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Tagungsbericht 9903 ., ,’!y;.- ‘ i ,> , ‘. ,,1 . .. ., ,,. .,” ‘, .,. “j’ DGMK German Society for Petroleum and Coal ,. Science and Technology Tagungsbericht 9903 Proceedings of the DGMK-Conference “The Future Role of Aromatics in Refining and Petrochemistry” October 13-15, 1999, Erlangen, Germany ,. (Authors’ Manuscripts) edited by G. Emig, M. Rupp &J. Weitkamp ,: .\ .,, 1111111111111111 Ksoo25199giI R: Ks DEoi362250g ,,., , -. .,, :- . ,, ; .“ ‘/ “.. < t. 6, ‘ t ~’t.” ,. .. ,, .,, .. ,. , . ,. # .“. .4 . .. ’.’ “. .,” .. ,’, ,”,, . ......, .; ,’ ,~..~;, , , y ,,, ,.. I ,, , !,< ,, ,’”,,,’,. ; ,-. ,.,. ,, ,, ,-. ,- , ,,/ ..,1. .! ::,, , ,,.,,., : ,., ,., ;,, . ..4. .,[$ ,’, :,:. ,,, .,. ,,?, ,$ DISCLAIMER ,’,,,$ ,,4 ,., ,,;1,,,, ,. f:, ;,,,,;~j -, ‘ ,>. ,., :,.,,, I ,,.., ‘::,~portions of this document may be illegible ; ,,,c.,,,;.,, ,,a ,. ,{:,.”’,,’., ; in electronic image products. Images are ,.,,. , ,,.,,,.,,,.: ::\ produced from the best available original ; .. ‘, , !. -, -,, -,- . ,, I ,.....’....,.- ,. .<,.’:’> CONTENTS ., , ““?:,:’ .:;,.’,’,’. ,< ,, -,.’ ,.,. ,,.” ,.. ~ Page ,6 ., \ -, Aromatics: Bridging Refi~ng and Petrochemicals - 7 a major Challenge for the Future W. J. Petzny, C.-P. Halsig How will EU Environmental Legislation Impact on the 21 Aromatics Markets? M. Schuller, P. Hodges t The Role of Aromatics in Transportation Fuels 37 K. van Leeuwen Sulphur Tolerant Dearomatization of Middle Distillates - 45 A Cost Effective Way of Meeting 2005 Specifications ?’ D. Huang, E. Kohler The Roles of Aromatics and Catalytic Reforming in the 53 2000+ Refinery O. Genis, S. G. Simpson, D. W. Penner, R. Gautam, B. K. Glover Flexible Upgrading of Light Reformate 65 J. Cosyns, Q. Debuisscheti, B. Didillon, J. L. Ambrosino Separation Processes for the Recovery of Pure Aromatics 73 ,.. , B. Firnhaber, G. Emmrich, F. Ennenbach, U. Ranke ,-,., Developments in Aromatics Separation 99 G. Krekel, J. Eberhardt, T. Diehl, G. Birke, H. Schlichting, A. Glasmacher The Role of Pyrolysis Gasoline from Steam Crackers 115 beyond the Year 2000 C. Dembny Maximizing Paraxylene Production with ParamaX 131 J. Rault, P. Renard, F. Alario ,.,~,’,, i .,, ,, .’1 Recent Advances in the Oxidation and Ammoxidation of 139 ,., .1, ;,., ,- ,.,; “., ,’ ., Aromatics ‘ -, .’ ,. , f .2.. , ~~ B. Lticke, A. Martin .’~,,,,,, :,,1~; ,,, , ,., ,., ., Recent Progress and Challenges in the Electrophilic 153 .,-, 1 Substitution of Aromatics ,, .,,.. ,.,1‘J F.-J. Mais Fundamental Relations between Modification of the External 161 Surface of Zeolites and Catalytic Performance H. P. Roger, K. P. Moller, W. Bohringer, C.T. O’Connor ,’. Y.,,,< ... ,,7 II Gas Phase Hydrogenation of Benzene with Unusual 169 Cyclohexene Formation “ E. Dietzsch, D. Honicke SulfurTolerance ofAIkali Exchanged Zeolites for Benzene 177 Hydrogenation L. Simon, J. G. van Ommen, P. J. Kooyman, A. Jentys, J. A. Lercher Postersession PolycyclicArenes and Heteroarenes asBackbonesof 185 Diphosphine/amine Ligands forThermostable Homogeneous Catalysts M. W. Haenel, St. Oevers, St. Hillebrand, W. C. Kaska Low Temperature o-XyIene Oxidation to Phthalic Anhydride 193 on V-Ti-O Catalysts Prepared by Mechanochemistry V.A. Zazhigalov, Al. Kharlamdv, L. Depero, A. Marine, I.V. Bacherikova, J. Stoch, J. Haber A New Calculation Method for Arenes Solubilities in the Whole 201 Composition Range of Water-Sulfuric Acid System A. L Lutsyk, E. S. Rudakov, V. N. Mochalin A New Oxidic Catalyst System for Selective CG+Paraffine 207 Aromatization D. L. Hoang, A. Trunschke, A. Bruckner, J. Radnik, H. Lieske Benzene Oxidation to Phenol by Molecular Oxygen on 215 Medicated MoOS L. V. Bogutskaya, S.V. Khalamejda, V.A. Zazhigalov Selective Hydrogenation of light Reformate for Production 217 of high-purity Benzene M. Walter, E. Schwab, M. G. Koch, P. Trubenbach, S. Dining Supported Ru-catalysts for the partial Gas Phase 223 Hydrogenation of Benzene E. Dietzsch, P. Claus, D. Honicke Heterogeneously catalyzed liquid-phase Hydrogenation 23i of nitro-aromatics using Microchannel Reactors R. Fodisch, W. Reschetilowski, D. Honicke Safety of large Reactors for the Cumene Oxidation 239 M. Weber Ill ., Base-catalyzed Synthesis of Ethylbenzene by 247 .. Dehydroisomerization of 4-Viny Icyclohexene J. Ackermann, E. Klemm, G. Emig Catalytic Behaviour of modified ZSM-5 Type Zeolites in the 255 Hydroxylation of Benzene-using nitrous Oxide A. Reitzmann, G, Konig, F. M. Petrat, E. Klemm, G. Emig 263 Effect of ZSM-5 Zeolite Synthesis Following Different Routes on ..’ the Isomerization of Xylenes ,:, R. Monnig, W. Schwieger .,7 Alkylation of Napthalene on a Zeolite Catalyst in Supercritical 271 ,,. and Gaseous Reaction Phases R. Glilser, J. Weitkamp On Selectivity Aspects of the Alkylation of Toluene with 279 Methanol over Zeolites M. Rep, A. E. Palomares, G. Eder-Mirth, J. G. van Ommen, J. A. Lercher ;., ,. ,,, , “ ,. ,.,..:,,:.,.,:. ,., ,,., . .,, ‘ .,, , ~,.