BUTYROLACTAMandLAUROLACTAM

Transcription

1 Report No. 118 BUTYROLACTAMandLAUROLACTAM by ROBERT H. SCHWAAR and TOHRU YAMADA September 1977 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA

2 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. ii

3 CONTENTS 1 INTRODUCTION..., 1 2 SUMMARY.. Laurolactam... 3 General Aspects... 3 Economic Aspects... 3 Technical Aspects... 6 Y-Butyrolactam... 8 General Aspects Economic Aspects... 8 Technical Aspects INDUSTRY STATUS Laurolactam Butyrolactam CYCLODODECANE FROM BUTADIENE VIA CYCLODODECATRIENE. 19 Chemistry Cyclododecatriene Production Cyclododecatriene Hydrogenation Review of Processes Cyclododecatriene Production Removal of Ziegler Catalyst Hydrogenation of Cyclododecatriene Process Description Process Discussion Butadiene Purification Catalyst Removal Removal of Heavy Residue Hydrogenation Processing of Recycle Streams from Other Units Waste Streams Cost Estimates Capital Costs Production Costs LAUROLACTAM FROM CYCLODODECANE VIA CYCLODODECANONE. 51 Chemistry. 51 Oxidation of Cyclododecane to Cyclododecanol Dehydrogenation of Cyclododecanol to Cyclododecanone Conversion of Cyclododecanone to Cyclododecanone Oxime.. 54 Vii

4 CONTF,NTS 5 LAUROLACTAM FROM CYCLODODECANE VIA CYCLODODECANONE (Continued) Hydroxylamine Preparation Rearrangement of Cyclododecanone Oxime to Laurolactam.. 55 Review of Processes Oxidation of Cyclododecane to Cyclododecanol Dehydrogenation of Cyclododecanol to Cyclododecanone Conversion of Cyclododecanone to Cyclododecanone Oxime.. 67 Production of Hydroxylamine Rearrangement of Cyclododecanone Oxime to Laurolactam.. 74 Ammonium Sulfate Recovery Purification of Laurolactam Coproduction of Laurolactam and Caprolactam Process Description Oxidation of Cyclododecane to Cyclododecanol Dehydrogenation of Cyclododecanol to Cyclododecanone Conversion of Cyclododecanone to Cyclododecanone Oxime.. 93 Rearrangement of Cyclododecanone Oxime to Laurolactam.. 93 Purification of Laurolactam Ammonium Sulfate Recovery Process Discussion Recovery of Boric Acid Recovery of Unreacted Cyclododecane Oximation Hydroxylamine Sulfate Ammonium Sulfate By-Product Handling Product Handling Tempered Water System Cost Estimates Capital Costs Production Costs LAUROLACTAM FROM CYCLODODECANE VIA PHOTOOXIMATION... Chemistry... Review of Processes... Cyclododecanone Oxime by Photooximation... Rearrangement of Cyclododecanone Oxime Hydrochloride to Laurolactam... Purification of Laurolactam... Process Description... Nitrosyl Chloride Preparation... Photooximation... Rearrangement viii

5 CONTENTS 6 LAUROLACTAM FROM CYCLODODECANE VIA PHOTOOXIMATION (Continued) Purification Ammonium Sulfate Recovery Chlorinated Waste Disposal Process Discussion Photooximation Productivity Photooximation Reaction Selectivity Operation Without a Solvent Form of the Oxime Hydrochloride Rearrangement Reaction Purification of Laurolactam Product Handling Ammonium Sulfate By-Product Handling Tempered Water System Materials of Construction Cost Estimates Capital Costs Production Costs OTHER LAUROLACTAM PROCESSES 157 Cyclododecanone Oxime from Cyclododecane via Nitrocyclododecane 157 Cyclododecanone Oxime from Cyclododecatriene via Chlorocyclododecadiene Oxime Cyclododecanol or Cyclododecanone from Cyclododecatriene via Epoxycyclododecadiene. 159 Cyclododecene from Cyclododecatriene 160 Cyclododecanol from Cyclododecene. 160 Cyclododecanone Oxime from Cyclododecene Laurolactam from Cyclododecene via 0x0 Reaction to Cyclododecane Carboxylic Acid Aminododecanoic Acid from Cyclododecene via Nitrocyclododecanone Aminododecanoic Acid from Cyclohexanone via l,l'-peroxydicyclohexylamine Miscellaneous Processes BUTYROLACTAM VIA BUTYROLACTONE Chemistry Butyrolactone from Maleic Anhydride Butyrolactone from 1,4-Butanediol Conversion of Butyrolactone to Butyrolactam ix

