Explore the wide array of uses for aromatic hydrocarbons in this comprehensive reference
Aromatics are a class of compounds - normally but not exclusively organic - which tend to be produced as by-products of various industrial processes. Their importance as petrochemical materials in themselves, along with the range of inter-relations between different aromatic chemicals, creates a complex and opportunity-filled market for aromatics.
Industrial Arene Chemistry provides a thorough look at the conventional techniques required to use and produce these aromatic hydrocarbons. Beginning with an overview of the global aromatic market - including, but not limited to, manufacturers, markets of BTX, and downstream functional aromatics, aromatics derived from renewable sources, and economic forecasts - the book will also explore the impact shifting environmental factors will have on the future of aromatic chemistry. The text further explores BTX production processes differentiated according to the raw materials used. Importantly, this will establish the importance and growth of the biobased chemical industry.
Industrial Arene Chemistry readers will also find: - Case studies that describe major elements of specific technologies prototyped by contributors/companies as part of ongoing market development efforts - Process chapters that include summaries of the conventional techniques and a more detailed discussion of recent high-impact studies - Recent advances in conventional aromatic reactions, including alkylation, acylation and carboxylation, hydrogenation/reduction, oxidation, nitration/amination, sulfonation, and halogenation
Industrial Arene Chemistry is a useful reference for chemists and chemical engineers who work with aromatics.
Table of Contents
Volume 1
Foreword xxi
Preface xxv
Section 1 The Markets for Aromatic Commodities 1
1 The Fossil-Based BTX Market 3
Andy Nicholson
2 The Downstream Functional Aromatics Market 19
Andy Nicholson
3 Crude Oil to Chemicals: Industry Development and Strategic Implications 43
Rong J. Chang
Section 2 BTX, Naphthalene and Higher Aromatics from Fossil-Based Sources 71
4 BTX from Light Hydrocarbons 73
Minghui Tan, Li Tan, Guohui Yang, and Yisheng Tan
5 BTX Aromatics from Naphtha Hydrocarbons 111
Arno de Klerk
6 BTX Aromatics from Heavier Material than Naphtha 145
Arno de Klerk
7 BTX Aromatics from Other Conversion Processes 171
Arno de Klerk
8 Bi- and Tri-nuclear Aromatic Production 195
Arno de Klerk
9 Extraction Separation of Aromatics 209
Weize Wu
10 The Honeywell UOP CCR PlatformingTM Process for BTX Production (Case Study) 269
Bryan Egolf, David Lafyatis, Manuela Serban, Ka Lok, and Mark Lapinski
11 The Honeywell UOP ParexTM Process: Fifty Years of Growth for the Petrochemical Industry (Case Study) 297
Patrick C. Whitchurch and James A. Johnson
12 Forty Years of Xylene Isomerization Technology Deployment at ExxonMobil (Case Study) 327
Michel Molinier, Robert G. Tinger, Arnaud Cotte, and Jeevan S. Abichandani
13 ExxonMobil PxMaxSM Process: Production of Paraxylene (Case Study) 357
Michel Molinier and Jeevan S. Abichandani
14 BP/Amoco Paraxylene Crystallization Technology (Case Study) 383
Jeffrey A. Amelse
15 Reactions and Mechanisms of Xylene Isomerization and Related Processes 403
Jeffrey A. Amelse
16 Honeywell UOP Tatoray Process: Maximizing Feed Utilization for Aromatics Production (Case Study) 439
Raymond Shih and Eseoghene Jeroro
17 The Honeywell UOP MX SorbexTM Process: Enabling Growth of PET Resin Applications (Case Study) 453
James Johnson and Patrick Whitchurch
