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Contents
SUMMARY
………………………
General Aspects …………………..
Technical Aspects ………………….
Diglycidyl Ether of Bisphenol A …………..
Solid Epoxy Resin …………………
Epoxy Resin Solution ………………..
Epoxy Novolac Resin ………………..
Economics and Process Comparison ……………
Conventional Process Compared with
Two-Step Process for DGEBA ……………..
Advancement Process Compared with Taffy Process
for Solid BPA-Based Resin ……………..
Processes for Epoxy Novolac Resins ………….
INDUSTRY STATUS . . . . . . . . . . . . . . . . . . . . . . .
13
DIGLYCIDYL ETHER OF BISPHENOL A ……………
Chemistry ……………………..
Review of Processes …………………
Process Description–Batch Process
………….
Production of DCHEBA
. .
Production and Purificakon of DGEBA
…………
………..
Process Discussion–Batch Process …………..
Cost Estimates–Batch Process …………….
Process Description–Continuous Process ………..
Production of DCHEBA
Production and Purifica%’of
DCHEBA
…………………….
Process Discussion–Continuous Process
………..
Cost Estimates–Continuous Process
………….
Economic Comparison …………………
SOLID EPOXY RESIN AND EPOXY RESIN SOLUTION
………
Chemistry ……………………..
Review of Processes …………………
Process Description–Solid Epoxy Resin
by Advancement Process
…
Process Discussion–Solid’Epo;y’Resin
…………
by Advancement Process
……………….
Cost Estimates– Solid Epoxy Resin by Advancement Process …
76
Epoxy Resins, Supp. A., February 1984
CONTENTS
5
SOLID EPOXY RESIN AND EPOXY RESIN SOLUTION (Continued)
Updated Economics for Solid Epoxy Resin by Taffy Process . . .
85
Process Description–High MW Epoxy Resin Solution . . . . . .
90
Process Discussion–High MW Epoxy Resin Solution . . . . . . .
95
Cost Estimates–High MW Epoxy Resin Solution
. . . . . . . .
95
6
EPOXY NOVOLAC RESINS
. . . . . . . . . . . .
Chemistry . . . . . . . . . . . . . . . . . .
Review of Processes . . . . . . . . . . . . .
Process Description–Conventional Process . .
Production of Novolac Resin . . . . . . . .
Production of Epoxy Novolac Resin . . . . .
Process Discussion–Conventional
Process
. .
Cost Estimates–Conventional Process
. . . .
Process Description–Alternative Process
. .
Production of Glycylomonochlorohydrin Phenyl
Production of Epoxy Novolac Resin . . . . .
Process Discussion–Alternative Process . . .
Cost Estimates–Alternative Process . . . . .
Economics of the Advancement Process
. . . .
7
OTHER EPOXY RESINS
…………………
149
Hydantoin Epoxy Resins
……………….
149
Nonaromatic Epoxy Resins
………………
150
Epoxy Ester Resins
…………………
151
Other Epoxy Resins
…………………
152
8
CURING AGENTS AND COMPOSITIONS . . . . . . . . . . . . . . .
155
Catalysts for Curing Epoxy Resins …………..
155
Curing Agents . . . . . . ………………
157
Epoxy Compositions
. . . ………………
159
Powder Coatings . . . . ………………
159
Liquid Coatings . . . . ………………
160
Adhesives . . . . . . . ………………
161
Laminates . . . . . . . ………………
162
Casting and Molding . . ………………
163
PATENT SUMMARY TABLES
. . . . . . . . . . . . . . . . . . . . .
165
CITED REFERENCES
. . . . . . . . . . . . . . . . . . . . .
197
PATENT REFERENCES
. . . . . . . . . . . . . . . . . . . . .
209
iV
Epoxy Resins, Supp. A., February 1984

ILLUSTRATIONS
Diglycidyl Ether of Bisphenol A by Batch Process
FlowSheet
. . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Batch Process
Effect of Operating Level and Plant Capacity
on Production Cost . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Batch Process
Effect of BPA and ECH Prices on Product Value
. . .
