................................................ 182
6.5 CHINA ....................................................................................................................... 184
6.5.1 Consumption ................................................................................................ 184
6.5.2 Supply .......................................................................................................... 184
6.5.3 Supply, Demand, and Trade ........................................................................ 185
6.6 REST OF THE WORLD ............................................................................................ 186
6.6.1 Consumption ................................................................................................ 186
6.6.2 Supply .......................................................................................................... 186
6.6.3 Supply, Demand, and Trade ........................................................................ 187
7 Strategic Analysis ................................................................................................................... 188
7.1 MARKET OUTLOOK ................................................................................................. 188

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7.2 TECHNOLOGY OUTLOOK....................................................................................... 189

7.2.1 Conventional Technologies .......................................................................... 189
7.2.2 Bioprocesses ................................................................................................ 190
8 References ............................................................................................................................. 192

Appendix Page

A Additional Cost of Production Estimates ................................................................................ A-1

B Definitions of Capital Cost Terms Used in Process Economics ............................................. B-1
C Definitions of Operating Cost Terms Used in Process Economics ........................................ C-1
D PERP Program Title Index (2006 - 2015) .............................................................................. D-1

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Figure Page

1.1 Caprolactam and 6-Aminocaproic Acid .................................................................................. 1

1.2 Polyamide 6 ............................................................................................................................ 1
1.3 Summary of Caprolactam Production Chemistry from Aromatics .......................................... 2
1.4 Summary of Aromatics-Based Caprolactam Process Economics ......................................... 6
1.5 Summary of Butadiene, Adiponitrile and Sugar-Based Caprolactam Process Economics ... 6
1.6 Global Caprolactam Demand by Region (2009-2020, thousand tons) .................................. 8
1.7 Global Caprolactam Capacity by Region (2009-2020, thousand tons) .................................. 9
1.8 Global Caprolactam Supply, Demand, and Trade (thousand tons) ....................................... 10
2.1 Caprolactam and 6-Aminocaproic Acid .................................................................................. 11
2.2 Polyamide 6 ............................................................................................................................ 11
2.3 Molecular Structure of Polyamide 6 and Polyamide 6:6 ........................................................ 12
2.4 Summary of Caprolactam Production Chemistry from Aromatics .......................................... 13
3.1 Summary Chemistry of Cyclohexane-Cyclohexane Oxime Route to Caprolactam ............... 19
3.2 Primary Commercial Cyclohexanone Production Routes ...................................................... 20
3.3 Cyclohexanone Oxime Production Routes ............................................................................ 21
3.4 Hydroxylamine Salt Production Routes .................................................................................. 23
3.5 Main Commercial Cyclohexanone Production Routes ........................................................... 24
3.6 KA Oil From Cyclohexane: Boric Acid Route ........................................................................ 27
3.7 Cyclohexanone from Cyclohexanol/Cyclohexanone .............................................................. 31
3.8 Caprolactam Process with Conventional Beckmann Rearrangement ................................... 33
3.9 Caprolactam Final Purification ............................................................................................... 35
3.10 Schematic Flow Diagram Honeywell Phenol Route to Caprolactam .................................... 37
3.11 Cyclopol Caprolactam Production .......................................................................................... 39
3.12 Cyclopol Cyclohexanone Block Diagram ............................................................................... 40
3.13 Cyclopol Hydroxylamine Sulfate Block Diagram .................................................................... 41
3.14 Cyclopol Process Block Diagram ........................................................................................... 43
3.15 Toray Photonitrozation Block Diagram ................................................................................... 44
3.16 Syndial Ammoximation Process Flow Diagram .................................................................... 48
3.17 Sumitomo Fluid Beckmann Rearrangement ......................................................................... 51
3.18 SNIA Process Block Diagram................................................................................................. 53
3.19 DuPont/DSM/BASF Caprolactam from Butadiene: Block Flow Diagram ............................... 56
3.20 DuPont/DSM/BASF/ Caprolactam from Butadiene: Carbonylation and Esterification ........... 57
3.21 DuPont/DSM/BASF Caprolactam from Butadiene: Hydroformylation ................................... 58
3.22 DuPont/DSM/BASF Caprolactam from Butadiene: Amination and Cyclization ..................... 59
3.23 ADN from Butadiene DuPont Process: Adiponitrile Reaction ................................................ 63
3.24 ADN from Butadiene DuPont Process: Adiponitrile Recovery ............................................... 64
3.25 ADN via Solutia Acrylonitrile Process .................................................................................... 66

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3.26 ACN+HMDA DuPont/BASF Process: Hydrogenation ........................................................... 70

