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Report No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS ECONOMICS PROGRAM I STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA

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Page 1: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

Report No. 2C

PROPYLENE OXIDE AND

ETHYLENE OXIDE

SUPPLEMENT C

by YEN-CHEN YEN

April 1977

A private report by the

PROCESS ECONOMICS PROGRAM

I STANFORD RESEARCH INSTITUTE

I

MENLO PARK, CALIFORNIA

-- . I

Page 2: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

For detailed marketing data and information, the reader is

referred to one of the SRI programs specializing in marketing

research. The CHEMICAL ECONOMICS HANDBOOK Program covers

most major chemicals and chemical products produced in the

United States and the WORLD HYDROCARBONS Program covers major

hydrocarbons and their derivatives on a worldwide basis. In

addition, the SRI DIRECTORY OF CHEMICAL PRODUCERS services

provide detailed lists of chemical producers by company,

product, and plant for the United States and Western Europe.

Page 3: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

CONTENTS

1 INTRODUCTION. . . . . . . . . . . . . . . . . . . . . . . . 1

2 SUMMARY . . . . . . . . . . . . . . . . . . . . . . . . . . 3

General Aspects ...................... 3 Economic Aspects ...................... 3 Technical Aspects ..................... 8

3 INDUSTRYSTATUS ...................... 15

Ethylene Oxide ....................... 15 Propylene Oxide ...................... 21

4 ETHYLENE OXIDE ....................... 27

Chemistry ......................... 27 Review of Processes .................... 30 Catalysts ........................ 30 Composition of the Reaction Gas ............. 43 Reactors ......................... 44 Recovery of EO ...................... 45 Purification ....................... 50 Miscellaneous

Evaluation of the Manufacture of Ethylene Oxide ...... 50

by the Oxygen Process ................... 53 Process Description ................... 53 Process Discussion .................... 62 Cost Estimates ...................... 64

Evaluation of the Manufacture of Ethylene Oxide by the Air Process .................... 72 Process Description ................... 72 Process Discussion .................... 79 Cost Estimates ...................... 79

Comparison of Oxygen and Air Processes ........... 87

5 COMPARISON OF PROCESSES FOR MANUFACTURING PROPYLENE OXIDE ........................... 91

Process Characteristics .................. 91 Chlorohydrin Processes .................. 91 Indirect Oxidation Processes ............... 92 Direct Oxidation Processes ................ 93

Economics of the Processes ................. 94 Improvement and Future Development ............. 100 Chlorohydrin Processes .................. 100 Hydroperoxide Processes ................. 100

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Page 4: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

CONTENTS

5 COMPARISON OF PROCESSES FOR MANUFACTURING PROPYLENE OXIDE (Continued)

Peracid Processes . . . . . . . . . . . . . . . . . . . . 100 Direct Oxidation Process . . . . . . . . . . . . . . . . . 101

6 PROPYLENE OXIDE BY CHLOROHYDRIN PROCESSES ......... 103

Review of Processes .................... 103 Evaluation of a Conventional Chlorohydrin Process ..... 112 Process Description ................... 112 Process Discussion .................... 121 Cost Estimates. ..................... 122

Evaluation of Chlorohydrin Process Using Recycled Brine . . 129 Process Description ................... 129 Process Discussion .................... 138 Cost Estimates. ..................... 140

Electrochemical Process .................. 150 Lummus Process. ...................... 152

7 PROPYLENE OXIDE BY HYDROPEROXIDE PROCESSES ........ 155

Chemistry ......................... 155 Review of Processes .................... 156 Evaluation of a Process for Making Propylene Oxide, with Tertiary Butyl Hydroperoxide as an Epoxidation Agent (The Isobutane Process) ............... 166 Process Description ................... 166 Process Discussion .................... 181 Cost Estimates. ..................... 183

Evaluation of a Process for Making Propylene Oxide, with Ethylbenzene Hydroperoxide as an Epoxidation Agent (The Ethylbenzene Process) ............. 204 Process Description ................... 204 Process Discussion .................... 213 Cost Estimates ...................... 215

Evaluation of an Ethylbenzene Process Using a Heterogeneous Catalyst .................. 221

Other Hydroperoxides as Epoxidation Agents ......... 228 Ethylene Oxide by Hydroperoxide Process .......... 233

