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Report No. 85
ANTIOXIDANTS AND STABILIZERS FOR POLYMERS AND ELASTOMERS
by LESLIE A. CARMICHAEL
with oontributions by Peter J. Manno, Consultant
May 1973
l A private report by the
PROCESS ECONOMICS PROGRAM
l STANFORD RESEARCH INSTITWX MENLO PARK, CALIFORNIA
CONTENTS
1 INTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . 1
2 SUMMARY ............................ 3
General Aspects ........................ 3 Economic and Technical Aspects ................ 4
3 INDUSTRY STATUS ........................
Antioxidants and Antiozonants for Rubber ........... Antioxidants for Plastics ................... Stabilizers for PVC ...................... Stabilizers Against UV ....................
4 ANTIOXIDANT AND ANTIOZONANT PROTECTION FOR RUBBER . . . . . . . 27
Mechanism of Rubber Deterioration . . . . . .......... 27 Antioxidants . . . . . . . . . . . . . . . .......... 41 Phenolic Antioxidants . . . , . . . . . . .......... 42 Amine Antioxidants . . . . . . . . . . . .......... 46 Network-Bound Antioxidants . . . . . . . .......... 50 Other Antioxidants and Synergistic Blends .......... 51 Comparing Antioxidants . . . . . . . . . .......... 53
Antiozonants . . . . . . . . . . . . . . . .......... 55 p-Phenylenediamines as Antiozonants . . . .......... 56 Dihydroquinolines as Antiozonants . . . . .......... 58 Miscellaneous Antiozonants . . . . . . . .......... 58
Comparing Antiozonants . . . . . . . . . . .......... 59
5 MANUFACTURE OF ANTIOXIDANTS AND ANTIOZONANTS FOR RUBBER ....
Hindered Phenols: Review of Processes ............ Hindered Bisphenols ...................... Review of Processes ..................... Bisphenols ........................ Alkylene Bisphenols .................... Sulfur-Containing Bisphenols ............... Polyphenols ........ ...............
A Process for 2,2'-Methylenebis (4-methyl-6-tert- butylphenol) ........................ Process Description .................... Process Discussion .................... Cost Estimates ......................
Aminophenols: Review of Processes .............. Dihydroxybenzenes: Review of Processes ............
15
15 18 20 23
61
62 66 66 66 67 70 76
78 78 87 87 91 92
V
CONTENTS
5 (Continued)
Diphenylamines ........................ 93
Review of Processes ..................... 93 A Process for Octylated Diphenylamine ............ 93 Process Description .................... 93
Process Discussion .................... 102
Cost Estimates ...................... 102
Naphthylamines ........................ 107
Review of Processes ..................... 107
A Process for Phenyl-p-naphthylamine ............ 107
Process Description .................... 107
Process Discussion .................... 114
Cost Estimates ...................... 114
Quinolines .......................... 119 Review of Processes ..................... 119
A Process for 6-Ethoxy-1,2-dihydr*2,2,4- trimethylquinoline ..................... 121
Process Description .................... 121
Process Discussion .................... 133
Cost Estimates ...................... 133
Substituted p-Phenylenediamines and Their Precursors ..... 138
p-Chloronitrobenzene .................... 141 Review of Processes .................... 141
Process Description .................... 144
Process Discussion .................... 155
Cost Estimates ...................... 155
p-Phenylenediamine via p-Chloronitrobenzene ......... 161
Review of Processes .................... 161
Process Description .................... 162 Process Discussion .................... 173
Cost Estimates ...................... 173
p-Phenylenediamine Without Formation of the Ortho Isomer . . 179
Review of Processes .................... 179
A Process for p-Phenylenediamine by Diazotization ofAniline ........................ 181
Process Description ................... 181
Process Discussion ................... 188
Cost Estimates ..................... 188
N,N'-Diaryl-Substituted Phenylenediamines .......... 194
Review of Processes .................... 194
N,N'-Diphenyl-p-phenylenediamine (DPPD) ......... 194
N,N'-Di-5-naphthyl-p-phenylenediamine (DNPD) ...... 197
N-Phenyl-N'-cyclohexyl-p-phenylenediamine (PCPD) .... 198
vi
CONTENTS
5 (Continued)
A Process for p-Nitrophenol, a Precursor of DPPD . . Process Description ................ Process Discussion ................ Cost Estimates .............. ..
