SYNTHETIC LUBRICANTS, SUPP. A - IHS Markit

Synthetic Lubricants, Supp. A, September 1989ssECONOMICSPROGRAMSRI lNTERNATlONALMenlo Park, California94025AbstractProcess EconomicsSYNTHETICProgram Report No. 125ALUBRICANT(SeptemberBASE STOCKS1989)This report is an update of PEP Report 125, SyntheticLubricantsfirst report on the subject, this report evaluates the commercial(May 1979). As in thatprocesses for producing thefollowing synthetic lubricant base stocks:lPolyalphaolefinslNeopolyol esters (technical pentaerythritollDibasic acid esters (diisodecyl adipate).(1 -deceneOligomers)esters)The particular base stocks used in our analyses are shown in parenthesis.ing the capital and production cost estimates for these processes,In addition to updat-this report summarizesrelevant patents issued since the publication of PEP Report 125, and presents information onthe industry status of these and other synthetic lubricant base stocks.PEP’87REB

Synthetic Lubricants, Supp. A, September 1989Report No. 125ASYNTHETIC LUBRICANTBASE STOCKSSUPPLEMENT Aby ROBERT E. BOLANwith contributions byKIRTLAND E. McCALEBSeptember 1989A private report by thePROCESS ECONOMICS PROGRAMMenlo Park, California 94025

Synthetic Lubricants, Supp. A, September 1989For detailed marketing data and information,programsthe reader is referred to one of the SRIspecializingin marketingresearch.The CHEMlCALECONOMICS HANDBOOKProgram covers most major chemicals and chemical products produced in the UnitedStates and the WORLD PETROCHEMICALStheir derivativesPRODUCERSProgram covers major hydrocarbonsandon a worldwidebasis. In addition,the SRI DIRECTORYOF CHEMICALservicesprovidedetailedlists of chemicalproduct, and plant for the United States and Western Europeproducersby company,

Synthetic Lubricants, Supp. A, September 1989CONTENTSLIST OF ILLUSTRATIONSLIST OF TABLES.1INTRODUCTION2SUMMARYl-l.2-lGENERAL ASPECTS.2-lPOLYALPHAOLEFINS.2-l.2-3DIBASIC ACID ESTERS L ESTERS4ix.NEOPOLYOL ESTERS3vii.i.3-7DIBASIC ACID ESTERS .3-10POLYALPHAOLEFINS4-lCHEMISTRY.4-lLOW VERSUS HIGH VISCOSITY PAOs .4-8REVIEW OF PATENTS .4-12REACTlON VARlABLES4-18.BFs RECOVERY METHODS .4-19PROCESS DESCRIPTION .4-20OligomerizationRecovery.Hydrogenationand Purification.PROCESS DISCUSSION .4-204-224-234-29Choice of Design Basis .4-29Oiigomerization4-30Reaction Conditions .Catalyst Removal and TreatmentMaterials of ConstructionCOST ESTIMATES.Capital investmentProduction Costs.- III -4-314-324-324-324-33

Synthetic Lubricants, Supp. A, September 1989CONTENTS5NEOPOLYOLCHEMISTRYESTERS.EFFECT OF ESTER COMPOSITIONREVIEW OF PATENTSPROCESSON PHYSICAL PROPERTIES tion .5-11PROCESS DISCUSSION .5-l 6Choice of Design Basis .Esterification ConsiderationsOther ConsiderationsWaste Streams.Materials of Construction.COST ESTIMATES.Capital InvestmentProduction Costs.DIBASIC ACID ESTERSCHEMISTRY.Purification 05-216-l6-lEFFECT OF ESTER COMPOSITION ON PHYSICAL PROPERTIES. .6-3REVIEW OF PATENTS .6-4PROCESS DESCRlPTlON .6-5Esterification.6-5Purification .6-7PROCESS DISCUSSION .6-12Choice of Design Basis .Esterification ConsiderationsPurification ConsiderationsOther ConsiderationsWaste Streams.Materials of Construction.- iv -6-126-126-136-136-146-15