8 PROPYLENE OXIDE BY EPOXIDATION USING PERACID OR HYDROGENPEROXIDE . . . . . . . . . . . . . . . . . . . . . 235

Peracid Processes . . . . . . . . . . . . . . . . . . . . . 235 Asahi Process . . . . . . . . . . . . . . . . . . . . . . 235 Metallgesellschaft Process Using Perbenzoic Acid . . -. . . 238

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Page 5: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

CONTENTS

8 PROPYLENE OXIDE BY EPOXIDATION USING PERACID OR HYDROGEN PEROXIDE (Continued)

Interox Process . . . . . . . . . . . . . . . Petrocarbon Peracid Process . . . . . . . . . . . . . . .

Hydrogen Peroxide Processes . . . . . . . . . . . . . . . . Evaluation of a Process for Making Propylene Oxide by Peracetic Acid Epoxidation Based on Daicel Patents . . . Process Description . . . . . . . . . . . . . . . . . . . Process Discussion . . . . . . . . . . . . . . . . . . . . Cost Estimates . . . . . . . . . . . . . . . . . . . . . .

9 PROPYLENE OXIDE BY OXIDATION WITH MOLECULAR OXYGEN .....

Review of Processes .................... Vapor Phase Oxidation with Silver Catalyst ........ Vapor Phase Oxidation with Other Catalysts ........ Vapor Phase Noncatalytic Oxidation ............ Liquid Phase Cooxidation ................. Liquid Phase Catalytic Oxidation ............. Liquid Phase Noncatalytic Oxidation ...........

Evaluation of a Process for Making Propylene Oxide by Acetaldehyde Cooxidation ................ Process Description ................... Process Discussion .................... Cost Estimates ......................

Evaluation of a Process for Making Propylene Oxide by Liquid Phase Catalytic Oxidation Using Molecular Oxygen, Based on USSR Patent ............... Process Description ................... Process Discussion .................... Cost Estimates ......................

Noncatalytic Oxidation Process ...............

10 OTHER PROCESSES FOR MAKING PROPYLENE OXIDE ......... 303

Propylene Oxide, from an Allylic Sulfonium Salt (Dow) ... 303 Silent Discharge Process .................. 303 Anodic Oxidation Processes ................. 304 Phosgenation Process (Hoechst) ............... 304 Conversion of Ethylene Oxide to Propylene Oxide (Mitsui) . . 304 Glycol Monoacetate Pyrolysis Process ............ 305 Mercuric Acetate Process (Aquitaine) ............ 305 Propylene Oxide from Vinyl Acetate (Bayer) ......... 305

239 240 241

244 244 252 252

259

259 259 259 259 260 265 265

279 279 286 286

291 291 296 296 301

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Page 6: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

CONTENTS

10 OTHER PROCESSES FOR MAKING PROPYLENE OXIDE (Continued)

Evaluation of a Process for Making Propylene Oxide by Propylene Glycol Monoacetate Pyrolysis . . . . . . . . . 306 Process Description . . . . . . . . . . . . . . . . . . . 306 Process Discussion . . . . . . . . . . . . . . . . . . . . 312 Cost Estimates. . . . . . . . . . . . . . . . . . . . . . 313

CITED REFERENCES . . . . . . . . . . . . . . . . . . . . . . . . 319

PATENT REFERENCES BY COMPANY . . . . . . . . . . . . . . . . . . 341

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Page 7: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

ILLUSTRATIONS

4.1 Ethylene Oxide by Oxygen Process Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . 349

4.2 Ethylene Oxide by Oxygen Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . 70

4.3 Ethylene Oxide by Air Process Flow Sheet . . . ..,..... . . . . . . . . . . . . . . . 353

4.4 Ethylene Oxide by Air Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . 86

4.5 Comparison of the Processes for Making Ethylene Oxide Effect of Plant Capacity on Product Value . . . . . . . . . . 89

5.1 Comparison of the Processes for Making Propylene Oxide Product Values, 400 Million lb/yr Plant . . . . . . . . . . . 95

5.2 Comparison of the Processes for Making Propylene Oxide Product Values, 700 Million lb/yr Plant . . . . . . . . . . . 98

6.1 Propylene Oxide by Conventional Chlorohydrin Process Flow Sheet ....................... 355

6.2 Propylene Oxide by Chlorohydrin Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . l . . . . l l l l l l l l l l 128