A Process for N,N'-Diphenyl-p-phenylenediamiie (DPPDj Process Description ................ Process Discussion ................ Cost Estimates ..................
A Process for N,N'-Di-p-naphthyl-p- phenylenediamine (DNPD) ............... Process Description ................ Process Discussion ................ Cost Estimates ..................
Aryl-, Alkyl-Substituted p-Phenylenediamines ..... Review of Processes ............... A Process for N-Isopropyl-;I-phenyi-p- phenylenediamine (IPPD) ............... Process Description ................ Process Discussion ................ Cost Estimates ..................
Dialkyl-Substituted p-Phenylenediamines ........ Review of Processes ................. A Process for N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) ............... Process Description ................ Process Discussion ................ Cost Estimates ..................
6 STABILIZERS FOR POLYOLEFINS . . . . . . . . . . . . . . . . . .
Chemistry of Stabilizer Action ........ ........ Stabilization of Polyethylene ......... ........ Stabilization of Polypropylene ........ ........ Review of Processes .............. ........ A Process for Dilauryl Thiodipropionate (DLTDP) ........ Process Description ............. ........ Process Discussion ............. ........ Cost Estimates ............... ........
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . . 223
. . . 223
. . . 230
. . . 230
. . . 235
. . . 235
. . . 242
. . . 242
. . . 251
. . . 251
. . . 257
. . . 257
. . . 265
. . . 265
. . . 270
. . . 270
199 199 204 204 209 209 217 217
275
275 284 284 286 287 287 294 294
Vii
CONTENTS
STABILIZERS FOR POLYVINYL CHLORIDE . . . . . . . . . . . . . . 299
Mechanism of PVC Degradat Types of PVC Stabilizers Primary Stabilizers . . Secondary Stabilizers .
ion . . . . . . . . . . . . . . ................ ................ ................
Mechanisms of PVC Stabilization ............. Manufacture of PVC Stabilizers ............. Metallic Soaps .................... Organotin Stabilizers .................
. . . 299
. . . 303
. . . 309
. . . 310
. . . 311
. . . 314
. . . 315
. . . 316
STABILIZERS FOR OTHER PLASTICS .............
Polystyrene ....................... Polyamines (Nylon) ................... Polyesters ....................... Polyurethanes ...................... OtherPolymers .....................
STABILIZERS AGAINST ULTRAVIOLET LIGHT ..........
UV Degradation of Polymers ............... Protective Measures ................... UV Absorbers ..................... UVQuenchers .....................
Selection of UV Stabilizers ............... Review of Processes ...................
2,4-Dihydroxybenzophenone and Its 4-Alkoxy Derivatives Phenylesters ..................... Benzotriazoles .................... Nickel Complexes ...................
A Process for 2-Hydroxy-4-octyloxy-benzophenone ..... Process Description .................. Process Discussion .................. Cost Estimates ....................
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
. . .
APPENDIX A DESIGN AND COST BASIS ................
APPENDIX B PHYSICAL PROPERTIES .................
CITED REFERENCES .........................
PATENT REFERENCES BYCOMPANY ...................
319
319 320 320 320 321
323
323 324 325 332 332 334 334 339 340 341 342 342 351 351
357
361
369
387
Viii
ILLUSTRATIONS
4.1
5.1
5.2
5.3
5.4
5.5
5.6
5.7
5.8
5.9
5.10
5.11
5.12
5.13
5.14
5.15
Dependence of Inhibiting Activity on Ionization Potential of Amines . . , . . . . . . . . . . . . . . . . 48
Hindered Phenols Change in Composition of Reaction Mixture as p-Cresol Is Alkylated with Isobutylene . , , , . . . . . . . . . . 64
Manufacture of 2246 . . . . . . . . . . . . . . . . , . . 83
Manufacture of 2246 Effect of Plant Capacity on Total Fixed Capital . . . . , 89
Manufacture of 2246 Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . 90
Manufacture of Octylated Diphenylamine . . . . . . . . . . 99
Manufacture of Octylated Diphenylamine Effect of Plant Capacity on Total Fixed Capital . , , . . 104
Manufacture of Octylated Diphenylamine Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . 106
Manufacture of Phenyl-5-naphthylamine , . . . , . , . . . 111
Manufacture of Phenyl-8-naphthylamine Effect of Plant Capacity on Total Fixed Capital . . . . , 116
Manufacture of Phenyl-5-naphthylamine Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . 118
Manufacture of EDTQ . . , . . . . . . . . . . . . . . . , 127
Manufacture of EDTQ Effect of Plant Capacity on Total Fixed Capital . . . . . 135
Manufacture of EDTQ Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . 137
Substituted p-Phenylenediamines Process Routes . . . . . . . . . . , . . . . . . . . . . . 139
Manufacture of p-Chloronitrobenzene Effect of Nitration Temperature . . . . . . , . . . . . . 142
