PHENOL/ACETONE/CUMENE (96/97-2) DECEMBER 1997

CONTENTS
I SUMMARY A. CURRENT COMMERCIAL TECHNOLOGY B. DEVELOPING TECHNOLOGIES C. COMMERCIAL ANALYSIS 1. Introduction 2. Phenol 3. Cumene 4. Acetone (a) Demand (b) Supply (c) Supply/Demand Balance

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1 1 4 6 6 7 11 12 12 14 14 16 16 17 17 18 18 18 19 19 20 20 22 26 29 35 35 35 35 39 42 49 53 53 55 56 57 59

II INTRODUCTION A. HISTORICAL ROUTES TO PHENOL B. CURRENT COMMERCIAL TECHNOLOGY 1. Cumene Hydroperoxide Route 2. DSM Toluene Oxidation Route C. DEVELOPING TECHNOLOGIES 1. Mitsui Acetone Recycle Route 2. Solutia/BIC N2O Benzene Oxidation Route 3. Asahi Cyclohexene Route III CUMENE PRODUCTION TECHNOLOGY A. CHEMISTRY B. SOLID PHOSPHORIC ACID CATALYZED CUMENE PROCESS C. ALUMINUM CHLORIDE CATALYZED CUMENE PROCESS D. ZEOLITE BASED CATALYZED CUMENE PROCESS IV PHENOL AND ACETONE PRODUCTION TECHNOLOGY A. CUMENE BASED PHENOL/ACETONE PROCESS TECHNOLOGY 1. Chemistry (a) Cumene Oxidation to Cumene Hydroperoxide (b) Cumene Hydroperoxide Cleavage to Phenol and Acetone 2. Process Technology B. MITSUI ACETONE RECYCLE PROCESS C. SOLUTIA NITROUS OXIDE BENZENE OXIDATION PROCESS 1. Chemistry 2. Reaction Mechanism 3. Oxidation Catalysts 4. Process Basis 5. Process Description

PHENOL/ACETONE/CUMENE (96/97-2) DECEMBER 1997

CONTENTS
D. PHENOL FROM TOLUENE 1. Benzoic Acid from Toluene 2. Phenol from Benzoic Acid (a) Chemistry (b) Process Description PHENOL FROM BENZENE VIA HYDROGENATION TO CYCLOHEXENE: THE ASAHI PROCESS ACETONE FROM PROPYLENE 1. Chemistry 2. Process Description

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60 61 62 62 65 70 74 74 76

E. F.

V ECONOMICS A. ECONOMICS OF CUMENE PRODUCTION B. ECONOMICS OF PHENOL PRODUCTION 1. Phenol Production via Cumene 2. Phenol Production via Benzene and Propylene 3. Phenol Production via Acetone 4. Phenol Production via Solutia Process C. ECONOMICS OF ACETONE PRODUCTION VI COMMERCIAL ANALYSIS A. INTRODUCTION B. PHENOL 1. United States (a) Demand (1) Phenolic Resins (2) Bisphenol A (3) Caprolactam (4) Other (b) Supply (c) Supply/Demand Balance 2. Western Europe (a) Demand (1) Phenolic Resins (2) Bisphenol A (3) Caprolactam (4) Other (b) Supply (c) Supply/Demand Balance 3. Japan (a) Demand (1) Phenolic Resins (2) Bisphenol A

79 79 85 85 85 89 92 96 98 98 99 99 99 100 100 100 101 101 102 103 103 104 104 105 105 105 106 107 107 108 108

PHENOL/ACETONE/CUMENE (96/97-2) DECEMBER 1997

CONTENTS
(3) Other (b) Supply (c) Supply/Demand Balance Other Far East (a) Demand (b) Supply (c) Supply/Demand Balance Latin America Rest of the World

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108 109 110 110 110 110 112 112 113

4.

5. 6.

