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PERP Report

Propylene Oxide

02/03-8 October 2003

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

Contents

Section 1 Summary...................................................................................................................... 1.1 1.2 BACKGROUND .............................................................................................. COMMERCIAL ROUTES ............................................................................... 1.2.1 1.2.2 1.2.3 1.3 1.3.1 1.3.2 1.3.3 1.4 1.5 Chlorohydrin Route .............................................................................. PO/SM Route ........................................................................................ Cumene Hydroperoxide Route ............................................................. Hydrogen Peroxide Route..................................................................... Direct Oxidation of Propylene with Oxygen ........................................ Hydro-Oxidation of Propylene with Oxygen and Hydrogen................ Page 1 1 4 4 4 6 8 8 10 11 12 14 14 16 17 18 19 24 24 24 25 29 29 32 36 36 41 47 47

i

DEVELOPING ROUTES.................................................................................

ECONOMICS ................................................................................................... COMMERCIAL ASPECTS ............................................................................. 1.5.1 1.5.2 1.5.3 1.5.4 Applications Overview ......................................................................... U.S. Supply/Demand Balance............................................................... West European Supply/Demand and Trade.......................................... Japanese Supply/Demand Balance .......................................................

2 3

Introduction................................................................................................................. Commercial Processes ................................................................................................ 3.1 CHLOROHYDRIN ROUTE INTEGRATED WITH CHLOR-ALKALI ........ 3.1.1 3.1.2 3.2 Chemistry.............................................................................................. Process Description...............................................................................

ETHYLBENZENE HYDROPEROXIDE ROUTE WITH STYRENE COPRODUCT (PO/SM) ........................................................................................ 3.2.1 3.2.2 Chemistry.............................................................................................. Process Description............................................................................... Chemistry.............................................................................................. Process Description...............................................................................

3.3

CUMENE HYDROPEROXIDE ROUTE WITHOUT CO-PRODUCT .......... 3.3.1 3.3.2

4

Developing Processes .................................................................................................. 4.1 EPOXIDATION WITH IN-SITU HYDROGEN PEROXIDE.........................

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Contents

4.1.1 4.1.2 4.2 4.2.1 4.2.2 4.3 4.3.1 4.3.2 4.4

Chemistry.............................................................................................. Process Description............................................................................... Chemistry.............................................................................................. Process Description............................................................................... Chemistry.............................................................................................. Process Description...............................................................................

47 50 52 52 55 57 57 59 62 62 63 66 66 66 67 67 67 68 68 71 75 75 75 83 86 88 91 91 91 92

EPOXIDATION WITH PURCHASED HYDROGEN PEROXIDE ...............

DIRECT OXIDATION OF PROPYLENE WITH OXYGEN .........................

HYDRO-OXIDATION OF PROPYLENE WITH OXYGEN AND HYDROGEN .................................................................................................... 4.4.1 4.4.2 Chemistry.............................................................................................. Process Description...............................................................................

5

Economic Analysis ...................................................................................................... 5.1 BASES .............................................................................................................. 5.1.1 5.1.2 5.1.3 5.2 5.2.1 5.2.2 5.2.3 5.3 5.3.1 5.3.2 5.3.3 5.3.4 5.4 Pricing ................................................................................................... Investment............................................................................................. Cost of Production ................................................................................ Chlorohydrin Process............................................................................ Ethylbenzene Hydroperoxidation Process (PO/SM) ............................ Cumene Hydroperoxidation Process (No Co-Product) ........................ Epoxidation with In-Situ Hydrogen Peroxide ...................................... Epoxidation with Purchased Hydrogen Peroxide ................................. Direct Oxidation of Propylene with Oxygen ........................................ Hydro-Oxidation of Propylene with Oxygen and Hydrogen................

COMMERCIAL PROCESSES ........................................................................

DEVELOPING PROCESSES ..........................................................................