~..,-,c.~,.., ~ ,., , ., .,<,’,.>, ,-, , ,. -,, ‘, .,., ;..,,... : ,,,. .’, “’?: :, , ,.,.,,J :,, .. !,, :, ..” ,,,. .$ ,.’ t *, ., ‘.. ,-,’,,’ ,.. ..,.: . ‘~,,i ..’ i .:.,; ;. .’, ,, ,..,,:, >, ,,~’,,, ..- DGMK-Conference “The Future Role of Aromatics in Refining and Petrochemistry”, Erlangen 1999 ., !,.,;:. ,. ,, W. J. Petzny ‘), C.-P. Halsig 2)” 1,BP Amoco Chemicals, London, United Kingdom 3 Fluo~ Daniel, Haar\em, The Netherlands Aromatics: Bridging Refining and Petrochemicals - a major Challenge for the Future ‘, Introduction t, In the last decade the European and North American Refining and Petrochemical Industries have faced increasing challenges in providing an attractive return on investment. The principal reasons for this situation includes overcapacity, slow down of economic growth, environmental pressurea, environmentally mandated fisel composition changes, ‘dkselisation’, price erosion, and low margins resulting in mergers and plant shut downs. The only potentially beneficial effect of this is less tlagmentation of these European industries. The marketa for both industries are regarded as cyclic. However, while the petrochemical industry cycle was at least in an upturn in 1988 and 1994/95, the refining industry has been in an economic trough since the mid 80s and still is. It is apparent that both industries are .,, ,.,, .,..,- , continuously searching for opportunities to stay competitive and to improve profitability by ., J.. { adding value to their products and product slates. Obviously, there is no general advice that one can offer for these challenges. Trends can be recognized and compared with each individual local situation. Newly applied techniques and new technological developments can enable refiners and petrochemical plant operators to increase utilization of existing equipment and, as usual, every situation is ‘special’. The demand for petrochemical products is now rising at a rate of about twice that of oil products. WMe currently about 8% of the crude oil barrel processed goes into petrochemicals this is predicted to rise clearly above 10% within the next few years, at some locations it is already at 200A.Growth in this area will require fhrther initiatives to search for opportunities for the benefit of both the refiner and petrochemical plants to increase return on existing assets. 7 OGMK-Tagungsbericht 9903, ISBN 3-931850-59-5 The title of this conference is ‘The Future Role of Aromatics in Refining and Petrochemistry’. As a contribution to this conference this presentation therefore aims to review the trends in refining and petrochemical industries, reviews the aromatics of common interest and the challenges and opportunities for both industries in this area, analysing the bridging opportunities and providing a basis for some of the presentations to follow. Trends in the Petrochemical and Refining Industries The considerable overlap of the two industries started with the introduction of the reforming process into the refineries more than 40 years ago, the extraction of aromatics produced, substituting and replacing the aromatics recovered from coke oven gas. The new gasoline specifications in place or coming in place in North America and in Europe, and finally the rest of the world - demands the reduction of total aromatics and benzene in particular in gasoline more and more will have a significant influence on this relationship. This offers challenges for fiture opportunities but also chances for conflicts. Though the world wide economy is still a bit in a trough, unprecedented petrochemical development is still taking place in Asia and in the Gulf area in terms of expansion as WCIIas vertical integration from feedstock to product. Though the Asian flue has reduced or delayed some investments many were already on their way when the flue hit. A majority of these new plants are integrated petrochemical - refining complexes with refining capacities between 150,000 and 250,000 bpsd (equivalent to 8-12 m t/year) and ethylene capacities from 0.4 to 1 m t/year of ethylene. These significant investments in integrated petrochemical / refining complexes are driven by the desire to have an optimal operation, benefiting from the synergy between the retincry and petrochemical plant, energy utilisation and security of petrochemical feedstock supply. Of the more than one hundred refineries in Western Europe about twenty, mostly the larger ones, are integrated with petrochemical operation. Major revamps have been carried out or are in progress at several locations to firther increase utilisation of refinery originating streams. In Central Europe, most petrochemical facilities are associated
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