iX
ILLUSTRATIONS
5.16
5.17
5.18
5.19
5.20
5.21
5.22
5.23
5.24
5.25
5.26 Diaryl-p-phenylenediamines Process Routes . . . . . . . . . . . . . . . . . . . . . .
5.27
5.28
Manufacture of p-Nitrophenol via p-Chloronitrobenzene . .
Manufacture of p-Nitrophenol via p-Chloronitrobenzene Effect of Plant Capacity on Total Fixed Capital . . . . ,
5.29 Manufacture of p-Nitrophenol via p-Chloronitrobenzene Effect of Operating Level and Plant Capacity on Production Cost . . , . . . . . . . . , . . , . . . . ,
Manufacture of p-Chloronitrobenzene Effect of Sulfuric Acid Strength . , . , . , , , . . . . ,
Manufacture of p- and o-Chloronitrobenzene , . . . . , , .
142
149
Manufacture of p- and o-Chloronitrobenzene Effect of Plant Capacity on Total Fixed Capital , . . . . 158
Manufacture of p- and o-Chloronitrobenzene Effect of Operating Level and Plant Capacity on Production Cost , . , . . . . . . . . , . . . . , , . . 160
Manufacture of p-phenylenediamine via p-Chloronitrobenzene . . . . . , . . . . , . . , . . . . . 167
Manufacture of p-Phenylenediamine via p-Chloronitrobenzene Effect of Plant Capacity on Total Fixed Capital . . , . . 176
Manufacture of p-Phenylenediamine via p-Chloronitrobenzene Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . , . . , 178
Manufacture of p-Phenylenediamine by Diazotization ofAniline......................,, 185
Manufacture of p-Phenylenediamine by Diazotization of Aniline Effect of Plant Capacity on Total Fixed Capital . . . . , 191
Manufacture of p-Phenylenediamine by Diazotization of Aniline Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . , , . . . . . . 193
195
201
206
208
X
ILLUSTRATIONS
5.30
5.31
5.32
5.33
5.34
5.35
5.36
5.37
5.38
5.39
5.40
5.41
5.42
5.43
Manufacture of N,N'-Diphenyl-p-phenylenediamine (DPPD) . . 213
Manufacture of N,N'-Diphenyl-p-phenylenediamine (DPPD) Effect of Plant Capacity on Total Fixed Capital . , . . . 220
Manufacture N,N'-Diphenyl-p-phenylenediamine (DPPD) Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . 222
Manufacture of N,N'-Di-@-naphthyl-p- phenylenediamine (DNPD) . . . . . . . . . . . . . . , . . 227
Manufacture of N,N'-Di-S-naphthyl-p- phenylenediamine (DNPD) Effect of Plant Capacity on Total Fixed Capital . . . . . 231
Manufacture of N,N'-Di-B-naphthyl-p- phenylenediamine (DNPD) Effect of Operating Level and Plant Capacity on Production Cost . , , , . . . . . , . . . . , . , . . . 234
N-Isopropyl-N'-phenyl-p-phenylenediamine (IPPD) Process Routes . , . , . , . . . . . . . . . . . . . , . . 237
Manufacture of N-Isopropyl-N'-phenyl-p- phenylenediamine (IPPD) . . . .,, . . . , , . . . . . . . 247
Manufacture of N-Isopropyl-N'-phenyl-p- phenylenediamine (IPPD) Effect of Plant Capacity on Total Fixed Capital . . . . . 254
Manufacture of N-Isopropyl-N'-phenyl-p- phenylenediamine (IPPD) Effect of Operating Level and Plant Capacity on Production Cost . . . . . . , . . . . . . . . , . . . , 256
Dialkyl-p-phenylenediamines Process Routes . . , . . . , . . . , . . . . . . , . . , . 259
Reductive Alkylation. Effect of Hz/Ketone Ratio on Alcohol Formation . . , . . . 264
Manufacture of N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) . . . . . . . . , . . . . . . . , 267
Manufacture of N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) Effect of Plant Capacity on Total Fixed Capital . . . . . 272
Xi
ILLUSTRATIONS
5.44 Manufacture of N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) Effect of Operating Level and Plant Capacity on Production Cost . . , . . . . . . , . . , . . . . . , . 274
