Skip to main content
SpringerLink
Log in

Progress in the research and development of p-xylene liquid phase oxidation process

  • Review Article
  • Published:
Frontiers of Chemical Engineering in China Aims and scope Submit manuscript

Abstract

The process of p-xylene liquid phase oxidation to produce purified terephthalic acid (PTA) involves a series of liquid phase radical reactions, chemical absorption, reactive crystallization, and evaporation. A commercial PTA production flow sheet includes a number of unit operations, which construct a complex process system. In this paper, a review of research and development (R&D) works on PTA process carried out in Zhejiang University during recent years is introduced. The works cover the oxidation and crystallization kinetics, gas-liquid mass transfer and evaporation, reactor modeling, database development, novel reactor design, process modeling, simulation, and optimization. The author emphasizes the viewpoint through this case study that chemical reaction engineering should be developed to process system engineering to extend its scope, and particular attention should be paid on reactor and process modeling.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Process Economics Program (PEP) Report 9E: Terephthalic Acid and Dimethyl Terephthalate. SRI Consulting, January 1997

  2. Process Economics Program (PEP) Report 9F: Terephthalic Acid. Marcos A C SRI Consulting, August 2005

  3. Suresh A, Sharma M, Sridhar T. Engineering aspects of industrial liquid-phase air oxidation of hydrocarbons. Ind Eng Chem Res, 2000, 39(11): 3,958–3,997

    Article  CAS  Google Scholar 

  4. Raghavendrachar P, Ramachandran S. Liquid-phase catalytic oxidation of p-xylene. Ind Eng Chem Res, 1992, 31: 453–462

    Article  CAS  Google Scholar 

  5. Partenheimer W. Methodology and scope of meta/bromide autoxidation of hydrocarbons. Catalysis Today, 1995, 23: 69–158

    Article  CAS  Google Scholar 

  6. Partenheimer W. A Chemical Model for the Amoco ‘MC’ Oxygenation Process to Produce Terephthalic Acid in “Catalysis of Organic Reactions”. Blackburn D W, ed. Marcel Dekker, Inc., 1990

  7. Partenheimer W. The complex synergy of water in the metal/bromide autoxidation of hydrocarbons caused by benzylic bromide formation. Adv Synth Catal, 2004, 346: 297–306

    Article  CAS  Google Scholar 

  8. Cincotti A., Orrù R, Cao G. Kinetics and related engineering aspects of catalytic liquid-phase oxidation of p-xylene to terephthalic acid. Catalysis Today, 1999, 52: 331–347

    Article  CAS  Google Scholar 

  9. Cao G, Pisu M, Morbidelli M. A lumped kinetic model for liquid-phase catalytic oxidation of p-xylene to terephthalic acid. Chem Eng Sci, 1994, 49(24): 5,775–5,788

    CAS  Google Scholar 

  10. Cao G, Servida A, Pisu M. Kinetics of p-xylene liquid-phase catalytic oxidation. AIChE J, 1994, 40(7): 1,156–1,166

    Article  CAS  Google Scholar 

  11. Cincotti A, Orrù R, Bori A. Effect of catalyst concentration and simulation of precipitation processes on liquid-phase catalytic oxidation of p-xylene to terephthalic acid. Chem Eng Sci, 1997, 52(21): 4,205–4,213

    CAS  Google Scholar 

  12. Li X. Toward process system engineering from chemical reaction engineering — The road of PTA process development. Chemical Reaction Engineering and Technology, 2005, 21(5): 385–391 (in Chinese)

    Google Scholar 

  13. Cheng Y W, Zhang L, Xie G, Li X. Experiment technique of p-xylene liquid phase catalytic oxidation. Chemical Reaction Engineering and Technology, 2003, 19(2): 182–187 (in Chinese)

    CAS  Google Scholar 

  14. Cheng Y W. Studies on hydrocarbon liquid phase catalytic oxidation in the MC process. Dissertation for the Doctoral Degree. Hangzhou: Zhejiang University, 2004 (in Chinese)

    Google Scholar 

  15. Wang L J, Li X, Xie G, Cheng Y W. Kinetic of p-xylene liquid phase catalytic oxidation (I): Mechanism and kinetic model. Journal of Chemical Industry and Engineering, 2003, 54(7): 946–952 (in Chinese)

    CAS  Google Scholar 

  16. Xie G, Li X, Niu J F. Kinetic of p-xylene liquid phase catalytic oxidation (II): Temperature effect. Journal of Chemical Industry and Engineering, 2003, 54(7): 1,013–1,016 (in Chinese)

    CAS  Google Scholar 

  17. Cheng Y W, Niu J F, Li X. Kinetic of p-xylene liquid phase catalytic oxidation (III): Catalyst effect. Journal of Chemical Industry and Engineering, 2004, 55(4): 580–585 (in Chinese)

    CAS  Google Scholar 

  18. Cheng Y W, Li X, Sima J. Kinetic of p-xylene liquid phase catalytic oxidation (IV): Kinetics for PX and solvent burning. Journal of Chemical Industry and Engineering, 2004, 55(11): 1,894–1,899 (in Chinese)

