WILEY CRITICAL CONTENT PETROLEUM TECHNOLOGY VOLUME 1-2 WILEY-INTERSCIENCE WILEY-VCH A JOHN WILEY & SONS, INC., PUBLICATION Copyright#2007byJohnWiley&Sons,Inc.,andWILEY-VCHVerlagGmbH&Co.KGaA, Weinheim.Allrightsreserved. PublishedbyJohnWiley&Sons,Inc.,Hoboken,NewJersey. PublishedsimultaneouslyinCanada. Nopartofthispublicationmaybereproduced,storedinaretrievalsystem,ortransmittedinany formorbyanymeans,electronic,mechanical,photocopying,recording,scanning,orotherwise,except aspermittedunderSection107or108ofthe1976UnitedStatesCopyrightAct,withouteitherthe priorwrittenpermissionofthePublisher,orauthorizationthroughpaymentoftheappropriate per-copyfeetotheCopyrightClearanceCenter,Inc.,222RosewoodDrive,Danvers,MA01923, (978)750-8400,fax(978)750-4470,oronthewebatwww.copyright.com.RequeststothePublisher forpermissionshouldbeaddressedtothePermissionsDepartment,JohnWiley&Sons,Inc., 111RiverStreet,Hoboken,NJ07030,(201)748-6011,fax(201)748-6008,oronline athttp://www.wiley.com/go/permission. 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WileyCriticalContent:PetroleumTechnology,2V ISBN 978-0-470-13402-3 PrintedintheUnitedStatesofAmerica 10 9 8 7 6 5 4 3 2 1 CONTRIBUTORS ColinBarker,UniversityofTulsa,Tulsa, M.LarryCampbell,ExxonChemicalCompany, Oklahoma,UnitedStates,Petroleum, FlorhamPark,NewJersey,UnitedStates, Introduction Cyclohexane ScottD.Barnicki,EastmanChemical MartinCarrera,AmocoCorporation, Company,Kingsport,Tennessee,United Naperville,Illinois,UnitedStates,Propylene States,SeparationsProcessSynthesis ClarenceD.Chang,MobilResearchand CalvinBartholomew,BrighamYoung DevelopmentCorporation,Princeton, University,Provo,Utah,UnitedStates, NewJersey,UnitedStates,Fuels,Synthetic, CatalystDeactivationandRegeneration Liquid Ju¨rgenBa¨ssler,UhdeGmbH,Dortmund, W.C.Cheng,W.R.Grace&Company, Germany,Acetylene Columbia,Maryland,UnitedStates,Fluid ArnoBehr,HenkelKGaA,Du¨sseldorf, CatalyticCracking,CatalystsandAdditives Germany,Hydrocarbons T.T.PeterCheung,PhillipsPetroleum HartmutBehringer,Hoechst Company,Bartlesville,Oklahoma,United Aktiengesellschaft,WerkKnapsack, States,Cyclopentadieneand Germany,Acetylene Dicyclopentadiene L.E.Bell,UOPLLC,DesPlaines,Illinois, P.D.Clark,UniversityofCalgary,Calgary, UnitedStates,FluidCatalyticCracking,Units, Alberta,Canada,SulfurandHydrogenSulfide Regeneration Recovery RosemarieBerger,Ludwigshafen,Germany, GerdCollin,DECHEMAe.V.,Frankfurtam Liquid–LiquidExtraction Main,Germany,Anthracene;Hydrocarbons; RonaldL.Berglund,Terracon,Kingwood, NaphthaleneandHydronaphthalenes Texas,UnitedStates,EmissionControl, AxelCommichau,MobilEuropeGasInc.,The Industrial Hague,TheNetherlands,NaturalGas DieterBiedenkapp,BASFAktiengesellschaft, WernerDabelstein,DeutscheShellAG, Ludwigshafen,Germany,Hydrocarbons Hamburg,Germany,OctaneEnhancers GeoffJ.Bishop,ShellAviationLtd.,London, RulaDeeb,MalcolmPirnie,Inc.,Emeryville, UnitedKingdom,AviationTurbineFuels California,UnitedStates,MethylTert-Butyl EckhartBlass,TechnischeUniversita¨t Ether Mu¨nchen,Mu¨nchen,Germany,Liquid–Liquid JamesR.Dickey,LubricantsConsultant, Extraction BaskingRidge,NewJersey,UnitedStates, KlausBoehlke,BASFAktiengesellschaft, LubricationandLubricants Ludwigshafen,Germany,Waxes WolframDietsche,BASFAktiengesellschaft, JohnT.Boepple,NexantChemSystems,White