PROCESS ECONOMICS PROGRAM

Transcription

1 PROCESS ECONOMICS PROGRAM SRI INTERNATIONAL Menlo Park, California Abstract Process Economics Program Report No. 22C PHENOL (March 1991) This is the fourth in a series of reports on the manufacture of phenol. The report contains preliminary process designs and cost estimates for the cumene peroxidation process, the toluene oxidation process, and a conceptual process based on a Mitsui Petrochemicals patent that entails partially hydrogenating benzene to cyclohexene, reacting the cyclohexene with water to form cyclohexanol, and dehydrogenating the cyclohexanol to produce phenol. In addition, this report includes a discussion of research developments since the last PEP report was written (1977), a discussion of the basic chemistry of the manufacturing processes, and a discussion of the industry status. PEP 88 MKG

2 Report No. 22C PHENOL by MARTHA K. GUERRA a 0 I - A private report by the March 1991 Menlo Park, California 94025

3 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 PETROCHEMlCALS Program covers major hydrocarbons their derivatives on a worldwide basis. In addition, the SRI D/RECTORY OF CHEMICAL PRODUCERS services provide detailed lists of chemical producers by company, product, and plant for the United States and Western Europe and

4 CONTENTS 1 INTRODUCTION I... l-l 2 SUMMARY... 2-l GENERAL ASPECTS ECONOMIC ASPECTS... 2-l TECHNICAL ASPECTS Cumene Peroxidation Process Toluene Oxidation Process Phenol from Benzene via Cyclohexene INDUSTRY STATUS... 3-l PHENOL PRODUCTION AND GROWTH PHENOL MARKETS IMPORTS/EXPORTS ACETONE PRODUCTION PHENOL PRICES CHEMISTRY CUMENE PEROXIDATION PROCESS... 4-l TOLUENE OXIDATION PROCESS PHENOL FROM BENZENE VIA CYCLOHEXENE CUMENE PEROXIDATION PROCESS REVIEW OF PATENTS PROCESS DESCRIPTION Cumene Oxidation Cleavage Product Recovery Water Treatment ar-methylstyrene Hydrogenation Ill -

5 CONTENTS (Continued) 5 CUMENE PEROXlDATlON PROCESS (Concluded) PROCESS DISCUSSION Cumene Oxidation and Stripping Cleavage Reaction Neutralization of Cleavage Product Product Recovery Water Treatment Hydrogenation of a-methylstyrene Materials of Construction Utilities Purity and Yield COST ESTIMATES TOLUENE OXIDATION PROCESS... 8-l REVIEW OF PATENTS... 6-l PROCESS DESCRIPTION Toluene Oxidation Phenol Production and Separation Catalyst Recovery Gas Treatment PROCESS DISCUSSION Toluene Oxidation Steam Injection Intermediates Heat Removal Excess Oxygen Catalyst Usage Yields and Purity Benzoic Acid CxidationIDecarboxylation Catalyst Usage and Recovery Benzene Production Phenol Losses and Overall Yield Materials of Construction Gas Treatment iv -

6 CONTENTS (Continued) 6 TOLUENE OXIDATION PROCESS (Concluded) PROCESS DISCUSSION (Concluded) Waste Treatment ,.,...,., Distillation....,...,,...,.,...,..., COST ESTIMATES...., * PHENOL FROM BENZENE VIA CYCLOHEXENE... 7-l REVIEW OF PATENTS... 7-l PROCESS DESCRIPTION Benzene Hydrogenation Cyclohexanol Formation Cyclohexanol Dehydrogenation Cyclohexane Dehydrogenation PROCESS DISCUSSION Hydrogenation Reaction Catalyst... 7-l 8 Other Additives Hydrogen Usage... 7-l 8 Phase Separation in S-101 A-C... 7-l 9 Materials of Construction Water Addition Reaction p-toluene Sulfonic Acid Recovery Materials of Construction Cyclohexanol Dehydrogenation Reaction Cyclohexane Dehydrogenation Reaction Extractive Distillation Columns Alternative Design Reaction Time Catalyst Separation Cyclohexanol vs. Cylohexanone Dehydrogenation, Conversions Cyclohexanol vs. Cylohexanone Dehydrogenation, Selectivities COST ESTIMATES v-

7 CONTENTS (Concluded) 8 OTHER PROCESSES... 8-l DIRECT OXIDATION OF BENZENE... 8-l Kyushu University University of Tokyo... 8-l Mftsui Toatsu Process HYDROLYSIS OF HALOBENZENES DEALKYLATION OF ALKYL PHENOLS MISCELLANEOUS PROCESSES Oxidation of Benzaldehyde Fhehyl Esters Cyclohexylbenzene COMPARlSON OF PROCESSES... 9-l COMPARfSON OF ECONOMICS... 9-l EFFECT OF ACETONE VALUE ON PHENOL PRODUCTION LOCATION FACTOR APPENDIX A: PATENT SUMMARY TABLES A-l APPENDlX B: DESIGN AND COST BASES... B-l DESIGN CONDITIONS... B-3 COST BASES... B-3 CAPlTAL INVESTMENT... B-3 PRODUCTION COSTS... B-4 EFFECT OF OPERATING LEVEL ON PRODUCTION COSTS... B-5 APPENDIX c: CITED REFERENCES C-l APPENDIX D: PATENT REFERENCES BY COMPANY D-l APPENDIX E: PROCESS FLOW DIAGRAMS E-l - vi -