6.1 Manufacture of Dilauryl Thiodipropionate . . . , . , . , , 291
6.2 Manufacture of Dilauryl Thiodipropionate Effect of Plant Capacity on Total Fixed Capital' . , . , , 296
6.3 Manufacture of Dilauryl Thiodipropionate Effect of Operating Level and Plant Capacity on Production Cost . . , . . . . . . . . . . . . , . . . . 298
9.1 Manufacture of 2-Hydroxy-4-octyloxy-benzophenone . . . . , 347
9.2 Manufacture of 2-Hydroxy-4-octyloxy-benzophenone Effect of Plant Capacity on Total Fixed Capital . , . . . 353
9.3 Manufacture of 2-Hydroxy-4-octyloxy-benzophenone Effect of Operating Level and Plant Capacity on Production Cost . . , . . . . . , . . . , , , . . . . , 355
xii
TABLES
2.1
2.2
2.3
2.4
2.5
3.1
3.2
3.3
3.4
3.5
4.1
4.2
4.3
4.4
5.1
5.2
5.3
5.4
5.5
Manufacture of Miscellaneous Antioxidants Summary of Economics ...................
Manufacture of p-Phenylenediamine Derivatives Summary of Economics ...................
Manufacture of p-Phenylenediamine Summary of Economics ...................
Manufactureof Dilauryl Thiodipropionate (DLTDP) Summary of Economics ...................
Manufacture of 2-Hydroxy-4-octyloxy-benzophenone Summary of Economics ...................
Production of Antioxidants and Antiozonants forRubber ........................
Principal Producers of Antioxidants and Antiozonants for Rubber .................
Consumption of Antioxidants in Plastics .........
Consumption of Stabilizers in PVC ............
Consumption of UV Stabilizers in Plastics ........
Classification of Antioxidants and Antiozonants forRubber ........................
Relative Effectiveness of Selected Phenolic Antioxidants .......................
Comparison of Antioxidants ................
Comparison of Antiozonants ................
Manufacture of 2246 Bases and Assumptions ..................
Manufacture of 2246 Major Process Equipment and Utilities Summary . . , . . ,
Manufacture of 2246 Stream Flows .......................
Manufacture of 2246 Total Capital Investment .................
Manufacture of 2246 Production Costs .....................
5
7
8
11
12
17
18
19
22
24
29
45
54
60
79
81
85
88
94
Xiii
TABLES
5.6
5.7
5.8
5.9
5.10
5;11
5.12
5.13
5.14
5.15
5.16
5.17
5.18
5.19
5.20
5.21
5.22
Manufacture of Octylated Diphenylamine Bases and Assumptions . . . . . . . . . . . . . . . . . .
Manufacture of Octylated Diphenylamine Major Process Equipment and Utilities Summary , . . . . .
Manufacture of Octylated Diphenylamine Stream Flows , . . . . . . . . . . , . . . . . , . . , . .
Manufacture of Octylated Diphenylamine Total Capital Investment . . . . . . . . . . . . . . . . ,
Manufacture of Octylated Diphenylamine Production Costs , . . . . . . , . . . . . . . . . . . . .
Manufacture of Phenyl-Ij-naphthylamine Bases and Assumptions . . . . . . . . , . . . . . . . . .
Manufacture of Phenyl-@-naphthylamine Major Process Equipment and Utilities Summary . . . . . .
Manufacture of Phenyl-p-naphthylamine Stream Flows . . . . . . . . . . . . . . . . . , . . . . .
Manufacture of Phenyl-5-naphthylamine Total Capital Investment . . . . . . . . . . . . . . . . .
Manufacture of Phenyl-5-naphthylamine Production Costs . . . . . . . . . . . . . . . . . . . . .
Manufacture of EDTQ Bases and Assumptions . . . . . . . . . . . . . . . . . .
Manufacture of EDTQ Major Process Equipment and Utilities Summary . . . , . .
Manufacture of ED!@ Stream Flows . . . . . . . . . . . . . . . , . . . . . . .