6.3 Propylene Oxide by Chlorohydrin Process with Recycled Brine Flow Sheet ......................~~ 359

7.1 Propylene Oxide by Isobutane Process Flow Sheet......................... 363

7.2 Propylene Oxide by Isobutane Process Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . 202

7.3 Propylene Oxide by Ethylbenzene Process Using Homogeneous Catalyst Flow Sheet . . . . . . . . . . . . . . . . . . . . . . . . . 369

7.4 Propylene Oxide by Ethylbenzene Process Using Homogeneous Catalyst Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . . 220

7.5 Propylene Oxide by Ethylbenzene Process Using Heterogeneous Catalyst Reaction Section . . . . . . . . . . . . . . . l . . . . . l 223

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Page 8: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

ILLUSTRATIONS

7.6 Propylene Oxide by Hydroperoxide Processes Effect of Plant Capacity on "Reduced Value of PO" . . . . . 231

8.1 Propylene Oxide by Peracetic Acid Epoxidation Based on Daicel Patents

Flow sheet......................... 375

8.2 Propylene Oxide by Perocetic Acid Epoxidation Based on Daicel Patents Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . 258

9.1 Propylene Oxide by #Acetaldehyde Cooxidation Flow sheet......................... 379

9.2 Propylene Oxide by Acetaldehyde Cooxidation Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . 290

9.3 Propylene Oxide by Liquid Phase Catalytic Oxidation Using Molecular Oxygen, Based on USSR Patent Flow sheet......................... 381

9.4 Propylene Oxide by Liquid Phase Catalytic Oxidation Using Molecular Oxygen, Based on USSR Patent Effect of Operating Level and Plant Capacity on Production Cost . . . . . . . . . . . . . . . . . . . . 300

10.1 Propylene Oxide by Propylene Glycol Monoacetate Pyrolysis Flow sheet......................... 383

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Page 9: PROPYLENE OXIDE AND ETHYLENE OXIDE - IHS Markit · PDF fileReport No. 2C PROPYLENE OXIDE AND ETHYLENE OXIDE SUPPLEMENT C by YEN-CHEN YEN April 1977 A private report by the PROCESS

TABLES

2.1 Processes for Making Ethylene Oxide Summary of Economics . . . . . . . . . . . . . . . . . .

2.2 Processes for Making Propylene Oxide Summary of Economics . . . . . . . . . . . . . . . . . .

3.1 Producers of Ethylene Oxide in the United States . . . . . . . . . . . . . . . . . . l . .

3.2 Producers of Ethylene Oxide Outside of the United States . . . . . . . . . . . . . . . . . . . . .

3.3 Producers of Propylene Oxide in the United States . . . . . . . . . . . . . . . . . . . . .

3.4 Producers of Propylene Oxide Outside of the United States . . . . . . . . . . . . . . . . . . . . .

4.1 Catalysts for Ethylene Oxide Preparation Patent Summary, l............ . . . . . . . .

4.2 Catalysts for Ethylene Oxide Preparation Patent Summary, 2.................. . .

4.3 Catalysts for Ethylene Oxide Preparation Patent Summary, 3 . . . . . . . . . . . . . . . . . . . .

4.4 Catalysts for Ethylene Oxide Preparation Patent Summary, 4....................

4.5 Reactor and Reaction Conditions for Ethylene Oxide Manufacture Patent Summary . . . . . . . . . . . . . . . . . . . . .

