PERP Report

Oxo 01/02-8

April 2003

44 South Broadway, White Plains, New York 10601, USA Tel: +1 914 609 0300 Fax: +1 914 609 0399

Disclaimer

This Report was prepared by Nexant, Inc. (“Nexant”) and is part of Chem Systems Process Evaluation/Research Planning (PERP) Program. Except where specifically stated otherwise in this Report, the information contained herein is prepared on the basis of information that is publicly available, and contains no confidential third party technical information to the best knowledge of Nexant. The aforesaid information has not been independently verified or otherwise examined to determine its accuracy, completeness, or feasibility.

Neither Nexant, Subscriber, nor any person acting on behalf of either assumes any liabilities with respect to the use of, or for damages resulting from the use of, any information contained in this Report. Nexant does not represent or warrant that any assumed conditions will come to pass.

The Report is submitted on the understanding that the Subscriber will maintain the contents confidential except for the Subscriber’s internal use. The Report shall not be reproduced, distributed, or used outside Subscriber’s organization without first obtaining prior written consent by Nexant. Each Subscriber agrees to use reasonable effort to protect the confidential nature of the Report.

PERP 01/02-8, Oxo Alcohols

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Contents

Section Page

1 Executive Summary...... 1 1.1 INTRODUCTION ...... 1 1.2 PROCESS TECHNOLOGY...... 4 1.3 PROCESS ECONOMICS...... 6 1.3.1 Health, Safety, Environmental Concerns Re Plasticizers...... 8 1.4 COMMERCIAL STATUS...... 10 1.4.1 Consumption...... 10 1.4.1.1 n-Butanol...... 10 1.4.1.2 2-EH ...... 12 1.4.2 Production...... 13 1.4.2.1 N-Butanols ...... 13 1.4.2.2 2-EH ...... 14 1.4.3 Asia ...... 14 1.4.3.1 Supply/Demand...... 14 2 Introduction...... 16 2.1 OXO CHEMISTRY...... 16 2.2 INDUSTRIAL PROCESSES ...... 18 2.3 PRODUCTS FROM OXO ALCOHOLS ...... 20 3 Conventional Technology and New Developments...... 21 3.1 OVERVIEW ...... 21 3.2 OXO TECHNOLOGY DEVELOPMENT...... 21 3.3 OXO TECHNOLOGY EVOLUTION ...... 22 3.3.1 First Generation - Unmodified Cobalt...... 22 3.3.2 Second Generation - Phosphine-Modified Cobalt...... 22 3.3.3 Third Generation - Phosphine-Modified Rhodium...... 22 3.3.4 Fourth Generation - Bis-phosphite-Modified Rhodium ...... 23 3.4 MODIFIED RHODIUM TECHNOLOGY ...... 24

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3.4.1 Oxo Production ...... 24 3.4.2 Oxo Alcohols Production...... 26 3.4.2.1 Butanol Production via ...... 26 3.4.2.2 2-Ethylhexanol Production via Hydrogenation...... 27 3.5 NEW DEVELOPMENTS OVERVIEW ...... 29 4 Process Economics ...... 33 4.1 OVERVIEW ...... 33 4.1.1 Case Descriptions...... 33 4.2 COST OF PRODUCTION METHODOLOGY ...... 33 4.2.1 Battery Limits ...... 33 4.2.2 Production Costs...... 34 4.2.2.1 Labor ...... 34 4.3 PRODUCTION COSTS...... 35 4.3.1 Overview...... 35 4.3.2 Synthesis Gas from Heavy Fuel Oil ...... 35 4.3.3 n-Butanol and 2-Ethylhexanol...... 35 4.3.4 Isononanol...... 35 4.3.5 Isodecanol ...... 36 4.3.6 2-Propylheptanol...... 36 4.4 HEALTH, SAFETY, ENVIRONMENTAL CONCERNS RE PLASTICIZERS ...... 49 5 Commercial Analysis...... 50 5.1 OVERVIEW ...... 50 5.2 UNITED STATES...... 51 5.2.1 Applications and Trends ...... 51 5.2.1.1 n-Butanol...... 51 5.2.1.2 2-Ethylhexanol ...... 51 5.2.2 Demand...... 52 5.2.2.1 n-Butanol...... 52 5.2.2.2 2-Ethylhexanol ...... 53

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5.2.3 Production...... 53 5.2.4 Supply/Demand and Projections...... 55 5.2.4.1 n-Butanol...... 55 5.2.4.2 2-EH ...... 56 5.3 WESTERN EUROPE...... 57 5.3.1 Demand...... 57 5.3.1.1 n-Butanol...... 57 5.3.1.2 2-Ethylhexanol - Consumption ...... 59 5.3.2 Production...... 60 5.3.3 Supply/Demand and Projections...... 62 5.3.3.1 n-Butanol...... 62 5.3.4 i-butanol...... 63 5.3.4.1 2-Ethylhexanol ...... 63 5.4 CENTRAL AND EASTERN EUROPE...... 65 5.4.1 2-Ethyl-Hexanol (2-EH)...... 65 5.4.1.1 Consumption ...... 65 5.4.1.2 Supply ...... 66 5.4.2 Butanols ...... 68 5.4.2.1 n-Butanol...... 68 Consumption ...... 68 Supply...... 69 Trade...... 70 Supply/Demand Balance ...... 71 5.4.2.2 I-Butanol ...... 71 Consumption ...... 71 Trade...... 73 5.5 ASIA ...... 74 5.5.1 Demand...... 74 6 References...... 79