6 CONTENTS 8 BUTYROLACTAM VIA BUTYROLACTONE (Continued) Review of Processes Butyrolactone from Maleic Anhydride by Liquid-Phase Processes Butyrolactone from Maleic Anhydride by Vapor-Phase Processes Butyrolactone from 1,4-Butanediol Butyrolactone from Other Starting Materials Ethylene Tetrahydrofuran x0 Process Conversion of Butyrolactone to Butyrolactam Butyrolactone from Maleic Anhydride Process Description Process Discussion Choice of Process Feed Preparation Reactor Design Solvent Product Purification Waste Products Materials of Construction Cost Estimates Capital Costs Production Costs Butyrolactone from 1,4-Butanediol Process Description Process Discussion Materials of Construction Waste Products Cost Estimates Capital Costs Production Costs Conversion of Butyrolactone to Butyrolactam Process Description Process Discussion Reaction Conditions Selection of Reactor Configuration Ammonia Recovery Final Distillation of Butyrolactam Product Ammonia Supply Heating Media Materials of Construction Waste Disposal X

7 CONTENTS 8 BUTYROLACTAM VIA BUTYROLACTONE (Continued) Cost Estimates Capital Costs Production Costs OTHER BUTYROLACTAM PROCESSES 239 Review of Processes Butyrolactam from Maleic Anhydride Butyrolactam from Succinonitrile Butyrolactam from Other Starting Materials Butyrolactam from Maleic Anhydride Process Description Process Discussion Feed Preparation First-Stage Reactor Second-Stage Reactor Recycle Water Stripping Product Purification Waste Products Materials of Construction Cost Estimates Capital Costs Production Costs APPENDIX A DESIGN AND COST BASES APPENDIX B PROPERTIES OF RAW MATERIALS AND INTERMEDIATES CITED REFERENCES 279 PATENT REFERENCES BY COMPANY Xi

8 ILLUSTRATIONS 4.1 Cyclododecane from Butadiene via Cyclododecatriene Process Flow Diagram Cyclododecane from Butadiene via Cyclododecatriene Effect of Plant Capacity on Total Fixed Capital Cyclododecane from Butadiene via Cyclododecatriene on Production Cost Laurolactam from Cyclododecane via Cyclododecanone Process Flow Diagram Laurolactam from Cyclododecane via Cyclododecanone Effect of Plant Capacity on Total Fixed Capital Laurolactam from Cyclododecane via Cyclododecanone Effect of Cyclododecane Price on Production Cost Laurolactam from Cyclododecane via Cyclododecanone on Production Cost Laurolactam from Cyclododecane by Photooximation Process Flow Diagram..., Laurolactam from Cyclododecane by Photooximation Effect of Plant Capacity on Total Fixed Capital Laurolactam from Cyclododecane by Photooximation Effect of Cyclododecane Price on Production Cost Laurolactam from Cyclododecane by Photooximation on Production Cost Routes from Cyclododecatriene to Laurolactam Y-Butyrolactone from Maleic Anhydride Process Flow Diagram y-butyrolactone from Maleic Anhydride Effect of Plant Capacity on Total Fixed Capital y-butyrolactone from Maleic Anhydride on Production Cost Y-Butryolactone from 1,4-Butanediol Process Flow Diagram xiii

9 ILLUSTRATIONS 8.5 Y-Butyrolactone from 1,4-Butanediol Effect of Plant Capacity on Total Fixed Capital Y-Butyrolactone from 1,4-Butanediol on Production Cost Conversion of Y-Butyrolactone to Y-Butyrolactam Process Flow Diagram Conversion of Y-Butyrolactone to Y-Butyrolactam Effect of Plant Capacity on Total Fixed Capital Conversion of Y-Butyrolactone to Y-Butyrolactam on Production Cost Y-Butyrolactam from Maleic Anhydride Process Flow Diagram Y-Butyrolactam from Maleic Anhydride Effect of Plant Capacity on Total Fixed Capital Y-Butyrolactam from Maleic Anhydride on Production Cost B.l Vapor Pressures of Butyrolactam and Related Compounds B.2 Vapor Pressures of Cyclododecane and Related Compounds B.3 Vapor Pressures of Laurolactam and Related Compounds xiv

10 TABLES 2.1,Summary of Cost Estimates for Laurolactam Manufacture Summary of Cost Estimates for Y-Butyrolactone and Y-Butyrolactam Manufacture ,4-Butanediol, Tetrahydrofuran, Butyrolactone, and Butyrolactam Production Plants Cyclododecatriene from Butadiene Through the Use of a Ziegler Catalyst Summary of Patents on Catalyst Systems Cyclododecatriene from Butadiene Through the Use of a Ziegler Catalyst Summary of Other Patents Hydrogenation of Cyclododecatriene to Cyclododecane Patent Summary. 4.4 Cyclododecane from Butadiene via Cyclododecatriene Bases and Assumptions Cyclododecane from Butadiene via Cyclododecatriene Major Equipment and Utilities Summary Cyclododecane from Butadiene via Cyclododecatriene Stream Flows Cyclododecane from Butadiene via Cyclododecatriene Total Capital Investment Cyclododecane from Butadiene via Cyclododecatriene Major Capital Equipment Costs Cyclododecane from Butadiene via Cyclododecatriene Production Costs Oxidation of Cyclododecane to Cyclododecanol Patent Summary Dehydrogenation of Cyclododecanol to Cyclododecanone Patent Summary Oximation of Cyclododecanone Patent Summary Rearrangement of Cyclododecanone Oxime to Laurolactam Patent Summary Rearrangement of Cycloalkanone Oximes to Lactams Patent Summary xv