7. Summary C. CUMENE 1. United States (a) Demand (b) Supply (c) Supply/Demand Balance 2. Western Europe (a) Demand (b) Supply (c) Supply/Demand Balance 3. Japan (a) Demand (b) Supply (c) Supply/Demand Balance 4. East Asia (a) Demand (b) Supply (c) Supply/Demand Balance 5. Latin America (a) Demand (b) Supply (c) Supply/Demand Balance 6. Rest of the World (a) Demand (b) Supply 7. Summary D. ACETONE 1. Demand (a) Methyl Methacrylate (b) Bisphenol A (c) Solvents (d) Other Uses 2. Supply 3. Supply/Demand Balance REFERENCES

114 120 120 120 120 121 121 121 121 122 123 123 123 124 125 125 125 125 126 126 126 127 128 128 128 128 132 132 132 133 133 133 135 136 138

PHENOL/ACETONE/CUMENE (96/97-2) DECEMBER 1997

TABLES Page
Table I.A.1 U.S. Gulf Coast Cumene Production Economic Comparison, 1st Qtr 1996 Table I.A.2 U.S. Gulf Coast Phenol Production Economic Comparsion: Cumene Route, 1st Qtr 1997 Table I.A.3 U.S. Gulf Coast Acetone Production Economic Summary, 1st Qtr 1997 Table I.B.1 U.S. Gulf Coast Phenol Production Economic Comparison of Developing Technologies, 1st Qtr 1997 Table I.C.1 Global Phenol Demand by Region, 1990-2010 Table I.C.2 Global Phenol Capacity by Region, 1993-2010 Table I.C.3 Global Cumene Demand by Region, 1993-2010 Table I.C.4 Global Cumene Capacity by Region, 1993-2010 Table I.C.5 Acetone Demand by Major Region, 1990-2010 Table I.C.6 Global Acetone Capacity in Major Producing Regions, 1990-2010 Table I.C.7 Global Acetone Supply/Demand Balance, 1990-2010 Table III.A.1 Benzene Feedstock Specifications Table III.A.2 Propylene Feedstock Specifications Table III.B.1 Typical Cumene Specifications for Chlorination Grade Phenol Manufacture Table IV.A.1 Typical Acetone Product Specifications Table IV.A.2 Typical Phenol Product Specifications Table IV.C.1 Effect of Catalyst Water Vapor Treatment on Benzene Conversion Table IV.C.2 Various Operating Conditions for N2O Oxidation of Benzene to Phenol Table IV.C.3 Process Parameters for N2O Oxidation of Benzene to Phenol Table IV.D.1 Toluene Oxidation Reactor Design Bases Table V.A.1 U.S. Gulf Coast Cumene Production Economics Comparison, 1st Qtr 1997 Table V.A.2 Cost Estimate of Cumene Production via Benzene/Propylene Transalkylation, Phosphoric Acid Catalyst Table V.A.3 Cost Estimate of Cumene Production via Benzene/Propylene Transalkylation, Aluminum Chloride Catalyst Table V.A.4 Cost Estimate of Cumene Production via Benzene/Propylene Transalkylation, Zeolite Catalyst Table V.B.1 Cost Estimate of Phenol Production via Cumene Table V.B.2 Cost Estimate of Phenol Production from Benzene and Propylene, Phosphoric Acid Catalyst Table V.B.3 Cost Estimate of Phenol Production from Benzene and Propylene, Zeolite Catalyst Table V.B.4 Cost Estimate of Phenol Production via Mitsui Process with Acetone Recycle Table V.B.5 Cost Estimate of Phenol Production from Benzene (Solutia) 2 3 4 6 8 9 11 12 13 14 15 21 22 26 46 48 56 58 59 67 80 82 83 85 86 87 88 90 93

