Citation: Nor Aqilah Mohd Fadzil, Mohd Hasbi Ab. Rahim, Gaanty Pragas Maniam. A brief review of para-xylene oxidation to terephthalic acid as a model of primary C-H bond activation[J]. Chinese Journal of Catalysis, ;2014, 35(10): 1641-1652. doi: 10.1016/S1872-2067(14)60193-5 shu

A brief review of para-xylene oxidation to terephthalic acid as a model of primary C-H bond activation

1.
Faculty of Industrial Sciences & Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak, 26300 Gambang Kuantan, Pahang, Malaysi

Corresponding author: Mohd Hasbi Ab. Rahim,
Received Date: 20 May 2014
Available Online: 8 July 2014
Fund Project: This work was supported by Universiti Malaysia Pahang and the Ministry of Education, Malaysia for Exploratory Research Grant Scheme (ERGS) (RDU 120605) (ERGS) (RDU 120605)again Ministry of Education, Malaysia support for MyPhD funding aid (Nor Aqilah Mohd Fadzil). (Nor Aqilah Mohd Fadzil)

The oxidation of para-xylene to terephthalic acid has been commercialised as the AMOCO process (Co/Mn/Br) that uses a homogeneous catalyst of cobalt and manganese together with a corrosive bromide compound as a promoter. This process is conducted in acidic medium at a high temperature (175-225 ℃). Concerns over environmental and safety issues have driven studies to find milder oxidation reactions of para-xylene. This review discussed past and current progress in the oxidation of para-xylene process. The discussion concentrates on the approach of green chemistry including (1) using heterogeneous catalysts with promising high selectivity and mild reaction condition, (2) application of carbon dioxide as a co-oxidant, and (3) application of alternative promoters. The optimisation of para-xylene oxidation was also outlined.
- Heterogeneous catalyst,
- Optimisation,
- Oxidation,
- para-Xylene,
- Promoter,
- Terephthalic acid
1. [1]
  [1] Li M, Niu F, Zuo X, Metelski P D, Busch D H, Subramaniam B. Chem Eng Sci, 2013, 104: 93
2. [2]
  [2] Partenheimer W. Catal Today, 1995, 23: 69
3. [3]
  [3] Wang L J, Cheng Y W, Wang Q B, Li X. Front Chem Eng China, 2007, 1: 317
4. [4]
  [4] Giacomo C, Silber P. Ber Deutsch Chem Ges, 1912, 45: 38
5. [5]
  [5] Xiao Y, Zhang X Y, Wang Q B, Tan Z, Guo C C, Deng W, Liu Z G, Zhang H F. Chin Chem Lett, 2011, 22: 135
6. [6]
  [6] Stephens H N. J Am Chem Soc, 1926, 48: 2920
7. [7]
  [7] Scheirs J, Long T E. Modern Polyesters: Chemistry and Technology of Polyesters and Copolyesters. Chichester: Wiley, 2013. 67
8. [8]
  [8] Raghavendrachar P, Ramachandran S. Ind Eng Chem Res, 1992, 31: 453
9. [9]
  [9] Saffer A, Barker R S. GB Patent 807091. 1959
10. [10]
  [10] Whinfield J R, Dickson J T. GB Patent 578079. 1946
11. [11]
  [11] Saffer A, Barker R S. US Patent 2833816. 1958
12. [12]
  [12] Saffer A, Barker R S. US Patent 3089906. 1963
13. [13]
  [13] Landau R, Saffer A. Chem Eng Progr, 1968, 64: 20
14. [14]
  [14] Ghiaci M, Mostajeran M, Gil A. Ind Eng Chem Res, 2012, 51: 15821
15. [15]
  [15] Tomás R A F, Bordado J C M, Gomes J F P. Chem Rev, 2013, 113: 7421
16. [16]
  [16] Li K T, Li S W. Appl Catal A, 2008, 340: 271
17. [17]
