SYNTHETIC LUBRICANTS, SUPP. A - ihsmarkit.com · SYNTHETIC LUBRICANT BASE STOCKS (September 1989) Menlo Park, California 94025 This report is an update of PEP Report 125, Synthetic

ss ECONOMICS

PROGRAM SRI lNTERNATlONAL

Abstract

Process Economics Program Report No. 125A

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:

l Polyalphaolefins (1 -decene Oligomers)

l Neopolyol esters (technical pentaerythritol esters)

l Dibasic acid esters (diisodecyl adipate).

The particular base stocks used in our analyses are shown in parenthesis. In addition to updat-

ing the capital and production cost estimates for these processes, this report summarizes

relevant patents issued since the publication of PEP Report 125, and presents information on

the industry status of these and other synthetic lubricant base stocks.

PEP’87 REB

Report No. 125A

SYNTHETIC LUBRICANT BASE STOCKS

SUPPLEMENT A

by ROBERT E. BOLAN

with contributions by

KIRTLAND E. McCALEB

September 1989

A private report by the

PROCESS ECONOMICS PROGRAM

Menlo Park, California 94025

For detailed marketing data and information, the reader is referred to one of the SRI

programs specializing in marketing research. The CHEMlCAL ECONOMICS HANDBOOK Program covers most major chemicals and chemical products produced in the United

States and the WORLD PETROCHEMICALS Program covers major hydrocarbons and

their derivatives on a worldwide basis. In addition, the SRI DIRECTORY OF CHEMICAL PRODUCERS services provide detailed lists of chemical producers by company,

product, and plant for the United States and Western Europe

CONTENTS

LIST OF ILLUSTRATIONS ............................................... vii

LIST OF TABLES ...................................................... ix

1 INTRODUCTION .................................................... l-l

2 SUMMARY ......................................................... 2-l

GENERAL ASPECTS ................................................. 2-l

POLYALPHAOLEFINS ................................................. 2-l

NEOPOLYOL ESTERS ................................................ 2-3

DIBASIC ACID ESTERS ............................................... 2-3

3 INDUSTRY STATUS ................................................. 3-l

POLYALPHAOLEFINS ................................................. 3-4

NEOPOLYOL ESTERS ............................ ..i. ................ 3-7

DIBASIC ACID ESTERS ............................................... 3-10

4 POLYALPHAOLEFINS ................................................ 4-l

CHEMISTRY ........................................................ 4-l

LOW VERSUS HIGH VISCOSITY PAOs ................................... 4-8

REVIEW OF PATENTS ................................................ 4-12

REACTlON VARlABLES ............................................... 4-18

BFs RECOVERY METHODS ............................................ 4-19

PROCESS DESCRIPTION .............................................. 4-20

Oligomerization .................................................. 4-20

Recovery ....................................................... 4-22

Hydrogenation and Purification ..................................... 4-23

PROCESS DISCUSSION ............................................... 4-29

Choice of Design Basis ........................................... 4-29

Oiigomerization Reaction Conditions ................................. 4-30

Catalyst Removal and Treatment ................................... 4-31

Materials of Construction ........................................... 4-32

COST ESTIMATES ................................................... 4-32

Capital investment ............................................... 4-32

Production Costs ................................................ 4-33

... - III -

CONTENTS

5 NEOPOLYOL ESTERS ...............................................

CHEMISTRY ........................................................

EFFECT OF ESTER COMPOSITION ON PHYSICAL PROPERTIES ...............

REVIEW OF PATENTS ................................................

PROCESS DESCRIPTION ..............................................

Esterification ....................................................

Purification ......................................................

PROCESS DISCUSSION ...............................................

Choice of Design Basis ...........................................

Esterification Considerations .......................................

Purification Considerations .........................................

Other Considerations .............................................

Waste Streams ..................................................

Materials of Construction ..........................................

COST ESTIMATES ...................................................

Capital Investment ...............................................

Production Costs ................................................