Section 3 Aromatics from Methanol and Synthesis Gas 479
18 Methanol-to-Aromatics Compounds (MTA) Process 481
Ning Wang, Huiqiu Wang, Hao Xiong, Wenlong Song, and Weizhong Qian
19 Carbon Monoxide and Carbon Dioxide for Aromatics Production 533
Yuebing Xu, Bing Liu, Feng Jiang, and Xiaohao Liu
Volume 2
Foreword xxiii
Preface xxvii
Section 4 The Chemistry of Downstream Functional Aromatics 555
Section 4.1 Alkylation 555
20 Homogeneous Friedel-Crafts Alkylation 557
Venkata D. B. C. Dasireddy, Gurwinder Singh, Stalin Joseph, Yoshihiro Sugi, and Ajayan Vinu
21 Heterogeneous Friedel-Crafts Alkylation 595
Yoichi Nishimura, Venkata D. B. C. Dasireddy, Stalin Joseph, Yoshihiro Sugi, and Ajayan Vinu
22 Badger Ethylbenzene Technology (Case Study) 645
Raghavender Bhoomi and Brian Maerz
23 Exelus Styrene Monomer (ExSyM) Process (Case Study) 673
Vamsi M. Vadhri, Tom Hickey, and Mitrajit Mukherjee
24 INEOS Phenol Cumene Chemistry (Case Study) 715
Ralf Bonmann, Manfred Weber, and Markus Weber
25 Linear Alkylbenzenes: An Overview of the Commercial HF and DetalTM Process Unit Alkylation Technology (Case Study) 729
Stephen Sohn and Phuong Do
26 Frontiers in Arene Chemistry: Direct Methylation of Benzene with Methane on Metal-Loaded Zeolites 747
Etsushi Tsuji and Naonobu Katada
Section 4.2 Acylation and Carboxylation 769
27 Acylation of Arenes 771
Chandrakanth R. Gadipelly, Gunjan Deshmukh, Suresh Bhargava, Selvakannan Periasamy, and Lakshmi Kantam Mannepalli
28 Carboxylation Reaction Based on the Direct and Indirect Uses of CO2: Sustainable Syntheses of C - CO2, O - CO2, and N - CO2 Bonds 807
Francesco Nocito and Angela Dibenedetto
Section 4.3 Reduction of Aromatic Nuclei 849
29 Homogeneously Catalyzed Aromatic Reduction 851
Tsuyoshi Yamada, Kwihwan Park, and Hironao Sajiki
30 Heterogeneously Catalyzed Aromatic Reduction 883
Yoshinari Sawama, Kazuho Ban, and Hironao Sajiki
31 Partial Hydrogenation of Benzene 919
Minghua Qiao and Baoning Zong
32 Cyclohexane Process: An Overview of the Axens Technology (Case Study) 951
Chiara Friggeri and Arnaud Cotte
33 The Fibrant Hydranone® and HPOplus Technologies for Cyclohexanone and 𝛆-Caprolactam Production (Case Study) 971
Johan T. Tinge, Marijke H.L. Groothaert, and Yu-Hwa E. Sheu
34 Hexamoll® DINCH, A Non-phthalate Plasticizer by BASF (Case Study) 1007
Rainer Papp, Matthias Pfeiffer, Axel Grimm, Diana Brunnenkant, Angelika Langsch, and Rainer Otter
35 Storage of Hydrogen in Reversible Aromatic Organic Liquids 1037
Phillimon Modisha and Dmitri Bessarabov
Volume 3
Foreword xxiii
Preface xxvii
Section 4.4 Oxidation 1067
36 Catalytic Aromatic Oxidations 1069
Madhav Ghanta, Shankha S. Acharyya, Raghunath V. Chaudhari, and Bala Subramaniam
37 BP-Amoco Mid-Century Process for Terephthalic Acid Production (Case Study) 1107
William H. Gong
38 Spray Reactor for Terephthalic Acid Production (Case Study) 1137
Madhav Ghanta, Xiaobin Zuo, Raghunath V. Chaudhari, and Bala Subramaniam
39 Oxidation of o-Xylene and Naphthalene to Phthalic Anhydride 1153
Nico A. de Munck, Oliver Richter, Hans-Jürgen Eberle, and Gerhard Mestl
40 Oxidation of o-Xylene and Naphthalene to Phthalic Anhydride - Catalyst Development (Case Study) 1203
Oliver Richter, Hans-Jürgen Eberle, Nico A. de Munck, Robert Marx, Thomas Turek, and Gerhard Mestl
41 Oxidation of Metaxylene to Isophthalic Acid and Its Application 1251
Xiang-li Long and Zhi-hao Wang
42 Ethylbenzene Dehydrogenation to Styrene 1293
Hong-Xia Fan, Antony Rajendran, and Wen-Ying li
43 Badger’s Styrene Monomer Production Technology (Case Study) 1327