11 TABLES 5.6 Purification of Laurolactam PatentSummary Purification Processes Possibly Applicable to Laurolactam Patent Summary Laurolactam from Cyclododecane via Cyclododecanone Bases and Assumptions Laurolactam from Cyclododecane via Cyclododecanone Major Equipment and Utilities Summary Laurolactam from Cyclododecane via Cyclododecanone Stream Flows Laurolactam from Cyclododecane via Cyclododecanone Total Capital Investment Laurolactam from Cyclododecane via Cyclododecanone Major Capital Equipment Costs Laurolactam from Cyclododecane via Cyclododecanone Production Costs Laurolactam from Cyclododecane by Photooximation Patent Summary Rearrangement of Cyclododecanone Oxime Produced by Photooximation Patent Summary Purification of Laurolactam Produced by Photooximation Patent Summary Laurolactam from Cyclododecane via Photooximation Bases and Assumptions Laurolactam from Cyclododecane via Photooximation Major Equipment and Utilities Summary Laurolactam from Cyclododecane by Photooximation Stream Flows Laurolactam from Cyclododecane by Photooximation Waste Treatment Laurolactam from Cyclododecane by Photooximation Total Capital Investment Laurolactam from Cyclododecane by Photooximation Major Capital Equipment Costs xvi

12 TABLES Laurolactam from Cyclododecane by Photooximation Production Costs Laurolactam from Cyclododecane by Photooximation Sensitivity of Production Cost to Selectivity.. Selective Hydrogenation of Cyclododecatriene to Cyclododecene Patent Summary. Y-Butyrolactone from Maleic Anhydride by Liquid-Phase Processes Patent Summary. Y-Butyrolactone from Maleic Anhydride by Vapor-Phase Process Patent Summary. Y-Butyrolactone from Other Starting Materials Patent Summary. Conversion of Y-Butyrolactone to Y-Butyrolactam Patent Summary. Y-Butyrolactone from Maleic Anhydride Bases and Assumptions.. Y-Butyrolactone from Maleic Anhydride Major Equipment and Utilities Summary... Y-Butyrolactone from Maleic Anhydride Stream Flows.. Y-Butyrolactone from Maleic Anhydride Total Capital Investment Y-Butyrolactone from Maleic Anhydride Major Capital Equipment Costs.. Y-Butyrolactone from Maleic Anhydride Production Costs Y-Butyrolactone from 1,4-Butanediol Bases and Assumptions.. Y-Butyrolactone from 1,4-Butanediol Major Equipment and Utilities Summary.. Y-Butyrolactone from 1,4-Butanediol Stream Flows.. Y-Butyrolactone from 1,4-Butanediol Total Capital Investment xvii

13 TABLES B.l B.2 B.3 B.4 Y-Butyrolactone from 1,4-Butanediol Major Capital Equipment Costs.. Y-Butyrolactone from 1,4-Butanediol Production Costs Conversion of Y-Butyrolactone to Y-Butyrolactam Bases and Assumptions.. Conversion of Y-Butyrolactone to Y-Butyrolactam Major Equipment and Utilities Summary.. Conversion of Stream Flows Conversion of Total Capital Conversion of Major Capital Y-Butyrolactone to Y-Butyrolactam.. Y-Butyrolactone to Y-Butyrolactam Investment Y-Butyrolactone to Y-Butyrolactam Equipment Costs.. Conversion of Y-Butyrolactone to Y-Butyrolactam Production Costs... Y-Butyrolactam from Starting Materials Other Than Y-Butyrolactone Patent Summary... Y-Butyrolactam from Maleic Anhydride Bases and Assumptions... ;... Y-Butyrolactam from Maleic Anhydride Major Equipment and Utilities Summary... Y-Butyrolactam from Maleic Anhydride Stream Flows... Y-Butyrolactam from Maleic Anhydride Total Capital Investment... Y-Butyrolactam from Maleic Anhydride Major Capital Equipment Costs... Y-Butyrolactam from Maleic Anhydride Production Costs... Butadiene Specifications (Commercial Grade)... Properties of Selected Compounds... Properties of Maleic Anhydride, Butyrolactone, and Butyrolactam... 1,4-Butanediol Properties xviii