Synthetic Lubricants, Supp. A, September 1989CONTENTS6DIBASIC ACID ESTERS (Concluded)COST ESTIMATES.6-15.Capital InvestmentProduction Costs6-15.6-16.TABLESAppendixA: PATENT SUMMARYAppendixB: DESIGN AND COST BASES .DESIGN CONDITIONSProduction Costs.B-3.B-4Appendix C: PROPERTIES OF RAW MATERIALS ANDSYNTHETIC LUBRICANT BASE STOCKS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .D: HANDLINGHANDLINGB-5C-lD-lD-4.D-4Linear Alpha Olefin Oligomer Production .D-4Neopolyol Ester Production .D-4Dibasic Acid Ester ProductionSAFETY.AND SAFETY INFORMATION.MATERIALS OF CONSTRUCTIONB-lB-3Effect of Operating Level on Production Costs .AppendlxA-lB-3COST BASES .Capital Investment6-l.D-4D-5.LINEAR ALPHA OLEFIN OLIGOMER PRODUCTION.D-5Linear Alpha Olefins .D-5Boron Trifluoride (BF3)D-5.Linear Alpha Olefin Oligomer Lubricant Base Stock .NEOPOLYOL ESTER PRODUCTION .Neopolyols.Short-ChainFatty AcidsNeopolyol Ester Lubricant Base Stock .0x0 Alcohols.-v-D-6D-6D-6D-6.D-7Adipic Acid .Dibasic Acid Ester Lubricant Base StockD-5D-5.DIBASIC ACID ESTER PRODUCTIOND-5.D-7

Synthetic Lubricants, Supp. A, September 1989CONTENTSAppendlxE: EQUIPMENTSUPPLIERSAppendlxF: CITED REFERENCES .E-lF-lAppendix G: PATENT REFERENCESBY COMPANY.G-lAppendixH-lH: PROCESS FLOW DIAGRAMS.- vi -

Synthetic Lubricants, Supp. A, September 1989ILLUSTRATIONS4.1EFFECT OF REACTION TIME ON 1-DECENEOLIGOMER PRODUCT DISTRIBUTION . . . . . . . . . . . . . . . . . . . . . . . .a.4-34.2POSSIBLE STRUCTURAL FORMULAS OF 1-DECENE OLIGOMERS . . . . . . . .4-44.3GENERAL CATIONIC POLYMERIZATION REACTION MECHANISM4-74.4VISCOSITY OF 1-DECENE OLIGOMERS AT 40 C4.5PRODUCT DlSTRlBUTlON FROM THE OLIGOMERIZATIONOF l-DECENE4.64-l 84.7PRODUCTION OF POLYALPHAOLEFINS FROM I-DECENEH-34.8PRODUCTION OF POLYALPHAOLEFINS FROM I-DECENEEFFECT OF PLANT CAPACITY ON INVESTMENT COST . . . . . . , . . . . , . . . .4-37PRODUCTION OF POLYALPHAOLEFINS FROM I-DECENEEFFECT OF OPERATING LEVEL ANDPLANT CAPACITY ON PRODUCT VALUE . . . . . . . . . . . . . . . . . . . . . . . . . . . .4-40PRODUCTION OF POLYALPHAOLEFINS FROM l-DECENEEFFECT OF I-DECENE PRICE ON PRODUCT VALUE . . . . . . . . . . . . . . , . . .4-415.1THERMAL DECOMPOSITION OF ESTERS . . .I.,.5-45.2EFFECT OF MOLECULAR WEIGHT ONNEOPOLYOL ESTER VISCOSITY . . . . . . . . . .I.5-6EFFECT OF BRANCHING ONVISCOSITY OF PENTAERYTHRITOL ESTERS . . . . . . . . . . . . . . . . . . . . . . . . . .5-7PRODUCTION OF NEOPCLYOL ESTERS FROM TECHNICALPENTAERYTHRITOL AND Cs TO Cg MIXED n-FATTY ACIDSH-55.35.45.5I.4-104-184.10lCONVERSION). o. . . . . , . . . . , . . . , , . . .PRODUCT DISTRIBUTION FROM THE OLIGOMERIZATIONOF l-DECENE (83.5% CONVERSION) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .4.9l(57.5%.5.6.PRODUCTION OF NEOPOLYOL ESTERS FROMTECHNICAL PENTAERYTHRITOL AND C5 TO Cg MIXED n-FATTY ACIDSEFFECT OF PLANT CAPACITY ON INVESTMENT COST . , . . . . , . . , , . . , . .5-23PRODUCTION OF NEOPOLYOL ESTERS FROMTECHNICAL PENTAERYTHRITOL AND C5 TO Cg MIXED n-FAllYACIDSEFFECT OF OPERATING LEVELAND PLANT CAPACITY ON PRODUCT VALUE . . . . . . . . . . . . . . . . . . . . . . . .5-26- vii -