  [17] Evans S, Lindsay Smith J R. J Chem Soc, Perkin Trans, 2000, 2: 1541
18. [18]
  [18] Shaabani A, Rahmati A. Catal Commun, 2008, 9: 1692
19. [19]
  [19] Gupta M, Paul S, Gupta R, Loupy A. Tetrahedron lett, 2005, 46: 4957
20. [20]
  [20] Poling B E, Prausnitz J M, O’Connell J P. The Properties of Gases and Liquids. New York: McGraw-Hill, 2001. 28
21. [21]
  [21] Savage P E. J Supercrit Fluids, 2009, 47: 407
22. [22]
  [22] Dunn J B, Savage P E. Ind Eng Chem Res, 2002, 41: 4460
23. [23]
  [23] Osada M, Savage P E. AIChE J, 2009, 55: 710
24. [24]
  [24] Garcia-Verdugo E, Venardou E, Thomas W B, Whiston K, Partenheimer W, Hamley P A, Poliakoff M. Adv Synth Catal, 2004, 346: 307
25. [25]
  [25] Garcia-Verdugo E, Fraga-Dubreuil J, Hamley P A, Thomas W B, Whiston K, Poliakoff M. Green Chem, 2005, 7: 294
26. [26]
  [26] Fraga-Dubreuil J, Poliakoff M. Pure Appl Chem, 2006, 78: 1971
27. [27]
  [27] Hamley P A, Ilkenhans T, Webster J M, Garcia-Verdugo E, Venardou E, Clarke M J, Auerbach R, Thomas W B, Whiston K, Poliakoff M. Green Chem, 2002, 4: 235
28. [28]
  [28] Chavan S A, Srinivas D, Ratnasamy P. J Catal, 2001, 204: 409
29. [29]
  [29] Sabater M J, Corma A, Domenech A, Forn’es V, Garcia H. Chem Commun, 1997: 1285
30. [30]
  [30] Hutchings G J. Chem Commun, 1999: 301
31. [31]
  [31] Falcon H, Campos-Martin J M, Al-Zahrani S M, Fierro J L G. Catal Commun, 2010, 12: 5
32. [32]
  [32] Hermans I, Peeters J, Jacobs P A. Top Catal, 2008, 50: 124
33. [33]
  [33] Frank C E. Chem Rev, 1950, 46: 155
34. [34]
  [34] Russell G A. J Chem Educ, 1959, 36: 111
35. [35]
  [35] Mayo F R. Acc Chem Res, 1968, 1: 193
36. [36]
  [36] Ichikawa Y, Yamashita G, Tokashiki M, Yamaji T. Ind Eng Chem, 1970, 62(4): 38
37. [37]
  [37] Fan J W, Zhang R Y. J Phys Chem A, 2006, 110: 7728
38. [38]
  [38] Guo Z, Liu B, Zhang Q H, Deng W P, Wang Y, Yang Y H. Chem Soc Rev, 2014, 43: 3480
39. [39]
  [39] Hronec M, Hrabe Z. Ind Eng Chem Prod Res Dev, 1986, 25: 257
40. [40]
  [40] Jacob C R, Varkey S P, Ratnasamy P. Appl Catal A, 1999, 182: 91
41. [41]
  [41] Tibbitt J M, Gong W H, Schammel W P, Hepfer R P, Adamian V, Brugge S P, Metelski P D, Zhou C X. WO Patent 133976 A2. 2007
42. [42]
  [42] Kesavan L, Tiruvalam R, Ab Rahim M H, bin Saiman M I, Enache D I, Jenkins R L, Dimitratos N, Lopez-Sanchez J A, Taylor S H, Knight D W, Kiely C J, Hutching S G J. Science, 2011, 331: 195
43. [43]
  [43] Ab Rahim M H, Forde M M, Jenkins R L, Hammond C, He Q, Dimitratos N, Lopez-Sanchez J A, Carley A F, Taylor S H, Willock D J, Murphy D M, Kiely C J, Hutching S G J. Angew Chem Int Ed, 2013, 52: 1280
44. [44]
  [44] Ab Rahim M H, Forde M M, Hammond C, Jenkins R L, Dimitratos N, Lopez-Sanchez J A, Carley A F, Taylor S H, Willock D J, Hutchings G J. Top Catal, 2013, 56: 1843
45. [45]
  [45] Deori K, Gupta D, Saha B, Awasthi S K, Deka S. J Mater Chem A, 2013, 1: 7091
46. [46]
  [46] Qin Z Z, Su T M, Jiang Y X, Ji H B, Qin W G. Chem Eng J, 2014, 242:414
47. [47]
  [47] Liu H L, Li Y W, Jiang H F, Vargas C, Luque R. Chem Commun, 2012, 48: 8431
48. [48]
  [48] Della Pina C, Falletta E, Rossi M. Chem Soc Rev, 2012, 41: 350