3.27 Caprolactam from Aminocapronitrile DuPont/BASF: Cyclization ........................................... 72
4.1 Innovative Sumitomo Caprolactam Crystallization Block Flow .............................................. 74
4.2 BASF Caprolactam Purification Block Flow ........................................................................... 75
4.3 Fibrant (DSM) Caprolactam Membrane Separation System ................................................. 76
4.4 Synthesis of Caprolactam via Glucaric Acid and Adipic Acid ................................................ 78
4.5 Rennovia Process Adipic Acid ............................................................................................... 82
4.6 Sugar to Acetyl-CoA and Succinyl-CoA ................................................................................. 85
4.7 Syngas to Acetyl-CoA and Succinyl-CoA ............................................................................... 86
4.8 Biochemical Pathways to Adipyl-CoA from Succinyl-CoA and Acetyl-CoA ........................... 88
4.9 Biochemical Pathways to Caprolactam from Adipate ............................................................ 89
4.10 DSM Routes to Biologically Derived Caprolactam ................................................................. 94
4.11 Draths Process for Caprolactam from Lysine ........................................................................ 96
5.1 Aromatic-Based Caprolactam Process Comparison (USGC, Q1 2015) ................................ 118
5.2 Aromatic-Based Caprolactam Process Comparison (USGC, Q1 2015) ................................ 118
5.3 Butadiene/Adiponitrile Based Process Comparison (USGC, Q1 2015) ................................. 124
5.4 Butadiene/Adiponitrile Based Process Comparison (USGC, Q1 2015) ................................. 124
5.5 Regional Cost Competitiveness for Cyclohexane Oxidation with Raschig Process
(Q1 2015) ............................................................................................................................... 128
5.6 Regional Cost Competitiveness for Cyclohexane Oxidation with Raschig Process
(Q1 2015) ............................................................................................................................... 128
5.7 Regional Cost Competitiveness for Cyclohexane Oxidation with NO Reduction Process .... 132
5.8 Regional Cost Competitiveness for Cyclohexane Oxidation with NO Reduction Process .... 133
5.9 Regional Cost Competitiveness for Cyclohexane Oxidation with HPO Process ................... 136
5.10 Regional Cost Competitiveness for Cyclohexane Oxidation with HPO Process ................... 137
5.11 Regional Cost Competitiveness for Honeywell Phenol Process ............................................ 140
5.12 Regional Cost Competitiveness for Honeywell Phenol Process ............................................ 141
5.13 Regional Cost Competitiveness for Cyclohexane Ammoxidation with Vapor-Phase
Rearrangement ...................................................................................................................... 144
5.14 Regional Cost Competitiveness for Cyclohexane Ammoxidation with Vapor-Phase
Rearrangement ...................................................................................................................... 145
5.15 Regional Cost Competitiveness for Photonitrozation Process ............................................... 148
5.16 Regional Cost Competitiveness for Photonitrozation Process ............................................... 149
5.17 Regional Cost Competitiveness for SNIA Toluene Process .................................................. 152
5.18 Regional Cost Competitiveness for SNIA Toluene Process .................................................. 153
5.19 Regional Cost Competitiveness for DuPont/DSM Altam Process ......................................... 156
5.20 Regional Cost Competitiveness for DuPont/DSM Altam Process ......................................... 157
5.21 Regional Cost Competitiveness for Adiponitrile Process ....................................................... 160
5.22 Regional Cost Competitiveness for Adiponitrile Process ....................................................... 161
5.23 Regional Cost Competitiveness for Rennovia Process ......................................................... 164
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5.24 Regional Cost Competitiveness for Rennovia Process ......................................................... 165

5.25 Sensitivity of Caprolactam Cost to Feedstock Price Movements ........................................... 168
5.26 Sensitivity of Caprolactam Cost to Production Scale ............................................................. 169
5.27 Sensitivity of Caprolactam Cost of Production Inputs – Cyclohexane Oxidation with
Raschig Process .................................................................................................................... 169
5.28 Sensitivity of Caprolactam Cost of Production Inputs – NO Reduction Process ................... 170
5.29 Sensitivity of Caprolactam Cost of Production Inputs – DSM HPO Process ......................... 170
5.30 Sensitivity of Caprolactam Cost of Production Inputs – Honeywell Phenol Process ............. 171
5.31 Sensitivity of Caprolactam Cost of Production Inputs – Cyclohexane Ammoxidation with
Vapor-Phase Rearrangement ................................................................................................ 171
5.32 Sensitivity of Caprolactam Cost of Production Inputs – Toray Photonitrozation Process...... 172
5.33 Sensitivity of Caprolactam Cost of Production Inputs – Toluene SNIA Process ................... 172
5.34 Sensitivity of Caprolactam Cost of Production Inputs – DuPont/DSM Altam Process........... 173
5.35 Sensitivity of Caprolactam Cost of Production Inputs – Butadiene with HMDA Byproduct ... 174
5.36 Sensitivity of Caprolactam Cost of Production Inputs – Rennovia Glucose Process ............ 174
6.1 Global Caprolactam Demand by Region (2009-2020, thousand tons) .................................. 176
6.2 Global Caprolactam Capacity by Region (2009-2020, thousand tons) .................................. 177
6.3 Global Caprolactam Supply, Demand, and Trade (thousand tons) ....................................... 178
6.4 North America Caprolactam Supply, Demand, and Trade (thousand tons) .......................... 179
6.5 Western Europe Caprolactam Supply, Demand, and Trade .................................................. 181
6.6 Asia Pacific Caprolactam Supply, Demand, and Trade ......................................................... 183
6.7 China Caprolactam Supply, Demand, and Trade .................................................................. 185
6.8 Rest of the World Caprolactam Supply, Demand, and Trade ................................................ 187