Ludwigshafen,Germany,Waxes Plains,NewYork,UnitedStates, MichaelF.Doherty,UniversityofCalifornia, PetrochemicalFeedstocks SantaBarbara,SantaBarbara,California, JohnK.Borchardt,ShellDevelopment UnitedStates,Distillation,Azeotropicand Company,Houston,Texas,UnitedStates, Extractive EnhancedOilRecovery T.J.Dougan,W.R.Grace&Company, JamesA.Brient,MerichemCompany, Columbia,Maryland,UnitedStates,Fluid Houston,Texas,UnitedStates,Naphthenic CatalyticCracking,CatalystsandAdditives Acids MaryNoonDoyle,ShepherdChemical P.F.Bryan,ChevronResearchandTechnology Company,Cincinnati,Ohio,UnitedStates, Company,Richmond,California,United NaphthenicAcids States,BTXProcessing LawrenceJ.Drew,U.S.GeologicalSurvey, KlausBuckl,LindeAG,Ho¨llriegelskreuth, Reston,Virginia,UnitedStates,Petroleum, Germany,Acetylene Introduction NarasimhanCalamur,AmocoCorporation, Gu¨nterEbersberg,Degussa-Hu¨lsAG,Marl, Naperville,Illinois,UnitedStates,Propylene Germany,Acetylene ix x CONTRIBUTORS Vol. 1 Jo¨rgFabri,DeutscheShellAG,Hamburg, GerdHohner,HoechstAktiengesellschaft,Werk Germany,OctaneEnhancers;Xylenes Gersthofen,Augsburg,Germany,Waxes JamesR.Fair,TheUniversityofTexasat HartmutHo¨ke,Weinheim,Germany, Austin,Austin,Texas,UnitedStates, Anthracene;Hydrocarbons;Naphthalene Distillation andHydronaphthalenes KevinJ.Fallon,WashingtonGroup CraigA.Hoyme,EastmanChemicalCompany, International,Inc.,Cambridge, Kingsport,Tennessee,UnitedStates, Massachusetts,UnitedStates,Ethylbenzene SeparationsProcessSynthesis WilliamFruscella,UnocalCorporation,El ChangSamuelHsu,ExxonResearchand Segundo,California,UnitedStates,Benzene EngineeringCompany,Annandale,New DorotheaGarbe,Haarmann&ReimerGmbH, Jersey,UnitedStates,Petroleum,Introduction Holzminden,Germany,Hydrocarbons WaltherW.Irion,DeutscheShellAG, BruceC.Gates,UniversityofCalifornia, Hamburg,Germany,OilRefining, Davis,Davis,California,UnitedStates, EnvironmentalConsiderations Catalysis MichaelKavanaugh,MalcolmPirnie,Inc., EugenGehrer,BASFAktiengesellschaft, Emeryville,California,UnitedStates,Methyl Ludwigshafen,Germany,Acylationand Tert-ButylEther Alkylation RolandKettner,MobilErdgas–Erdo¨lGmbH, Heinz-PeterGelbke,BASFAktiengesellschaft, Celle,Germany,NaturalGas Ludwigshafen,Germany,Ethylbenzene JeffreyP.Knapp,E.I.duPontdeNemours UlrichGraeser,VebaO¨lAG,Gelsenkirchen, &Company,Wilmington,Delaware,United Germany,Xylenes States,Distillation,AzeotropicandExtractive HelmutGreim,Institutfu¨rToxikologieund ChristianKu¨chen,Institutfu¨rWirtschaftliche Umwelthygiene,TechnischeUniversita¨t Oelheizung,Hamburg,Germany,HeatingOil Mu¨nchen,Freising-Weihenstephan,Germany, G.R.Lappin,AlbemarleCorporation,Baton NaphthaleneandHydronaphthalenes Rouge,Louisiana,UnitedStates,Olefins, KarlGriesbaum,Universita¨tKarlsruhe(TH), Higher Karlsruhe,Germany,Hydrocarbons MarylineLaugier,MalcolmPirnie,Inc., BaruchGrinbaum,IMI(TAMI)Institutefor Emeryville,California,UnitedStates,Methyl ResearchandDevelopment,DSBG,HaifaBay, Tert-ButylEther Israel,DrillingFluids GeorgeM.Long,InstituteofGasTechnology, GeorgHammer,MobilErdgas–Erdo¨lGmbH, Chicago,Illinois,UnitedStates,Pipelines Celle,Germany,NaturalGas EckhardLoser,BayerAG,Wuppertal, ScottHan,MobilResearchandDevelopment Germany,Isoprene Corporation,Princeton,NewJersey,United TorstenLu¨bcke,MobilErdgas–Erdo¨lGmbH, States,Fuels,Synthetic,Liquid