49. [49]
  [49] Khan N A, Kennedy E M, Dlugogorski B Z, Adesina A A, Stockenhuber M. Catal Commun, 2014, 53: 42
50. [50]
  [50] Impeng S, Khongpracha P, Warakulwit C, Jansang B, Sirijaraensre J, Ehara M, Limtrakul J. RSC Adv, 2014, 4: 12572
51. [51]
  [51] Liu H L, Chen G Z, Jiang H F, Li Y W, Luque R. ChemSusChem, 2012, 5: 1892
52. [52]
  [52] Sheehan R J. Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid. Wiley-VCH, 2002. 156
53. [53]
  [53] Shigeyasu M, Kusano N. US Patent 4160108. 1979
54. [54]
  [54] Seko M, Miyake T, Takeuchi H, Tanouchi M. US Patent 4230882A. 1980
55. [55]
  [55] Scott L S, Sommers R W. US Patent 158738. 1979
56. [56]
  [56] Kahsar K R, Schwartz D K, Medlin J W. J Am Chem Soc, 2014, 136: 520
57. [57]
  [57] Bramucci M G, McCutchen C M, Nagarajan V, Thomas S M. Google Patents, 2002
58. [58]
  [58] Bramucci M G, McCutchen C M, Nagarajan V, Thomas S M. US Patent 0170836. 2003
59. [59]
  [59] Robert R, Ratnasamy P. J Mol Catal A, 1995, 100: 93
60. [60]
  [60] Mki-Arvela P, Kumar N, Nasir A, Salmi T, Murzin D U. Ind Eng Chem Res, 2005, 44: 9376
61. [61]
  [61] Marimuthu A, Zhang J W, Linic S. Science, 2013, 339: 1590
62. [62]
  [62] Lee I, Delbecq F, Morales R, Albiter M A, Zaera F. Nat Mater, 2009, 8: 132
63. [63]
  [63] Wang Y, Zhang S J, Zhao Y X, Lin M. J Mol Catal A, 2014, 385:1
64. [64]
  [64] Yoo J S, Jhung S H, Lee K H, Park Y S. Appl Catal A, 2002, 223: 239
65. [65]
  [65] Zuo X B, Niu F H, Snavely K, Subramaniam B, Busch D H. Green Chem, 2010, 12: 260
66. [66]
  [66] Zuo X B, Subramaniam B, Busch D H. Ind Eng Chem Res, 2008, 47: 546
67. [67]
  [67] Park S E, Yoo J S. Stud Surf Sci Catal, 2004, 153: 303
68. [68]
  [68] Jhung S H, Park Y S, Lee K H, Chae J H, Yoo J S. WO Patent 037407Al. 2000
69. [69]
  [69] Raju G, Reddy B M, Park S E. Indian J Chem A, 2012, 51: 1315
70. [70]
  [70] Ali A M, Emanuelsson E A C, Patterson D A. Appl Catal B, 2010, 97: 168
71. [71]
  [71] Wang S B, Zhu Z H. Energy Fuels, 2004, 18: 1126
72. [72]
  [72] Yan N, Fu X Z, Chuang K T, Luo J L. J Power Sources, 2014, 254: 48
73. [73]
  [73] Ma Z, Zaera F. Encyclopedia of Inorganic and Bioinorganic Chemistry. Hoboken, New Jersey: John Wiley and Sons, 2014. 418
74. [74]
  [74] Pakhare D, Spivey J. Chem Soc Rev, 2014
75. [75]
  [75] Ansari M B, Park S E. Energy Environ Sci, 2012, 5: 9419
76. [76]
  [76] Brill W F. Ind Eng Chem, 1960, 52: 837
77. [77]
  [77] Tashiro Y, Iwahama T, Sakaguchi, Ishii Y. Adv Synth Catal, 2001, 343: 220
78. [78]
  [78] Coseri S. Catal Rev-Sci Eng, 2009, 51: 218
79. [79]
  [79] Xu H F, Tang R R, Gong N H, Liu C H, Zhou Y P. Progr Chem, 2007, 19: 1736
80. [80]
  [80] Saha B, Koshino N, Espenson J H. J Phys Chem A, 2004, 108: 425
81. [81]
  [81] Cheng Y W, Li X, Wang L J, Wang Q B. Ind Eng Chem Res, 2006, 45: 4156
82. [82]
  [82] Cao N, Chang E, Kaufman M. Senior Design Report. University of Pennsylvania, 2011
83. [83]
  [83] Zhang Y, Feng J, Lyu Z, Li X. Modern Res Catal, 2014, 3: 19
84. [84]
  [84] Horst A, Holmstrand H, Andersson P, Thornton B F, Wishkerman A, Keppler F, Gustafsson O. Geochim Cosmochim Acta, 2014, 125: 186