J. Alex Bishop and Peter Vallieres
44 INEOS Phenol - Phenol and Acetone Chemistry (Case Study) 1343
Manfred Weber, Ralf Bonmann, and Markus Weber
45 The MEXEO Bisphenol A (BPA) Technology (Case Study) 1359
Maciej Kiedik, Arkadiusz Chru´sciel, and Wiesław Hreczuch
46 Direct Hydroxylation of Benzene to Phenol on Solid-State Catalyst 1385
Cheng Wang, Jinwen Zhang, Wentao Zheng, Yuanhang Ren, Bin Yue, and Heyong He
47 Aromatic Oxidation Technologies at Eni/Versalis (Case Study) 1411
Carlo Perego, Vittorio Milanesi, Roberto Buzzoni, Marco Ricci, and Daniele Bianchi
Section 4.5 Nitration/Amination 1439
48 The NORAM Process for the Production of Nitrobenzene (Case Study) 1441
Steven Buchi, Alfred Guenkel, and Rob Pistner
49 The Josef Meissner Processes for the Manufacture of Nitroaromatics: On the Way to Sustainability (Case Study) 1463
Jürgen Pöhlmann, Heinrich Hermann, and Stefan Fankel
50 Selective Catalytic Hydrogenation of Nitroarenes to Anilines 1479
Ruijie Gao, Chong Peng, and Ji-Jun Zou
51 Methylene Diphenyl Diisocyanate (MDI) and Toluene Diisocyanate (TDI) 1525
Helge Braun
52 The Production of Methylene Diphenyl Diisocyanate (MDI) and Toluene Diisocyanate (TDI) at Wanhua Chemical Group (Case Study) 1575
Fang Wen, Miao Hu, Yongfeng Li, Hongmin Zhang, Shiyuan Wan, Zhijun Fang, Qishan Huang, and Weiqi Hua
Section 4.6 Sulfonation 1611
53 Alkylbenzene Sulfonation Technologies at Desmet Ballestra (Case Study) 1613
Ilio Sebastiani, Antonino Milicia, and Icilio Adami
54 Sulfonated Aromatic Polymers and Copolymers for Membrane Engineering 1659
Piyachai Khomein and Gao Liu
55 Green Sulfonation 1701
Ming Wang and Xuefeng Jiang
Volume 4
Foreword xxi
Preface xxv
Section 4.7 Halogenation 1723
56 Fluoroarenes 1725
Takashi Okazoe and Yuichiro Ishibashi
57 Chloroaromatics: Advances in Synthesis and Applications 1769
Vitor S.C. de Andrade and Marcio C.S. de Mattos
58 Bromo- and Iodoaromatics 1803
Tsugio Kitamura
59 Aromatic Halogenation at WeylChem Group (Case Study) 1841
Andrea Missio and Michael Badine
Section 5 Sustainable Aromatics Production and Technology 1859
Section 5.1 Biobased Aromatics 1859
60 BTX from Lignin 1861
William H. Gong
61 Bio-based Aromatics from Carbohydrates 1909
Gangavaram V. M. Sharma, Kajjam Ravindranath, Kondreddi R. Reddy, and Kota S. Rao
62 Bio-Based Aromatics from Lipids and Fatty Acids 1953
Wayne Seames, Evguenii Kozliak, Alena Kubátová, and Brian Tande
63 Biobased Paraxylene 1981
William H. Gong and Robert Rozmiarek
64 Biobased Terephthalic Acid 2037
William H. Gong
65 Naturally Occurring Phenolic Sources for Industrial Applications 2059
Marion Thébault, Antonio Pizzi, and Franco Policardi
Section 5.2 Recycling Polymers 2101
66 Chemical Recycle of PET 2103
Peter D. Metelski
67 Depolymerization of PET Polymers at Ioniqa Technologies (Case Study) 2117
Marianne Gravendeel, Michiel de Groot, Lonneke Slenders, Becky Stevens, Maarten Stolk, Joost Wolters, Alexander Wolters, and Fabian Wouters
68 Chemical Recycling of Mixed Plastic Waste for the Production of Aromatics and Olefins as Monomers for Circular Polyolefins and Polycarbonate. SABIC TRUCIRCLETM (Case Study) 2143
Lara Galan-Sanchez, Christoph Dittrich, Anthoni van Zijl, Tom Housmans, Maria Soliman, and Frank Kuijpers
69 Chemical Recycling of Polystyrene: From Post-Consumer Polystyrene Waste to High-Quality Polystyrene Products (Case Study) 2163
Norbert Niessner, Bianca Wilhelmus, Michiel Verswyvel, Tristan Kolb, Andreas Schedl, Hans-Werner Schmidt, Philipp Schäfer, Laura Hollerbach, and Karoline Raulf
Index 2185
Company Index 2239