Diglycidyl Ether of Bisphenol A by Continuous Process
FlowSheet
. . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Continuous Process
Effect of Operating Level and Plant Capacity
on Production Cost . . . . . . . . . . . . . . . . .
Solid Epoxy Resin from DGEBA and Bisphenol A
FlowSheet
. . . . . . . . . . . . . . . . . . . . .
Solid Epoxy Resin from DGEBA and Bisphenol A
Effect of Operating Level and Plant Capacity
on Production Cost . . . . . . . . . . . . . . . . .
Solid Epoxy Resin from DGEBA and Bisphenol A
Effect of BPA and DGEBA Prices on Product Value
. .
High MW Epoxy Resin Solution from DGEBA and Bisphenol
FlowSheet
. . . . . . . . . . . . . . . . . . . . .
High MW Epoxy Resin Solution from DGEBA and Bisphenol
Effect of Operating Level and Plant Capacity
on Production Cost . . . . . . . . . . . . . . . . .
High MW Epoxy Resin Solution from DGEBA and Bisphenol
Effect of BPA and DGEBA Prices on Product Value
. .
Epoxy Novolac Resin by Conventional Process
FlowSheet
. . . . . . . . . . . . . . . . . . . . .
Epoxy Novolac Resin by Conventional Process
Effect of Operating Level and Plant Capacity
on Production Cost . . . . . . . . . . . . . . . . .
Epoxy Novolac Resin by Conventional Process
Effect of Epichlorohydrin and Phenol Prices
onProductValue
. . . . . . . . . . . . .
Epoxy Resins, Supp. A., February 1984
ILLUSTRATIONS
6.4
Epoxy Novolac Resin by Alternative Process
Flowsheet…………………….
223
6.5
Epoxy Novolac Resin by Alternative Process
Effect of Operating Level and Plant Capacity
on Production Cost
. . . . . . . . . . . . . . . . . . . .
143
vi
Epoxy Resins, Supp. A., February 1984
TABLES
2.1

Processes for BPA-Based Epoxy Resins
Summary of Economics . . . . . . . . . . . . . . . . . . . .
Processes for Phenol-Based Epoxy Resins
Summary of Economics . . . . . . . . . . . . . . . . . . . .
Major Producers of Epoxy Resins in the United States,
Western Europe, and Japan . . . . . . . . . . . . . . . . .
Producers of Epoxy Resins in Other Countries
. . . . . . .
Announced Production Capacity Expansion for Epoxy Resins . .
Consumption of Epoxy Resins in the United States,
Western Europe, and Japan . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A
PatentSummary
. . . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Batch Process
Design Bases and Assumptions
. . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Batch Process
Stream Flows
. . . . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Batch Process
Maj’or Equipment . . . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Batch Process
Utilities Summary . . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Batch Process
Total Capital Investment
. . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Batch Process
Production Costs
. . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Continuous Process
Design Bases and Assumptions
. . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Continuous Process
Stream Flows
. . . . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Continuous Process
Major Equipment . . . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Continuous Process
Utilities Summary . . . . . . . . . . . . . . . . . . . . .
Diglycidyl Ether of Bisphenol A by Continuous Process
Total Capital Investment
. . . . . . . . . . . . . . . . .
Vii
Epoxy Resins, Supp. A., February 1984
TABLES
4.13
Diglycidyl Ether of Bisphenol A by Continuous Process
Production Costs . . . . . . . . . . . . . . . . . . . . .
57
4.14
Diglycidyl Ether of Bisphenol A Updated Batch Process
Production Costs
. . . . . . . . . . . . . . . . . . . .
62
4.15
Diglycidyl Ether of Bisphenol A
Updated Continuous Process
Production Costs . . . . . . . . . . . . . . . . . . . . .
64
5.1
Solid Epoxy Resins
PatentSummary………………….
169
5.2
Solid Epoxy Resin from DGEBA and Bisphenol A
Design Bases and Assumptions . . . . . . . . . . . . . . .
71
5.3
Solid Epoxy Resin from DGEBA and Bisphenol A
Stream Flows . . . . . . . . . . . . . . . . . . . . . . .