85. [85]
  [85] Schammel W P, Huggins B J, Kulzick M A, Nubel P O, Rabatic B M, Zhou C X, Adamian V A, Gong W H, Metelski P D, Miller J T. US Patent 8624055. 2014
86. [86]
  [86] Masuno M N, Smith P B, Hucul D A, Dumitrascu A, Brune K, Smith R L, Bissell J, Foster M. US Patent 0245316 A1. 2013
87. [87]
  [87] Pacheco J J, Davis M E. Proceedings of the National Academy of Sciences of USA. 2014. 345
88. [88]
  [88] Han I S, Kim M, Han C. Theor Appl Chem Eng, 2002, 8: 2989
89. [89]
  [89] Han I S, Kim M, Lee C H, Cha W, Ham B K, Jeong J H, Lee H, Chung C B, Han C. Korean J Chem Eng, 2003, 20: 977
90. [90]
  [90] Liu R L, Su H Y, Mu S J, Jia T, Chen W Q, Chu J. Chin J Chem Eng, 2004, 12: 234
91. [91]
  [91] Zhan Y, Su H Y, Liu R L, Chu J. Chin J Chem Eng, 2005, 13: 642
92. [92]
  [92] He H, Du W L, Qian F, Zhong W M. Ind Eng Chem Res, 2010, 49: 5683
93. [93]
  [93] Makareviciene V, Skorupskaite V, Levisauskas D, Andruleviciute V, Kazancev K. Int J Green Energy, 2014, 11: 527
94. [94]
  [94] Rasouli F, Aber S, Salari D, Khataee A R. Appl Clay Sci, 2014, 87: 228
95. [95]
  [95] Salman J M. Arabian J Chem, 2014, 7: 101
96. [96]
  [96] Roosta M, Ghaedi M, Daneshfar A, Darafarin S, Sahraei R, Purkait M K. Ultrason Sonochem, 2014, 21: 1441
97. [97]
  [97] Torrades F, García-Montao J. Dyes Pigments, 2014, 100: 184
98. [98]
  [98] Wang S, Liu H P, Zhang Y, Yu J, Yuan W. Appl Mechanics Mater, 2014, 464: 77
99. [99]
  [99] Pasma S A, Daik R, Maskat M Y, Hassan O. Int J Polym Sci, 2013, 10:1
100. [100]
  [100] Krbahti B K, Rauf M A. Chem Eng J, 2008, 136: 25
101. [101]
  [101] Jeganathan P M, Venkatachalam S, Karichappan T, Ramasamy S. Preparative Biochem Biotechnol, 2014, 44: 56
102. [102]
  [102] Sharif K M, Rahman M M, Azmir J, Mohamed A, Jahurul M H A, Sahena F, Zaidul I S M. J Food Eng, 2014, 124: 105
103. [103]
  [103] Grilc M, Likozar B, Levec J. Appl Catal B, 2014, 150-151: 275
104. [104]
  [104] Mujtaba A, Ali M, Kohli K. Chem Eng Res Des, 2014, 92: 156
1. [1]
  Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
2. [2]
  Jia-Cheng Hou , Hong-Tao Ji , Yu-Han Lu , Jia-Sheng Wang , Yao-Dan Xu , Yan-Yan Zeng , Wei-Min He . Sustainable and practical semi-heterogeneous photosynthesis of 5-amino-1,2,4-thiadiazoles over WS₂/TEMPO. Chinese Chemical Letters, 2024, 35(8): 109514-. doi: 10.1016/j.cclet.2024.109514
3. [3]
  Xiaoxue Li , Hongwei Zhou , Rongrong Qian , Xu Zhang , Lei Yu . A concise synthesis of Se/Fe materials for catalytic oxidation reactions of anthracene and polyene. Chinese Chemical Letters, 2025, 36(3): 110036-. doi: 10.1016/j.cclet.2024.110036
4. [4]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
5. [5]
  Chen Lian , Si-Han Zhao , Hai-Lou Li , Xinhua Cao . A giant Ce-containing poly(tungstobismuthate): Synthesis, structure and catalytic performance for the decontamination of a sulfur mustard simulant. Chinese Chemical Letters, 2024, 35(10): 109343-. doi: 10.1016/j.cclet.2023.109343
6. [6]
  Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H₄PMo₁₁VO₄₀ catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298
7. [7]