8 DIBASIC ACID ESTERS .............................................. 6-l

CHEMISTRY ........................................................ 6-l

EFFECT OF ESTER COMPOSITION ON PHYSICAL PROPERTIES. .............. 6-3

REVIEW OF PATENTS ................................................ 6-4

PROCESS DESCRlPTlON .............................................. 6-5

Esterification .................................................... 6-5

Purification ...................................................... 6-7

PROCESS DISCUSSION ............................................... 6-12

Choice of Design Basis ........................................... 6-12

Esterification Considerations ....................................... 6-12

Purification Considerations ......................................... 6-13

Other Considerations ............................................. 6-13

Waste Streams .................................................. 6-14

Materials of Construction .......................................... 6-15

5-l

5-l

5-3

5-a

5-9

5-9

5-11

5-l 6

5-16

5-16

5-16

5-18

5-19

5-20

5-20

5-20

5-21

- iv -

CONTENTS

6 DIBASIC ACID ESTERS (Concluded) ................................... 6-l

COST ESTIMATES ................................................... 6-15

Capital Investment ............................................... 6-15

Production Costs ................................................ 6-16

Appendix A: PATENT SUMMARY TABLES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . A-l

Appendix B: DESIGN AND COST BASES ................................... B-l

DESIGN CONDITIONS ................................................ B-3

COST BASES ....................................................... B-3

Capital Investment ............................................... B-3

Production Costs ................................................ B-4

Effect of Operating Level on Production Costs ........................ B-5

Appendix C: PROPERTIES OF RAW MATERIALS AND

SYNTHETIC LUBRICANT BASE STOCKS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . C-l

Appendlx D: HANDLING AND SAFETY INFORMATION. ....................... D-l

HANDLING ......................................................... D-4

MATERIALS OF CONSTRUCTION .................................... D-4

Linear Alpha Olefin Oligomer Production .......................... D-4

Neopolyol Ester Production ..................................... D-4

Dibasic Acid Ester Production .................................. D-4

SAFETY ........................................................... D-5

LINEAR ALPHA OLEFIN OLIGOMER PRODUCTION ...................... D-5

Linear Alpha Olefins ........................................... D-5

Boron Trifluoride (BF3) ........................................ D-5

Linear Alpha Olefin Oligomer Lubricant Base Stock ................. D-5

NEOPOLYOL ESTER PRODUCTION ................................... D-5

Neopolyols .................................................. D-5

Short-Chain Fatty Acids ....................................... D-6

Neopolyol Ester Lubricant Base Stock ............................ D-6

DIBASIC ACID ESTER PRODUCTION ................................. D-6

0x0 Alcohols ................................................ D-6

Adipic Acid .................................................. D-7

Dibasic Acid Ester Lubricant Base Stock ......................... D-7

-v-

CONTENTS

Appendlx E: EQUIPMENT SUPPLIERS ..................................... E-l

Appendlx F: CITED REFERENCES ......................................... F-l

Appendix G: PATENT REFERENCES BY COMPANY .......................... G-l

Appendix H: PROCESS FLOW DIAGRAMS ................................. H-l

- vi -

ILLUSTRATIONS

4.1 EFFECT OF REACTION TIME ON 1-DECENE

OLIGOMER PRODUCT DISTRIBUTION . . . . . . . . . . . . . . . . . . . . . . . ..a...... 4-3

4.2 POSSIBLE STRUCTURAL FORMULAS OF 1-DECENE OLIGOMERS . . . . . . . . 4-4

4.3 GENERAL CATIONIC POLYMERIZATION REACTION MECHANISM . . . . . . . . . 4-7

4.4 VISCOSITY OF 1-DECENE OLIGOMERS AT 40°C . o . . . . . , . . . . , . . . , , . . . 4-10

4.5 PRODUCT DlSTRlBUTlON FROM THE OLIGOMERIZATION

OF l-DECENE (57.5% CONVERSION) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4-l 8

4.6 PRODUCT DISTRIBUTION FROM THE OLIGOMERIZATION

OF l-DECENE (83.5% CONVERSION) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4-18

4.7 PRODUCTION OF POLYALPHAOLEFINS FROM I-DECENE . . . . . . . . . . . . . . H-3

4.8 PRODUCTION OF POLYALPHAOLEFINS FROM I-DECENE EFFECT OF PLANT CAPACITY ON INVESTMENT COST . . . . . . , . . . . , . . . . 4-37