Manufacture of EDTQ Total Capital Investment . . . . , . . . . . . . . . . . .
Manufacture of EDTQ Production Costs . . . . . . . . . . . . . , . . . . . . .
Manufacture of p- and o-Chloronitrobenzene Bases and Assumptions . . . . . , . . . . , . . . . . . .
Manufacture of p- and o-Chloronitrobenzene Major Process Equipment and Utilities Summary . . . . . .
95
97
101
103
105
108
110
113
115
117
122
126
129
134
136
145
149
xiv
TABLES
5.23
5.24
5.25
5.26
5.27
5.28
5.29
5.30
5.31
5.32
5.33
5.34
5.35
5.36
5.37
5.38
Manufacture of p- and o-Chloronitrobenzene Stream Flows . . . . . . . . . . . . . . . . . . . , . . .
Manufacture of p- and o-Chloronitrobenzene Total Capital Investment . . . . . . . . . . . . . . . . .
Manufacture of p- and o-Chloronitrobenzene Production Costs . . . . . . . . . . , . . . . . , . . . ,
Manufacture of p-Phenylenediamine via p-Chloronitrobenzene Bases and Assumptions . . . . . . . . . . . . . . . . . .
Manufacture of p-Phenylenediamine via p-Chloronitrobenzene Major Process Equipment and Utilities Summary . . . . . .
Manufacture of p-Phenylenediamine via p-Chloronitrobenzene Stream Flows . . . . . . . . . . . . . . . . . . . . . . .
Manufacture of p-Phenylenediamine via p-Chloronitrobenzene Total Capital Investment . . . . . . . . . . . . . . . . .
Manufacture of p-Phenylenediamine via p-Chloronitrobenzene Production Costs . . . . . . . . . . . . . . . . . . . , .
Manufacture of p-Phenylenediamine by Diazotization of Aniline Bases and Assumptions . . . . . . . . . . . , . . . . . ,
Manufacture of p-Phenylenediamine by Diazotization of Aniline Major Process Equipment and Utilities Summary . . . . . ,
Manufacture of p-Phenylenediamine by Diazotization of Aniline Stream Flows . . . . . . . . . . . . . , . . . . . . . . .
Manufacture of p-Phenylenediamine by Diazotization of Aniline Total Capital Investment . , . . . , . . . . . . . . . . ,
Manufacture of p-Phenylenediamine by Diazotization of Aniline Production Costs . . . . . , . . . . . . . . . . . . . . .
Manufacture of p-Nitrophenol via p-Chloronitrobenzene Bases and Assumptions . . . . . . . . . . . . . . . . . .
Manufacture of p-Nitrophenol via P-Chloronitrobenzene Major Process Equipment and Utilities Summary . , . . . .
Manufacture of p-Nitrophenol via p-Chloronitrobenzene Stream Flows . . . . . . . , . . . . . , . . . . . . . . .
153
157
159
163
166
169
175
177
182
184
187
190
192
200
201
203
xv
TABLES
5.39 Manufacture of p-Nitrophenol via p-Chloronitrobenzene Total Capital Investment . . . . . . . . . . . . . . . . . 205
5.40 Manufacture of p-Nitrophenol via p-Chloronitrobenzene Production Costs . . . . , . . . . . . . . . . . . . . . l 207
5.41 Manufacture of N,N'-Diphenyl-p-phenylenediamine (DPPD) Bases and Assumptions . . . . , . . . . . . . . . . . . . 210
5.42 Manufacture of N,N'-Diphenyl-p-phenylenediamine (DPPD) Major Process Equipment and Utilities Summary . . . . . . 212
5.43 Manufacture of N,N'-Diphenyl-p-phenylenediamine (DPPD) Stream Flows . . . . . . . . . . . . . . . . . . . . . . . 215
5.44 Manufacture of N,N'-Diphenyl-p-phenylenediamine (DPPD) Total Capital Investment . . . . . . . . . , . . . . . . . 219
5.45 Manufacture of N,N'-Diphenyl-p-phenylenediamine (DPPD) Production Costs . . . . . . . . . . . . . . . . . . . . . 221
5.46 Manufacture of N,N'-Di-B-naphthyl-p- phenylenediamine (DNPD) Bases and Assumptions . . . . . , . . . . . . . . . . . . 224
5.47 Manufacture of N,N'-Di-B-naphthyl-p- phenylenediamine (DNPD) Major Process Equipment and Utilities Summary . . . . . . 225
