p-Xylene oxidation to terephthalic acid: a literature review oriented toward process optimization and development.

Oriented toward Process Optimization and Development Rogeŕio A. F. Tomaś,† Joaõ C. M. Bordado,‡ and Joaõ F. P. Gomes*,‡,§ †ARTLANT, Zona Industrial e Logística de Sines, Zona 2, Lote 2E1, Monte Feio, 7520-064 Sines, Portugal ‡Instituto de Biotecnologia e Bioengenharia/Instituto Superior Tećnico (IBB), Universidade Tećnica de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal Instituto Superior de Engenharia de Lisboa (ISEL), Área Departamental de Engenharia Química, R. Conselheiro Emídio Navarro, 1959-007 Lisboa, Portugal

[1]  W. Partenheimer.  The Complex Synergy of Water in Metal/Bromide Autoxidations. Part II. Effect of Water and Catalyst on the Aerobic Oxidation of Benzaldehydes and the Effect of Water on the Elementary Catalytic Pathways , 2005 .

[2]  Massimo Pisu,et al.  A lumped kinetic model for liquid-phase catalytic oxidation ofp-xylene to terephthalic acid , 1994 .

[3]  D. Ravens.  The kinetics and mechanism of the auto-oxidation of p-toluic acid in acetic acid solution catalyzed by cobalt and manganese bromides , 1959 .

[4]  G. A. Russell,et al.  Fundamental processes of autoxidation , 1959 .

[5]  J. Dunn,et al.  Terephthalic Acid Synthesis in High-Temperature Liquid Water , 2002 .

[6]  W. Partenheimer.  The Complex Synergy of Water in the Metal/Bromide Autoxidation of Hydrocarbons Caused by Benzylic Bromide Formation , 2004 .

[7]  P. Roffia,et al.  Methyl acetate: by-product in the terephthalic acid production process. Mechanisms and rates of formation and decomposition in oxidation , 1988 .

[8]  Y. Kamiya.  The autoxidation of tetralin catalysed by cobalt salt and sodium bromide in acetic acid , 1966 .

[9]  W. Partenheimer.  The effect of zirconium in metal/bromide catalysts on the autoxidation of p-xylene: Part II. Alternative metals to zirconium and the effect of zirconium on manganese(IV) dioxide formation and precipitation with pyromellitic acid , 2003 .

[10]  Fritz Haber,et al.  The catalytic decomposition of hydrogen peroxide by iron salts , 1934 .

[11]  A. Chester,et al.  Kinetics of the cobalt-catalyzed autoxidation of toluene in acetic acid. Role of cobalt , 1972 .

[12]  G. A. Russell.  The Rates of Oxidation of Aralkyl Hydrocarbons. Polar Effects in Free Radical Reactions1,2 , 1956 .

[13]  G. Ciamician,et al.  Chemische Lichtwirkungen. XXII. Autooxydationen. I , 1912 .

[14]  S. Sakaguchi,et al.  Innovation of Hydrocarbon Oxidation with Molecular Oxygen and Related Reactions , 2001 .

[15]  Ki Hwa Lee,et al.  Liquid Phase Oxidation of Xylenes: Effects of Water Concentration and Alkali Metals , 2002 .

[16]  D. H. Busch,et al.  Liquid phase oxidation of p-xylene to terephthalic acid at medium-high temperatures: multiple benefits of CO2-expanded liquids , 2010 .

[17]  C. Bawn,et al.  Autoxidation of p-toluic acid catalyzed by cobalt bromide , 1968 .

[18]  F. Mayo.  Free radical autoxidations of hydrocarbons , 1968 .

[19]  M. Poliakoff,et al.  Organic reactions in high-temperature and supercritical water , 2006 .

[20]  KamiyaYoshio,et al.  The Autoxidation of p-Xylene Catalyzed with Cobalt Monobromide in Acetic Acid , 1966 .

[21]  I. Yavari,et al.  N-Hydroxyphthalimide-Catalyzed Oxidative Production of Phthalic Acids from Xylenes Using O2/HNO3 in an Ionic Liquid , 2009 .

[22]  Xi Li,et al.  Kinetics of Burning Side Reaction in the Liquid-phase Oxidation of p-Xylene , 2009 .

[23]  S. B. Halligudi,et al.  Formation and role of cobalt and manganese cluster complexes in the oxidation of p-xylene , 2000 .