4.6 Recover of Ethylene Oxide Patent Summary . . . . . . . . . . . . . . . . . . . . .

4.7 Purification of Ethylene Oxide Patent Summary . . . . . . . . . . . . . . . . . . . . .

4.8 Other Ethylene Oxide Related Innovations Patent Summary . . . . . . . . . . . . . . . . . . . . .

4.9 Ethylene Oxide by Oxygen Process Design Bases and Assumptions . . . . . . . . . . . . . .

4.10 Ethylene Oxide by Oxygen Process Stream Flows . . . . . . . . . . . . . . . . . . . . . .

4.11 Ethylene Oxide by Oxygen Process Major Equipment and Utilities Summary . . . . . . . . . .

4.12 Ethylene Oxide by Oxygen Process Total Capital Investment . . . . . . . . . . . . . . . .

xiii

4

6

17

18

22

23

32

34

36

38

46

48

51

52

54

58

59

66

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TABLES

4.13 Ethylene Oxide by Oxygen Process Production Costs . . . . . . . . . . . . . . . . . . . . 68

4.14 Ethylene Oxide by Air Process Design Bases and Assumptions . . . . . . . . . . . l . . 73

4.15 Ethylene Oxide by Air Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . 15

4.16 Ethylene Oxide by Air Process Major Equipment and Utilities Summary . . . . . . . . . . 76

4.17 Ethylene Oxide by Air Process Total Capital Investment . . . . . . . . . . . . . . . . 82

4.18 Ethylene Oxide by Air Process Production Costs . . . . . . . . . . . . . . . . . . . . 84

6.1 Propylene Oxide by Chlorohydrin Process Patent Summary, Chlorohydrin . . . . . . . . . . . . . . 105

6.2 Propylene Oxide by Chlorohydrin Process Patent Summary, Saponification . . . . . . . . . l . . . 106

6.3 Propylene Oxide by Chlorohydrin Process Patent Summary, Recovery and Purification . . . . . . . . 109

6.4 Propylene Oxide by Chlorohydrin Process Patent Summary, Waste or By-Product Treatment . . . . . . 109

6.5 Propylene Oxide by Modified Chlorohydrin Process Patent Summary . . . . . . . . . . . . . . . . . . . . . 110

6.6 Propylene Oxide by Electrochemical Chlorohydrin Process Patent Summary . . . . . . . . . . . . . . . . . . . . . 111

6.7 Propylene Oxide by Conventional Chlorohydrin Process

Design Bases and Assumptions . . . . . . . . . . . . . . 113

6.8 Propylene Oxide by Conventional Chlorohydrin Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . 116

6.9 Propylene Oxide by Conventional Chlorohydrin Process

Major Equipment and Utilities Summary . . . . . . . . . . 118

6.10 Propylene Oxide by Conventional Chlorohydrin Process Total Capital Investment . . . . . . . . . . . . . . . . 121

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l

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TABLES

6.11 Propylene Oxide by Conventional Chlorohydrin Process Production Costs . . . . . . . . . . . . . . . . . . . . 126

6.12 Propylene Oxide by Chlorohydrin Process with Recycled Brine Design Bases and Assumptions . . . . . . . . . . . . . . 130

6.13 Propylene Oxide by Chlorohydrin Process with Recycled Brine Stream Flows . . . . . . . . . . . . . . . . . . . . . . 133

6.14 Propylene Oxide by Chlorohydrin Process with Recycled Brine Major Equipment and Utilities Summary . . . . . . . . . . 135

6.15 Propylene Oxide by Chlorohydrin Process with Recycled Brine Total Capital Investment . . . . . . . . . . . . . . . . 142

6.16 Propylene Oxide by Chlorohydrin Process with Recycled Brine Production Costs . . . . . . . . . . . . . . . . . . . . 144

6.17 Propylene Oxide Chlorohydrin Process Associated with Large Chlorine Plant Total Capital Investment . . . . . . . . . . . l . . . . 146

6.18 Propylene Oxide Chlorohydrin Process Associated with Large Chlorine Plant Production Costs . . . . . . . . . . . . . . . . . . . . 148

7.1 Preparation of Hydroperoxides Patent Summary . . . . . . . . . . . . . . . . . . . . . 157

7.2 Homogeneous Catalysts for Epoxidation by Hydroperoxide8

Patent Summary . . . . . . . . . . . . . . . . . . . . . 159

7.3 Heterogeneous Catalysts for Epoxidation by Hydroperoxides Patent Summary . . . . . . . . . . . . . . . . . . . . . . 160

7.4 Epoxidation of Propylene by Hydroperoxide Process Patent Summary . . . . . . . . . . . . . . . . . . . . . 161

7.5 Hydroperoxide Process, Recovery of Catalyst Patent Summary . . . . . . . . . . . . . . . . . . . . . 163

7.6 Hydroperoxide Process, Recovery and Purification of Propylene Oxide Patent Summary . . . . . . . . . ..d . . . . . . . . . 164

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TABLES

7.7 Processing of Alcohols from Hydroperoxides Patent Summary . . . . . . . . . . . . . . . . . . . . . 165

7.8 Propylene Oxide by Isobutane Process Design Bases and Assumptions . . . . . . . . . . . . . . 167

7.9 Propylene Oxide by Isobutane Process Stream Flows . . . . . . . . . . . . . . . . . . . . . . 174

7.10

7.11

7.12

7.13

Propylene Oxide by Isobutane Process Major Equipment.. . . . . . . . . . . . . . . . . . . . 176

Propylene Oxide by Isobutane Process Utilities Summary . . . . . . . . . . . . . . . . . . . . 180

Propylene Oxide by Isobutane Process with Butyl Alcohol Coproduction Total Capital Investment . . . . . . . . . . . . . . . . 188

Propylene Oxide by Isobutane Process with Butyl Alcohol Coproduction Production Costs . . . . . . . . . . . . . . . . . . . . 190

7.14 Propylene Oxide by Isobutane Process with Isobutane Recycle Total Capital Investment . . . . . . . . . . . . . . . . 192

7.15 Propylene Oxide by Isobutane Process with Isobutane Recycle Production Costs . . . . . . . . . . . . . . . . . . . . 194

7.16 Propylene Oxide by Isobutane Process with Isobutylene Coproduction Total Capital Investment . . l . . . . . . . . . . . . . 196

7.17 Propylene Oxide by Isobutane Process with Isobutylene Coproduction Production Costs . . . . . . . . . . . . . . . . . . . . 198

7.18 Propylene Oxide by Isobutane Process Cost Features of Various Versions of Process . . . . . . 200

7.19 Propylene Oxide by Isobutane Process Effect of Design Variations on Costs . . . . . . . . . . 203

7.20 Propylene Oxide by Ethylbenzene Process Using Homogeneous Catalyst Design Bases and Assumptions . . . . . . . . . . . . . . 205

7.21 Propylene Oxide by Ethylbenzene Process Using Homogeneous Catalyst Stream Flows . . . . . . . . . . . . . . . . . . . . . . 208

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TABLES

7.22 Propylene Oxide by Ethylbenzene Process Using Homogeneous Catalyst

Major Equipment and Utilities Summary . . . . . . . . . . 210

7.23 Propylene Oxide by Ethylbenzene Process Using Homogeneous Catalyst Total Capital Investment . . . . . . . . . . . . . . . . 216

7.24 Propylene Oxide by Ethylbenzene Process Using Homogeneous Catalyst Production Costs . . . . . . . . . . . . . . . . . . . . 218

7.25 Propylene Oxide by Ethylbenzene Process Using Heterogeneous Catalyst Design Bases and Assumptions . . . . . . . . . . . . . . 222

7.26 Propylene Oxide by Ethylbenzene Process Using Heterogeneous Catalyst Total Capital Investment . . . . . . . . . . . . . . . . 224

7.27 Propylene Oxide by Ethylbenzene Process Using Heterogeneous Catalyst Production Costs . . . . . . . . . . . . . . . . . . . . 226

7.28 Epoxidation by Other Hydroperoxides . . . . . . . . . . . 229

7.29 Screening Evaluation of Some Hydroperoxide Processes for Making Propylene Oxide with Various Coproducts . . . 232

8.1 Propylene Oxide by Peracid Processes Patent Summary . . . . . . . . . . . . . . . . . . . . . 236

8.2 Propylene Oxide by Hydrogen Peroxide Processes Patent Summary . . . . . . . . . . . . . . . . . . . . . 242

8.3 Propylene Oxide by Peracetic Acid Epoxidation Based on Daicel Patents

Design Bases and Assumptions . . . . . . . . . . . . . . 245

8.4 Propylene Oxide by Peracetic Acid Epoxidation Based on Daicel Patents

8.5

8.6

Stream Flows . . . . . . . l . . . . . . . . . . . . . . 248

Propylene Oxide by Peracetic Acid Epoxidation Based on Daicel Patents

Major Equipment and Utilities Summary . . . . . . . . . . 250

Propylene Oxide by Peracetic Acid Epoxidation Based on Daicel Patents Total Capital Investment . . . . . . . . . . . . . . . . 254

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TABLES

8.7 Propylene Oxide by Peracetic Acid Epoxidataon Based on Daicel Patents Production Costs . . . . . . . . . . . . . . . . . . l . 256

