PROCESS ECONOMICS PROGRAM
SRI INTERNATIONAL
Menlo Park, California 94025 Abstract Process Economics Program Report No. 193 ETHYLENE OXIDE DERIVATIVES
(January 1991)
This report covers the technology and economics for producing ethylene glycol ether, tert-butyl glycol ether, ethanolamines, ethyleneamines, and ethylene carbonate. Product slate flexibility is addressed for the ethanolamines, and four routes to ethyleneamines are evaluated: from ethylene oxide, from monoethanolamine, from ethylene dichloride, and by an integrated ethylene oxide/ethylene dichloride process.
Information on producers, plant capacities, and current supply and demand for these products is included.
PEP’87 TIM - Report No. 193
ETHYLENE OXIDE a DERIVATIVES
by THOMAS I. McMlLLAN l
January 1991
A private report by the PROCESS ECONOMICS PROGRAM
Menlo Park, California 94025 For detailed marketing data and information, the reader is referred to one of the SRI programs specializing in marketing research. The CHEMCAL ECONOMlCS HANDBOOK Program covers most major chemicals and chemical products produced In the United States and the WORLD PETRocHEMlcdLS Program covers major hydrocarbons and their derivatives on a worldwide basis. In addition, the SRI Dl/?ECTO/?Y OF CHEMlCAL PRODUCERS services provide detailed lists of chemical producers by company, product, and plant for the United States and Western Europe
Ii 1 INTRODUCTION I...... ,..,...... ,,...... l-l
2 SUMMARY ...... 2-l
GENERAL ASPECTS ...... 2-l Ethylene Glycol Ethers ...... 2-2 Ethylene Glycol t-Butyl Ether ...... 2-2 Ethanolamines ...... 2-2 Ethyleneamines ...... 2-3 Ethylene Carbonate ...... 2-3
ECONOMICS ...... 2-3 Glycol Ethers ...... 2-3 Ethanolamines ...... 2-4 Ethyleneamines ...... 2-5 Ethylene Carbonate ...... 2-6
3 INDUSTRY STATUS ...... 3-l
ETHYLENE OXIDE ...... 3-l
ETHYLENE GLYCOL ETHERS ...... 3-6 United States ...... 3-l 1 Ethylene Glycol Monomethyl Ether ...... 3-l 1 Ethylene Glycol Monobutyl Ether ...... 3-l 1 Diethylene Glycol Monomethyl Ether ...... 3-l 2 Diethylene Glycol Ethyl Ether ...... 3-l 2 Diethylene Glycol Monobutyl Ether ...... 3-l 2 Triethylene Glycol Monoethers ...... 3-13 Western Europe ...... 3-13 Japan ...... 3-13 ETHANOLAMINES ...... 3-14 United States ...... 3-18 Western Europe ...... 3-22 Japan ...... 3-23
.. . - Ill - CONTENTS (Continued)
3 INDUSTRY STATUS (Concluded)
ETHYLENEAMINES ...... 3-24 United States ...... 3-27 Western Europe ...... 3-30
Japan ...... 3-31
ETHYLENE CARBONATE ...... 3-32 United States ...... 3-33 Western Europe ...... 3-33 Japan ...... 3-34
4 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE ...... 4-l
CHEMISTRY ...... 4-l
PROCESS REVIEW ...... 4-3 Homogeneous Catalysts ...... 4-4 Heterogeneous Catalyst Systems ...... 4-8 REVIEW OF ESTIMATE BASES ...... 4-7