  Ruonan Guo , Heng Zhang , Changsheng Guo , Ningqing Lv , Beidou Xi , Jian Xu . Degradation of neonicotinoids with different molecular structures in heterogeneous peroxymonosulfate activation system through different oxidation pathways. Chinese Chemical Letters, 2024, 35(9): 109413-. doi: 10.1016/j.cclet.2023.109413
8. [8]
  Yanling Yang , Zhenfa Ding , Huimin Wang , Jianhui Li , Yanping Zheng , Hongquan Guo , Li Zhang , Bing Yang , Qingqing Gu , Haifeng Xiong , Yifei Sun . Dynamic tracking of exsolved PdPt alloy/perovskite catalyst for efficient lean methane oxidation. Chinese Chemical Letters, 2024, 35(4): 108585-. doi: 10.1016/j.cclet.2023.108585
9. [9]
  Hao WANG , Kun TANG , Jiangyang SHAO , Kezhi WANG , Yuwu ZHONG . Electro-copolymerized film of ruthenium catalyst and redox mediator for electrocatalytic water oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2193-2202. doi: 10.11862/CJIC.20240176
10. [10]
  Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
11. [11]
  Meng Wang , Yan Zhang , Yunbo Yu , Wenpo Shan , Hong He . High-temperature calcination dramatically promotes the activity of Cs/Co/Ce-Sn catalyst for soot oxidation. Chinese Chemical Letters, 2025, 36(1): 109928-. doi: 10.1016/j.cclet.2024.109928
12. [12]
  Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
13. [13]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
14. [14]
  Wenjing Dai , Lan Luo , Zhen Yin . Interface reconstruction of hybrid oxide electrocatalysts for seawater oxidation. Chinese Journal of Structural Chemistry, 2025, 44(3): 100442-100442. doi: 10.1016/j.cjsc.2024.100442
15. [15]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
16. [16]
  Yang Yang , Jing-Li Luo , Xian-Zhu Fu . Water-oxidation intermediates enabling electrochemical propylene epoxidation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100269-100269. doi: 10.1016/j.cjsc.2024.100269
17. [17]
  Gu Gong , Mengzhu Li , Ning Sun , Ting Zhi , Yuhao He , Junan Pan , Yuntao Cai , Longlu Wang . Versatile oxidized variants derived from TMDs by various oxidation strategies and their applications. Chinese Chemical Letters, 2024, 35(6): 108705-. doi: 10.1016/j.cclet.2023.108705
18. [18]
  Erzhuo Cheng , Yunyi Li , Wei Yuan , Wei Gong , Yanjun Cai , Yuan Gu , Yong Jiang , Yu Chen , Jingxi Zhang , Guangquan Mo , Bin Yang . Galvanostatic method assembled ZIFs nanostructure as novel nanozyme for the glucose oxidation and biosensing. Chinese Chemical Letters, 2024, 35(9): 109386-. doi: 10.1016/j.cclet.2023.109386
19. [19]
  Zhipeng Wan , Hao Xu , Peng Wu . Selective oxidation using in-situ generated hydrogen peroxide over titanosilicates. Chinese Journal of Structural Chemistry, 2024, 43(6): 100298-100298. doi: 10.1016/j.cjsc.2024.100298
20. [20]
  Huangjie Lu , Yingzhe Du , Peng Lin , Jian Lin . Separation of americium from lanthanides based on oxidation state control. Chinese Journal of Structural Chemistry, 2024, 43(10): 100344-100344. doi: 10.1016/j.cjsc.2024.100344

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(360)
HTML views(29)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142