73
5.4
Solid Epoxy Resin from DGEBA and Bisphenol A
Major Equipment . . . . . . . . . . . . . . . . . . . . .
74
5.5
Solid Epoxy Resin from DGEBA and Bisphenol A
Utilities Summary . . . . . . . . . . . . . . . . . . . .
75
5.6
Solid Epoxy Resin from DGEBA and Bisphenol A
Total Capital Investment . . . . . . . . . . . . . . . . .
78
5.7
Solid Epoxy Resin from DGEBA and Bisphenol A
Production Costs . . . . . . . . . . . . . . . . . . . . .
79
5.8
Solid Epoxy Resin by Taffy Process
Total Capital Investment . . . . . . . . . . . . . . . . .
87
5.9
Solid Epoxy Resin by Taffy Process
Production Costs . . . . . . . . . . . . . . . . . . . . .
88
5.10
High MW Epoxy Resin Solution from DGEBA and Bisphenol A
Design Bases and Assumptions . . . . . . . . . . . . . . .
91
5.11
High MW Epoky Resin Solution from DGEBA and Bisphenol A
Stream Flows . . . . . . . . . . . . . . . . . . . . . . .
92
5.12
High MW Epoxy Resin Solution from DGEBA and Bisphenol A
Major Equipment . . . . . . . . . . . . . . . . . . . . .
93
5.13
High MW Epoxy Resin Solution from DGEBA and Bisphenol A
Utilities Summary . . . . . . . . . . . . . . . . . . . .
94
5.14
High MW Epoxy Resin Solution from DGEBA and Bisphenol A
Total Capital Investment . . . . . . . . . . . . . . . . .
97
.
Viii
Epoxy Resins, Supp. A., February 1984
TABLES
?
5.15
High MW Epoxy Resin Solution from DGEBA and Bisphenol A
Production Costs . . . . . . . . . . . . . . . . . . . . .
98
6.1
Epoxy Novolac Resins
Patentsummary………………….
172
6.2
Epoxy Novolac Resin by Conventional Process
Design Bases and Assumptions . . . . . . . . . . . . . . .
111
6.3
Epoxy Novolac Resin by Conventional Process
Stream Flows . . . . . . . . . . . . . . . . . . . . . . .
114
6.4
Epoxy Novolac Resin by Conventional Process
Major Equipment . . . . . . . . . . . . . . . . . . . . .
116
6.5
Epoxy Novolac Resin by Conventional Process
Utilities Summary . . . . . . . . . . . . . . . . . . . .
117
6.6
Epoxy Novolac Resin by Conventional Process
Total Capital Investment . . . . . . . . . . . . . . . . .
120
6.7
Epoxy Novolac Resin by Conventional Process
Production Costs . . . . . . . . . . . . . . . . . . . . .
122
6.8
Epoxy O-Cresol Novolac Resin by Conventional Process
Production Costs . . . . . . . . . . . . . . . . . . . . .
127
6.9
Epoxy Novolac Resin by Alternative Process
Design Bases and Assumptions . . . . . . . . . . . . . . .
130
6.10
Epoxy Novolac Resin by Alternative Process
Stream Flows . . . . . . . . . . . . . . . . . . . . . . .
133
6.11
Epoxy Novolac Resin by Alternative Process
Major Equipment . . . . . . . . . . . . . . . . . . . . .
135
6.12
Epoxy Novolac Resin by Alternative Process
Utilities Summary . . . . . . . . . . . . . . . . . . . .
136
6.13
Epoxy Novolac Resin by Alternative Process
Total Capital Investment . . . . . . . . . . . . . . . . .
138
6.14
Epoxy Novolac Resin by Alternative Process
Production Costs . . . . . . . . . . . . . . . . . . . . .
140
6.15
Epoxy o-Cresol Novolac Resin by Alternative Process
Production Costs . . . . . . . . . . . . . . . . . . . . .
144
6.16
Solid Epoxy Novolac Resin by Integrated Process
Production Costs . . . . . . . . . . . . . . . . . . . . .