PHENOL/ACETONE/CUMENE (96/97-2) DECEMBER 1997

TABLES Page
Table V.C.1U.S. Gulf Coast Acetone Production Economics Summary, 1st Qtr 1997 Table V.C.2Cost Estimate of Acetone Production via IPA Dehydration Table VI.B.1 U.S. Phenol Demand by Application, 1997 Table VI.B.2 U.S. Phenol Demand by End Use, 1990-2010 Table VI.B.3 U.S. Synthetic Phenol Capacity, 1997 Table VI.B.4 U.S. Phenol Supply/Demand Balance, 1993-2010 Table VI.B.5 West European Phenol Demand by Application, 1997 Table VI.B.6 West European Phenol Demand by End Use, 1990-2010 Table VI.B.7 West European Phenol Capacity, 1997 Table VI.B.8 West European Phenol Supply/Demand Balance, 1993-2010 Table VI.B.9 Japanese Phenol Demand by Application, 1997 Table VI.B.10 Japanese Phenol Demand by End Use, 1990-2010 Table VI.B.11 Japanese Phenol Capacity, 1997 Table VI.B.12 Japanese Phenol Supply/Demand Balance, 1993-2010 Table VI.B.13 East Asian Phenol Capacity, 1997 Table VI.B.14 East Asian Phenol Supply/Demand Balance, 1993-2010 Table VI.B.15 Latin American Phenol Supply/Demand Balance, 1993-2010 Table VI.B.16 Phenol Capacity, Rest of the World, 1997 Table VI.B.17 Global Phenol Demand by Region, 1990-2010 Table VI.B.18 Global Phenol Capacity by Region, 1993-2010 Table VI.C.1 U.S. Cumene Capacity, 1997 Table VI.C.2 U.S. Cumene Supply/Demand Balance, 1993-2010 Table VI.C.3 West European Cumene Capacity, 1997 Table VI.C.4 West European Cumene Supply/Demand Balance, 1993-2010 Table VI.C.5 Japanese Cumene Capacity, 1997 Table VI.C.6 Japanese Cumene Supply/Demand Balance, 1993-2010 Table VI.C.7 East Asian Cumene Capacity, 1997 Table VI.C.8 East Asian Cumene Supply/Demand Balance, 1993-2010 Table VI.C.9 Latin American Cumene Capacity, 1997 Table VI.C.10 Latin American Cumene Supply/Demand Balance, 1993-2010 Table VI.C.11 Rest of the World Cumene Capacity, 1997 Table VI.C.12 Global Cumene Demand by Region, 1993-2010 Table VI.C.13 Global Cumene Capacity by Region, 1993-2010 Table VI.D.1 Acetone Demand by Major Region, 1990-2010 Table VI.D.2 Acetone Capacity in Major Producing Regions, 1990-2010 Table VI.D.3 Global Acetone Supply/Demand Balance, 1990-2010 96 97 99 100 102 103 103 104 106 107 107 108 109 110 111 112 113 114 116 118 120 121 122 123 124 124 125 126 127 127 128 130 132 135 136 137

FIGURES Page
Figure I.C.1 Global Phenol Net Trade by Region, 1996 Figure III.B.1 Phosphoric Acid Catalyst, UOP Cumene Synthesis 10

and Purification

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PHENOL/ACETONE/CUMENE (96/97-2) DECEMBER 1997

FIGURES Page
Figure III.C.1 Figure III.D.1 Figure III.D.2 Figure IV.A.1 Figure IV.A.2 Figure IV.B.1 Figure IV.B.2 Figure IV.C.1 Figure IV.D.1 Figure IV.D.2 Figure IV.E.1 Figure IV.F.1 Figure V.A.1 Figure V.B.1 Figure V.B.2 Figure VI.B.1 Figure VI.B.2 Figure VI.B.3 Figure VI.C.1 Figure VI.C.2 Figure VI.D.1 Solutia/Kellogg Cumene Synthesis and Purification UOPs Qmax Process: Zeolite Catalyst CDTech CDCumene Process, Zeolite Catalyst Phenol from Cumene Oxidation and Cleavage Phenol from Cumene: Phenol/Cumene Recovery and AMS Hydrogenation Mitsui Process: Hydrogenation of Acetone to Isopropanol Simplified Flow Diagram of Mitsui Process: Isopropanol to Propylene Simplified Flow Diagram of Solutia Process: Benzene to Phenol Phenol via Toluene: Benzoic Acid Synthesis and Purification Area Phenol via Toluene: Liquid Phase Phenol Synthesis and Purification Phenol via Benzene Hydrogenation to Cyclohexene Acetone from Propylene via IPA Sensitivity of Cumene Production Cost to Benzene and Propylene Price, Zeolite Catalyst Sensitivity of Phenol Production Cost to Acetone Price in Conventional and Mitsui Processes Sensitivity of Phenol Production Cost to N2O Price in Conventional and Solutia Processes Global Phenol Demand by Region, 1997 Global Phenol Capacity by Region, 1997 Global Phenol Net Trade by Region, 1996 Global Cumene Demand by Region, 1997 Global Cumene Capacity by Region, 1997 Acetone Consumption in Major Regions, 1997 27 30 31 43 47 50 51 54 66 69 73 78 81 91 95 115 117 119 129 131 134