Celle,Germany,NaturalGas R.H.Harding,W.R.Grace&Company, DieterMayer,HoechstAktiengesellschaft, Columbia,Maryland,UnitedStates,Fluid Frankfurt,Germany,Acetylene;Hydrocarbons CatalyticCracking,CatalystsandAdditives HelmutMeinass,LindeAG,Ho¨llriegelskreuth, B.W.Hedrick,UOPLLC,DesPlaines,Illinois, Germany,Acetylene UnitedStates,FluidCatalyticCracking,Units, GeorgMichalczyk,DEAMineralo¨lAG, Regeneration Hamburg,Germany,Waxes WernerHefner,BASFAktiengesellschaft, JohnJ.Mooney,EnvironmentalandEnergy Ludwigshafen,Germany,Acetylene TechnologyandPolicyInstitute,Wyckoff, Franz-LeoHeinrichs,Hoechst NewJersey,UnitedStates,EmissionControl, Aktiengesellschaft,WerkGersthofen, Automotive Augsburg,Germany,Waxes PatrickMoran,U.S.NavalAcademy, RobertN.Heistand,Consultant,Englewood, Annapolis,Maryland,UnitedStates, Colorado,UnitedStates,OilShale CorrosionandCorrosionControl C.L.Hemler,UOPLLC,DesPlaines,Illinois, SanfordL.Moskowitz,AmericanEconomics UnitedStates,FluidCatalyticCracking,Units, GroupandChemicalHeritageFoundation, Regeneration Abington,Pennsylvania,UnitedStates, AlbertM.Hochhauser,ExxonMobilResearch SyntheticOrganicChemicals,Economic andEngineeringCompany,Paulsboro,New Evaluation Jersey,UnitedStates,GasolineandOther EckartMu¨ller,FrankfurtamMain,Germany, MotorFuels Liquid–LiquidExtraction Vol. 1 CONTRIBUTORS xi RichardMu¨ller,Degussa-Hu¨lsAG,Marl, W.J.Reagan,UOPLLC,DesPlaines, Germany,Acetylene Illinois,UnitedStates,FluidCatalytic ThomasNarbeshuber,BASF Cracking,Units,Regeneration Aktiengesellschaft,Ludwigshafen,Germany, HertaRecknagel,RuhrgasAG,Essen, AcylationandAlkylation Germany,NaturalGas PaulNatishan,NavalResearchLaboratory, ArnoReglitzky,DeutscheShellAG,Hamburg, Washington,DC,UnitedStates, Germany,OctaneEnhancers CorrosionandCorrosionControl J.R.Riley,W.R.Grace&Company, J.R.D.Nee,W.R.Grace&Company, Columbia,Maryland,UnitedStates, Columbia,Maryland,UnitedStates,Fluid FluidCatalyticCracking,Catalystsand CatalyticCracking,CatalystsandAdditives Additives L.H.Nemec,AlbemarleCorporation,Baton HeinrichRischmu¨ller,TechnischeUniversita¨t Rouge,Louisiana,UnitedStates,Olefins, Clausthal,Clausthal-Zellerfeld,Germany, Higher Exploration,Drilling,andProduction Hans-JoachimNeumann,GermanPetroleum Engineering Institute,Clausthal-Zellerfeld,Germany, WinstonK.Robbins,ExxonResearchand NaturalGas EngineeringCompany,Annandale,New OttoS.Neuwirth,UKWesseling,Wesseling, Jersey,UnitedStates,Petroleum, Germany,OilRefining,Environmental Introduction Considerations MichaelRo¨per,BASFAktiengesellschaft, FranzNierlich,OxenoOlefinchemieGmbH, Ludwigshafen,Germany,Acylationand Marl,Germany,MethylTert-ButylEther Alkylation E.DicksonOzokwelu,AmocoChemical F.S.Rosser,UOPLLC,DesPlaines,Illinois, Company,Naperville,Illinois,UnitedStates, UnitedStates,FluidCatalyticCracking,Units, Toluene Regeneration BarbaraPaczynska-Lahme,Consultant, MichaelSakuth,Hu¨lsInfracorGmbH,Marl, Osterode,Germany,NaturalGas Germany,MethylTert-ButylEther ChristianPaetz,BayerAG,Leverkusen, J.D.Sauer,AlbemarleCorporation,Baton Germany,Hydrocarbons Rouge,Louisiana,UnitedStates,Olefins, P.Palmas,UOPLLC,DesPlaines,Illinois, Higher UnitedStates,FluidCatalyticCracking,Units, AlanW.Scaroni,PennsylvaniaState Regeneration