Synthetic Lubricants, Supp. A, September 1989ILLUSTRATIONS6.16.2PRODUCTION OF DIISODECYL ADIPATE (DIBASIC ACID ESTER)FROM ADlPlC ACID AND ISODECYL ALCOHOL . . . . , . . . . . . . . . . . . . . . . . .H-7PRODUCTION OF DIISODECYL ADIPATE (DIBASIC ACID ESTER)FROM ADlPlC ACID AND ISODECYL ALCOHOLEFFECT OF PLANT CAPACITY ON INVESTMENT COST . . . . . . . . , . . . . . . a 6-186.3PRODUCTION OF DIISODECYL ADIPATE (DIBASIC ACID ESTER)FROM ADlPlC ACID AND ISODECYL ALCOHOLEFFECT OF OPERATING LEVEL ANDPLANT CAPACITY ON PRODUCT VALUE-.VIII -. .*.,.,.6-21

Synthetic Lubricants, Supp. A, September 1989TABLES2.1PERFORMANCE PROPERTIES OF SYNLUBES BY CLASS .2-23.1CLASSIFICATION3-l3.2PERFORMANCE PROPERTIES OF SYNLUBES BY CLASS .3-33.3U.S. CONSUMPTION OF SYNLUBE BASE STOCKS, 1987 .3-43.4OF SYNTHETIC BASE FLUIDSPRODUCERS OF POLYALPHAOLEFIN BASE STOCKSAND THEIR 1989 PRODUCTION CAPACITIES3-53-8PRODUCERS OF DIBASIC ACID ESTER BASE STOCKSAND THEIR PRODUCTION CAPACITIES, 1988 .3-124.1PRINCIPAL POLYALPHAOLEFIN VISCOSITY GRADES .4-94.2TYPICAL VISCOSITY REQUIREMENTS FORSELECTED MULTIGRADE OILS .4-12OLEFIN OLIGOMERSPATENT SUMMARY .A-3PRODUCTION OF POLYALPHAOLEFINS FROM 1-DECENEDESIGN BASES AND ASSUMPTIONS .4-24PRODUCTION OF POLYALPHAOLEFINS FROM 1-DECENEMAJOR EQUIPMENT .4-25PRODUCTION OF POLYALPHAOLEFINS FROM 1-DECENESTREAM FLOWS .4-27PRODUCTION OF POLYALPHAOLEFINS FROM 1-DECENETOTAL CAPITAL INVESTMENT .4-353.64.34.44.54.64.7-.PRODUCERS OF NEOPOLYOL ESTER BASE STOCKSAND THEIR PRODUCTION CAPACITIES, 1987 .3.5-.4.84.95.105.2PRODUCTION OF POLYALPHAOLEFINS FROM 1-DECENECAPITAL INVESTMENT BY SECTION .4-36PRODUCTION OF PCLYALPHAOLEFINS FROM 1-DECENEPRODUCTION COSTS .4-38NEOPOLYOL ESTERSPATENT SUMMARY .A-15PRODUCTION OF NEOPOLYOL ESTERS FROMTECHNICAL PENTAERYTHRITOL AND Cs TO Cg MIXED n-FATTY ACIDSDESIGN BASES AND ASSUMPTIONS .- ix -5-13