8 ILLUSTRATIONS 4.1 PHENOL FROM CUMENE PRODUCTS, BY-PRODUCTS, AND INTERMEDIATES CUMENE PEROXIDATION PROCESS FLOW DIAGRAM *.... E CUMENE PEROXIDATION PHENOL PRODUCT VALUE VERSUS BENZENE COST AND ACETONE VALUE..,..., TOLUENE OXIDATION PROCESS PROCESS FLOW DIAGRAM ,,...,...,... E-7 TOLUENE OXIDATION PROCESS TOLUENE COST VERSUS PRODUCT VALUE PHENOL FROM BENZENE VIA CYCLOHEXENE PROCESS FLOW DIAGRAM E-l 1 PHENOL FROM BENZENE VIA CYCLOHEXENE TOTAL FIXED CAPITAL VERSXUS PHENOL VALUE EFFECT OF BENZENE AND TOLUENE PRICES ON PHENOL PRODUCT VALUE......a vii -

9 TABLES 2.1 PHENOL MANUFACTURING COST SUMMARY WORLD PHENOL PRODUCERS WORLD DEMAND FOR PHENOL BY END-USE APPLICATIONS IN PHENOL PRICES CUMENE HYDROPEROXIDE PREPARATION PATENT SUMMARY... A CLEAVAGE OF CUMENE HYDROPEROXIDE PATENT SUMMARY... A PRODUCT RECOVERY PATENT SUMMARY... A CUMENE PEROXIDATION PROCESS DESIGN BASES CUMENE PEROXIDATION PROCESS MAJOR EQUIPMENT CUMENE PEROXIDATION PROCESS STREAM FLOWS CUMENE PEROXIDATION PROCESS UTILITIES SUMMARY CUMENE PEROXIDATION PROCESS COMPARISON OF UTILITIES CUMENE PEROXIDATION PROCESS COMPARISON OF RAW MATERIAL CONSUMPTIONS CUMENE PEROXIDATION PROCESS TOTAL CAPITAL INVESTMENT CUMENE PEROXIDATION PROCESS CAPITAL INVESTMENT BY SECTION CUMENE PEROXIDATION PROCESS PRODUCTION COSTS CUMENE FROM BENZENE AND PROPYLENE PRODUCTION COSTS PHENOL FROM BENZENE AND PROPYLENE VIA CUMENE PRODUCTION COSTS ix -

10 TABLES (Continued) 6.1 PHENOL FROM BENZOIC ACID OXIDATION-DECARBOXYLATION LIQUID PHASE PATENT SUMMARY A PHENOL FROM BENZOIC ACID OXIDATION-DECARBOXYLATION VAPOR PHASE PATENT SUMMARY A TOLUENE OXIDATION PROCESS DESlGN BASES TOLUENE OXIDATION PROCESS MAJOR EQUIPMENT...,..., TOLUENE OXIDATION PROCESS STREAM FLOWS *..* TOLUENE OXIDATION PROCESS UTlLlTlES SUMMARY TOLUENE OXIDATION PROCESS TOTAL CAPlTAL INVESTMENT TOLUENE OXIDATION PROCESS CAPlTAL INVESTMENT BY SECTION n.,.,.., TOLUENE OXIDATION PROCESS PRODUCTION COSTS , PHENOL FROM BENZENE VIA CYCLOHEXENE DESIGN BASES.....* PHENOL FROM BENZENE VIA CYCLOHEXENE MAJOR EQUIPMENT I PHENOL FROM BENZENE VIA CYCLOHEXENE STREAM FLOWS *...* PHENOL FROM BENZENE VIA CYCLOHEXENE UTILITIES SUMMARY # PHENOL FROM BENZENE VIA CYCLOHEXENE TOTAL CAPlTAL INVESTMENT B PHENOL FROM BENZENE VIA CYCLOHEXENE CAPlTAL INVESTMENT BY SECTION a e -x-

11 TABLES (Concluded) 7.7 PHENOL FROM BENZENE VIA CYCLOHEXENE PRODUCTION COSTS.....I PHENOL BY OXIDATION OF BENZENE PATENT SUMMARY #..#... A PHENOL FROM HALOBENZENES PATENT SUMMARY A DEALKYLATION OF ALKYLATED PHENOLS PATENT SUMMARY A MISCELLANEOUS PATENTS PATENT SUMMARY.a*...*... A COMPARISON OF PROCESSES *...*..* xi -