University,UniversityPark,Pennsylvania, PeterPa¨ssler,BASFAktiengesellschaft, UnitedStates,CombustionScienceand Ludwigshafen,Germany,Acetylene Technology WolfgangPayer,HoechstAktiengesellschaft, KunoScha¨dlich,VEBAOELAG, WerkRuhrchemie,Oberhausen,Germany, Gelsenkirchen,Germany,OctaneEnhancers Waxes HansSchmidt,HoechstAktiengesellschaft, UdoPeters,OxenoOlefinchemieGmbH,Marl, WerkGersthofen,Augsburg,Germany, Germany,MethylTert-ButylEther Waxes MarkR.Pillarella,AirProductsand PeterSchug,VEBAOELAG,Gelsenkirchen, Chemicals,Inc.,Allentown,Pennsylvania, Germany,OctaneEnhancers UnitedStates,NaturalGas EkkehardSchulte-Ko¨rne,OxenoOlefinchemie EdwinM.Piper,PiperDesignsLLC,Littleton, GmbH,Marl,Germany,MethylTert-Butyl Colorado,UnitedStates,OilShale Ether SarmaV.Pisupati,PennsylvaniaState RezaSharifi,PennsylvaniaStateUniversity, University,UniversityPark,Pennsylvania, UniversityPark,Pennsylvania,UnitedStates, UnitedStates,CombustionScienceand CombustionScienceandTechnology Technology WolfgangSiegel,BASFAktiengesellschaft, HeinrichPredel,MiROGmbH&Company Ludwigshafen,Germany,Acylationand KG,Karlsruhe,Germany,PetroleumCoke Alkylation RogerC.Prince,ExxonResearchand JeffreyJ.Siirola,EastmanChemical EngineeringCompany,Annandale, Company,Kingsport,Tennessee,United NewJersey,UnitedStates,Bioremediation States,SeparationsProcessSynthesis Gu¨nterPusch,TechnischeUniversita¨t ThomasA.Simo,LurgiO¨lGasChemieGmbH, Clausthal,Clausthal-Zellerfeld,Germany, Frankfurt,Germany,Xylenes Exploration,Drilling,andProduction DomienSluyts,BayerAG,Antwerpen, Engineering Belgium,Liquid–LiquidExtraction xii CONTRIBUTORS Vol. 1 JamesG.Speight,Consultant,Laramie, KlausWeggen,Hemmingen,Germany, Wyoming,UnitedStates,Asphalt;Fuels, Exploration,Drilling,andProduction Synthetic,Gaseous;PetroleumRefinery Engineering Processes;TarSands HansMartinWeitz,BASFAktiengesellschaft, KnutSpitzmu¨ller,Hamburg,Germany, Ludwigshafen,Germany,Isoprene HeatingOil VincentA.Welch,WashingtonGroup H.N.Sun,ExxonChemicalCompany,Baytown, International,Inc.,Cambridge, Texas,UnitedStates,Butadiene Massachusetts,UnitedStates,Ethylbenzene MarttiSuominen,FortumOilandGasOy, Hans-Ju¨rgenWernicke,LindeAG, Finland,MethylTert-ButylEther Ho¨llriegelskreuth,Germany,Acetylene W.A.Sweeney,ChevronResearchand PeterJ.Wessner,MerichemCompany, TechnologyCompany,Richmond,California, Houston,Texas,UnitedStates, UnitedStates,BTXProcessing NaphthenicAcids Jo¨rgTalbiersky,Dorsten,Germany, ThomasP.Whaley,Consultant,SunCity, Anthracene Arizona,UnitedStates,Pipelines R.RayTaylor,PhillipsPetroleumCompany, JosefWildgruber,HoechstAktiengesellschaft, Bartlesville,Oklahoma,UnitedStates, WerkGersthofen,Augsburg,Germany,Waxes LiquefiedPetroleumGas UweWolfmeier,HoechstAktiengesellschaft, ShmuelD.Ukeles,IMI(TAMI)Institutefor WerkGersthofen,Augsburg,Germany, ResearchandDevelopment,DSBG,HaifaBay, Waxes Israel,DrillingFluids J.P.Wristers,ExxonChemicalCompany, L.L.Upson,UOPLLC,DesPlaines,Illinois, Baytown,Texas,UnitedStates,Butadiene UnitedStates,FluidCatalyticCracking,Units, G.Yaluris,W.R.Grace&Company, Regeneration Columbia,Maryland,UnitedStates, Heinz-WernerVoges,Hu¨lsAktiengesellschaft, FluidCatalyticCracking,Catalysts Marl,Germany,Hydrocarbons andAdditives J.D.Wagner,AlbemarleCorporation,Baton X.Zhao,W.R.Grace&Company,Columbia, Rouge,Louisiana,UnitedStates,Olefins, Maryland,UnitedStates,FluidCatalytic