Synthetic Lubricants, Supp. A, September 1989TABLES5.35.4PRODUCTION OF NEOPOLYOL ESTERS FROMTECHNICAL PENTAERYTHRITOL AND C5 TO Cg n-FATTY ACIDSMAJOR EQUIPMENT . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .PRODUCTION OF NEOPOLYOL ESTERS FROMTECHNICAL PENTAERYTHRITOLAND C5 TO CQ n-FATTY ACIDSSTREAM FLOWS . . . . . . . . . . . . . . . . .I.5.55-145-l 5PRODUCTIONOF NEOPOLYOL ESTERS FROMTECHNICAL PENTAERYTHRITOL AND C5 TO Cg MIXED n-FATTY ACIDSTOTAL CAPITAL INVESTMENT *.,.,.,.,.5.66.16.26.36.46.56.85-22PRODUCTION OF NEOPOLYOL ESTERS FROMTECHNICAL PENTAERYTHRITOL AND C5 TO Cg MIXED n-FATTY ACIDSPRODUCTIONCOSTS . . . . . . . .*.*.5-24DIBASIC ACID ESTERSPATENT SUMMARY . . .,,.,*.,.**.*.,,.A-18PRODUCTION OF DIISODECYL ADIPATE FROMADIPIC ACID AND ISODECYL ALCOHOLDESIGN BASES AND ASSUMPTIONS . . . . . . . . . . .**.6-9PRODUCTION OF DIISODECYL ADIPATE FROMADIPIC ACID AND ISODECYL ALCOHOLMAJOR EQUIPMENT . . . . . . . . . . . . . . . . . . . . . . . .#.6-10PRODUCTION OF DIISODECYL ADIPATE FROMADIPIC ACID AND ISODECYL ALCOHOLSTREAM FLOWS . . . . . . . . . . . . . . .*.**.6-11PRODUCTION OF DIISODECYL ADIPATE FROMADIPIC ACID AND ISODECYL ALCOHOLTOTAL CAPITAL INVESTMENT ,.,,.a.6-l 7PRODUCTION OF DIISODECYL ADIPATE FROMADIPIC ACID AND ISODECYL ALCOHOLPRODUCTION COSTS . . . . .*.*.,.*.8.7ESTIMATED PRODUCTION COSTS FOR OTHER DIESTERS . . . . . . . . . . . . . .C.1PROPERTIES OF DECENE-1C.2PROPERTIES OF POLYALPHAOLEFINSYNTHETIC LUBRICANT BASE STOCKS . . . . . . .a. . . . . . . . . . .*.**.*.-x-6-196-22c-3c-4

Synthetic Lubricants, Supp. A, September 1989TABLESC.3PROPERTIES OF NEOPOLYOLS . . . . . . . . . . . . . . . . . . . . .*.c-5C.4PROPERTIES OF TECHNICAL PENTAERYTHRITOL,.,.,,,.,.,.C-6C.5PROPERTIES OF SHORT-CHAIN.,.,,.,.,.,.,C-7C.6FATTY ACIDSPROPERTIES OF PENTAERYTHRITOL FAITY ACID ESTERSYNTHETIC LUBRICANT BASE . . . . . . . . . . . . .*.m.*.C-8C.7PROPERTIES OF STRAIGHT CHAIN DIBASIC ACIDS . . . . . . . . . . . . . . . . . , . .C-9C.8PROPERTIES OF OX0 ALCOHOLSc-10C.9PROPERTIES OF DIBASIC ACID ESTER SYNTHETIC BASE STOCKS . . . . . . . . . . . . . . . . . . . . . . .a.- xi -C-10

SYNTHETIC LUBRICANT BASE STOCKS (September 1989) Menlo Park, California 94025 This report is an update of PEP Report 125, Synthetic Lubricants (May 1979). As in that first report on the subject, this report evaluates the commercial processes for producing the following synthetic lubricant base stocks: