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1,4-Butanediol/THF 02/03-7 PERP Report 1,4-Butanediol/THF 02/03-7 January 2004 44 South Broadway, White Plains, New York 10601, USA Tel: +1 914 609 0300 Fax: +1 914 609 0399 “This report was prepared by Nexant, Inc (“Nexant”) and is part of the Process Evaluation/Research Planning Program (PERP). Except where specifically stated otherwise in this Report, the information contained herein is prepared on the basis of information that is publicly available, and contains no confidential third party technical information to the best knowledge of Nexant. Aforesaid information has not been independently verified or otherwise examined to determine its accuracy, completeness or financial feasibility. Neither NEXANT, Subscriber nor any person acting on behalf of either assumes any liabilities with respect to the use of or for damages resulting from the use of any information contained in this Report. Nexant does not represent or warrant that any assumed conditions will come to pass. The report is submitted on the understanding that the Subscriber will maintain the contents confidential except for the Subscriber’s internal use. The Report should not be reproduced, distributed or used without first obtaining prior written consent by Nexant. Each Subscriber agrees to use reasonable effort to protect the confidential nature of the Report.” Contents Section Page 1 Executive Summary ............................................................................................................. 1 1.1 SYNOPSIS................................................................................................................ 1 1.2 OVERVIEW ............................................................................................................. 2 1.3 PROCESS CONCEPTS............................................................................................ 4 1.4 PROCESS TECHNOECONOMICS......................................................................... 6 1.5 COMMERCIAL STATUS........................................................................................ 11 1.5.1 Butanediol Market Summary ....................................................................... 11 1.5.2 Tetrahydrofuran Market Summary .............................................................. 13 1.6 STRATEGIC ISSUES.............................................................................................. 15 1.6.1 Captive/Merchant Market Balance .............................................................. 15 1.6.2 Emergence of Industrial Scale Biotransformation Processes....................... 15 1.7 SUMMARY .............................................................................................................. 17 2 Introduction.......................................................................................................................... 18 2.1 TECHNOLOGY EVOLUTION ............................................................................... 18 2.1.1 Overview...................................................................................................... 18 2.1.2 Phase One Acetylene – The Early Years ..................................................... 18 2.1.3 Phase Two – The New Challengers ............................................................. 20 2.1.3.1 Mitsubishi – Butadiene Acetoxylation....................................... 20 2.1.3.2 ARCO (Now Lyondell) – Propylene Oxide............................... 20 2.1.3.3 Davy Process Technology – Maleic Anhydride......................... 21 2.1.3.4 DuPont – Transport Bed – A New Philosophy .......................... 21 2.1.3.5 BP/Lurgi GEMINOX® - Fluid Bed Revisited........................... 21 2.1.4 Phase Three – Industry Commoditization through Technology .................. 21 2.1.4.1 Drive to World Scale Units........................................................ 21 2.1.4.2 Innovation in BDO/THF Technology Still Apparent................. 22 Darien – Allyl Alcohol............................................................... 22 Eastman – Butadiene Revisited.................................................. 22 Succinic Acid – Biotransformation Makes an Entrance ............ 22 2.2 BUTANEDIOL VALUE CHAIN............................................................................. 25 2.3 METHODOLOGY AND STUDY OUTLINE ......................................................... 27 3 Commercial Technology...................................................................................................... 28 3.1 PROCESSES FOR 1,4-BUTANEDIOL................................................................... 28 3.1.1 Acetylene/Formaldehyde (Reppe Concept) ................................................. 28 3.1.1.1 Process Chemistry...................................................................... 28 3.1.1.2 Process Description.................................................................... 30 Synthesis of 1,4-Butynediol ....................................................... 30 3.1.1.3 Hydrogenation Sections............................................................. 30 Butanediol i 02/03-7 4117-Butanediol Contents 3.1.2 Mitsubishi Chemical Butadiene Acetoxylation............................................ 32 3.1.2.1 Process Chemistry...................................................................... 32 3.1.2.2 Process Description.................................................................... 34 Acetoxylation Process................................................................ 34 Hydrogenation/Hydrolysis Processes......................................... 35 3.1.3 Lyondell Propylene Oxide Route................................................................. 37 3.1.3.1 Process Chemistry...................................................................... 37 3.1.3.2 Process Description.................................................................... 37 Propylene Oxide Isomerization to Allyl Alcohol....................... 37 Hydroformylation and Extraction .............................................. 39 Hydrogenation and Purification ................................................. 41 3.1.4 Darien Propylene Acetoxylation/Hydroformylation.................................... 43 3.1.4.1 Propylene Acetoxylation to Allyl Acetate ................................. 43 3.1.4.2 Allyl Acetate Cracking............................................................... 45 3.1.4.3 Allyl Alcohol Conversion to 1,4-Butanediol ............................. 45 3.1.5 Davy Process Technology - 1,4-Butanediol Process using Maleic Anhydride 46 3.1.5.1 Process Chemistry...................................................................... 46 Basic Maleic Anhydride Chemistry ........................................... 46 Conversion of Maleic Anhydride Into γ-Butyrolactone, Butanediol, Tetrahydrofuran...................................................... 47 3.1.5.2 Process Descriptions.................................................................. 48 Maleic Anhydride Synthesis ...................................................... 48 The Huntsman Mars V/Mars VI Process - Oxidation ................ 49 The Huntsman Mars V/Mars VI Process - Recovery................. 49 Conversion of Crude Maleic Anhydride in 1,4-Butanediol via Davy Process Technology.......................................................... 50 3.1.6 Eurodiol (Now BASF) Concept Based on Maleic Anhydride ..................... 53 3.1.6.1 Process Chemistry...................................................................... 53 3.1.6.2 Process Description.................................................................... 55 3.1.7 BP/Lurgi Geminox from n-Butane via Maleic Acid.................................... 59 3.1.7.1 Process Chemistry...................................................................... 59 3.1.7.2 Process Description.................................................................... 59 Maleic Acid Production ............................................................. 59 Hydrogenation of Maleic Acid to 1,4-Butanediol and Tetrahydrofuran ......................................................................... 60 3.2 PROCESSES FOR TETRAHYDROFURAN .......................................................... 62 3.2.1 Dehydration of 1,4-Butanediol..................................................................... 62 3.2.1.1 Process Chemistry...................................................................... 62 3.2.1.2 Process Description.................................................................... 62 3.2.2 Mitsubishi Chemical Butadiene Acetoxylation............................................ 63 Butanediol ii 02/03-7 4117-Butanediol Contents 3.2.2.1 Process Chemistry...................................................................... 63 3.2.2.2 Process Description.................................................................... 63 3.2.3 DuPont Transport Bed Concept ................................................................... 65 3.2.3.1 Overview.................................................................................... 65 3.2.3.2 Process Description.................................................................... 66 Maleic Acid................................................................................ 66 Tetrahydrofuran Synthesis ......................................................... 69 3.2.4 Pentose/Furfural Approach.......................................................................... 71 3.2.4.1 Process Chemistry.....................................................................
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