[24]  H. N. Stephens.  OXIDATION IN THE BENZENE SERIES BY GASEOUS OXYGEN. IV. MECHANISM OF THE SLOW OXIDATION OF SATURATED HYDROCARBONS , 1928 .

[25]  Phillip E. Savage,et al.  A perspective on catalysis in sub- and supercritical water , 2009 .

[26]  M. Edge,et al.  Spectroscopic analysis of organic contaminants in terephthalic acid: colour implications in poly(ethylene terephthalate) manufacture , 1998 .

[27]  R. J. Sheehan,et al.  Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid , 2011 .

[28]  W. Partenheimer,et al.  Methodology and scope of metal/bromide autoxidation of hydrocarbons , 1995 .

[29]  K. Jun,et al.  The promotional effect of CO2 in ethylbenzene oxidation with MC-type catalytic system , 2003 .

[30]  J. Hanotier,et al.  Mechanism of the liquid phase homogeneous oxidation of alkylaromatic hydrocarbons by cobalt salts , 1981 .

[31]  P. V. Leeuwen,et al.  Homogeneous Catalysis: Understanding the Art , 2004 .

[32]  Martyn Poliakoff,et al.  Selective partial oxidation in supercritical water: the continuous generation of terephthalic acid from para-xylene in high yield , 2002 .

[33]  H. N. Stephens.  STUDIES IN AUTO-OXIDATION. I. CYCLOHEXENE PEROXIDE. (PRELIMINARY COMMUNICATION)1 , 1928 .

[34]  R. Sheldon.  Catalytic reactions in ionic liquids. , 2001, Chemical communications.

[35]  A. S. Hay,et al.  AUTOXIDATION REACTIONS CATALYZED BY COBALT ACETATE BROMIDE , 1965 .

[36]  Qinbo Wang,et al.  Effects of Guanidine on the Liquid-Phase Catalytic Oxidation of p-Xylene to Terephthalic Acid , 2005 .

[37]  H. H. Jaffé,et al.  A Reëxamination of the Hammett Equation. , 1953 .

[38]  M. Hartmann,et al.  Über ein Tetralin‐peroxyd , 1932 .

[39]  J. Ilavsky,et al.  Oxidation of polyalkylaromatic hydrocarbons. 12. Technological aspects of p-xylene oxidation to terephthalic acid in water , 1982 .

[40]  M. Poliakoff,et al.  Selective aerobic oxidation of para-xylene in sub- and supercritical water. Part 1. Comparison with ortho-xylene and the role of the catalyst , 2011 .

[41]  W. Brill.  Terephthalic Acid by Single-Stage Oxidation , 1960 .

[42]  Lozar Jean,et al.  Cinetique de la reduction de l'acetate de CoIII dans l'acide acetique , 2010 .

[43]  Ling Zhao,et al.  Kinetics of COx formation in the homogeneous metal/bromide‐catalyzed aerobic oxidation of p‐xylene , 2012 .

[44]  W. Partenheimer.  The structure of metal/bromide catalysts in acetic acid/water mixtures and its significance in autoxidation , 2001 .

[45]  W. J. Koehl,et al.  Oxidation by metal salts. V. Cobaltic acetate oxidation of alkylbenzenes , 1969 .

[46]  J. Bolland.  Kinetics of olefin oxidation , 1949 .

[47]  C. Lee,et al.  Combined Promotional Effect of CO2 and Ni on Co/Mn/Br Catalyst in the Liquid-Phase Oxidation of p-Xylene , 2002 .

[48]  P. Raghavendrachar,et al.  Liquid-phase catalytic oxidation of p-xylene , 1992 .

[49]  L. Hammett.  The Effect of Structure upon the Reactions of Organic Compounds. Benzene Derivatives , 1937 .

[50]  M. Poliakoff,et al.  Simultaneous continuous partial oxidation of mixed xylenes in supercritical water , 2005 .

[51]  P. Roffia,et al.  Byproduct identification in the terephthalic acid production process and possible mechanisms of their formation , 1984 .

[52]  S. Benson.  Effects of Resonance and Structure on the Thermochemistry of Organic Peroxy Radicals and the Kinetics of Combustion Reactions1 , 1965 .

[53]  G. Xie,et al.  Effect of Water Content on the Kinetics of p-Xylene Liquid-Phase Catalytic Oxidation to Terephthalic Acid , 2005 .

[54]  J. Weiß,et al.  Über die Katalyse des Hydroperoxydes , 1932, Naturwissenschaften.

