PHENOL PROCESS ECONOMICS PROGRAM. Report No. 22A. Supplement A. by YEN-CHEN. September A private report by the PARK, CALIFORNIA

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1 Report No. 22A PHENOL Supplement A by YEN-CHEN YEN September 1972 A private report by the PROCESS ECONOMICS PROGRAM.-. _ STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA

2 CONTENTS 1 INTRODUCTION SUMMARY General Aspects... 3 Technical Aspects INDUSTRY STATUS CUMENE FROM BENZENE AND PROPYLENE Chemistry Review of Processes Process Description Process Discussion Cost Estimates PHENOL FROM CUMENE Chemistry Oxidation of Cumene Decomposition of Hydroperoxide By-Products Review of Processes Oxidation of Cumene Concentration of Hydroperoxide Acid Cleavage and Neutralization Distillation Purification of Recycled Cumene Treatment of Heavy Ends Purification of Phenol Process Description Process Discussion Cost Estimates PHENOL FROM SECONDARY BUTYLBENZENE AND OTHER ALKYLBENZENES.. 87 Chemistry sec-butylbenzene by Alkylation Oxidation of sec-butylbenzene to Hydroperoxide Acid Cleavage of sec-butylbenzene Hydroperoxide Preparation of and Acid Cleavage of Ethylbenzene Hydroperoxide Preparation of Cyclohexylbenzene Preparation of and Acid Cleavage of Cyclohexylbenzene Hydroperoxide V

3 CONTENTS (Continued) Review of Processes A Process for Manufacture of sec-butylbenzene from Butene.. 92 Process Description Process Discussion Cost Estimates A Rough Evaluation of the Manufacture of Phenol from sec-butylbenzene PHENOL FROM BENZENE VIA PHENYL ACETATE Process Description Process Discussion Cost Estimates PHENOL FROM BENZENE BY DIRECT OXIDATION WITH MOLECULAR OXYGEN Chemistry Review of Processes Process Description Cost Estimates PHENOL BY OTHER PROCESSES The Toluene Process The Raschig Process The Sulfonation Process The Chlorination Process The Cyclohexane Process Phenol by Dealkylation or Disproportionation of Cresol. Phenol by Oxidation with a Hydroperoxide, Peroxides, or Peracids Phenol from Benzene by Oxidation with Cupric Chloride. Phenol from Benzaldehyde by Oxidation Phenol from Oxidation of Diphenylethane Phenol from the By-Product of Salicylic Acid Manufacture Phenol from Oxidation of Toluene and Methane Phenol from Benzene Through a Thallium Compound.... Phenol from cr-methylstyrene Vi

4 CONTENTS APPENDIX A DESIGN AND COST BASIS APPENDIX B PHYSICAL AND CHEMICAL DATA APPENDIX C PRODUCT SPECIFICATIONS CITED REFERENCES PATENT REFERENCES BY COMPANY Vii

5 ILLUSTRATIONS 4.1 Cumene from Benzene and Propylene.,.,,.,,., Cumene from Benzene and Propylene Production Cost at Different Production Levels,...,, Phenol from Cumene Products, By-Products, and Intermediates ,., Phenol from Cumene.,., , Phenol from Cumene Production Cost at Different Production Levels.., ,.,.....,., Production Cost at Different Production Levels...., Phenol from Secondary Butylbenzene Production Cost at Different Production Levels ,., , Phenol by Raschig Process , ix

6 TABLES 2.1 Phenol from Cumene or Secondary Butylbenzene Summary of Economics, Cumene or Secondary Butylbenzene Production Summary of Economics, Phenol by Various Processes Summary of Economics Synthetic Phenol Producers and Capacities.., Cumene Producers and Capacities Cumene from Benzene and Propylene Patent Summary,...,., ,....., Cumene from Benzene and Propylene Major Process Equipment and Utilities Summary Cumene from Benzene and Propylene Stream Flows ,,...,,, Cumene from Benzene and Propylene Total Capital Investment Cumene from Benzene and Propylene Production Costs..., , Oxidation of Cumene Patent Summary..., Cleavage of Cumene Hydroperoxide Patent Summary..., Distillation for Recovery of Products in Cumene Process for Phenol Manufacture Patent Summary Hydrogenation of CY-Methylstyrene Patent Summary...,,......, Treatment of Heavy Ends in Phenol Manufacture from Cumene Patent Summary Purification of Phenol Patent Summary., ,....,, Phenol from Cumene Major Process Equipment and Utilities Summary...,,. 67 Xi

7 TABLES 5.8 Phenol from Cumene Stream Flows Phenol from Cumene Waste Products Summary Phenol from Cumene Production Costs,...., , Phenol from Cumene Total Capital Investment......,....., Major Process Equipment and Utilities Summary Stream Flows Waste Products Summary Total Capital Investment Production Costs Phenol from Secondary Butylbenzene Major Process Equipment and Utilities Summary Phenol from Secondary Butylbenzene Total Capital Investment Phenol from Secondary Butylbenzene Production Costs ,.... Major Process Equipment and Utilities Summary Stream Flows,., ,,. Waste Products Summary.., Total Capital Investment Production Costs *.. 95,, , , , ,, , ,.,.. s ,.... a xii

8 TABLES Patent Summary.....,..., Major Process Equipment and Utilities Summary..., Stream Flows, , Waste Products Summary Total Capital Investment Production Costs....,., Phenol from Toluene via Benzoic Acid Patent Summary Phenol from Toluene Production Costs...,......,...., Phenol by Raschig Process Patent Summary , Phenol by Raschig Process Production Costs....., , Phenol by Sulfonation Process Patent Summary..., , Phenol by Sulfonation Process Production Costs , Chlorination of Benzene and Alkali Hydrolysis of Chlorobenzene Patent Summary Phenol by Chlorination Process Production Costs xiii

9 TABLES 9.9 Phenol by Cyclohexane Process Patent Summary..,...,,...,....., Phenol by Cyclohexane Process Production Costs xiv

CHLORINE PROCESS ECONOMICS PROGRAM. Report No. 61A. Supplement A. by YEN CHEN YEN. May A private report by the STANFORD RESEARCH INSTITUTE

CHLORINE PROCESS ECONOMICS PROGRAM. Report No. 61A. Supplement A. by YEN CHEN YEN. May A private report by the STANFORD RESEARCH INSTITUTE Report No. 61A CHLORINE Supplement A by YEN CHEN YEN May 1074 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I I MENLO PARK, CALIFORNIA CONTENTS 1 2 3 INTRODUCTION... 1 SUMMARY...