PROCESS DESCRIPTION ...... 4-10 PROCESS DISCUSSION ...... 4-l 8 Product Switching ...... 4-l 9 Tankage ...... 4-19
COST ESTlMATES ...... 4-20 Capital Costs ...... 4-20 Production Costs ...... 4-20
5 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE ...... 5-l
CHEMISTRY ...... 5-1 PROCESS REVIEW ...... 5-3 - PROCESS DESCRIPTION ...... 5-5 Review of Estimate Bases ...... 5-5
PROCESS DISCUSSION ...... 5-l 2 COST ESTIMATES ...... 5-12 a
- iv - CONTENTS (Continued)
- 5 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE (Concluded) ...... 5-l Capital Costs ...... 5-l 2 Production Costs ...... 5-13 a Feedstock Costs ...... 5-14 6 ETHANOLAMINES ...... 6-l
CHEMISTRY ...... 6-l
PROCESS REVIEW ...... 6-5 Reaction Conditions, Process Energy Efficiency ...... 6-8 Color Stabilization ...... 8-9 Product Recycle and Multiple Reactor Systems ...... 8-10
PROCESS DESCRIPTION ...... 6-11
PROCESS DISCUSSION ...... 6-25 a Materials of Construction ...... 8-25 Reactor Design ...... 6-25 Product Slate ...... 6-26 Product Separation and Purification ...... 6-26
COST ESTIMATES ...... 6-28 Capital Costs ...... 6-28 Production Costs ...... 6-34 Variable Costs ...... 6-34 Product Value-Case A ...... 6-34 Product Value-Case B ...... 6-35
7 ETHYLENEAMINES ...... 7-l
CHEMISTRY ...... 7-l
PROCESS REVIEW ...... 7-3 Ethyleneamines from Monoethanolamine ...... 7-3 Ethyleneamines from Ethylene Oxide via Monoethanolamine ...... 7-5 Polyethylene Polyamines by non-EDC Processes ...... 7-5 Other Related Processes ...... 7-7
-v- CONTENTS (Continued)
7 ETHYLENEAMINES (Concluded)
INDUSTRIAL PRCCESSES AND THEIR ECONOMICS ...... 7-7 Case A: Ethyleneamines from Ethylene Oxide ...... 7-9 Process Description ...... 7-9 Process Discussion ...... 7-l 8 Cost Estimates ...... 7-18 Case B: Ethyleneamines from Monoethanolamine ...... 7-27 Process Description ...... 7-27 Process Discussion ...... 7-35 Cost Estimates ...... 7-35 Case C: Ethyleneamines from Ethylene Dichloride ...... 7-42 Process Description ...... 7-42 Process Discussion ...... 7-53 Cost Estimates ...... 7-53 Case D: Ethyleneamines from Ethylene Oxide-and Ethylene Dichloride .... 7-60 Process Description ...... 7-60 Process Discussion ...... 7-75 Cost Estimates ...... 7-75
8 OHYLENE CARBONATE ...... 6-l CHEMISTRY ...... 8-l PROCESS REVIEW ...... 8-2 PROCESS DESCRIPTION ...... 8-8 PROCESS DISCUSSION ...... 6-15 COST ESTIMATES ...... 8-l 6 Capital Costs ...... 8-16 Production Costs ...... 8-16
APPENDIX A: PATENT SUMMARY TABLES ...... A-l
APPENDIX B: DESIGN AND COST BASES ...... B-l
DESIGN CONDlTIONS ...... B-3
COST BASES ...... B-3
CAPlTAL INVESTMENT ...... B-3 PRODUCTIONCOSTS ...... B-4 EFFECT OF OPERATING LEVEL ON PRODUCTIONCOSTS ...... B-5
- vi - CONTENTS (Concluded)
