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.I
Report No. 9
TEREPHTHALIC ACID AND
DIMETHYL TEREPHTHALATE
by LLOYD M. ELKIN
contributions by SHIGEYOSHI TAKAOKA
February 19 6 6
A private report by the
PROCESS ECONOMICS PROGRAM
STANFORD RESEARCH INSTITUTE MENLO PARK. CALIFORNIA
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CONTENTS
I INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . 1
II SUMMARY . . . . . . . . . . . . . . . . . . . . . . . . . . 3
III INDUSTRY STATUS . . . . . . . . . . . . . . . . . . . . . . 11
IV CHEMISTRY . . . . . . . . . . . . . . . . . . . . . .
Terephthalic Acid by Bromine-Promoted Catalytic Air Oxidation of p-Xylene . . . . . . . . . . . . . . . .
Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator . .
Terephthalic Acid from Phthalic Anhydride . . . . . . Terephthalic Acid by Nitric Acid Oxidation of p-Xylene Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications . . . . . . . . . . . First Oxidation . . . . . . . . . . . . . . . . . . First Esterification . . . . . . . . . . . . . . . . Second Oxidation . . . . . . . . . . . . . . . . . . Second Esterification . . . . . . . . . . . . . . .
. . . 21
. . . 21
. . . 24
. . . 26
. . . 28
. . . 29
. . . 29
. . . 32
. . . 33
. . . 35
V PROCESSES FOR THE PRODUCTION OF TEREPHTHALIC ACID ..... 37
Terephthalic Acid by Bromine-Promoted Catalytic Air Oxidation of p-Xylene ................... 37
Review of Processes ................... 37 Basic Patents ..................... 37 Raw Materials ..................... 37 Catalysts ....................... 37 Promotors ....................... 38 Solvents ........................ 30 Reactor Design and Reaction Conditions ......... 39 Separation of Products ................. 40 Purification ...................... 40 Catalyst Recovery ................... 42
iii
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CONTENTS
V (continued)
Process Description for Crude Acid Production ...... Process Discussion for Crude Acid Production .......
Process Description and Discussion for Purification of Crude Acid .......................
Cost Estimates ......................
Capital Costs .....................
Production Costs ....................
Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl-Ethyl Ketone Activator ....... Review of Processes ...................
Production of Crude Terephthalic Acid .........
Purification of Crude Terephthalic Acid ........
Process Description ...................
Process Discussion ....................
Capital Costs ......................
Production Costs ......... '. ........... Terephthalic Acid from Phthalic Anhydride .........
Review of Processes ...................
Raw Materials .....................
Catalysts .......................
Reactor Conditions and Design .............
Work-Up of Reactor Products ..............
Other Process Details .................
Process Description ...................
Process Discussion ....................
Capital Costs ......................
Production Costs .....................
Terephthalic Acid by Nitric Acid Oxidation of p-Xylene ... Review of Processes ...................
Process Description ...................
Process Discussion ....................
Capital Costs ......................
Production Costs .....................
42 48
49 55 55 59
59 59 59 65 65 73 75 75 79 79 79 79 85 85 85 86 93 94 94 98 98
103 110 110 110
iv
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CONTENTS
V (continued)
Dimethyl Terephthalate by Esterification of Terephthalic Acid ........................... 114 Review of Processes ................... 114 Process Description ................... 117 Process Discussion .................... 125
Feed Treatment Section ................. 125 Reactor Section .................... 125 Methanol Recovery Section ............... 126 Product Distillation Section .............. 126
Capital Costs ...................... 126
. Production Costs ..................... 129 Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications .............. 129
Review of Processes ................... 129 Production of Crude Dimethyl Terephthalate ....... 129 Purification of Dimethyl Terephthalate ......... 134
Process Description .................... 134 Process Discussion .................... 145 Capital Costs ...................... 146 Production Costs ..................... 149
Other Processes ...................... 149 Oxidation with Nitrogen Dioxide ............. 149 Oxidation with Sulfur Dioxide .............. 149 Decarboxylation of Trimellitic Acid ........... 151 Reaction with Sodium Metal and Carbon Dioxide ...... 151 Reaction with Alkali Metal Alkyl Carbonate ........ 152 Oxidation in Alkaline Solution .............. 152 Oxidation in Alkaline Solution in Presence of Catalyst . . 152 Oxidation with Sodium Hypochlorite ............ 153 Oxidation with Sulfur Compounds ............. 153
V
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CONTENTS
APPENDIX A Design and Cost Basis ............... 155
APPENDIX B Physical Data ................... 159
APPENDIX C Raw Material and Product Specifications ...... 163
APPENDIX D Handling and Safety ................ 167
Cited References ......................... 169
Supplementary References .. ; .................. 183
vi
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Crude Terephthalic Acid by Bromine-Promoted Air Oxidation of p-Xylene . . . . . . . . . . . . . . . . . . . . . . . . . 43
Purification of Crude Terephthalic Acid . . . . . . . . . . . 51
Crude Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator . . . . . . . . 67
Crude Terephthalic Acid from Phthalic Anhydride . . . . . . . 87
Crude Terephthalic Acid by Nitric Acid Oxidation of p-Xylene . 105
Dimethyl Terephthalate by Esterification of Terephthalic Acid.... , . . . . . . . . . . . . . . . . . . . . . . . . 119
Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications . . . . . . . . . . . . . . . . . . . . . 137
Vii
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TABLES
7
8
9
10
11
12
13
14
Summary of Economics of Evaluated Processes . . . . . . . . .
Summary of Processes Evaluated . . . . . . . . . . . . . . .
