DIBASIC ACIDS PROCESS ECONOMICS PROGRAM. Report No. 75. by YEN-CHEN. October A private report by the

Transcription

1 Report No. 75 FOR NYLON DIBASIC ACIDS MANUFACTURE by YEN-CHEN YEN October 1971 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE MENLO PARK, CALIFORNIA

2 CONTENTS INTRODUCTION,... 1 SUMMARY... General Aspects... Technical Aspects... INDUSTRY STATUS... Applications and Consumption of Sebacic Acid... Applications and Consumption of Azelaic Acid... Applications of Dodecanedioic and Suberic Acids... Applications of Cyclododecatriene and Cyclooctadiene... Producers... Prices DIBASIC ACIDS FOR MANUFACTURE OF POLYAMIDES CYCLOOLIGOMERIZATION OF BUTADIENE... Ziegler Catalyst... Nickel Catalyst... Other Catalysts... Co-Cyclooligomerization... Mechanism... By-products and Impurities... A Process for Manufacture of Cyclododecatriene... Process Description... Process Discussion... A Process for Manufacture of Cyclooctadiene... Process Description... Process Discussion... A Process for Manufacture of Cyclodecadiene... DODECANEDIOIC ACID FROM CYCLODODECATRIENE... Hydrogenation of Cyclododecatriene... Oxidation of Cyclododecane... Oxidation of Cyclododecanol or Cyclododecanone V

3 CONTENTS 6 (continued) Epoxidation of Cyclododecatriene... Ozonization of Cyclododecene... Hydrogenation of Cyclododecatriene... Dodecanedioic Acid from Cyclododecane... Dodecanedioic Acid from Cyclododecatriene Through Epoxidation... Purification... A Process via Cyclododecane... Process Description... Process Discussion... A Process via Cyclododecene... Process Description... Process Discussion... 7 SUBERIC ACID FROM CYCLOOCTADIENE AND SEBACIC ACID FROM CYCLODECADIENE... A Process for Suberic Acid from Cyclooctadiene via Cyclooctane... Process Description and Discussion... A Process for Sebacic Acid from Cyclodecadiene via Cyclodecane... Process Description and Discussion... 8 SEBACIC ACID FROM CASTOR OIL... Process Description... Process Discussion SEBACIC ACID FROM ADIPIC ACID vi

4 CONTENTS 9 (continued) Process Description... Process Discussion AZELAIC ACID FROM OLEIC ACID Process Description... Process Discussion DIBASIC ACIDS FROM FATTY ACIDS OR PARAFFINS...., Process Description... Process Discussion OTHER PROCESSES FOR PREPARATION OF DODECANEDIOIC ACID From Malonic Acid and Butadiene... From Cyclohexanone... From Castor Oil or Ricinoleic Acid... From 1,10-Decanediol... From Pentane... From l0-undecenoic... By Fermentation OTHER PROCESSES FOR PREPARATION OF SEBACIC ACID From Decalin (Decahydronaphthalene)... From Butadiene via Isosebacic Acid... From Furfural From Butadiene Through 1,4-Dichloro-2-butene... From Octadiene... From Resorcinal... From Pentin Acid.... From 1-Cyclodecanol-2-one... From lo-undecenoic Acid... From Tetrachlorononane... From Tetrahydrofurfural Chloride... By Fermentation Vii

5 CONTENTS OTHER PROCESSES FOR PREPARATION OF AZELAIC ACID... From an Acetylene Compound and Butadiene... From Cyclooctadiene... From Resorcinol and Acrylic Acid... From Cyclohexanone... From Ethylene and Chlorocyanogen... From Cyclooctanone... From Thiophene... From Cyclopentanone-Carboxylic Acid... By Fermentation... OTHER PROCESSES FOR PREPARATION OF SUBERIC ACID... From Acetylene via Cyclooctatetraene... From Chloromethyl-methylether and Butadiene... From Acetylene and Carbon Monoxide... From Ethylene and Carbon Tetrachloride via Tetrachloroheptane... From Acrylic Acid via 1-Hexene-6-oic Methyl Ester... From Acrolein via Hexanediol... From Resorcinol Through 1,3-Cyclohexanedione... From Butadiene and Acetylene... From 1,5-Hexadiene... By Fermentation APPENDIX A DESIGN AND COST BASIS... APPENDIX B SPECIFICATIONS AND TYPICAL ANALYSES... APPENDIX C PHYSICAL DATA... CITED REFERENCES... PATENT REFERENCES BY COMPANY Viii