[55]  Youwei Cheng,et al.  Optimum Ratio of Co/Mn in the Liquid-Phase Catalytic Oxidation of p-Xylene to Terephthalic Acid , 2006 .

[56]  P. Gund.  Guanidine, trimethylenemethane, and "Y-delocalization." Can acyclic compounds have "aromatic" stability? , 1972 .

[57]  Qian Feng,et al.  Operation Condition Optimization of p-Xylene Oxidation Reaction Process Based on a Fuzzy Adaptive Immune Algorithm , 2010 .

[58]  Vladimir Agabekov,et al.  Effect of catalyst composition on decreasing of CO2 and CO formation in synthesis of aromatic acids , 1995 .

[59]  C. Chung,et al.  Application of partial least squares methods to a terephthalic acid manufacturing process for product quality control , 2003 .

[60]  Hsi-Ya Huang,et al.  Determining organic impurities in mother liquors from oxidative terephthalic acid synthesis by microemulsion electrokinetic chromatography. , 2009, Journal of chromatography. A.

[61]  S. Jhung,et al.  Effects of alkali metals on the liquid phase oxidation of p-xylene , 2002 .

[62]  H. N. Stephens.  OXIDATIONS IN THE BENZENE SERIES BY GASEOUS OXYGEN I. OXIDATION OF METHYLBENZENES , 1926 .

[63]  Y. Kamiya,et al.  Autoxidation of Aromatic Hydrocarbons Catalyzed with Cobaltic Acetate in Acetic Acid Solution. II. Oxidation of Ethylbenzene and Cumene , 1973 .

[64]  E. R. Bell,et al.  Oxidation of Ethane and Related Compounds , 1949 .

[65]  I. Watt,et al.  The kinetics of oxidation of benzaldehyde. I , 1953, Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences.

[66]  Ling Zhao,et al.  Simplified Free-Radical Reaction Kinetics for p-Xylene Oxidation to Terephthalic Acid , 2008 .

[67]  Y. Ichikawa,et al.  New Oxidation Process for Production of Terephthalic Acid from p-Xylene , 1970 .

[68]  Igor V. Khudyakov,et al.  Mechanisms of action and reactivities of the free radicals of inhibitors , 1987 .

[69]  M. Hronec,et al.  Liquid-phase oxidation of p-xylene catalyzed by metal oxides , 1986 .

[70]  Youwei Cheng,et al.  Kinetics of p-Xylene Liquid-Phase Catalytic Oxidation to Terephthalic Acid , 2005 .

[71]  H. N. Stephens.  OXIDATIONS IN THE BENZENE SERIES BY GASEOUS OXYGEN II. ALKYL BENZENES WITH TWO OR MORE CARBON ATOMS IN THE SIDE CHAIN , 1926 .

[72]  J. Howarth.  Oxidation of aromatic aldehydes in the ionic liquid [bmim]PF6 , 2000 .

[73]  H. G. Khorana.  The Chemistry of Carbodiimides. , 1953 .

[74]  Y. Kamiya.  Catalysis by cobalt and bromide ions in the autoxidation of alkylbenzenes in acetic acid , 1974 .

[75]  J. Rubim,et al.  Analysis of impurities in crude and highly-purified terephthalic acid by capillary electrophoresis , 2004 .

[76]  A. Baeyer,et al.  Einwirkung des Caro'schen Reagens auf Ketone , 1899 .

[77]  Chong Yan,et al.  Selective aerobic oxidation of para-xylene in sub- and supercritical water. Part 2. The discovery of better catalysts , 2011 .

[78]  P. Savage,et al.  Terephthlic Acid Synthesis in Supercritical Water , 2002 .

[79]  D. Busch,et al.  Liquid-Phase Oxidation of Toluene and p-toluic Acid under Mild Conditions: Synergistic Effects of Cobalt, Zirconium, Ketones, and Carbon Dioxide , 2008 .

[80]  Sang-Eon Park,et al.  New CO2 chemistry – Recent advances in utilizing CO2 as an oxidant and current understanding on its role , 2004 .

[81]  Y. Kamiya,et al.  The autoxidation of aromatic hydrocarbons catalyzed with cobaltic acetate in acetic acid solution: I. The oxidation of toluene , 1972 .

[82]  Kuo-Tseng Li,et al.  CoBr2-MnBr2 containing catalysts for catalytic oxidation of p-xylene to terephthalic acid , 2008 .

[83]  S. Jhung,et al.  Precipitation of Manganese in the p-Xylene Oxidation with Oxygen-Enriched Gas in Liquid Phase , 2002 .

