AROMATIC AMINES PROCESS ECONOMICS PROGRAM. Report No. 76Al Interim. by YEN-CHEN. July A private report by the MENLO PARK, CALIFORNIA

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1 Report No. 76Al Interim AROMATIC AMINES by YEN-CHEN YEN July 1975 A private report by the PROCESS ECONOMICS PROGRAM STANFORD RESEARCH INSTITUTE I MENLO PARK, CALIFORNIA

2 CONTENTS 1 INTRODUCTION INDUSTRY STATUS AND SUMMARY... 3 Industry Status... 3 Summary of Process Descriptions... 4 Dinitrobenzene... 4 m-phenylenediamine from Dinitrobenzene... 4 m-phenylenediamine by Direct Amination... 5 Cost Comparisons DINITROBENZENE... 9 Chemistry... 9 Review of Processes Nitration Reactor Type Raw Materials Acid Composition and Recycling Separation, Washing and Purification Process Description Process Discussion Cost Estimates META-PHENYLENEDIAMINE FROM DINITROBENZENE Chemistry Review of Processes Reduction Purification of Meta-phenylenediamine Process Description Process Discussion Cost Estimates m-phenylenediamine BY DIRECT AMINATION Process Description Process Discussion Cost Estimates Alternative Cases Possibilities for Future Development vii

3 L CONTENTS 6 OTHER PROCESSES FOR MANUFACTURING m-phenylenediamine Reduction of Dinitrobenzene by Iron and Hydrochloric Acid (Bechamp Process) i: Reduction of Chlorodinitrobenzene From Isophthalic Acid via Amide Direct Amination of Isophthalic Acid Amination of Aniline by Hydroxylamine Hydrochloride From Resorcinol APPENDIX A DESIGN AND COST BASES APPENDIX B PHYSICAL DATA APPENDIX C SPECIFICATIONS OF p-phenylenediamine APPENDIX D HAZARDS CITED REFERENCES PATENT REFERENCES BY COMPANY viii

4 ILLUSTRATIONS 3.1 Reaction Rates for Nitration of Benzene and Nitrobenzene Compositions of Mixed Acids Used in the Manufacture of Dinitrobenzene Flow Sheet Acid Cycle in the Process Dinitrobenzene Effect of Operating Level and Plant Capacity on Production Cost , m-phenylenedismine from Dinitrobenzene Flow Sheet Integrated Production of m-phenylenediamine from Benzene via DNB Effect of Operating Level and Plant Capacity on Production Cost m-phenylenediamine by Direct Amination Flow Sheet m-phenylenediamine by Direct Amination Effect of Operating Level and Plant Capacity on Production Cost B.l System Nitrobenzene-Sulfuric Acid-Water ix

5 TABLES Comparison of Processes for Making m-phenylenediamine... 6 Production of Aniline and m-phenylenediamine., Washing, Separation, and Purification of Nitrobenzene and Dinitrobenzene Patent Summary Design Bases and Assumptions , 21 Major Process Equipment and Utility Summary Compositions of Stream Flows Waste Streams Total Capital Investment Production Costs Reduction of Dinitro Aromatic Compounds to Diamines by Hydrogen Patent Summary Purification of Meta-Phenylenediamine Patent Summary m-phenylenediamine from Dinitrobenzene Design Basis and Assumptions m-phenylenediamine from Dinitrobenzene Based on Du Pont Patents Major Process Equipment and Utilities Summary m-phenylenediamine from Dinitrobenzene Composition of Stream Flows...., m-phenylenediamine from Dinitrobenzene Based on Du Pont Patents Total Capital Investment m-phenylenediamine from Dinitrobenzene Based on Du Pont Patents Production Costs xi

6 TABLES 5.1 m-phenylenediamine by Direct Amination Design Bases and Assumptions m-phenylenediamine by Direct Amination Major Process Equipment and Utilities Summary 5.3 m-phenylenediamine by Direct Amination Compositions of Stream Flows....., m-phenylenediamine by Direct Amination Total Capital Investment m-phenylenediamine by Direct Amination Production Costs m-phenylenediamine by Direct Amination Comparison of Costs Aniline by Direct Amination with Coproduction of m-phenylenediamine Cost Features xii