Skip to main content
SpringerLink
Log in

Catalytic Oxidation of Oleic Acid in Supercritical Carbon Dioxide Media with Molecular Oxygen

  • Original Paper
  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

Oxidation of oleic acid was performed over various ordered porous catalysts containing transition metal in supercritical carbon dioxide (scCO2) media with molecular oxygen. Oleic acid was completely decomposed into mono- and dicarboxylic acids over porous catalysts, viz., mesoporous molecular sieves (CrMCM-41, MnMCM-41, CoMCM-41) and microporous molecular sieves (CrAPO-5, CoMFI, MnMFI) using scCO2 at 353 K for 8 h. Among the different catalysts studied, microporous and mesoporous catalysts containing chromium, in presence of scCO2 showed high distribution of azelaic and pelargonic acids as compared to their analogs containing cobalt or manganese. The presence of scCO2 medium with the catalysts increased the distribution of azelaic and pelargonic acids. The effect of CO2 pressure, reaction temperature and reaction time on oxidation of oleic acid over CrMCM-41 was also investigated. Additionally it is noticed that the catalyst can be recycled with negligible loss of catalytic activity.

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

Fig. 1
Fig. 2
Fig. 3
Scheme 1

Similar content being viewed by others

References

  1. Biermann U, Friedt W, Lang S, Lühs W, Machmüller G, Metzger JO, Klaas MR, Schäfer HJ, Schneider MP (2000) Angew Chem Int Ed 39:2206

    Article  CAS  Google Scholar 

  2. Hill K (2000) Pure Appl Chem 72:1255

    Article  CAS  Google Scholar 

  3. Johnson RW (1989) Dibasic acids. In: Johnson RW, Fritz E (eds) Fatty acids in industry. Marcel Dekker, New York, pp 327–350

    Google Scholar 

  4. Garti N, Avni E (1981) J Am Oil Chem Soc 58:840

    Article  CAS  Google Scholar 

  5. Nakano Y, Foglia TA (1982) J Am Oil Chem Soc 59:163

    Article  CAS  Google Scholar 

  6. Fujitani K, Nakazawa M (1988) A process for the preparation of carboxylic acid. Japanese Patent 63-93,746 to New Japan Chemical Ltd, 25 April 1998

