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

About the Author

Jacques Mortier, PhD, is Professor of Organic Chemistry at Le Mans University (former University of Maine) in France, where he teaches classes on Industrial Organic Chemistry and Reaction Mechanisms in Aromatic and Heteroaromatic Chemistry. Dr. Mortier started his career as a research chemist in the crop protection industry. At Le Mans University, his research is focused on various topics dealing with polar organometallics, directed aromatic metalation methodologies, and the study of reaction mechanisms. He has extensive experience as a consultant for the chemical industry. In recognition of his research expertise, he was distinguished as a member of the University Institute of France (IUF).