COMPARISON OF PROCESSES ................................................................... PROPYLENE OXIDE CHARACTERISTICS................................................. 6.1.1 6.1.2 Properties, Storage, and Handling ........................................................ Health and Safety..................................................................................

6

Commercial Analysis .................................................................................................. 6.1

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Contents

6.2

APPLICATIONS OVERVIEW........................................................................ 6.2.1 6.2.2 6.2.3 6.2.4 6.2.5 Polyether Polyols .................................................................................. Propylene Glycols................................................................................. Glycol Ethers ........................................................................................ 1,4-Butanediol....................................................................................... Isopropanolamines ................................................................................ Demand ................................................................................................. Supply ................................................................................................... Supply/Demand Balance....................................................................... Demand ................................................................................................. Supply ................................................................................................... Supply/Demand and Trade ................................................................... Demand ................................................................................................. Supply ................................................................................................... Supply/Demand Balance.......................................................................

93 93 95 95 95 95 96 96 98 99 100 100 101 102 104 104 105 105 106

6.3

UNITED STATES ............................................................................................ 6.3.1 6.3.2 6.3.3

6.4

WESTERN EUROPE ....................................................................................... 6.4.1 6.4.2 6.4.3

6.5

JAPAN .............................................................................................................. 6.5.1 6.5.2 6.5.3

7

References....................................................................................................................

Appendix A B C Elements of Nexant/Chem Systems' Capital Cost Estimates.................................. Propylene Oxide ­ Material Safety Data Sheet........................................................ PERP Program Title Index ........................................................................................

Page A-1 B-1 C-1

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Contents

Figure 1.1 Propylene Oxide Capacity Share by Process, 1970-2002............................................. 1.2 Comparison of Propylene Oxide Costs......................................................................... 1.3 Propylene Oxide Industry Structure Overview............................................................. 1.4 U.S. Propylene Oxide Supply and Demand.................................................................. 1.5 West European Propylene Oxide Supply/Demand Balance ......................................... 2.1 Propylene Oxide Capacity Share by Process, 1970-2002............................................. 2.2 Summary of PO Patent Activity, 1998-2003 ................................................................ 2.3 Selectivity-Conversion for Propylene Oxidation via Hydro-Oxidation and Direct Oxidation....................................................................................................................... 2.4 PO Yield Data via Hydro-Oxidation and Direct Oxidation.......................................... 3.1 Propylene Oxide Chlorohydrin Process....................................................................... 3.2 Block Flow Diagram of PO (Chlorohydrin) Plant with Integral Caustic/Chlorine ..... 3.3 Styrene/Propylene Oxide via Lyondell Process: Peroxidation & Epoxidation ............ 3.4 Styrene/Propylene Oxide via Lyondell Process: Recovery .......................................... 3.5 Speculative Sumitomo Co-Product Free PO Process: Block Diagram......................... 3.6 Speculative Sumitomo PO Process ­ Oxidation & Epoxidation .................................. 3.7 Speculative Sumitomo PO Process ­ Recovery & Hydrogenolysis ............................. 4.1 Propylene Oxide via Epoxidation with In-situ Hydrogen Peroxide ............................ 4.2 Propylene Oxide via Epoxidation with Purchased Hydrogen Peroxide ...................... 4.3 Propylene Oxide by Direct Oxidation of Propylene .................................................... 4.4 Propylene Oxide by Hydro-Oxidation of Propylene .................................................... 5.1 Styrene Price Effect on PO Cost; Hydroperoxidation Process ..................................... 5.2 Styrene Price Trend (USGC) ........................................................................................ 5.3 H2O2 Price Effect on PO Cost....................................................................................... 5.4 Capacity Effect on H2O2 Cost Anthraquinone Process ................................................ 5.5 Capacity Effect on PO Cost via Direct H2O2 Process ................................................. 5.6 Comparison of Propylene Oxide Costs......................................................................... 6.1 Propylene Oxide Industry Structure Overview............................................................. 6.2 U.S. Propylene Oxide End-Use Analysis, 2002 ...........................................................