4.9 PRODUCTION OF POLYALPHAOLEFINS FROM I-DECENE EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4-40

4.10 PRODUCTION OF POLYALPHAOLEFINS FROM l-DECENE EFFECT OF I-DECENE PRICE ON PRODUCT VALUE . . . . . . . . . . . . . . , . . . 4-41

5.1 THERMAL DECOMPOSITION OF ESTERS . . ..I................,...... 5-4

5.2 EFFECT OF MOLECULAR WEIGHT ON

NEOPOLYOL ESTER VISCOSITY . . . . . . . . . ..I....................... 5-6

5.3 EFFECT OF BRANCHING ON VISCOSITY OF PENTAERYTHRITOL ESTERS . . . . . . . . . . . . . . . . . . . . . . . . . . 5-7

l 5.4 PRODUCTION OF NEOPCLYOL ESTERS FROM TECHNICAL PENTAERYTHRITOL AND Cs TO Cg MIXED n-FATTY ACIDS . . . . . . . . . . . . H-5

5.5 PRODUCTION OF NEOPOLYOL ESTERS FROM

TECHNICAL PENTAERYTHRITOL AND C5 TO Cg MIXED n-FATTY ACIDS

l EFFECT OF PLANT CAPACITY ON INVESTMENT COST . , . . . . , . . , , . . , . . 5-23


TECHNICAL PENTAERYTHRITOL AND C5 TO Cg MIXED n-FAllY ACIDS

EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE . . . . . . . . . . . . . . . . . . . . . . . . 5-26

I - vii -

ILLUSTRATIONS

6.1 PRODUCTION OF DIISODECYL ADIPATE (DIBASIC ACID ESTER)

FROM ADlPlC ACID AND ISODECYL ALCOHOL . . . . , . . . . . . . . . . . . . . . . . . H-7

6.2 PRODUCTION OF DIISODECYL ADIPATE (DIBASIC ACID ESTER)

FROM ADlPlC ACID AND ISODECYL ALCOHOL EFFECT OF PLANT CAPACITY ON INVESTMENT COST . . . . . . . . , . . . . . . a 6-18

6.3 PRODUCTION OF DIISODECYL ADIPATE (DIBASIC ACID ESTER) FROM ADlPlC ACID AND ISODECYL ALCOHOL EFFECT OF OPERATING LEVEL AND

PLANT CAPACITY ON PRODUCT VALUE . ..*.....,..........,....... 6-21

. . . - VIII -

-

-

0

2.1

3.1

3.2

3.3

3.4

3.5

3.6

4.1

4.2

4.3

4.4

4.5

4.6

4.7

4.8

4.9

5.1

5.2

TABLES

PERFORMANCE PROPERTIES OF SYNLUBES BY CLASS ................ 2-2

CLASSIFICATION OF SYNTHETIC BASE FLUIDS ...................... 3-l

PERFORMANCE PROPERTIES OF SYNLUBES BY CLASS ................ 3-3

U.S. CONSUMPTION OF SYNLUBE BASE STOCKS, 1987 ............... 3-4

PRODUCERS OF POLYALPHAOLEFIN BASE STOCKS

AND THEIR 1989 PRODUCTION CAPACITIES ......................... 3-5

PRODUCERS OF NEOPOLYOL ESTER BASE STOCKS

AND THEIR PRODUCTION CAPACITIES, 1987 ........................ 3-8

PRODUCERS OF DIBASIC ACID ESTER BASE STOCKS

AND THEIR PRODUCTION CAPACITIES, 1988 ........................ 3-12

PRINCIPAL POLYALPHAOLEFIN VISCOSITY GRADES ................... 4-9

TYPICAL VISCOSITY REQUIREMENTS FOR SELECTED MULTIGRADE OILS .................................... 4-12

OLEFIN OLIGOMERS PATENT SUMMARY ............................................. A-3

PRODUCTION OF POLYALPHAOLEFINS FROM 1 -DECENE

DESIGN BASES AND ASSUMPTIONS ............................... 4-24


MAJOR EQUIPMENT ............................................. 4-25


STREAM FLOWS ................................................ 4-27


TOTAL CAPITAL INVESTMENT ..................................... 4-35


CAPITAL INVESTMENT BY SECTION ................................ 4-36

PRODUCTION OF PCLYALPHAOLEFINS FROM 1 -DECENE

PRODUCTION COSTS ............................................ 4-38

NEOPOLYOL ESTERS

PATENT SUMMARY ............................................. A-15

PRODUCTION OF NEOPOLYOL ESTERS FROM

TECHNICAL PENTAERYTHRITOL AND Cs TO Cg MIXED n-FATTY ACIDS DESIGN BASES AND ASSUMPTIONS ............................... 5-13