6 ILLUSTRATIONS 5.1 Cyclododecatriene from Butadiene.....,., Cyclododecatriene from Butadiene Production Costs as Different Production Levels....., Cyclooctadiene from Butadiene ,.,. 67 Cyclooctadiene from Butadiene Production Costs at Different Production Levels.., Dodecanedioic Acid from Cyclododecatriene Summary of Routes , Dodecanedioic Acid from Cyclododecatriene via Cyclododecane ,..., Dodecanedioic Acid from Cyclododecatriene via Cyclododecane Production Costs at Different Production Levels Dodecanedioic Acid from Cyclododecatriene via Cyclododecene , 125 Dodecanedioic Acid from Cyclododecatriene via Cyclododecene Production Costs at Different Production Levels,...., 132 Suberic Acid from Cyclooctadiene Summary of Routes ,.., Suberic Acid from Cyclooctadiene via Cyclooctane Purification Section Suberic Acid from Cyclooctadiene via Cyclooctane Production Costs at Different Production Levels,...,. 149 Sebacic Acid from Cyclodecadiene via Cyclodecane Purification Section Sebacic Acid from Cyclodecadiene via Cyclodecane Production Costs at Different Production Levels., Sebacic Acid from Castor Oil., Sebacic Acid from Castor Oil Production Costs at Different Production Levels Sebacic Acid from Adipic Acid by Electrolysis., Sebacic Acid from Adipic Acid by Electrolysis Production Costs at Different Production Levels,..,

7 ILLUSTRATIONS C.1 C.2 c.3 C.4 C.5 Production Costs at Different Production Levels Dibasic Acids from Tallow by Oxidation.,... Dibasic Acids from Tallow by Oxidation Production Costs at Different Production Levels Solubilities of Dibasic Acid in Water..... Solubilities of Sebacic Acid, Azelaic Acid, and Suberic Acid in 25% Aqueous Nitric Acid,... Solubilities of Sebacic Acid, Azelaic Acid, and Suberic Acid in 40% Aqueous Nitric Acid.... Solubilities of Sebacic Acid, Azelaic Acid and Suberic Acid in 58% Aqueous Nitric Acid..,. Vapor Pressures of Selected Compounds.,....,......, ,

8 TABLES Manufacture of Sebacic Acid Cost Estimates , 4 Manufacture of Dodecanedioic Acid, Suberic Acid, and Sebacic Acid via Cycloalkenes.., Cost Estimates ,., Cost Estimates Dibasic Acids from Tallow Cost Estimates Manufacture of Cyclododecatriene, Cyclooctadiene, and Cyclodecadiene Cost Estimates Producers of Dibasic Acids and Precursors Dibasic Acids for Polyamide Manufacture...., Cyclododecatriene from Butadiene Patent Summary Cyclooctadiene from Butadiene by Catalytic Oligomerization Patent Summary....., Cyclooligomerization of Butadiene and Ethylene Patent Summary.,......,....., Cyclododecatriene from Butadiene Major Process Equipment and Utilities Summary Cyclododecatriene from Butadiene Stream Flows....., Cyclododecatriene from Butadiene Total Capital Investment ,. 62 Cyclododecatriene from Butadiene Production Costs....., Cyclooctadiene from Butadiene Major Process Equipment and Utilities Summary Cyclooctadiene from Butadiene Stream Flows Cyclooctadiene from Butadiene Total Capital Investment xi

9 TABLES Dodecanedioic Acid from Cyclododecatriene via Cyclododecene Total Capital Investment Dodecanedioic Acid from Cyclododecatriene via Cyclododecene Production Costs Processes Related to Suberic Acid from Cyclootadiene Patent Summary Patents Related to Processes for Sebacic Acid from Cyclodecadiene Suberic Acid from Cyclooctadiene via Cyclooctane Major Process Equipment and Utilities Summary Suberic Acid from Cyclooctadiene via Cyclooctane Total Capital Investment Suberic Acid from Cyclooctadiene via Cyclooctane Production Costs Sebacic Acid from Cyclodecadiene via Cyclodecane Major Process Equipment and Utilities Summary Sebacic Acid from Cyclodecadiene via Cyclodecane Total Capital Investment Sebacic Acid from Cyclodecadiene via Cyclodecane Production Costs Sebacic Acid from Castor Oil or Related Substances Patent Summary Sebacic Acid from Castor Oil Major Process Equipment and Utilities Summary Sebacic Acid from Castor Oil Stream Flows Sebacic Acid from Castor Oil Total Capital Investment Sebacic Acid from Castor Oil Production Costs Sebacic Ester from Adipic Monoester Patent Summary Xiii

10 TABLES Sebacic Acid from Adipic Acid by Electrolysis Major Process Equipment and Utilities Summary Sebacic Acid from Adipic Acid by Electrolysis Stream Flows Sebacic Acid from Adipic Acid by Electrolysis Total Capital Investment, Sebacic Acid from Adipic Acid by Electrolysis Production Costs Patent summary Major Process Equipment and Utilities Summary Stream Flows Total Capital Investment ,,. 224 Production Costs..., Dibasic Acids from Fatty Acids or Fatty Oils Literature Summary Dibasic Acids from Hydrocarbons by Oxidation Literature Summary Recovery and Purification of Dibasic Acids Patent Summary Dibasic Acids from Tallow by Oxidation Major Process Equipment and Utilities Summary Dibasic Acids from Tallow by Oxidation Stream Flows Dibasic Acids from Tallow by Oxidation Total Capital Investment Dibasic Acids from Tallow by Oxidation Production Costs , xiv