Page 1 14 15 16 17 19 20 22 23 26 28 33 34 42 43 44 51 56 60 64 71 72 79 82 83 90 94 96

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Contents

6.3 U.S. Propylene Oxide Supply and Demand.................................................................. 6.4 West European Propylene Oxide End-Use Analysis, 2002 .......................................... 6.5 West European Propylene Oxide Supply/Demand Balance ......................................... 6.6 Japanese Propylene Oxide Demand Components, 2002...............................................

99 100 103 104

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Contents

Table 1.1 Summary of Propylene Oxide Economics .................................................................... 1.2 U.S. Propylene Oxide Supply/Demand Balance........................................................... 1.3 West European Propylene Oxide Supply/Demand Balance ......................................... 1.4 Japanese Propylene Oxide Supply/Demand Balance ................................................... 3.1 Selectivity in Ethylbenzene Oxidation ......................................................................... 3.2 Comparison of Hydroperoxidation Parameters ............................................................ 4.1 PO Yields via Oxidation with Hydrogen Peroxide....................................................... 4.2 Operating Parameters Employed in Speculative Direct Oxidation Propylene Oxide Process .......................................................................................................................... 5.1 Feedstock and By-Product Prices ................................................................................. 5.2 Cost of Production Estimate for: Propylene Oxide Process: Chlorohydrin Integ. w/Chlor-Alkali............................................................... 5.3 Cost of Production Estimate for: Propylene Oxide Process: Hydroperoxide ­ Styrene Co-Product ............................................................ 5.4 Cost of Production Estimate for: Propylene Oxide Process: PO/SM, Materials & Utilities @ 13-Yr Average ........................................... 5.5 Cost of Production Estimate for: Propylene Oxide Process: Sumitomo Hydroperoxide­No Co-Product .................................................... 5.6 Cost of Production Estimate for: Propylene Oxide Process: C3H6 Epox. w/In-Situ H2O2 ............................................................................ 5.7 Cost of Production Estimate for Propylene Oxide Process: C3H6 Epox. w/ Purchased H2O2...................................................................... 5.8 Cost of Production Estimate for: Hydrogen Peroxide (100% Basis, as 70% Soln.) Process: Anthraquinone Auto-Oxidation (Extrapolated to Large Scale) ..................... 5.9 Cost of Production Estimate for: Propylene Oxide Process: C3H6 Epox. w/Crude 43% H2O2 High ............................................................ 5.10 Cost of Production Estimate for: Propylene Oxide Process: C3H6 Epox. w/Crude 43% H2O2 Low ........................................................... 5.11 Cost of Production Estimate for: Propylene Oxide Process: Direct Oxidation of Propylene ­ Patent Results............................................. 5.12 Cost of Production Estimate for: Propylene Oxide Process: Direct Oxidation of Propylene - Improved.....................................................

Page 13 16 17 18 30 39 53 59 66 69 70 73 74 76 77 78 80 81 84 85

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Contents

5.13 Cost of Production Estimate for: Propylene Oxide Process: Hydro-Oxidation of Propylene (5.8% Conv/Pass) ......................................... 5.14 Summary of Propylene Oxide Economics .................................................................... 6.1 Physical Properties of Propylene Oxide ....................................................................... 6.2 U.S. Propylene Oxide Demand..................................................................................... 6.3 U.S. Propylene Oxide Capacity .................................................................................... 6.4 U.S. Propylene Oxide Supply/Demand Balance........................................................... 6.5 West European Propylene Oxide Demand ................................................................... 6.6 West European Capacities for Propylene Oxide........................................................... 6.7 West European Propylene Oxide Supply/Demand Balance ......................................... 6.8 Japanese Propylene Oxide Demand.............................................................................. 6.9 Japanese Propylene Oxide Capacity by Producer, 2003............................................... 6.10 Japanese Propylene Oxide Supply/Demand Balance ...................................................

87 89 91 96 98 99 101 102 103 104 105 105

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