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Contents

Appendix Page

A Elements of Nexant’s/Chem Systems’ Capital Cost Estimates A-1 B PERP Program Title Index B-1

Figure Page

1.1 Products from Propylene ...... 3 1.2 Oxo Alcohol Production Costs ...... 7 1.3 Oxo Alcohol Production Costs ...... 8 1.4 United States n-Butanol Consumption by End Use, 2001...... 10 1.5 West European n-Butanol Consumption by End Use, 2002 (Estimate)...... 11 1.6 United States 2-Ethyl Hexanol Consumption by End Use, 2001 ...... 12 1.7 West European 2-EH Consumption, 2002, Estimate...... 13 1.8 Production of n-Butanol ...... 13 1.9 Production of 2-EH...... 14 2.1 Products from Propylene Hydroformylation ...... 20 3.1 Flow Scheme of LP Oxo Process – Mark IV Butraldehyde Process...... 25 3.2 Simplified Flow Scheme for n-Butanol Production ...... 27 3.3 Simplified Flow Scheme for 2-ethylhexanol Production ...... 28 3.4 Oxeno - Simple Flowsheet for Higher Oxo Production from Two-Stage Hydroformation 30 4.1 Oxo Alcohol Production Costs ...... 48 4.2 Oxo Alcohol Production Costs ...... 48 5.1 United States n-Butanol Consumption by End Use, 2001...... 52 5.2 United States 2-Ethylhexanol Consumption by End Use, 2001 ...... 53 5.3 United States Commodity Oxo Alcohol Producers ...... 55 5.4 West European n-Butanol Consumption by End Use, 2002 (Estimate)...... 57 5.5 West European i-Butanol Consumption, 2002, Estimate ...... 58 5.6 West European 2-EH Consumption, 2002, Estimate...... 59 5.7 West European Commodity Oxo Alcohol Producers...... 61 5.8 West European n-Butanol Supply/Demand and Trade...... 63

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5.9 West European 2-EH Supply/Demand and Trade ...... 64

Table Page

1.1 Comparison of the Various Oxo Processes...... 1 1.2 Oxo Alcohol Production Cost Summary ...... 6 1.3 Recent Asian 2-EH Projects ...... 15 2.1 Comparison of the Various Oxo Processes...... 18 3.1 Oxo Alcohol Process Development...... 21 3.2 Comparison of LP Oxo Processes ...... 25 3.3 Typical Compositions Hydroformylation Mixtures ...... 31 4.1 Cost of Production Estimate for : Synthesis Gas (1:1) Process : Partial Oxidation of Heavy Fuel Oil...... 37 4.2 Cost of Production Estimate for : n-Butanol Process Davy/Dow MK IV...... 38 4.3 Cost of Production Estimate for : n-Butanol) Process : Celanese (RCH)...... 39 4.4 Cost of Production Estimate for : 2-Ethylhexanol Process : Davy/Dow MK IV...... 40 4.5 Cost of Production Estimate for : 2-Ethylhexanol Process : Celanese (RCH)...... 41 4.6 Cost of Production Estimate for : Mixed Octenes Process : Dimersol X™ ...... 42 4.7 Cost of Production Estimate for : Isononanol Process : Classic Cobalt...... 43 4.8 Cost of Production Estimate for : Isodecanol Process : Classic Cobalt...... 44 4.9 Cost of Production Estimate for : 2-Propylheptanol Process : Dow/Davy MK IV...... 45 4.10 Oxo Alcohol Production Cost Summary ...... 46

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5.1 United States Commodity Oxo Alcohol Capacity, End 2001 ...... 54 5.2 United States Supply/Demand Balance for n-Butanol, 1998-2010 ...... 56 5.3 2-EH Supply, Demand and Trade in the United States 1998-2010...... 56 5.4 West European n-Butanol Consumption ...... 58 5.5 West European i-Butanol Consumption ...... 59 5.6 West European 2-EH Consumption...... 60 5.7 West European Commodity Oxo Alcohol Capacity, End 2001 ...... 60 5.8 West European n-Butanol Supply/Demand and Trade...... 62 5.9 West European 2-EH Supply/Demand and Trade ...... 64 5.10 2-EH Consumption - Central and Eastern Europe...... 65 5.11 2-EH Capacity - Central and Eastern Europe ...... 66 5.12 Central and Eastern Europe Oxo Alcohol Capacity ...... 66 5.13 2-EH Net Trade - Central and Eastern Europe(1)...... 67 5.14 2-EH Supply/Demand Balance - Central and Eastern Europe ...... 68 5.15 n-Butanol Consumption - Central and Eastern Europe ...... 69 5.16 n-butanol Capacity - Central and Eastern Europe ...... 69 5.17 n-butanol Net Trade - Central and Eastern Europe(1)...... 70 5.18 n-butanol Supply/Demand Balance - Central and Eastern Europe...... 71 5.19 i-Butanol Consumption - Central and Eastern Europe ...... 72 5.20 i-Butanol Capacity - Central and Eastern Europe...... 72 5.21 i-Butanol Net Trade - Central and Eastern Europe...... 73 5.22 i-Butanol Supply/Demand Balance - Central and Eastern Europe...... 73 5.23 Recent Asian 2-EH Projects ...... 74 5.24 Annual 2-EH Capacity in Asia Pacific ...... 75 5.25 Annual n-Butanol Capacity in Asia Pacific...... 75 5.26 Annual i-Butanol Capacity in Asia Pacific...... 76 5.27 Phthalates Supply/Demand in Japan 1998 to 2000...... 77 5.28 2-EH Supply/Demand Japan 1996-2000 ...... 78

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