147
ix
Epoxy Resins, Supp. A., February 1984
TABLES
7.1
Hydantoin Derivatives and their Diglycidyl Compounds
Patentsummary…………………..
174
7.2
Cycloaliphatic Epoxy Resins
PatentSummary…………………..
176
7.3
Epoxy Ester Resins
PatentSummary…………………..
177
7.4
Other Glycidyl-Type Epoxy Resins
PatentSummary…………………..
180
7.5
Modified Epoxy Resins
PatentSummary…………………..
182
8.1
Catalysts for Curing Epoxy Resins
PatentSummary…………………..
184
8.2
Curing Agents for Epoxy Resins
PatentSummary…………………..
187
8.3
Epoxy Resin Compositions
Patent Summary. . . . . . . . . . . . . . . . . . . . . . . 190

Contents
Contents ……………………………………………………………………………………………………………………………………. iii
Figures ……………………………………………………………………………………………………………………………………… vi
Tables ………………………………………………………………………………………………………………………………………. vii
1. Introduction ………………………………………………………………………………………………………………………….. 1-1
2. Conclusions ………………………………………………………………………………………………………………………….. 2-1
3. Executive Summary ………………………………………………………………………………………………………………. 3-1
Commercial overview ……………………………………………………………………………………………………………. 3-1
Technology overview …………………………………………………………………………………………………………….. 3-2
Process economics …………………………………………………………………………………………………………………. 3-2
4. Industry status ………………………………………………………………………………………………………………………. 4-1
Uses …………………………………………………………………………………………………………………………………….. 4-1
Supply and demand ……………………………………………………………………………………………………………….. 4-2
Capacities …………………………………………………………………………………………………………………………….. 4-2
Health concerns and regulatory issues ……………………………………………………………………………………… 4-4
Worldwide producers of BPA …………………………………………………………………………………………………. 4-5
Planned worldwide capacities …………………………………………………………………………………………………. 4-6
Feedstock ……………………………………………………………………………………………………………………………… 4-7
Phenol ………………………………………………………………………………………………………………………………. 4-7
Acetone …………………………………………………………………………………………………………………………….. 4-7
BPA product ……………………………………………………………………………………………………………………… 4-8
Feedstock and product specifications ……………………………………………………………………………………….. 4-9
Phenol ………………………………………………………………………………………………………………………………. 4-9
Acetone …………………………………………………………………………………………………………………………….. 4-9
BPA product ……………………………………………………………………………………………………………………… 4-9
5. Chemistry review ………………………………………………………………………………………………………………….. 5-1
Process Chemistry …………………………………………………………………………………………………………………. 5-1
Condensation reactions ……………………………………………………………………………………………………….. 5-1
Cracking reactions ……………………………………………………………………………………………………………… 5-2
Rearrangement reactions …………………………………………………………………………………………………….. 5-3
Production process ………………………………………………………………………………………………………………… 5-4
Condensation reactors …………………………………………………………………………………………………………. 5-4
Condensation catalysts ………………………………………………………………………………………………………… 5-4
Product recovery and purification…………………………………………………………………………………………. 5-5
Patent review ………………………………………………………………………………………………………………………… 5-7
Badger ………………………………………………………………………………………………………………………………. 5-7
Bayer ………………………………………………………………………………………………………………………………… 5-8
Dow …………………………………………………………………………………………………………………………………. 5-8
Idemitsu/Chiyoda ……………………………………………………………………………………………………………….. 5-9
Mitsui ……………………………………………………………………………………………………………………………… 5-10
SABIC (GE) ……………………………………………………………………………………………………………………. 5-10
IHS Chemical Process Economics Program | Report 192A

Sinopec/Lummus ……………………………………………………………………………………………………………… 5-12
6. Bisphenol A by SABIC process ………………………………………………………………………………………………. 6-1
Process description ………………………………………………………………………………………………………………… 6-1
Reaction ……………………………………………………………………………………………………………………………. 6-1
Product separation and recovery …………………………………………………………………………………………… 6-1
Cracking and rearrangement ………………………………………………………………………………………………… 6-2
BPA purification ………………………………………………………………………………………………………………… 6-3