9.1 Propylene Oxide,by Vapor Phase Molecular Oxygen Oxidation Using Silver Catalyst Patent Summary . . . . . . . . . . . . . . . . . . . . . 261

9.2 Propylene Oxide by Vapor Phase Molecular Oxygen Oxidation Using Catalysts Other Than Silver Patent Summary . . . . . . . . . . . . . . . . . . . . . 262

9.3 Propylene Oxide by Vapor Phase Noncatalytic Molecular Oxygen Oxidation Patent Summary . . . . . . . . . . . . . . . . . . . . . 264

9.4 Propylene Oxide by Cooxidation of Acetaldehyde Patent Summary . . . . . . . . . . . . . . . . . . . . . 266

9.5 Propylene Oxide by Oxygen Cooxidation of Isobutyraldehyde

Patent Summary . . . . . . . . . . . . . . . . . . . . . 268

9.6 Propylene Oxide by Cooxidation of Chemicals Other Than Acetaldehyde and Isobutyraldehyde Patent Summary ..a . . . . . . . . . . . . . . . . . . 270

9.7 Propylene Oxide by Catalytic Liquid Phase Oxidation Using Molecular Oxygen Patent Summary . . . . . . . . . . . . . . . . . . . . . 272

9.8 Propylene Oxide by Noncatalytic Liquid Phase Oxidation Using Molecular Oxygen Patent Summary . . . . . . . . . . . . . . . . . . . . . 276

9.9 Separation and Purification of Propylene Oxide in Connection with Liquid Phase Oxidation Processes Patent Summary . . . . . . . . . . . . . . . . . . . . . 277

9.10 Propylene Oxide by Acetaldehyde Cooxidation Design Bases and Assumptions . . . . . . . . . . . . . . 279

9.11 Propylene Oxide by Acetaldehyde Cooxidation Stream Flows . . . . . . . . . . . . . . . . . . . . . . 282

9.12 Propylene Oxide by Acetaldehyde Cooxidation Major Equipment and Utilities Summary . . . . . . . . l . 284

9.13 Propylene Oxide by Acetaldehyde Cooxidation Total Capital Investment . . . . . . . . . . . . . . . . 287

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TABLES

9.14 Propylene Oxide by Acetaldehyde Cooxidatfon Production Costs . . . . . . . . . . . . . . . . . . . . 288

9.15

9.16

9.17

9.18

9.19

9.20

10.1

10.2

Propylene Oxide by Liquid Phase Catalytic Oxidation Using Molecular Oxygen, Based on USSR Patent Design Basis and Assumptions . . . . . . . . . . . . . . 291

Propylene Oxide by Liquid Phase Catalytic Oxidation Using Molecular Oxygen, Based on USSR Patent Stream Flows . . . . . . . . . . . . . . . . . . . . . . 293

Propylene Oxide by Liquid Phase Catalytic Oxidation Using Molecular Oxygen, Based on USSR Patent

Major Equipment and Utilities Summary . . . . . . . . . . 294

Propylene Oxide by Liquid Phase Catalytic Oxidation Using Molecular Oxygen, Based on USSR Patent Total Capital Investment . . . . . . . . . . l . . . . . 297

Propylene Oxide by Liquid Phase Catalytic Oxidation Using Molecular Oxygen, Based on USSR Patent Production Costs . . . . . . . . . . . . . . . . . . . . 298

Propylene Oxide by Noncatalytic Oxidation Using Molecular Oxygen Production Costs . . . . . . . . . . . . . . . . . . . . 302

Propylene Oxide by Propylene Glycol Monoacetate Pyrolysis Design Bases and Assumptions . . . . . . . . . . . . . . 307

Propylene Oxide by Propylene Glycol Monacetate Pyrolysis Stream Flows . . . . . . . . . . . . . . . . . . . . . . 309

10.3 Propylene Oxide by Propylene Glycol Monoacetate Pyrolysis Major Equipment and Utilities Sumnary . . . . . . . . . . 310

10.4 Propylene Oxide by Propylene Glycol Monoacetate Pyrolysis Total Capital Investment . . . . . . . . . . . . . . . . 314

10.5 Propylene Oxide by Propylene Glycol Monoacetate Pyrolysis Production Costs . . . . . . . . . . . . . . . . . . . . 316

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