5.48 Manufacture of N,N'-Di-@naphthyl-p- phenylenediamine (DNPD) Stream Flows . . . . . . . . . . . , . . . . . . . . . . . 229
5.49 Manufacture of N,N'-Di-p-naphthyl-p- phenylenediamine (DNPD) Total Capital Investment . . . . . . . . . . . . . . . . . 232
5.50 Manufacture of N,N'-Di-S-naphthyl-p- phenylenediamine (DNPD) Production Costs . . . . . . . . . . . . . . . . . . . . . 233
5.51 Aryl-, Alkyl-Substituted p-Phenylenediamine: Reductive Alkylation of p-Nitro- and Amino-DPA Patent Summary . . . . . . . . . . . . . . . . . . , . . . 239
5.52 Manufacture of N-Isopropyl-N'-phenyl-p- phenylenediamine (IPPD) Bases and Assumptions . . . . . . . . . . . . . . . . . . 243
5.53 Manufacture of N-Isopropyl-N'-phenyl-p- phenylenediamine (IPPD) Major Process Equipment and Utilities Summary . . . . . . 246
-
a xvi
TABLES
5.54
5.55
5.56
5.57
5.58
5.59
5.60
5.61
5.62
6.1
6.2
6.3
6.4
6.5
Manufacture of N-Isopropyl-N'-phenyl-p- phenylenediamine (IPPD) Stream Flows . . . . . . . . . . . . . . . . . . . . . . . 249
Manufacture of N-Isopropyl-N'-phenyl-p- phenylendiamine (IPPD) Total Capital Investment . . . . . . . . . . , . . . . . .
Manufacture of N-Isopropyl-N'-phenyl-p- phenylenediamine (IPPD)
253
Production Costs . . . . . . . . . . . . . . , . . . . . . 255
Dialkyl-Substituted-p-Phenylenediamines: Reductive Alkylation Processes Patent Summary . . . . . . . . . . . . . . . . . . . . . .
Manufacture of N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) Bases and Assumptions . . . . . . . . . . . . . . . . . .
Manufacture of N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) Major Process Equipment and Utilities Summary . . . . . .
Manufacture of N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) Stream Flows . . . . . . . . . . . , . . . . . . . . . . .
Manufacture of N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) Total Capital Investment . . . . . . , . . , , , . . . . .
Manufacture of N,N'-Di-sec-butyl-p- phenylenediamine (DSPD) Production Costs . . . . . . . , . , . . . . . . . , . . .
Antioxidants for Polyolefins . . . . . . . . . . . . . . .
Manufacture of Dilauryl Thiodipropionate Bases and Assumptions . . . . . . . . . . . . . . . . . .
Manufacture of Dilauryl Tbiodipropionate Major Process Equipment and Utilities Summary . . . . . .
Manufacture of Dilauryl Thiodipropionate Stream Flows . . , . . . . . . . . . . . , . . . . . . . .
Manufacture of Dilauryl Thiodipropionate Total Capital Investment . . . . . . . . . . . . . . . . .
261
266
267
269
271
273
277
288
291
293
295
xvii
TABLES
6.6
7.1
9.1
9.2
9.3
9.4
9.5
9.6
9.7
Manufacture of Dilauryl Thiodipropionate Production Costs ..................... 297
Stabilizers for PVC ................... 303
Chemical Stabilizers Against Ultraviolet Light ...... 326
2-Hydroxy-4-alkoxy-benzophenone Patent Summary , . . . . . . , , . . , . . . . . . . . . . 337
Manufacture of 2-Hydroxy-4-octyloxy-benzophenone Bases and Assumptions . . . . . . . . . . . . . . . . . . 343
Manufacture of 2-Hydroxy-4-octyloxy-benzophenone Major Process Equipment and Utilities Summary . . . , . . 346
Manufacture of 2-Hydroxy-4-octyloxy-benzophenone Stream Flows . . . . . . . . . . . . . . . . . . . . . . . 349
Manufacture of 2-Hydroxy-4-octyloxy-benzophenone Total Capital Investment . . . . . . . . . . . . . . . . . 352
Manufacture of 2-Hydroxy-4-octyloxy-benzophenone Production Costs . . . . . , . . . . . . . . . . . . . . . 354
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