APPENDIX c: PHYSICAL PROPERTIES ..,,,...... I...... C-l - APPENDIX D: HANDLING AND SAFETY INFORMATION ...... D-l
ETHYLENE OXIDE ...... D-3
GLYCOL ETHERS ...... D-4 l Storage and Handling ...... D-4 Environmental Issues ...... D-4
ETHANOLAMINES ...... D-4 Materials of Construction ...... D-4 Freeze Protection ...... D-5 Atmosphere ...... D-5 Safety ...... D-5 ETHYLENEAMINES...... D-5 Materials of Construction ...... D-6 Freeze Protection ...... D-6 Atmosphere ...... D-8 Safety ...... D-8 ETHYLENE CARBONATE ...... D-6
APPENDIX E: CITED REFERENCES ...... E-l
APPENDIX F: PATENT REFERENCES BY COMPANY ...... F-l
APPENDIX G: PROCESS FLOW DIAGRAMS ...... G-l
- vii - ILLUSTRATIONS
4.1 GLYCOL ETHERS PROCESS FLOW DIAGRAM ...... G-3
4.2 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENEOXIDE EFFECT OF RAW MATERIAL PRICES ON PRODUCT VALUE ETHYL ETHERS ...... 4-28
4.3 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE EFFECT OF RAW MATERIAL PRICES ON PRODUCT VALUE BUTYL ETHERS ...... 4-29
4.4 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE EFFECT OF OPERATING LEVEL ON PRODUCT VALUE ETHYL ETHERS ...... 4-30
4.5 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE EFFECT OF OPERATING LEVEL ON PRODUCT VALUE BUTYL ETHERS ...... 4-31
5.1 ETHYLENE GLYCOL TERTlARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE ISOBUTYLENECONVERSION AND PRODUCT YIELDS AS FUNCTIONS OF REACTION CONDITIONS . . . , ...... 5-6
5.2 ETHYLENE GLYCOL TERTIARY-BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE PROCESS FLOW DIAGRAM ...... G-5
5.3 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE EFFECT OF RAW MATERIAL COSTS ON PRODUCT VALUE ...... 5-18
5.4 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE ...... *...... 5-19
6.1 ETHANOLAMINES PRODUCT DISTRIBUTION AS A FUNCTION OF FEEDSTOCK MOL RATIO ...... , ...... 6-4
6.2 ETHANOLAMINES REPRESENTATIVE ETHANOLAMINES FLOWSHEET ...... 6-6
6.3 ETHANOLAMINES PROCESS FLOW DIAGRAM ...... G-7
- ix - ILLUSTRATIONS (Continued)
6.4 ETHANOLAMINES-CASE 8.5 FLEXIBLE PLANT, 5:l AMMONIA:EO MOL RATIO EFFECT OF RAW MATERIAL COSTS ON PRODUCT VALUE ...... 6-43
8.5 ETHANOLAMINES-CASE 8.5 FLEXIBLE PLANT, 5:l AMMONIA:EO MOL RATIO EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE ...... 8-46 l 7.1 ETHYLENEAMINESFROM ETHYLENEOXIDE PROCESS FLOW DIAGRAM ...... G-9
7.2 ETHYLENEAMINESFROM ETHYLENEOXIDE EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE ...... 7-26
7.3 ETHYLENEAMINESFROM MONOETHANOLAMINE PROCESS FLOW DIAGRAM ...... G-l 3
7.4 ETHYLENEAMINESFROM MONOETHANOLAMINE EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE ...... 7-41
7.5 ETHYLENEAMINESFROM ETHYLENE DICHLORIDE PROCESS FLOW DIAGRAM ...... G-15
7.6 ETHYLENEAMINESFROM ETHYLENE DICHLORIDE EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE ...... 7-59