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Table Page

1.1 Bio-Caprolactam Process Development ................................................................................ 3

1.2 Summary of Aromatics-Based Caprolactam Process Economics ......................................... 5
1.3 Summary of Butadiene, Adiponitrile, and Sugar-Based Caprolactam Process Economics .. 5
1.4 Global Caprolactam Demand by Region (2009-2020, thousand tons) .................................. 7
1.5 Global Caprolactam Capacity by Region (2009-2020, thousand tons) .................................. 8
1.6 Global Caprolactam Supply, Demand, and Trade (thousand tons) ....................................... 9
1.7 Summary of Strategic Outlook for Caprolactam ..................................................................... 10
2.1 Bio-Caprolactam Process Development ................................................................................ 14
2.2 Caprolactam Technology Licensors ....................................................................................... 15
2.3 Key Physical and Thermodynamic Properties of Caprolactam .............................................. 16
2.4 Caprolactam Product Specification ........................................................................................ 17
3.1 Ammonium Sulfate Production with Current Commercial Caprolactam Technology ............. 25
3.2 Typical Operating Conditions of KA Oil from Cyclohexane via the Boric Acid Route ........... 28
3.3 First Stage Ammoximation Reaction Summary ..................................................................... 46
3.4 Higher-Stage Ammoximation Reactions Summary ................................................................ 47
3.5 Caprolactam Technology Summary for Aromatic-Derived Feedstocks ................................. 60
3.6 Caprolactam Technology Summary for Aromatic-Derived Feedstocks ................................. 67
3.7 Caprolactam Technology Summary for Aromatic-Derived Feedstocks ................................. 67
4.1 Summary of Reactions for Producing Succinyl-CoA and Acetyl-CoA in Genomatica
GENO™ Fermentation ........................................................................................................... 87
4.2 Summary of Reactions for Producing Adipic Acid from Succinyl-CoA and Acetyl-CoA ........ 88
4.3 Summary of Reactions to Caprolactam from Adipate ............................................................ 90
5.1 Pricing Basis for Caprolactam ................................................................................................ 101
5.2 Cost of Production for: Caprolactam
Process: Cyclohexane Oximation with Raschig Process Hydroxylamine Production ........... 104
5.3 Cost of Production for: Caprolactam
Process: Cyclohexane Oximation with NO Reduction Process Hydroxylamine
Production .............................................................................................................................. 106
5.4 Cost of Production for: Caprolactam
Process: Cyclohexane Oximation with DSM HPO Process Hydroxylamine Production ........ 108
5.5 Cost of Production for: Caprolactam
Process: Honeywell Phenol Process with Raschig Hydroxylamine Production ..................... 110
5.6 Cost of Production for: Caprolactam
Process: EniChem Cyclohexane Ammoxidation Process with Sumitomo Vapor-Phase
Rearrangement ...................................................................................................................... 112
5.7 Cost of Production for: Caprolactam
Process: Toray Cyclohexane Photonitrozation Process ........................................................ 114
5.8 Cost of Production for: Caprolactam
Process: SNIA Toluene Process ............................................................................................ 116

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5.9 Summary of Aromatic-Based Caprolactam Process Economics ........................................... 117