    CAS  Google Scholar 

  19. Wang Q B, Li X, Wang L J. Kinetics of p-xylene liquid phase catalytic oxidation to terephthalic acid. Ind Eng Chem Res, 2005, 44(2): 261–266

    Article  CAS  Google Scholar 

  20. Sima J, Li X, Xie G. The effect of reactant content on burning in the oxidation of p-xylene. Journal of Chemical Engineering of Chinese Universities, 2003, 17: 20–25 (in Chinese)

    Google Scholar 

  21. Wang Q B, Li X, Wang L J, Cheng Y W, Xie G. Effect of water content on the kinetics of p-xylene liquid-phase catalytic oxidation to terephthalic acid. Ind Eng Chem Res, 2005, 44(13): 4,518–4,522

    CAS  Google Scholar 

  22. Xie G, Sima J, Wang Q B. Effect of oxygen volume fraction on p-xylene liquid phase catalytic oxidation. Journal of Zhejiang University (Engineering Science), 2004, 38(8): 1,024–1,028 (in Chinese)

    CAS  Google Scholar 

  23. Wang L J. Modeling, control and optimization of p-xylene oxidation process. Dissertation for the Doctoral Degree. Hangzhou: Zhejiang University, 2005 (in Chinese)

    Google Scholar 

  24. Xie G. Development of the novel PX oxidation reactor and the related chemical engineering studies. Dissertation for the Doctoral Degree. Hangzhou: Zhejiang University, 2004 (in Chinese)

    Google Scholar 

  25. Wang Q B. Studies on p-xylene oxidation and reactive crystallization. Dissertation for the Doctoral Degree. Hangzhou: Zhejiang University, 2006 (in Chinese)

    Google Scholar 

  26. Wang Q B, Xu H B, Li X. Solid-liquid equilibria of 1,4-benzenedicarboxylic acid in binary acetic acid + water solvent mixtures in the temperature range from 433.2 to 513.2 K. J Chem Eng Data, 2005, 50(1): 258–260

    Article  CAS  Google Scholar 

  27. Wang Q B, Xu H B, Li X. Solubility of 4-carboxybenzaldehyde and 1,4-benzenedicarboxylic acid in N-methyl-2-pyrrolidone in the temperature range from 323.2 to 468.2 K. J Chem Eng Data, 2005, 50(1): 243–245

    Article  CAS  Google Scholar 

  28. Wang Q B, Xu H B, Li X. Solubilities of terephthalic acid in dimethyl sulfoxide + water and in N,N-dimethylformamide + water from 301.4 to 373.7 K. J Chem Eng Data, 2005, 50(2): 719–721

    Article  CAS  Google Scholar 

  29. Wang Q B, Xu H B, Li X. Relation between the critical radius and particle size distribution during Ostwald ripening. Journal of Material Science and Technology, 2004, 22: 80–81 (in Chinese)

    Article  Google Scholar 

  30. Cheng Y W, Li X, Wang L J, Wang Q B. The optimum ratio of Co/Mn in the liquid-phase catalytic oxidation of p-xylene to terephthalic acid. Ind Eng Chem Res, 2006, 45(12): 4,156–4,162

    Article  CAS  Google Scholar 

  31. Cheng Y W, Li X, Wang Q B, Wang L J. Effects of guanidine on the liquid-phase catalytic oxidation of p-xylene to terephthalic acid. Ind Eng Chem Res, 2005, 44(20): 7,756–7,760

    Article  CAS  Google Scholar 

  32. Xie G, Li X. Oxygen concentration distribution along the p-xylene oxidation reactor at oxygen-enriched condition. Petrochemical Technology, 2004, 33(7): 627–631 (in Chinese)

    CAS  Google Scholar 

  33. Wang Q B, Chen X J, Xie G. Simulating of p-xylene oxidation reactor at oxygen-enriched process. Petrochemical Technology, 2003, 32(11): 967–972 (in Chinese)

    CAS  Google Scholar 

  34. Wang Q B, Li X, Xu H B. Effect of gas-liquid mass transfer on p-xylene oxidation. Journal of Zhejiang University (Engineering Science), 2004, 38(11): 1,515–1,519

    CAS  Google Scholar 

  35. Wang Q B, Xie G, Li X. Control step analysis of p-xylene oxidation. Chemical Reaction Engineering and Technology, 2004, 20(4): 300–304 (in Chinese)

    Google Scholar 

  36. Dai W. Studies on PX oxidation kinetics and reactor cold model. Dissertation for the Master Degree. Hangzhou: Zhejiang University, 2004 (in Chinese)

    Google Scholar 

  37. Wang L Y. Measurement of flow and transport parameters in the slurry bubble column. Dissertation for the Master Degree. Hangzhou: Zhejiang University, 2006 (in Chinese)

    Google Scholar 

  38. Li X, Wang L J, Chen B, Wang L Y. A bubble column reactor with resistance internals. Chinese Patent, CN 200510061602.9