7.7 ETHYLENEAMINESFROM ETHYLENE OXIDE AND ETHYLENE DICHLORIDE PROCESS FLOW DIAGRAM ...... G-19
7.8 ETHYLENEAMINESFROM ETHYLENE OXIDE AND ETHYLENE DICHLORIDE EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE ...... 7-83
8.1 ETHYLENE CARBONATE JEFFERSON CHEMICAL ETHYLENE CARBONATE PILOT PLANT ...... 8-3
8.2 ETHYLENE CARBONATE HiSLS ETHYLENE CARBONATE PLANT SAVINESTI INDUSTRIAL COMPLEX, ROMANIA ...... , ...... 6-5
8.3 ETHYLENE CARBONATE PROCESS FLOW DIAGRAM ...... G-25
-x- ILLUSTRATlONS (Concluded)
8.4 ETHYLENE CARBONATE EFFECT OF RAW MATERIAL COSTS ON PRODUCT VALUE ...... 8-21
8.5 ETHYLENE CARBONATE EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE ...... 8-22 c.1 ETHYLENE GLYCOL TERTIARY BUTYL ETHER (ETB) TRIANGULAR PHASE DIAGRAM FOR THE BUTANE-BUTENE FRACTION-ETHYLENE GLYCOL-ETB SYSTEM ...... C-9
- xi - TABLES
2.1 WORLD CONSUMPTION OF ETHYLENEOXIDE - 1989 ...... 2-l
2.2 COST FEATURES OF GLYCOL ETHERS PRODUCTION ...... 2-7
2.3 COST FEATURES OF ETHANOLAMINES PRODUCTlON ...... 2-8 l 2.4 COST FEATURES OF ETHYLENEAMINESPRODUCTION ...... 2-9 2.5 COST FEATURES OF ETHYLENE CARBONATE PRODUCTION ...... 2-10
3.1 PRODUCERSOF ETHYLENE OXIDE- UNlTED STATES, WESTERN EUROPE, AND JAPAN ...... 3-2
3.2 WORLD PRODUCTIONCAPACITY FOR ETHYLENEOXIDE ...... 3-4
3.3 WORLD SUPPLY/DEMAND FOR ETHYLENE OXIDE-1988 ...... 3-5
3.4 PRODUCERSOF GLYCOL ETHERS- UNlTED STATES, WESTERN EUROPE, AND JAPAN ...... 3-7
3.5 1988 CONSUMPTION OF ETHYLENEGLYCOL ETHERS- UNITED STATES, WESTERN EUROPE, AND JAPAN ...... 3-9
3.6 1993 WORLD CONSUMPTION OF GLYCOL ETHERS- UNiTED STATES, WESTERN EUROPE, AND JAPAN ...... 3-10
3.7 WORLD PRODUCERSOF ETHANOLAMINES ...... 3-15
3.8 WORLD SUPPLY/DEMAND OF ETHANOLAMINES-1987 ...... 3-17
3.9 PRODUCTlONOF ETHANOLAMINES-UNITED STATES ...... 3-18
3.10 U.S. CONSUMFllON OF ETHANOLAMINES-1986 ...... 3-l 9
3.11 WESTERN EUROPEANCONSUMPTION OF ETHANOLAMINES-1987 .... 3-23
3.12 JAPANESE CONSUMPTlONOF ETHANOLAMINES-1988 ...... 3-24
3.13 WORLD PRODUCERSOF ETHYLENEAMINES-1990 ...... 3-25
3.14 U.S. DISTRIBUTIONOF ETHYLENEAMINEPRODUCTION-l 987 ...... 3-27
3.15 U.S. CONSUMPTION OF ETHYLENEDIAMINE-1987 ...... 3-28
3.16 CONSUMPTION PATTERN OF ACYCLIC POLYAMINES- UNITED STATES ...... 3-29
3.17 WESTERN EUROPEAN CONSUMPTION OF ETHYLENEDIAMINE-1987 ... 3-30
... - XIII - TABLES (Continued)
3.18 JAPANESE CONSUMPTION OF ETHYLENEAMINES-1987 ...... 3-32
3.19 PRODUCERSOF ETHYLENE CARBONATE IN THE UNITED STATES, WESTERN EUROPE, AND JAPAN IN 1990 ,,.... 3-33
4.1 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE PATENT SUMMARY ...... A-3 l 4.2 HOMOGENEOUS CATALYSTS FOR PRODUCTIONOF BUTYL GLYCOL ETHER ...... 4-4
4.3 HETEROGENEOUSCATALYSTS FOR PRODUCTIONOF BUTYL GLYCOL ETHER ...... 4-6
4.4 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE DESIGN BASES AND ASSUMPTIONS ...... 4-9