5.10 Cost of Production for: Caprolactam
Process: DSM/DuPont Altam Process ................................................................................... 120
5.11 Cost of Production for: Caprolactam
Process: BASF/DuPont Adiponitrile Process with HMDA Co-product ................................... 122
5.12 Summary of Butadiene/Adiponitrile Based Process Economics ............................................ 123
5.13 Cost of Production for: Caprolactam
Process: Rennovia Process via Glucaric Acid and Adipic Acid ............................................. 126
5.14 Summary of Regional Cost Competitiveness for Cyclohexane Oxidation with Raschig
Process................................................................................................................................... 127
5.15 Cost of Production for: Caprolactam in Western Europe
Process: Cyclohexane Oxidation with Raschig Process ........................................................ 130
5.16 Cost of Production for: Caprolactam in China
Process: Cyclohexane Oxidation with Raschig Process ........................................................ 131
5.17 Summary of Regional Cost Competitiveness for Cyclohexane Oxidation with NO
Reduction Process ................................................................................................................. 132
5.18 Cost of Production for: Caprolactam in Western Europe
Process: Cyclohexane Oxidation with NO Reduction ............................................................ 134
5.19 Cost of Production for: Caprolactam in China
Process: Cyclohexane Oxidation with NO Reduction ............................................................ 135
5.20 Summary of Regional Cost Competitiveness for Cyclohexane Oxidation with HPO
Process................................................................................................................................... 136
5.21 Cost of Production for: Caprolactam in Western Europe
Process: Cyclohexane Oxidation with DSM HPO Process .................................................... 138
5.22 Cost of Production for: Caprolactam in China
Process: Cyclohexane Oxidation with DSM HPO Process .................................................... 139
5.23 Summary of Regional Cost Competitiveness for Honeywell Phenol Process ....................... 140
5.24 Cost of Production for: Caprolactam in Western Europe
Process: Honeywell Phenol Process ..................................................................................... 142
5.25 Cost of Production for: Caprolactam in China
Process: Honeywell Phenol Process ..................................................................................... 143
5.26 Summary of Regional Cost Competitiveness for Cyclohexane Ammoxidation with
Vapor-Phase Rearrangement ................................................................................................ 144
5.27 Cost of Production for: Caprolactam in Western Europe
Process: EniChem Cyclohexane Ammoxidation with Sumitomo Rearrangement ................ 146
5.28 Cost of Production for: Caprolactam in China
Process: EniChem Cyclohexane Ammoxidation with Sumitomo Rearrangement ................ 147
5.29 Summary of Regional Cost Competitiveness for Photonitrozation Process .......................... 148
5.30 Cost of Production for: Caprolactam in Western Europe
Process: Toray Cyclohexane Photonitrozation Process ........................................................ 150
5.31 Cost of Production for: Caprolactam in China
Process: Toray Cyclohexane Photonitrozation Process ........................................................ 151

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5.32 Summary of Regional Cost Competitiveness for SNIA Toluene Process .............................. 152
5.33 Cost of Production for: Caprolactam in Western Europe
Process: SNIA Toluene Process ............................................................................................ 154
5.34 Cost of Production for: Caprolactam in China
Process: SNIA Toluene Process ............................................................................................ 155
5.35 Summary of Regional Cost Competitiveness DuPont/DSM Altam Process .......................... 156
5.36 Cost of Production for: Caprolactam in Western Europe
Process: DuPont/DSM Altam Process ................................................................................... 158
5.37 Cost of Production for: Caprolactam in China
Process: DuPont/DSM Altam Process ................................................................................... 159
5.38 Summary of Regional Cost Competitiveness for Adiponitrile Process .................................. 160
5.39 Cost of Production for: Caprolactam in Western Europe
Process: BASF/DuPont Adiponitrile Process with HMDA Co-product ................................... 162
5.40 Cost of Production for: Caprolactam in China
Process: BASF/DuPont Adiponitrile Process with HMDA Co-product ................................... 163
5.41 Summary of Regional Cost Competitiveness for Rennovia Process ..................................... 164
5.42 Cost of Production for: Caprolactam in Western Europe
Process: Rennovia Process ................................................................................................... 166
5.43 Cost of Production for: Caprolactam in China
Process: Rennovia Process ................................................................................................... 167
6.1 Global Caprolactam Demand by Region (2009-2020, thousand tons) .................................. 175
6.2 Global Caprolactam Capacity by Region (2009-2020, thousand tons) .................................. 176
6.3 Global Caprolactam Supply, Demand, and Trade ................................................................. 177
6.4 North American Caprolactam Capacity .................................................................................. 178
6.5 North America Caprolactam Supply, Demand, and Trade ..................................................... 179
6.6 Western Europe Caprolactam Capacity ................................................................................. 180
6.7 Western Europe Caprolactam Supply, Demand, and Trade .................................................. 181
6.8 Asia Pacific (Excluding China) Caprolactam Capacity ........................................................... 182
6.9 Asia Pacific Caprolactam Supply, Demand, and Trade ......................................................... 183
6.10 China Caprolactam Capacity.................................................................................................. 184
6.11 China Caprolactam Supply, Demand, and Trade .................................................................. 185
6.12 Rest of the World Caprolactam Capacity ............................................................................... 186
6.13 Rest of the World Caprolactam Supply, Demand, and Trade ................................................ 187

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