- ix -

TABLES

5.3 PRODUCTION OF NEOPOLYOL ESTERS FROM TECHNICAL PENTAERYTHRITOL AND C5 TO Cg n-FATTY ACIDS

MAJOR EQUIPMENT . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5-14


TECHNICAL PENTAERYTHRITOL AND C5 TO CQ n-FATTY ACIDS STREAM FLOWS . . . . . . . . . . . . . . . . ..I............................. 5-l 5

5.5 PRODUCTION OF NEOPOLYOL ESTERS FROM TECHNICAL PENTAERYTHRITOL AND C5 TO Cg MIXED n-FATTY ACIDS

TOTAL CAPITAL INVESTMENT *............,.......,.........,...,. 5-22


TECHNICAL PENTAERYTHRITOL AND C5 TO Cg MIXED n-FATTY ACIDS

PRODUCTION COSTS . . . . . . . ..*.................*................ 5-24

6.1 DIBASIC ACID ESTERS

PATENT SUMMARY . . ..,,.....,*.,...........**.......*.,,...... A-18

6.2 PRODUCTION OF DIISODECYL ADIPATE FROM

ADIPIC ACID AND ISODECYL ALCOHOL

DESIGN BASES AND ASSUMPTIONS . . . . . . . . . . ..**................. 6-9

6.3 PRODUCTION OF DIISODECYL ADIPATE FROM ADIPIC ACID AND ISODECYL ALCOHOL

MAJOR EQUIPMENT . . . . . . . . . . . . . . . . . . . . . . . ..#................... 6-10



STREAM FLOWS . . . . . . . . . . . . . . ..*......**....................... 6-11


ADIPIC ACID AND ISODECYL ALCOHOL TOTAL CAPITAL INVESTMENT ,............,,.............a........ 6-l 7



PRODUCTION COSTS . . . . ...*.................*.. ,............*.. 6-19

8.7 ESTIMATED PRODUCTION COSTS FOR OTHER DIESTERS . . . . . . . . . . . . . . 6-22

C.1 PROPERTIES OF DECENE-1 . . . . . . . . . . ..*......**.............*... c-3

C.2 PROPERTIES OF POLYALPHAOLEFIN

SYNTHETIC LUBRICANT BASE STOCKS . . . . . . ..a.................... c-4

-x-

TABLES

C.3 PROPERTIES OF NEOPOLYOLS . . . . . . . . . . . . . . . . . . . . ..*............. c-5

C.4 PROPERTIES OF TECHNICAL PENTAERYTHRITOL , . . . . , . . , , , . . , . . . . , . . C-6

C.5 PROPERTIES OF SHORT-CHAIN FATTY ACIDS . . , . . . , , . . , . . . , . . . . , . . , C-7

C.6 PROPERTIES OF PENTAERYTHRITOL FAITY ACID ESTER

SYNTHETIC LUBRICANT BASE . . . . . . . . . . . . ..*.......m.......*...... C-8

C.7 PROPERTIES OF STRAIGHT CHAIN DIBASIC ACIDS . . . . . . . . . . . . . . . . . , . . C-9

C.8 PROPERTIES OF OX0 ALCOHOLS . . . . . . . . . . . . . . . . ..a.............. c-10

C.9 PROPERTIES OF DIBASIC ACID ESTER SYNTHETIC BASE STOCKS . . . . . . . C-10

- xi -

Documents

SYNTHETIC LUBRICANTS, SUPP. A - ihsmarkit.com · SYNTHETIC LUBRICANT BASE STOCKS (September 1989) Menlo Park, California 94025 This report is an update of PEP Report 125, Synthetic