4.5 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENEOXIDE STREAM FLOWS-ETHYL ETHERS OPERATION ...... , 4-12
4.6 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE STREAM FLOWS-BUTYL ETHERS OPERATIONS ...... 4-l 3 a
4.7 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE OPERATING TEMPERATURESAND PRESSURES ...... 4-14
4.8 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE MAJOR EQUIPMENT ...... 4-15
4.9 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE UTILITIES SUMMARY ...... 4-l 7
4.10 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENEOXIDE TOTAL CAPITAL INVESTMENT ...... 4-22
4.11 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE a PRODUCTION COSTS-ETHYL ETHERS ...... s.... 4-23
4.12 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE PRODUCTlONCOSTS-BUTYL ETHERS . . . ..*...... 4-25
4.13 GLYCOL ETHERS FROM ALCOHOLS AND ETHYLENE OXIDE FEED REQUIREMENTSAND COSTS OF INDIVIDUAL GLYCOL ETHERS . . 4-27
5.1 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE RATE CONSTANTS AND EQUILIBRIUMCONSTANTS ...... 5-2
- xiv - TABLES (Continued)
5.2 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE TYPICAL COMPOSITION OF A BUTANE-BUTENE FRACTION FROM NAPHTHA CRACKING ...... 5-3
5.3 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE l PATENT SUMMARY ...... A-9
5.4 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENEGLYCOL AND ISOBUTYLENE DESIGN BASES AND ASSUMPTIONS ..,....,...,...... a...... 5-7
5.5 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE STREAM FLOWS ...... 5-9
5.6 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE MAJOR EQUIPMENT . ..*...... 5-10
5.6 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE MAJOR EQUIPMENT ...... 5-11
5.7 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE UTILITIES SUMMARY ...... 5-11
5.8 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE TOTAL CAPITAL INVESTMENT ...... 5-15
5.9 ETHYLENE GLYCOL TERTIARY BUTYL ETHER FROM ETHYLENE GLYCOL AND ISOBUTYLENE PRODUCTIONCOSTS ...... 5-16
6.1 ETHANOLAMINES PATENT SUMMARY . . ..,...... ,...... A-12
6.2 ETHANOLAMINES DESIGN BASES AND ASSUMPTIONS ...... 6-11
6.3 ETHANOLAMINES 5:l AMMONIA:EO MOL RATIO IN REACTOR FEED STREAM FLOWS ...... 6-14
-xv- TABLES (Continued)
6.4 ETHANOLAMINES 2O:l AMMONIA:EO MOL RATIO IN REACTOR FEED l STREAM FLOWS ...... 6-16
6.5 ETHANOLAMINES CASE A.S-NARROW PRODUCT DlSTRIBUTlON 5:l AMMONIA:EO MOL RATIO IN REACTOR FEED MAJOR EQUIPMENT ...... 6-18
6.6 ETHANOLAMINES CASE A.PO-NARROW PRODUCT DISTRIBUTION 0 2O:l AMMONIA:EO MOL RATIO IN REACTOR FEED MAJOR EQUIPMENT ...... 6-20
6.7 ETHANOLAMINES CASE B-WIDE PRODUCT DISTRIBUTION 5:l TO 2O:l AMMONIA:EO MOL RATIO IN REACTOR FEED MAJOR EQUIPMENT ...... 6-22
6.6 ETHANOLAMINES UTiLlTlES SUMMARY ...... *...... 6-24
6.9 ETHANOLAMINES TOTAL CAPlTAL INVESTMENT ...... 6-30
