Report No. 7 CAPROLACTAM PART II. November A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE MENLO PARK, CALIFORNIA

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1 Report No. 7 CAPROLACTAM PART II by HAROLD C. RIES ROBERT G. MULLER November 1965 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA

2 CONTENTS PART II VIII INTRODUCTION IX SUMMARY Orientation.. General Aspects Technical Aspects X CYCIGHEXANONE FROM PHENOL.... Chemistry Review of Processes Raw Materials... Process Description Process Discussion costs Capital Investment Production Costs XI CYCLOHEXANONE FROM CYCLOHEXANOL... Chemistry of Dehydrogenation Review of Processes..... Vapor Phase... Liquid Phase... Other Processes Process Description, Vapor Phase.... Process Discussion..... Process Description, Liquid Phase... Process Discussion Costs.. Capital Investment Production Costs. Mixed Feed--Vapor Phase XII CYCLOHEXANOL AND CYCLOHEXANONE FROM CYCLOHEXANE 307 Introduction.... Review of Processes Process Description Costs.. Capital Investment Production Costs iii

3 CONTENTS XIII CYCLOHEXANONE OXIME FROM CYCLOHEXANONE. Chemistry... Oximation... Preparation of Hydroxylamine... Review of Processes. Oximation... Preparation of Hydroxylamine... Process Description. Hydroxylamine Preparation... Oximation of Cyclohexanone... Materials of Construction... costs... Capital Investment. Production Costs.. XIV CAPROLACTAM FROM CYCLOHEXANONE OXIME.. Introduction.... Chemistry... Review of Processes. VaporPhase... Reactors... Process Description. costs... Capital Investment. Production Costs.. xv CAPROLACTAM FROM CAPROLACToNE... Chemistry... Oxidation of Cyclohexanone to Caprolactone... Ammonolysis of Caprolactone... Review of Processes. Oxidation of Cyclohexanone to Caprolactone... Ammonolysis of Caprolactone... Preparation of Peracetic Acid... Process Description. Oxidation of Cyclohexanone to Caprolactone... Ammonolysis of Caprolactone... Purification of Caprolactam... Preparation of Peracetic Acid... Raw Materials iv

4 CONTENTS Materials of Construction costs Capital Investment. 400 Production Costs Variations Affecting Cost XVI PURIFICATION OF CAPROLACTAM 411 XVII COMPLETE CAPROLACTAM PROCESSES Introduction Capital Investment Production Costs XVIII OTHER PROCESSES Caprolactam from Aniline Hydrogenation of Aniline to Cyclohexylamine Oxidation of Cyclohexylamine Cyclohexylamine from Cyclohexanol or Cyclohexanone Schmidt Reaction Miscellaneous Processes APPENDIX D Design and Cost Basis. 431 APPENDIX E Physical Data 435 APPENDIX F Raw Material and Product Specifications APPENDIX G I.F.P. Cyclohexanone Process Cited References 451 Supplementary References. 467

5 ILLUSTRATIONS Caprolactam Processes Cyclohexanone from Phenol 267 Vapor Phase Dehydrogenation of Cyclohexanol 283 Liquid Phase Dehydrogenation of Cyclohexanol Effect of Variables on Costs of Liquid Phase Dehydrogenation of Cyclohexanol Effect of Mixing on Rate of Oximation Kinetics of the Beckmann Rearrangement of Cyclohexanone Oxime. 348 Caprolactam from Oxime. 355 Caprolactam from Caprolactone Caprolactam from Caprolactone Effect of Raw Material Costs on Caprolactam Cost Effect of By-product Acetic Acid Price on Caprolactam Cost Effect of Caprolactam Yield in Final Purification on Cost Caprolactam Production Costs vii

6 TABLES Caprolactam from Oxime Stream Flows Caprolactam from Oxime Process Unit & Utilities Investment Caprolactam from Oxime Total Capital Investment Caprolactam from Oxime Production Costs Caprolactam from Caprolactone--Sections 100 and 200 Major Process Equipment List. 384 Caprolactam from Caprolactone--Sections 300 and 400 Major Process Equipment List. 387 Caprolactam from Caprolactone Stream Flows Caprolactam from Caprolactone Process Unit & Utilities Investment, Caprolactam from Caprolactone Total Capital Investment Caprolactam from Caprolactone Production Costs Caprolactam from Phenol Total Capital Investment Caprolactam from Cyclohexane Total Capital Investment Caprolactam from Cyclohexane via Caprolactone Total Capital Investment Caprolactam Processes Production Costs ix

7 TABLES Process Index.... Summary of Caprolactam Processes.... Sensitivity Analysis of Caprolactam Processes Cyclohexanone from Phenol Major Process Equipment List Cyclohexanone from Phenol Process Unit &Utilities Investment Cyclohexanone from Phenol Total Capital Investment Cyclohexanone from Phenol Production Costs Dehydrogenation of Cyclohexanol--Vapor Phase Major Process Equiment List. 34 Dehydrogenation of Cyclohexanol--Vapor Phase Stream Flows Dehydrogenation of Cyclohexanol--Liquid Phase Major Process Equipment List. 36 Dehydrogenation of Cyclohexanol--Vapor Phase Process Unit & Utilities Investment..., Dehydrogenation of Cyclohexanol--Liquid Phase Process Unit & Utilities Investment Dehydrogenation of Cyclohexanol--Vapor Phase Total Capital Investment Dehydrogenation of Cyclohexanol--Liquid Phase Total Capital Investment... Dehydrogenation of Cyclohexanol--Vapor Phase Production Costs X

8 TABLES Dehydrogenation of Cyclohexanol--Liquid Phase Production Costs.. Dehydrogenation of Cyclohexanol - Mixed Feed--Vapor Phase Total Capital Investment... Dehydrogenation of Cyclohexanol - Mixed Feed--Vapor Phase Production Costs.. Major Process Equipment List. StreamFlows.... Process Unit & Utilities Investment... Total Capital Investment.., Production Costs..,.,.. Major Process Equipment List...,,. Stream Flows.... Process Unit & Utilities Investment... Total Capital Investment... Production Costs.. Caprolactam from Oxime--Section 400 Major Process Equipment List Xi