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View Table of Contents (PDF) Abstract Process Economics Program Report 7C CAPROLACTAM (May 1998) This supplementary report presents an overview of the technical and economic aspects of modern caprolactam manufacture and identifies specific process improvements developed since PEP Report 41B, Nylon 6 and Caprolactam , was issued in March 1988. Because the vast majority of today’s caprolactam is produced from cyclohexanone, we pri- marily focus on the cyclohexanone based routes in our review of recent technology improvements in caprolactam manufacturing technology. In particular, we highlight the environmental aspects of caprolactam production, especially for cyclohexane oxidation and hydroxylamine production technologies. Two process technologies are evaluated in detail: • DSM’s hydroperoxide process—a commercial cyclohexane oxidation process for cyclo- hexanone manufacture • EniChem’s ammoximation process—a newly commercialized oximation process for cy- clohexanone oxime manufacture Comparison economics are presented for major commercial and developing technologies for the production of cyclohexanone, cyclohexanone oxime, and caprolactam. For producers of caprolactam and its intermediates, this report will be useful for the compar- ative economics it provides, as well as for its extensive review of recently issued patents and published literature. PEP’95 7C AEH CONTENTS GLOSSARY........................................................................................................................ xv 1 INTRODUCTION........................................................................................................ 1-1 2 SUMMARY ................................................................................................................. 2-1 TECHNICAL ASPECTS ............................................................................................. 2-1 Cyclohexanone Production ........................................................................................ 2-1 Cyclohexanone Oxime Production............................................................................. 2-2 Caprolactam Production............................................................................................. 2-7 ECONOMIC ASPECTS.............................................................................................. 2-11 Cyclohexanone Production ........................................................................................ 2-11 Investment Capital................................................................................................. 2-11 Production Costs................................................................................................... 2-13 Cyclohexanone Oxime Production............................................................................. 2-15 Investment Capital................................................................................................. 2-15 Production Costs................................................................................................... 2-15 Caprolactam Production............................................................................................. 2-17 Investment Capital................................................................................................. 2-21 Production Costs................................................................................................... 2-21 Profitability............................................................................................................. 2-25 3 INDUSTRY STATUS.................................................................................................. 3-1 GLOBAL CAPACITY OVERVIEW.............................................................................. 3-1 SUPPLY AND DEMAND ............................................................................................ 3-4 North America ............................................................................................................ 3-5 Western Europe ......................................................................................................... 3-10 Japan.......................................................................................................................... 3-12 4 TECHNOLOGIES FOR MANUFACTURING CYCLOHEXANONE............................ 4-1 CYCLOHEXANONE VIA CYCLOHEXANE OXIDATION ........................................... 4-5 Cyclohexane Oxidation—Chemistry........................................................................... 4-5 Cyclohexane Oxidation—Process Design ................................................................. 4-6 i CONTENTS (Continued) 4 TECHNOLOGIES FOR MANUFACTURING CYCLOHEXANONE (Concluded) Cyclohexanone Recovery ..................................................................................... 4-24 Environmental Issues............................................................................................ 4-25 CYCLOHEXANONE FROM CYCLOHEXENE........................................................... 4-26 Cyclohexene Hydration .............................................................................................. 4-26 Cyclohexene Epoxidation........................................................................................... 4-26 Cyclohexene Oxidation .............................................................................................. 4-26 5 CYCLOHEXANONE FROM CYCLOHEXANE VIA THE HYDROPEROXIDE ROUTE.............................................................................. 5-1 PROCESS DESCRIPTION ........................................................................................ 5-2 Section 100—Cyclohexane Oxidation........................................................................ 5-2 Section 200—Cyclohexanone Production.................................................................. 5-3 Section 300—Cyclohexane Recovery........................................................................ 5-3 PROCESS DISCUSSION .......................................................................................... 5-16 Oxidation .................................................................................................................... 5-16 Decomposition............................................................................................................ 5-17 Cyclohexane Recycle................................................................................................. 5-17 By-products ................................................................................................................ 5-17 Wastewater ................................................................................................................ 5-18 Safety ......................................................................................................................... 5-18 COST ESTIMATES .................................................................................................... 5-18 Capital Investment Costs ........................................................................................... 5-18 Production Costs ........................................................................................................ 5-19 6 TECHNOLOGIES FOR MANUFACTURING CYCLOHEXANONE OXIME ............... 6-1 HYDROXYLAMINE PRODUCTION........................................................................... 6-3 HAS Production.......................................................................................................... 6-3 Commercial Raschig Processes ........................................................................... 6-5 “Direct” Raschig Processes................................................................................... 6-6 iii CONTENTS (Continued) 6 TECHNOLOGIES FOR MANUFACTURING CYCLOHEXANONE OXIME (Concluded) Nitric Oxide Reduction Process ............................................................................ 6-8 HAAS Production ....................................................................................................... 6-10 HAP Production.......................................................................................................... 6-10 Hydroxylamine Production from Ammonia ................................................................. 6-10 Environmental Issues ................................................................................................. 6-11 Wastewater ........................................................................................................... 6-11 Nitrogen Oxides..................................................................................................... 6-11 CYCLOHEXANONE OXIMATION.............................................................................. 6-14 Oximation by HAS—The Conventional Process ........................................................ 6-15 Oximation by HAAS—the HSO Process .................................................................... 6-16 Oximation by HAP—the HPO Process....................................................................... 6-18 Direct Oximation by Hydroxylamine ........................................................................... 6-20 Direct Ammoximation Processes—Liquid Phase ....................................................... 6-20 Direct Ammoximation Processes—Vapor Phase....................................................... 6-21 Other Cyclohexanone Oximation Processes ............................................................. 6-22 Environmental Issues ................................................................................................
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