6.10 ETHANOLAMINES CASE A.S-NARROW PRODUCT DISTRIBUTION 0 5:l AMMONIA:EO MOL RATIO IN REACTOR FEED CAPlTAL INVESTMENT BY SECTION ...... 6-31
6.11 ETHANOLAMINES CASE A.PO-NARROW PRODUCT DISTRIBUTION 2O:l AMMONIA:EO MOL RATIO IN REACTOR FEED CAPITAL INVESTMENT BY SECTION ...... 6-32
6.12 ETHANOLAMINES CASE B-WIDE PRODUCT DISTRIBUTION 5:l TO 2O:l AMMONIA:EO MOL RATIO IN REACTOR FEED CAPITAL INVESTMENT BY SECTION ...... ~..... 6-33
6.13 ETHANOLAMINES VARIABLE COSTS PEP COST INDEX: 515 ,...... 6-37 a 6.14 ETHANOLAMINES CASE A .5-NARROW PRODUCT DlSTRlBUTlON 5:l AMMONIA:EO MOL RATIO IN REACTOR FEED PRODUCTIONCOSTS ...... 6-38
6.15 ETHANOLAMINES CASE A. 20-NARROW PRODUCT DISTRIBUTION 2O:l AMMONIA:EO MOL RATIO IN REACTOR FEED a PRODUCTIONCOSTS ..,...... 6-39
6.16 ETHANOLAMINES CASE B.S-WIDE PRODUCT DISTRIBUTION 5:l AMMONIA:EO MOL RATIO IN REACTOR FEED PRODUCTIONCOSTS ...... 6-40
- xvi - TABLES (Continued)
6.17 ETHANOLAMINES CASE B. 1O-WIDE PRODUCT DlSTRlBUTlON 10: 1 AMMONIA:EO MOL RATIO IN REACTOR FEED PRODUCTIONCOSTS ...... 8-41
6.18 ETHANOLAMINES CASE B.SO-WIDE PRODUCT DISTRIBUTION 2O:l AMMONIA:EO MOL RATIO IN REACTOR FEED PRODUCTIONCOSTS ..,....,,,,..,...... ,...... 6-42
8.19 ETHANOLAMINES CASE A-NARROW PRODUCT DISTRIBUTION DIRECT COSTS BY SECTION ...... 6-44
6.20 ETHANOLAMINES CASE 8-WIDE PRODUCT DISTRIBUTION DIRECT COSTS BY SECTION ...... 6-45
7.1 ETHYLENEAMINES PATENT SUMMARY ...... *...... A-16
7.2 ETHYLENEAMINES COMPARISON OF PROCESSESEVALUATED ...... 7-8
7.3 ETHYLENEAMINESFROM ETHYLENEOXIDE DESIGN BASES AND ASSUMPTIONS ...... *..... 7-l 1
7.4 ETHYLENEAMINESFROM ETHYLENEOXIDE STREAM FLOWS ...... 7-12
7.5 ETHYLENEAMINESFROM ETHYLENE OXIDE MAJOR EQUIPMENT ...... 7-14
7.6 ETHYLENEAMINESFROM ETHYLENEOXIDE UTlLlTlESSUMMARY ...... 7-17
7.7 ETHYLENEAMINESFROM ETHYLENEOXIDE TOTAL CAFITAL INVESTMENT ..,...... ,...... , 7-21
7.8 ETHYLENEAMINESFROM ETHYLENEOXIDE CAPlTAL INVESTMENT BY SECTION ...... 7-22
7.9 ETHYLENEAMINESFROM ETHYLENE OXIDE PRODUCTIONCOSTS ...... 7-24
7.10 ETHYLENEAMINESFROM MONOETHANOLAMINE DESIGN BASES ...... I...... 7-29
7.11 ETHYLENEAMINESFROM MONOETHANOLAMINE STREAM FLOWS ...... I...... 7-30
- xvii - TABLES (Continued)
7.12 ETHYLENEAMINESFROM MONOETHANOLAMINE MAJOR EQUIPMENT ...... 7-32
7.13 ETHYLENEAMINESFROM MONOETHANOLAMINE UTlLlTlES SUMMARY ,.,...... ,...... ,,...... *...... 7-34
7.14 ETHYLENEAMINESFROM MONOETHANOLAMINE TOTAL CAPITAL INVESTMENT .,...... 7-37
7.15 ETHYLENEAMINESFROM MONOETHANOLAMINE CAPlTAL INVESTMENT BY SECTION ...... 7-38
7.16 ETHYLENEAMINESFROM MONOETHANOLAMINE PRODUCTIONCOSTS ...... 7-39
7.17 ETHYLENEAMINESFROM ETHYLENE DICHLORIDE DESIGN BASES AND ASSUMPTIONS ...... 7-45
7.18 ETHYLENEAMINESFROM ETHYLENE DICHLORIDE STREAM FLOWS ...... 7-46
7.19 ETHYLENEAMINESFROM ETHYLENE DICHLORIDE MAJOR EQUIPMENT ...... 7-49