  39. Li X, Xie G. A bubble column oxidation apparatus used in production of terephthalic acid. Chinese Patent, CN 200310107889.5

  40. Li X, Wang L J, Chen B, Wang L Y. Apparatus for production of aromatic acids. Chinese Patent, CN 200520116535.1

  41. Chen B, Wang L Y, Li X. Studies on the bubble column equipped with resistance internals (I): Effects on liquid velocity distribution. Chemical Reaction Engineering and Technology, 2006, 22(4): 317–323 (in Chinese)

    CAS  Google Scholar 

  42. Wang L J, Wang L Y, Zhang Y, Zhou Q N, Li X. Studies on the bubble column equipped with resistance internals (II): Effects of the internals on gas-liquid mass transfer. Chemical Reaction Engineering and Technology, 2007, 23(2): 109–113 (in Chinese)

    CAS  Google Scholar 

  43. Wang L Y, Zhuang H J, Song J Z, Chen B, Li X. The measurement of local gas holdup under high superficial velocity in a bubble column. Chemical Reaction Engineering and Technology, 2006, 22(1): 1–6 (in Chinese)

    Google Scholar 

  44. Wang L Y, Zhuang H J, Chen B, Li X. Wavelet analysis of turbulent structure at high superficial velocity in bubble column. Journal of Chemical Industry and Engineering, 2006, 57(4): 738–743 (in Chinese)

    CAS  Google Scholar 

  45. Chen B. Studies on the internals of bubble column reactor. Dissertation for the Master Degree. Hangzhou: Zhejiang University, 2006 (in Chinese)

    Google Scholar 

  46. Xie G, Wang L J, Wang Q B. CSTR model for p-xylene oxidation reactor. Chemical Reaction Engineering and Technology, 2003, 19(4): 330–336 (in Chinese)

    Google Scholar 

  47. Wang Q B, Li X, Xie G. Modeling of p-xylene oxidation reactor-condenser. Journal of Zhejiang University (Engineering Science), 2004, 38(8): 1,029–1,034 (in Chinese)

    CAS  Google Scholar 

  48. Xie G, Li X. An axial dispersion model for evaporating bubble column reactor. Chinese J Chem Eng, 2004, 12(2): 214–220

    CAS  Google Scholar 

  49. Xie G, Dai W, Li X. Modeling and comparing for hydrocarbon evaporative oxidation reactors. Petrochemical Technology, 2003, 32: 827–829 (in Chinese)

    Google Scholar 

  50. Xie G, Li X. Three-region model for p-xylene oxidation reactor. Journal of Chemical Engineering of Chinese Universities, 2004, 18(4): 430–436 (in Chinese)

    CAS  Google Scholar 

  51. Li W X, Wang L J, Zhuang H J, Wang Q B, Li X. Models of reactor-crystallizer connected in series in p-xylene oxidation process. Chemical Reaction Engineering and Technology, 2005, 21(6): 481–486 (in Chinese)

    CAS  Google Scholar 

  52. Xiao X J, Wang L J, Ding G H, Li X. Liquid-liquid equilibria for the ternary system of water + acetic acid + propyl acetate. J Chem Eng Data, 2006, 51(2): 582–583

    Article  CAS  Google Scholar 

  53. Wang L J, Zhang H J, Li X. Thermodynamics of HAc-H2O-NBA system and simulation of the azeotropic process. Journal of Chemical Industry and Engineering, 2005, 56(7): 1,324–1,330 (in Chinese)

    Google Scholar 

  54. Wang L J, Li X, Zhang H J, Wang Q B. Mathematical modeling of p-xylene oxidation/crystallization/distillation coupling processes. Journal of Chemical Industry and Engineering, 2005, 56(8): 1,504–1,510 (in Chinese)

    CAS  Google Scholar 

  55. Wang L J, Zhang H J, Li X. Synthesis of p-xylene oxidation reactor network. Journal of Zhejiang University (Engineering Science), 2005, 39(9): 1,413–1,417 (in Chinese)

    CAS  Google Scholar 

  56. Cheng Y W, Li X. Comparison and analysis of p-xylene oxidation techniques. Petrochemical Technology, 2003, 32: 212–215 (in Chinese)

    Google Scholar 

  57. Li X, Wang L J, Cheng Y W, Xiao X J. Method and apparatus for production of terephthalic acid. Chinese Patent, CN 200410067358.2

Download references

Author information

Authors and Affiliations

  1. College of Material Science and Chemical Engineering, Zheijiang University, Hangzhou, 310027, China

    Wang Lijun, Cheng Youwei, Wang Qinbo & Li Xi

Authors
  1. Wang Lijun
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Cheng Youwei
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wang Qinbo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Li Xi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Li Xi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, L., Cheng, Y., Wang, Q. et al. Progress in the research and development of p-xylene liquid phase oxidation process. Front. Chem. Eng. China 1, 317–326 (2007). https://doi.org/10.1007/s11705-007-0058-9

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11705-007-0058-9

Keywords

Search

Navigation