Process discussion …………………………………………………………………………………………………………………. 6-7
Patent selection ………………………………………………………………………………………………………………….. 6-7
Catalyst …………………………………………………………………………………………………………………………….. 6-7
Reactors ……………………………………………………………………………………………………………………………. 6-7
Feedstocks ………………………………………………………………………………………………………………………… 6-7
BPA recovery ……………………………………………………………………………………………………………………. 6-8
Materials of construction …………………………………………………………………………………………………….. 6-8
Waste treatment …………………………………………………………………………………………………………………. 6-8
Cost estimates ……………………………………………………………………………………………………………………… 6-12
Fixed-capital costs ……………………………………………………………………………………………………………. 6-12
Production costs ……………………………………………………………………………………………………………….. 6-12
7. Bisphenol A by Dow process ………………………………………………………………………………………………….. 7-1
Process description ………………………………………………………………………………………………………………… 7-1
Reaction ……………………………………………………………………………………………………………………………. 7-1
Product separation and recovery …………………………………………………………………………………………… 7-1
Cracking and rearrangement ………………………………………………………………………………………………… 7-2
BPA purification ………………………………………………………………………………………………………………… 7-2
Process discussion …………………………………………………………………………………………………………………. 7-6
Patent selection ………………………………………………………………………………………………………………….. 7-6
Catalyst …………………………………………………………………………………………………………………………….. 7-6
Reactors ……………………………………………………………………………………………………………………………. 7-6
Feedstocks ………………………………………………………………………………………………………………………… 7-6
BPA recovery ……………………………………………………………………………………………………………………. 7-7
Materials of construction …………………………………………………………………………………………………….. 7-7
Waste treatment …………………………………………………………………………………………………………………. 7-7
Cost estimates ……………………………………………………………………………………………………………………… 7-11
Fixed-capital costs ……………………………………………………………………………………………………………. 7-11
Production costs ……………………………………………………………………………………………………………….. 7-11
8. Bisphenol A by Badger process ………………………………………………………………………………………………. 9-1
Process description …………………………………………………………………………………………………………….. 9-1
Reaction ………………………………………………………………………………………………………………………… 9-1
Product separation and recovery ……………………………………………………………………………………….. 9-1
Cracking and rearrangement …………………………………………………………………………………………….. 9-2
BPA purification …………………………………………………………………………………………………………….. 9-2
Process discussion ……………………………………………………………………………………………………………… 9-6

Patent selection ………………………………………………………………………………………………………………. 9-6
Catalyst check ………………………………………………………………………………………………………………… 9-6
Reactors …………………………………………………………………………………………………………………………. 9-6
Feedstocks ……………………………………………………………………………………………………………………… 9-6
BPA recovery …………………………………………………………………………………………………………………. 9-7
Materials of construction …………………………………………………………………………………………………. 9-7
Waste treatment ………………………………………………………………………………………………………………. 9-7
Cost estimates ………………………………………………………………………………………………………………….. 9-11
Fixed-capital costs …………………………………………………………………………………………………………. 9-11
Production costs ……………………………………………………………………………………………………………. 9-11
Appendix A: Patent summary table ……………………………………………………………………………………………. A-1
Appendix B: Design and cost bases ……………………………………………………………………………………………. B-1
Appendix C: Cited references ……………………………………………………………………………………………………. C-1
Appendix D: Patent references by company ………………………………………………………………………………… D-1
Appendix E: Process flow diagrams …………………………………………………………………………………………… E-1

IHS Chemical Process Economics Program | Report 192A
Figures
Figure 3.1: Capital costs comparison …………………………………………………………………………………………… 3-5
Figure 3.2: Production costs comparison ……………………………………………………………………………………… 3-6
Figure 3.3: CO2 emissions comparison ……………………………………………………………………………………….. 3-7
Figure 3.4: Water usage comparison ……………………………………………………………………………………………. 3-7