7.20 ETHYLENEAMINESFROM ETHYLENE DICHLORIDE UTlLlTlES SUMMARY ..,...,...... ,...... 7-52
7.21 ETHYLENEAMINESFROM ETHYLENE DICHLORIDE TOTAL CAPlTAL INVESTMENT ...... 7-56
7.22 ETHYLENEAMINESFROM ETHYLENE DICHLORIDE PRODUCTION COSTS ...... 7-57
7.23 ETHYLENEAMINESFROM ETHYLENE OXIDE AND ETHYLENE DlCHLORlDE DESIGN BASES AND ASSUMPTIONS ...... 7-63
7.24 ETHYLENEAMINESFROM ETHYLENE OXIDE AND ETHYLENE DlCHLORlDE STREAM FLOWS ...... 7-64
7.25 ETHYLENEAMINESFROM ETHYLENE OXIDE AND ETHYLENE DICHLORIDE MAJOR EQUIPMENT ...... 7-69
7.26 ETHYLENEAMINESFROM ETHYLENE OXIDE AND ETHYLENE DICHLORIDE UTlLlTlES SUMMARY ,...,....,,.....,,...... ,....,,...... ,. 7-74
.. . - XVIII - TABLES (Continued)
7.27 ETHYLENEAMINESFROM ETHYLENE OXIDE AND ETHYLENE DICHLORIDE TOTAL CAPITAL INVESTMENT ...... 7-78
7.28 ETHYLENEAMINESFROM ETHYLENEOXIDE AND ETHYLENE DICHLORIDE CAPlTAL INVESTMENT BY SECTION ...... 7-79
7.29 ETHYLENEAMINESFROM ETHYLENEOXIDE AND ETHYLENE DICHLORIDE PRODUCTIONCOSTS n...... 7-80
7.30 ETHYLENEAMINESFROM ETHYLENE OXIDE AND ETHYLENE DICHLORIDE DIRECT COSTS BY SECTION ...... 7-82
6.1 HOLS ETHYLENE CARBONATE PLANT SAVINESTI INDUSTRIALCOMPLEX, ROMANIA ...... 6-6
6.2 ETHYLENE CARBONATE - PATENT SUMMARY ...... A-29 8.3 ETHYLENE CARBONATE DESIGN BASES ...... 8-9
8.4 ETHYLENE CARBONATE STREAM FLOWS ...... *...... 8-11
8.5 ETHYLENE CARBONATE MAJOR EQUIPMENT ...... 8-13
8.6 ETHYLENE CARBONATE UTILITIES SUMMARY ...... 8-14
8.7 ETHYLENE CARBONATE - TOTAL CAPITAL INVESTMENT ...... 8-18
8.8 ETHYLENE CARBONATE PRODUCTIONCOSTS ...... 8-l 9 a- c.1 PHYSICAL PROPERTIESOF ETHYLENEOXIDE ...... C-3 c.2 PHYSICAL PROPERTIESOF ETHYLENEGLYCOL ETHERS FROM ETHANOL OR BUTANOL AND ETHYLENEOXIDE ...... C-4
c.3 PHYSICAL PROPERTIESOF ETHYLENEGLYCOL ETHERS 0 FROM ETHANOL OR BUTANOL AND ETHYLENEOXIDE ...... C-5
- xix - TABLES (Concluded)
C.4 ETHYLENE GLYCOL TERTIARY BUTYL ETHER (ETB) BOILING POINTS OF THE COMPOUNDS IN THE REACTOR EFFLUENT . . . C-8 l
C.5 ETHYLENE GLYCOL TERTIARY BUTYL ETHER (ETB) BOlLlNG POINTS OF AZEOTROPES ,,,,..,,,,,....,...... C-6
C.6 ETHYLENE GLYCOL TERTIARY BUTYL ETHER (ETB) PHOTOCHEMICAL REACTIVITY OF GLYCOL ETHERS ...... C-7 l
C.7 ETHYLENE GLYCOL TERTIARY BUTYL ETHER (ETB) PHYSICAL PROPERTIESCOMPARISON FOR ETHYLENE GLYCOL TERTIARY BUTYL ETHER (ETB) AND ETHYLENE GLYCOL N-BUTYL ETHER (EB) ,...... C-8
C.6 PHYSICAL PROPERTIESOF ETHANOLAMINES ...... c-10
C.9 PHYSICAL PROPERTIESOF ACYCLIC ETHYLENEAMINES ...... s. . . . C-l 1
C.10 PHYSICAL PROPERTIESOF SOME CYCLIC ETHYLENEAMINES ...... C-l 1
C.11 COMPONENTS OF SOME COMMERCIAL HIGHER ETHYLENEAMINES. . . . C-l 2
C.12 PHYSICAL PROPERTIESOF ETHYLENE CARBONATE ...... c-13
C.13 AZEOTROPE OF ETHYLENE GLYCOL AND ETHYLENECARBONATE . . . . c-14
D.1 STORAGE TEMPERATURESFOR ETHANOLAMINES ...... D-5
-xx-