Plant Capacities, Americas . . . . . . . . . . . . . . . . .
Plant Capacities, Western Europe . . . . . . . . . . . . . .
Plant Capacities, Asia . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid by Bromine-Promoted Catalytic Air Oxidation of p-Xylene Major Process Equipment List . . . . . . . . . . . . . . . .
Crude Terephthalic Acid 'by Bromine-Promoted Catalytic Air Oxidation of p-Xylene
4
7
13
15
17
43
Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 45
Purification of Crude Terephthalic Acid Major Process Equipment List . . . . . . . . . . . . . . . . 51
Purification of Crude Terephthalic Acid Stream Flows . . . . . . . . . . . . . . . . . . . . . . . .
Terephthalic. Acid by Bromine-Promoted Catalytic Air Oxidation of p-Xylene Utilities Summary . . . . . . . . . . . . . . . . . . . . . .
'Terephthalic Acid by Bromine-Promoted Catalytic Air Oxidation of p-Xylene
53
56
Process Unit and Utilities Investment . . . . . . . . . . . . 57
Terephthalic Acid by Bromine-Promoted Catalytic Air Oxidation of p-Xylene Total Capital Investment . . . . . . . . . . . . . . . . . .
Terephthalic Acid by Bromine-Promoted Catalytic Air Oxidation of p-Xylene Production Costs . . . . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator Summary of Processes . . . . . . . . . . . . . . . . . . . .
58
60
63
viii
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TABLES
15
16
. 17
18
19
20
21
22
23
24
25
26
Crude Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator Major Process Equipment List . . . . . . . . . . . . . . . .
Crude Terephthalic &id by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator Stream Flows . . . . . . . . . . . . . . . . . . . . . . . .
Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator Utilities Summary . . . . . . . . . . . . . . . . . . . . . .
Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator Process Unit and Utilities Investment . . . . . . . . . . . .
Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator Total Capital Investment . . . . . . . . . . . . . . . . . .
Terephthalic Acid by Catalytic Oxidation of p-Xylene in the Presence of Methyl Ethyl Ketone Activator Production Costs . . . . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid from Phthalic Anhydride Summary of Processes . . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid from Phthalic Anhydride Major Process Equipment List . . . . . . . . . . . . . . . .
Crude Terephthalic Acid from Phthalic Anhydride Stream Flows . . . . . . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid from Phthalic Anhydride Utilities Summary......................
Crude Terephthalic Acid from Phthalic Anhydride Process Unit and Utilities Investment . . . . . . . . . . . .
Crude Terephthalic Acid from Phthalic Anhydride Total Capital Investment . . . . . . . . . . . . . . . . . .
IX
67
69
71
76
77
78
81
87
89
91
95
96
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TABLES
27
28
29
30
31
32
33
34
35
36
37
38
39
40
Crude Terephthalic Acid from Phthalic Anhydride Production Costs . . . . . . . . . . . . . . . . . . . . . .
Terephthalic Acid from Phthalic Anhydride Production Costs . . . . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid by Nitric Acid Oxidation of p-Xylene Summary of Processes . . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid by Nitric Acid Oxidation of p-Xylene Major Process Equipment List . . . . . . . . . . . . . . . .
Crude Terephthalic Acid' by Nitric Acid Oxidation of p-Xylene Stream Flows . . . . . . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid by Nitric Acid Oxidation of p-Xylene Utilities Summary . . . . . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid by Nitric Acid Oxidation of p-Xylene Process Unit and Utilities Investment . . . . . . . . . . . .
Crude Terephthalic Acid by Nitric Acid Oxidation of p-Xylene Total Capital Investment . . . . . . . . . . . . . . . . . .
Crude Terephthalic Acid by Nitric Acid Oxidation of p-Xylene Production Costs . . . . . . . . . . . . . . . . . . . . . .
Terephthalic Acid by Nitric Acid Oxidation of p-Xylene Production Costs . . . . . . . . . . . . . . . . . . . . . .
Dimethyl Terephthalate by Esterification of Terephthalic Acid Major Process Equipment List . . . . ; . . . . . . . . . . .
Dimethyl Terephthalate by Esterification of Terephthalic Acid Stream Flows . . . . . . . . . . . . . . . . . . . . . . . .
Dimethyl Terephthalate by Esterification of Terephthalic Acid Utilities Summary......................
Dimethyl Terephthalate by Esterification of Terephthalic Acid Process Unit and Utilities Investment . . . . . . . . . . . .
97
99
101
105
107
109
111
112
113
115
118
121
123
127
X
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TABLES
41
42
43
44
45
46
47
48
49
Dimethyl Terephthalate by Esterification of Terephthalic Acid Total Capital Investment . . . . . . . . . . . . . . . . . .
Dimethyl Terephthalate by Esterification of Terephthalic Acid Production Costs . . . . . . . . . . . . . . . . . . . . . .
Purification of Dimethyl Terephthalate Summary of Processes . . . . . . . . . . . . . . . . . . . .
130
131
135
Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications Major Process Equipment List . . . . . . . . . . . . . . . . 136
Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications Stream Flows . . . . . . . . . . . . . . . . . . . . . . . . 139
Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications Utilities Summary . . . . . . . . . . . . . . . . . . . . . . 143
Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications Process Unit and Utilities Investment . . . . . . . . . . . . 147
Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications Total Capital Investment . . . . . . . . . . . . . . . . . , 148
Dimethyl Terephthalate from p-Xylene by Successive Oxidations and Esterifications Production Costs . . . . . . . . . . . . . . . . . . . . . . 150
xi
DATE: Terephthalic Acid and Dimethyl Terephthalate, February 1966
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