[84]  S. Jhung.  Liquid Phase Oxidation of p-Xylene: Effects of Potassium with Various Reaction Conditions , 2002 .

[85]  C. Ritchie,et al.  An Examination of Structure‐Reactivity Relationships , 2007 .

[86]  J. Halpern.  General introduction—homogeneous catalysis of hydrogenation, oxidation and related reactions , 1968 .

[87]  P. Ratnasamy,et al.  Selective Oxidation of para-Xylene to Terephthalic Acid by μ3-Oxo-Bridged Co/Mn Cluster Complexes Encapsulated in Zeolite–Y , 2001 .

[88]  Qinbo Wang,et al.  Semicontinuous Studies on the Reaction Mechanism and Kinetics for the Liquid-Phase Oxidation of p-Xylene to Terephthalic Acid† , 2007 .

[89]  J. Hanotier,et al.  Effect of strong acids on the oxidation of alkylarenes by manganic and cobaltic acetates in acetic acid , 1973 .

[90]  J. E. McIntyre,et al.  The Historical Development of Polyesters , 2004 .

[91]  W. Partenheimer.  Chemistry of the oxidation of acetic acid during the homogeneous metal-catalyzed aerobic oxidation of alkylaromatic compounds , 2011 .

[92]  J. Clark,et al.  Mild, solvent-free oxidation of toluene and subsituted toluenes to their benzoic acids using carboxylic acid-promoted heterogeneous catalysis , 2002 .

[93]  S. Jhung,et al.  An advanced MC-type oxidation process — the role of carbon dioxide , 2002 .

[94]  B. Saha,et al.  N-Hydroxyphthalimides and Metal Cocatalysts for the Autoxidation of p-Xylene to Terephthalic Acid , 2004 .

[95]  K. R. Seddon,et al.  Paradigm confirmed: the first use of ionic liquids to dramatically influence the outcome of chemical reactions. , 2004, Organic letters.

[96]  W. Partenheimer.  Characterization of the reaction of cobalt(II) acetate, dioxygen and acetic acid, and its significance in autoxidation reactions , 1991 .

[97]  W. Vaughan,et al.  Oxidation of Hydrocarbons Catalyzed by Hydrogen Bromide - Summary , 1949 .

[98]  B. K. Das,et al.  Cobalt(III)-oxo cubane clusters as catalysts for oxidation of organic substrates , 2011 .

[99]  Kenneth R. Seddon,et al.  Ionic liquids. Green solvents for the future , 2000 .

[100]  Massimo Pisu,et al.  Kinetics of p‐xylene liquid‐phase catalytic oxidation , 1994 .

[101]  B. Saha,et al.  Low-bromide containing MC catalyst for the autoxidation of para-xylene , 2007 .

[102]  L. Csányi,et al.  Catalysis and Inhibition by Water during the Liquid-Phase Oxidation of Hydrocarbons , 1993 .

[103]  S. Sakaguchi,et al.  Recent progress in aerobic oxidation of hydrocarbons by N-hydroxyimides , 2006 .

[104]  J. Donaldson,et al.  Cobalt and Cobalt Compounds , 2005 .

[105]  Yong Gu,et al.  Scalable multi-objective optimization of industrial purified terephthalic acid (PTA) oxidation process , 2004, Comput. Chem. Eng..

[106]  P. Savage,et al.  Terephthalic acid synthesis at higher concentrations in high‐temperature liquid water. 1. Effect of oxygen feed method , 2009 .

[107]  M. Poliakoff,et al.  Is it Possible to Achieve Highly Selective Oxidations in Supercritical Water? Aerobic Oxidation of Methylaromatic Compounds , 2004 .

[108]  P. M. Heertjes,et al.  The Structure of Cobalt(II) Acetate and Cobalt(III) Acetate in Acetic Acid Solution , 1979 .

[109]  W. Partenheimer.  The effect of zirconium in metal/bromide catalysts during the autoxidation of p-xylene. Part I. Activation and changes in benzaldehyde intermediate formation , 2003 .

[110]  S. Sakaguchi,et al.  A New Strategy for the Preparation of Terephthalic Acid by the Aerobic Oxidation of p-Xylene using N-Hydroxyphthalimide as a Catalyst , 2001 .

[111]  T. Welton.  Ionic liquids in catalysis , 2004 .

[112]  K. Ingold.  Inhibition of the Autoxidation of Organic Substances in the Liquid Phase. , 1961 .