Phenol/Acetone/Cumene December 2015 Report Contents Phenol/Acetone/Cumene Table of Contents A Report by NexantThinking™ Process Evaluation/Research Planning (PERP) Program PERP Report 2015-6 – Published December 2015 www.nexantthinking.com Section Page 1 Executive Summary ............................................................................................................... 1 1.1 INDUSTRY OVERVIEW AND TECHNOLOGY LICENSORS ................................... 1 1.2 BUSINESS AND STRATEGIC ANALYSIS REVIEW ................................................ 2 1.3 COMMERCIAL PRODUCTION TECHNOLOGIES ................................................... 4 Cumene Consumption.................................................................................. 4 Selection of Phenol Technologies by Customers for Grassroots and Retrofitting Projects ...................................................................................... 6 1.4 ALTERNATIVE AND “DEVELOPING” TECHNOLOGIES ........................................ 7 SBB to Phenol Process ................................................................................ 7 Benzene Oxidation (with Nitrous Oxide) to Phenol Process ........................ 7 Green Technology Developments ................................................................ 8 1.5 PROCESS ECONOMICS.......................................................................................... 9 Sensitivity Analyses ...................................................................................... 10 Concluding Remarks .................................................................................... 10 1.6 COMMERCIAL MARKET ANALYSIS ....................................................................... 12 Global Cumene Supply, Demand, and Trade .............................................. 12 Global Phenol Supply, Demand, and Trade ................................................ 13 2 Introduction ............................................................................................................................. 16 2.1 CUMENE ................................................................................................................... 16 Technology Overview of Cumene Production .............................................. 17 Technology Licensing Status and Major Producers ..................................... 17 Strategic and Business Considerations ....................................................... 18 Physical and Thermodynamic Properties .................................................... 19 Specifications ............................................................................................... 19 Health Hazards ............................................................................................. 20 PERP PROGRAM 1 www.nexantthinking.com PERP 2015-6, Phenol/Acetone/Cumene A00101.0015.4106 Phenol/Acetone/Cumene December 2015 Report Contents Storage and Transportation ......................................................................... 20 2.2 PHENOL .................................................................................................................... 20 Technology Overview of Phenol Production ................................................ 20 Technology Licensing Status and Major Producers ..................................... 23 Strategic and Business Considerations ....................................................... 24 Physical and Thermodynamic Properties .................................................... 25 Specifications ............................................................................................... 25 Health Hazards ............................................................................................. 25 Storage and Transportation ......................................................................... 26 2.3 ACETONE ................................................................................................................. 27 Technology Overview of Acetone Production .............................................. 27 Technology Licensing Status and Major Producers ..................................... 27 Strategic and Business Considerations ....................................................... 28 Physical and Thermodynamic Properties .................................................... 29 Specifications ............................................................................................... 29 Health Hazards ............................................................................................. 30 Storage and Transportation ......................................................................... 30 3 Cumene Commercial Technologies ....................................................................................... 31 3.1 PROCESS CHEMISTRY ........................................................................................... 31 3.2 CATALYST COMPARISON ...................................................................................... 34 3.3 COMMERCIAL ZEOLITE CATALYZED PROCESSES ............................................ 35 Badger Licensing .......................................................................................... 35 Versalis/CB&I Technology ........................................................................... 38 UOP .............................................................................................................. 44 4 Cumene to Phenol Process Chemistry .................................................................................. 47 4.1 CUMENE OXIDATION TO CUMENE HYDROPEROXIDE ...................................... 47 4.2 CUMENE HYDROPEROXIDE CLEAVAGE TO PHENOL AND ACETONE ............ 50 5 Phenol Production - A Generic Description ............................................................................ 53 5.1 OXIDATION ............................................................................................................... 53 5.2 CHP CONCENTRATION (CUMENE STRIPPING) ................................................... 56 5.3 CHP CLEAVAGE ...................................................................................................... 57 5.4 NEUTRALIZATION ................................................................................................... 58 5.5 PRODUCT RECOVERY AND AMS HYDROGENATION ......................................... 58 5.6 ECONOMIC BENEFIT .............................................................................................. 59 Cumene Consumption.................................................................................. 59 PERP PROGRAM 2 www.nexantthinking.com PERP 2015-6, Phenol/Acetone/Cumene A00101.0015.4106 Phenol/Acetone/Cumene December 2015 Report Contents Selection of Phenol Technologies by Customers for Grassroots and Retrofitting Projects ...................................................................................... 60 6 Phenol and Acetone Commercial Technologies .................................................................... 62 6.1 ILLA INTERNATIONAL ............................................................................................. 62 Process Features ......................................................................................... 63 Process Description ..................................................................................... 63 6.2 KBR ........................................................................................................................... 84 Process Features ......................................................................................... 85 Process Description ..................................................................................... 86 6.3 MITSUI CHEMICALS (ACETONE RECYCLE PROCESS) ...................................... 90 Process Chemistry ....................................................................................... 91 Process Description ..................................................................................... 92 6.4 VERSALIS AND CB&I TECHNOLOGY .................................................................... 94 Process Features ......................................................................................... 94 Process Description ..................................................................................... 95 6.5 SUNOCO/UOP .......................................................................................................... 99 Process Features ......................................................................................... 99 Process Description ..................................................................................... 99 7 Developing Technologies ....................................................................................................... 103 7.1 CUMENE ................................................................................................................... 103 Cumene via Alkylation of Benzene with Isopropanol ................................... 103 7.2 SEC-BUTYLBENZENE (SBB)................................................................................... 104 Alkylation of Benzene to sec-Butylbenzene ................................................. 104 Shell Process for Alkylation of Benzene to sec-Butylbenzene (SBB) using trans-2-Butene .................................................................................... 107 ExxonMobil Process for Alkylation of Benzene to sec-Butylbenzene (SBB) using