  7. Klaas MR, Bavaj P, Warwel S (1995) Fat Sci Technol 97:359

    Google Scholar 

  8. Turnwald SE, Lorier MA, Wright LJ, Mucalo MR (1998) J Mater Sci Lett 17:1305

    Article  CAS  Google Scholar 

  9. Zimmermann F, Meux E, Mieloszynski J-L, Lecuire J-M, Oget N (2005) Tetrahedron Lett 46:3201

    Article  CAS  Google Scholar 

  10. Ioo TL, Mizukami F, Niwa S (1999) J Oil Palm Res 11:53

    Google Scholar 

  11. Antonelli E, D’Aloisio R, Gambaro M, Fiorani T, Venturello C (1998) J Org Chem 63:7190

    Article  CAS  Google Scholar 

  12. Oakley MA, Woodward S, Coupland K, Parker D, Temple-Heald C (1999) J Mol Catal A Chem 150:105

    Article  CAS  Google Scholar 

  13. Santacesaria E, Ambrosio M, Sorrentino A, Tesser R, Di Serio M (2003) Catal Today 79–80:59

    Article  Google Scholar 

  14. Noureddini H, Kanabur M (1999) J Am Oil Chem Soc 76:305

    Article  CAS  Google Scholar 

  15. Rebrovic L (1993) Catalyzed process for oxidation of ozonides of unsaturates to carboxylic acids. WO 93/05007

  16. Taguchi A, Schüth F (2005) Micropor Mesopor Mater 77:1

    Article  CAS  Google Scholar 

  17. Mbaraka IK, Shanks BH (2006) J Am Oil Chem Soc 83:79

    Article  CAS  Google Scholar 

  18. Anastas PT, Bartlett LB, Kirchhoff MM, Williamson TC (2000) Catal Today 55:11

    Article  CAS  Google Scholar 

  19. Oatkes RS, Clifford AA, Rayner CM (2001) J Chem Soc Perkin Trans 1:917

    Article  Google Scholar 

  20. Leitner W (2002) Acc Chem Res 35:746

    Article  CAS  Google Scholar 

  21. Beckman EJ (2004) J Supercrit Fluids 28:121

    Article  CAS  Google Scholar 

  22. Matsuda T, Harada T, Nakamura K (2005) Curr Org Chem 9:299

    Article  CAS  Google Scholar 

  23. Jessop PG, Subramaniam B (2007) Chem Rev 107:2666

    Article  CAS  Google Scholar 

  24. Ciriminna R, Carraro ML, Campestrini S, Pagliaro M (2008) Adv Synth Catal 350:221

    Article  CAS  Google Scholar 

  25. Sakthivel A, Dapurkar SE, Selvam P (2003) Appl Catal A Gen 246:283

    Article  CAS  Google Scholar 

  26. Kornatowski J, Zadrozna G, Rozwadowski M, Zibrowius B, Marlow F, Lercher JA (2001) Chem Mater 13:4447

    Article  CAS  Google Scholar 

  27. Robson H (ed) (2001) Verified synthesis of zeolitic materials, 2nd edn. Elsevier, Amsterdam

    Google Scholar 

  28. Beck JS, Vartuli JS, Roth WJ, Leonowicz ME, Kresge CT, Schmitt KD, Chu CT-W, Olson DH, Sheppard EW, McCullen SB, Higgins JB, Schlenker JL (1992) J Am Chem Soc 114:10834

    Article  CAS  Google Scholar 

  29. Treacy MMJ, Higgins JB (eds) (2001) Collection of simulated XRD patterns for zeolites. Elsevier, Amsterdam

    Google Scholar 

  30. Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquerol J, Siemieniewska T (1985) Pure Appl Chem 57:603

    Article  CAS  Google Scholar 

  31. Weckhuysen BM, Wachs IE, Schoonheydt RA (1996) Chem Rev 96:3327

    Article  CAS  Google Scholar 

  32. Zhu Z, Chang Z, Kevan L (1999) J Phys Chem B 103:2680

    Article  CAS  Google Scholar 

  33. Sakthivel A, Selvam P (2002) J Catal 211:134

    CAS  Google Scholar 

  34. Dapurkar SE, Sakthivel A, Selvam P (2003) New J Chem 27:1184

    Article  CAS  Google Scholar 

  35. Wang Y, Ohishi Y, Shishido T, Zhang Q, Yang W, Guo Q, Wan H, Takehira K (2003) J Catal 220:347

    Article  CAS  Google Scholar 

  36. El Haskouri J, Cabrera S, Gómez-Garcia SJ, Guillem C, Latorre J, Beltrán A, Beltrán D, Marcos MD, Amorós P (2004) Chem Mater 16:2805

    Article  CAS  Google Scholar 

  37. Zhang Q, Wang Y, Itsuki S, Shishido T, Takehira K (2002) J Mol Catal A Chem 188:189

    Article  CAS  Google Scholar 

  38. Lempers HEB, Sheldon RA (1998) J Catal 175:62

    Article  CAS  Google Scholar 

  39. Wang X, Venkataramanan NS, Kawanami H, Ikushima Y (2007) Green Chem 9:1352

    Article  CAS  Google Scholar 

  40. Chatterjee M, Ikushima Y, Hakuta Y, Kawanami H (2006) Adv Synth Catal 348:1580

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This work was financially supported by the Japan Society for the Promotion of Science (JSPS). S.E. Dapurkar is grateful to JSPS.

Author information

Authors and Affiliations

  1. Research Center for Compact Chemical Process, National Institute of Advanced Industrial Science and Technology (AIST), 4-2-1 Nigatake, Miyagino-Ku, Sendai, 983-8551, Japan

    Sudhir E. Dapurkar, Hajime Kawanami, Toshirou Yokoyama & Yutaka Ikushima

Authors
  1. Sudhir E. Dapurkar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hajime Kawanami
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Toshirou Yokoyama
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yutaka Ikushima
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Sudhir E. Dapurkar or Hajime Kawanami.

Additional information

Note that the term “Supercritical” in this paper is used for a reaction mixture exceeding the critical point of the solvent, despite several phases.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 167 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dapurkar, S.E., Kawanami, H., Yokoyama, T. et al. Catalytic Oxidation of Oleic Acid in Supercritical Carbon Dioxide Media with Molecular Oxygen. Top Catal 52, 707–713 (2009). https://doi.org/10.1007/s11244-009-9212-6

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-009-9212-6

Keywords

Search

Navigation