Figure 4.1: Global consumption by end uses ………………………………………………………………………………… 4-1
Figure 4.2: Worldwide supply and demand ………………………………………………………………………………….. 4-2
Figure 4.3: Global capacity by process type …………………………………………………………………………………. 4-2
Figure 4.4: Capacity growth by process type ………………………………………………………………………………… 4-3
Figure 4.5: Capacity growth by regions ……………………………………………………………………………………….. 4-4
Figure 4.6: Historical prices for phenol ……………………………………………………………………………………….. 4-7
Figure 4.7: Historical prices for acetone ………………………………………………………………………………………. 4-8
Figure 4.8: Historical prices for BPA ………………………………………………………………………………………….. 4-8
Figure 6.1: Bisphenol A production by SABIC process ………………………………………………………………… E-2
Figure 6.2: Effect of feedstock prices (SABIC process) ……………………………………………………………….. 6-14
Figure 6.3: Effect of plant capacity (SABIC process) ………………………………………………………………….. 6-14
Figure 7.1: Bisphenol A production by Dow process ……………………………………………………………………. E-3
Figure 7.2: Effect of feedstock prices (Dow process) …………………………………………………………………… 7-13
Figure 7.3: Effect of plant capacity (Dow process) ……………………………………………………………………… 7-13
Figure 8.1: Bisphenol A production by Badger process ………………………………………………………………… E-4
Figure 8.2: Effect of feedstock prices (Badger process) ……………………………………………………………….. 9-13
Figure 8.3: Effect of plant capacity (Badger process) …………………………………………………………………… 9-13

IHS Chemical Process Economics Program | Report 192A
July 2014
vii
© 2014 IHS
Tables
Table 3.1: Production economics comparison (English units) …………………………………………………………. 3-3
Table 3.2: Production economics comparison (Metric units) ………………………………………………………….. 3-4
Table 4.1: Worldwide producers of BPA ……………………………………………………………………………………… 4-5
Table 4.2: Planned worldwide capacities ……………………………………………………………………………………… 4-6
Table 4.3: Phenol feedstock specifications …………………………………………………………………………………… 4-9
Table 4.4: Acetone feedstock specifications …………………………………………………………………………………. 4-9
Table 4.5: BPA product specifications ………………………………………………………………………………………… 4-9
Table 6.1: Design basis and assumptions (SABIC process) ……………………………………………………………. 6-4
Table 6.2: Stream flows (SABIC process) ……………………………………………………………………………………. 6-5
Table 6.3: Major equipment (SABIC process) ……………………………………………………………………………… 6-9
Table 6.4: Utilities summary (SABIC process) …………………………………………………………………………… 6-11
Table 6.5: Total capital investment (SABIC process) ………………………………………………………………….. 6-15
Table 6.6: Production costs (SABIC process) …………………………………………………………………………….. 6-16
Table 6.7: Production costs in metric units (SABIC process) ……………………………………………………….. 6-18
Table 7.1: Design basis and assumptions (Dow process) ……………………………………………………………….. 7-3
Table 7.2: Stream flows (Dow process) ……………………………………………………………………………………….. 7-4
Table 7.3: Major equipment (Dow process) …………………………………………………………………………………. 7-8
Table 7.4: Utilities summary (Dow process) ………………………………………………………………………………. 7-10
Table 7.5: Total capital investment (Dow process) ……………………………………………………………………… 7-14
Table 7.6: Production costs (Dow process) ………………………………………………………………………………… 7-15
Table 7.7: Production costs in metric units (Dow process) …………………………………………………………… 7-17
Table 8.2: Stream flows (Badger process) ……………………………………………………………………………………. 9-4
Table 8.3: Major equipment (Badger process) ………………………………………………………………………………. 9-8
Table 8.4: Utilities summary (Badger process)……………………………………………………………………………. 9-10
Table 8.5: Total capital investment (Badger process) …………………………………………………………………… 9-14
Table 8.6: Production costs (Badger process) ……………………………………………………………………………… 9-15
Table 8.7: Production costs in metric units (Badger process) ………………………………………………………… 9-17
Table A.1: Bisphenol A production patent summary…………………………………………………………………….. A-2