Higher Cracking,CatalystsandAdditives RolandWalzl,LindeAG,Hoellriegelskreuth, HeinzZimmermann,LindeAG, Germany,Ethylene Hoellriegelskreuth,Germany,Ethylene PREFACE Wiley’s major reference works cover a multitude of subject disciplines and have earned many accolades over the years for their well-structured, accessible arti- cles, covering both fundamentals and cutting-edge topics. The Wiley Critical Content Series was conceived in response to demand from customers who have a strong interest in certain key topics covered within more than one of Wiley’s reference works and who have asked to see the most relevant articles brought together in one place. Wiley Critical Content: Petroleum Technology is the first title to be published in this series. It features articles from two of Wiley’s most prestigious encyclopedias—the Kirk-Othmer Encyclopedia of Chemical Technology and Ullmann’s Encyclopedia of Industrial Chemistry. Wiley Critical Content: Petroleum Technology provides comprehensive, up- to-date information on all aspects of petroleum: properties and origin, explora- tion, production and refining processes, economic issues, and environmental and health concerns. The two volumes contain over fifty articles, organized thematically: - Part I: Exploration, Production, and Refining - Part II: Refined Products and Fuels - Part III: Petrochemicals Written by prominent scholars from around the world, this reliable reference will be of particular interest to petroleum engineers, researchers in industry and academia, and other professionals and consultants in petroleum-related industries. vii CONTENTS VOLUME 1 PART I: EXPLORATION, PRODUCTION, AND REFINING Petroleum, Introduction 1 Catalysis 499 Exploration,Drilling, Catalyst Deactivation andProduction Engineering 43 andRegeneration 553 Enhanced OilRecovery 167 Distillation 621 OilShale 194 Distillation, Azeotropic TarSands 222 andExtractive 667 DrillingFluids 250 Separations Process PetroleumRefinery Synthesis 734 Processes 291 Liquid–Liquid Extraction 776 OilRefining,Environmental Considerations 334 Pipelines 851 NaturalGas 355 Sulfur andHydrogen Sulfide BTX Processing 427 Recovery 872 FluidCatalytic Cracking, Corrosion andCorrosion Units, Regeneration 442 Control 896 FluidCatalytic Cracking, Catalysts andAdditives 477 Bioremediation 920 v CONTENTS VOLUME 2 PART II: REFINED PRODUCTS AND FUELS LiquefiedPetroleum Gas 1 Fuels,Synthetic, Liquid 329 Lubrication andLubricants 14 Fuels,Synthetic, Gaseous 377 Waxes 85 OctaneEnhancers 406 Asphalt 169 MethylTert-Butyl Ether 428 PetroleumCoke 205 Gasolineand OtherMotorFuels 223 Combustion Science andTechnology 449 Aviation Turbine Fuels 273 Emission Control,Automotive 493 HeatingOil 293 Naphthenic Acids 317 Emission Control,Industrial 529 PART III: PETROCHEMICALS PetrochemicalFeedstocks 576 Ethylbenzene 974 Hydrocarbons 591 Cyclopentadiene and Dicyclopentadiene 991 Acetylene 652 Naphthaleneand Ethylene 727 Hydronaphthalenes 1007 Propylene 799 Anthracene 1020 Butadiene 820 Olefins,Higher 1028 Isoprene 849 Acylationand Cyclohexane 876 Alkylation 1047 Benzene 885 SyntheticOrganic Chemicals, Toluene 914 Economic Evaluation 1114 Xylenes 944 Index 1141 vi
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