Skip to main content
SpringerLink
Log in

Determination of Oxidation of Methyl Ricinoleates

  • Original Paper
  • Published:
Journal of the American Oil Chemists' Society

Abstract

Ricinoleate esters have desirable properties as biolubricants, but their oxidative stability has been questioned. To systematically study the stability of ricinoleate ester and its derivative, methyl esters of castor oil were prepared and methyl ricinoleate was isolated by solvent partitioning. Methyl 12-acetyl ricinoleate was synthesized from the methyl ricinoleate by interesterification with excess methyl acetate and was then purified by solvent partitioning. The rates of oxidation of methyl linoleate, methyl oleate and the two ricinoleate esters were measured by oxidation of lipid dispersed on glass beads under three temperatures (40–80 °C). The relative amounts of the unoxidized methyl esters were determined periodically by gas chromatography, and the peroxide value of the oils was also determined. The oxidation rates were determined as the peroxide value increase rate, as well as the ester disappearance rate, and the stability of the various esters was compared. Overall, methyl ricinoleate was much more oxidatively stable than methyl oleate at mildly elevated temperatures, and the acetylation of the hydroxyl group on the 12th carbon decreased the stability.

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
Fig. 4

Similar content being viewed by others

References

  1. Knothe G (2008) “Designer” biodiesel: optimizing fatty ester composition to improve fuel propertied. Energy Fuels 22:1358–1364

    Article  CAS  Google Scholar 

  2. Moser BR (2009) Comparative oxidative stability of fatty acid alkyl esters by accelerated methods. J Am Oil Chem Soc 86:699–706

    Article  CAS  Google Scholar 

  3. Yao L, Hammond EG, Wang T, Bhuyan S, Sundararajann S (2010) Synthesis and physical properties of potential biolubricants based on ricinoleic acid. J Am Oil Chem Soc 87:937–946

    Article  CAS  Google Scholar 

  4. Ogunniyi DS (2006) Castor oil: a vital industrial raw material. Bioresour Technol 97:1086–1091

    Article  CAS  Google Scholar 

  5. Conceicao MM, Fernandes VJ Jr, Araujo AS, Farias MF, Santos IMG, Souza AG (2007) Thermal and oxidative degradation of castor oil biodiesel. Energy Fuels 21:1522–1527

    Article  CAS  Google Scholar 

  6. Araújo SV, Luna FMT, Rola EM Jr, Azevedo DCS, Cavalcante CL Jr (2009) A rapid method for evaluation of the oxidation stability of castor oil FAME: influence of antioxidant type and concentration. Fuel Process Technol 90:1272–1277

    Article  Google Scholar 

  7. Tekin A, Hammond EG (2004) Products of the surface oxidation of methyl linoleate. J Am Oil Chem Soc 81:481–485

    Article  CAS  Google Scholar 

  8. Slawson V, Adamson AW, Mead JF (1973) Autoxidation of polyunsaturated fatty esters on silica. Lipids 8:129–134

    Article  CAS  Google Scholar 

  9. Wu G-S, Stein RS, Mead JF (1977) Autoxidation of fatty acid monolayers adsorbed on silica gel, II: rates and products. Lipids 12:971–978

    Article  CAS  Google Scholar 

  10. Porter WL, Levasseur LA, Jeffers JI, Henick AS (1971) UV spectrophotometry of autoxidized lipid monolayers while on silica gel. Lipids 6:16–25

    Article  CAS  Google Scholar 

  11. Wu GS, Mead JF (1977) Autoxidation of fatty acid monolayers adsorbed on silica gel, I: nature of adsorbtion sites. Lipids 12:965–970

    Article  CAS  Google Scholar 

  12. Togashi HJ, Heniek AS, Koch RB (1961) The oxidation of lipids in thin films. J Food Sci 26:186–191

    Article  CAS  Google Scholar 

  13. Wu G-S, Stein RA, Mead JF (1978) Autoxidation of fatty acid monolayers on silica gel: III effect of saturated fatty acids and cholesterol. Lipids 13:517–524

    Article  CAS  Google Scholar 

  14. Porter WL, Levasseur LA, Henick AS (1972) Effects of surface concentration, metals and acid synergists on autoxidation of linoleic acid on monolayers on silica. Lipids 7:699–709

    Article  CAS  Google Scholar 

  15. Koprucuoglu Y, Calkoglu E, Tekin A, Hammond EG (2011) Effect of some transition metals on the monolayer oxidation of methyl linoleate. J Am Oil Chem Soc 88:1845–1848

    Article  CAS  Google Scholar 

  16. Wong WD, Hammond EG (1977) Analysis of oleate and linoleate hydroperoxides in an oxidized ester mixtures. Lipids 12:475–479

    Article  CAS  Google Scholar 

  17. Fatemi SH, Hammond EG (1980) Analysis of oleate, linoleate and linolenate hydroperoxides in oxidized ester mixtures. Lipids 15:379–385

    Article  CAS  Google Scholar 

  18. Palacios LE, Wang T (2005) Egg-yolk lipid fractionation and lecithin characterization. J Am Oil Chem Soc 82:571–578

    Article  CAS  Google Scholar 

  19. Spruyt JP (1955) Accelerated stability test for vitamin A in oils and fats by means of surface-enlarging at room temperature. J Am Oil Chem Soc 32:197–200

    Article  CAS  Google Scholar 

  20. Berdeaux O, Christie WW, Gunstone FD, Sebeduio JL (1997) Large scale synthesis of methyl cis-9, trans-11-octadecadienolate from methyl ricinoleate. J Am Oil Chem Soc 74:1011–1015

    Article  CAS  Google Scholar 

  21. AOCS (2005) Official methods and recommended practices of the American Oil Chemists’ Society, Urbana

  22. Yao L, Hammond EG, Wang T (2010) Synthesis and physical properties of ricinoleate esters that are potential biolubricants. J Am Oil Chem Soc 87:937–945

    Article  CAS  Google Scholar 

  23. Knothe G, Cermak SC, Evangelista RL (2012) Methyl esters from vegetable oils with hydroxy fatty acids: comparison of lesquerella and castor methyl esters. Fuel 96:535–540

    Article  CAS  Google Scholar 

  24. Cvengroš J, Paligová J, Cvengrošova Z (2006) Properties of alkyl esters base on castor oil. Eur J Lipid Sci Technol 108:629–635

    Article  Google Scholar 

  25. Berman P, Nizri S, Wiesman Z (2011) Castor oil biodiesel and its blends as alternative fuel. Biomass Bioenergy 35:2861–2866

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Food Science and Human Nutrition, Iowa State University, 2312 Food Sciences Building, Ames, IA, 50011-1061, USA

    Tong Wang, Show-ling Lee, Earl Hammond & Linxing Yao

  2. Petrobras SA. Research Center, Lubricants and Special Products, Rio De Janeiro, RJ, Brazil

    José André C. da Silva

Authors
  1. Tong Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Show-ling Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. José André C. da Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Earl Hammond
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Linxing Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tong Wang.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, T., Lee, Sl., da Silva, J.A.C. et al. Determination of Oxidation of Methyl Ricinoleates. J Am Oil Chem Soc 92, 871–880 (2015). https://doi.org/10.1007/s11746-015-2649-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-015-2649-9

Keywords

Search

Navigation