Skip to main content
SpringerLink
Log in

Glycerolysis of Soybean Oil with Crude Glycerol Containing Residual Alkaline Catalysts from Biodiesel Production

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

Abstract

The glycerolysis reaction of soybean oil was evaluated using crude glycerol obtained from the transesterification of soybean oil with methanol, catalyzed by sodium methoxide and sodium hydroxide, without any purification step other than the methanol removal. Crude glycerol with the lower content of remaining inorganic catalyst produced the highest concentration of monoglycerides (about 42%). The effect of the addition of water on the glycerolysis reaction was analyzed, evidencing a low formation rate of products in the first stages of the reaction due to the transformation of the inorganic catalyst to soaps, which are weaker bases. The sample of crude glycerol that led to the best results was evaluated at several temperatures. It was observed that the reaction with crude glycerol exhibits a lower formation rate of monoglycerides at low temperatures (160 and 180 °C) compared with the reaction with pure glycerol and catalyzed with NaOH. This behavior was explained by the lower activity of the soaps present in the crude glycerol respect to the inorganic base. Above 200 °C the reaction is very fast and the monoglycerides formed are consumed to produce diglycerides.

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
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Duane TJ, Katherine AT (2007) The glycerin glut: options for the value-added conversion of crude glycerol resulting from biodiesel production. Environ Prog 26:338–348

    Article  Google Scholar 

  2. Pagliaro M, Rossi M (2008) The future of glycerol. New uses of a versatile raw material. RSC, Cambridge

    Google Scholar 

  3. Noureddini H, Harkey D, Gutsman M (2004) A continuous process for the glycerolysis of soybean oil. J Am Oil Chem Soc 8:203–207

    Article  Google Scholar 

  4. Wolfson A, Litvak G, Dlugy C, Shotland Y, Tavor D (2009) Employing crude glycerol from biodiesel production as an alternative green reaction medium. Ind Crop Prod 30:78–81

    Article  CAS  Google Scholar 

  5. Elfman-Börjesson I, Härröd M (1999) Synthesis of monoglycerides by glycerolysis of rapeseed oil using immobilized lipase. J Am Oil Chem Soc 76:701–707

    Article  Google Scholar 

  6. Lin KF (2005) Paints, varnishes, and related products. In: Shahidi F (ed) Bailey’s industrial oil and fat products. Wiley, Hoboken, pp 319–349

    Google Scholar 

  7. Sonntag N (1982) Glycerolysis of fats and methyl esters-status, review and critique. J Am Oil Chem Soc 59:795A–802A

    Article  CAS  Google Scholar 

  8. Kaufman V, Garti N (1982) Organic reactions in emulsions-preparation of glycerol and polyglycerol esters of fatty acids by transesterification reaction. J Am Oil Chem Soc 59:471–474

    Article  CAS  Google Scholar 

  9. Chetpattananondh P, Tongurai C (2008) Synthesis of high purity monoglycerides from crude glycerol and palm stearin. Songklanakarin J Sci Technol 30:515–521

    Google Scholar 

  10. Ma F, Hanna MA (1999) Biodiesel production: a review. Bioresour Technol 70:1–15

    Article  CAS  Google Scholar 

  11. Vicente G, Martínez M, Aracil J (2004) Integrated biodiesel production: a comparison of different homogeneous catalysts systems. Bioresour Technol 92:297–305

    Article  CAS  Google Scholar 

  12. BS EN 14103:2003 (2003) Fat and oil derivatives-fatty acid methyl esters (FAME)-determination of ester and linolenic acid methyl ester contents. European Committee for Standardization (CEN), Brussels

  13. ASTM D 6584-07 (2007) Standard test method for determination of free and total glycerin in b-100 biodiesel methyl esters by gas chromatography. American Society for Testing and Materials, West Conshohocken

  14. Brüschweiler H, Dieffenbacher A (1991) Determination of mono- and DG by capillary gas chromatography—results of a collaborative study and the standardized method. Pure Appl Chem 63:1153–1162

    Article  Google Scholar 

  15. Van Gerpen J, Shanks B, Pruszko R (2004) Biodiesel analytical methods. National Renewable Energy Laboratory, Colorado

    Book  Google Scholar 

  16. ASTM E 203-08 (2008) Standard test method for water using volumetric Karl Fischer titration. American Society for Testing and Materials, West Conshohocken

Download references

Acknowledgment

Authors thank the Ministerio de Agricultura y Desarrollo Rural de Colombia (Proyecto de Transición de la Agricultura-PTA) and the University of Antioquia (programa Estrategia de Sostenibilidad de Grupos) for financial support.

Author information

Authors and Affiliations

  1. Applied Physical–Chemical Processes Group, University of Antioquia, Calle 62 No. 52–59, A.A. 1226, Medellín, Colombia

    David A. Echeverri, Fernando Cardeño & Luis A. Rios

Authors
  1. David A. Echeverri
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fernando Cardeño
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Luis A. Rios
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Luis A. Rios.

About this article

Cite this article

Echeverri, D.A., Cardeño, F. & Rios, L.A. Glycerolysis of Soybean Oil with Crude Glycerol Containing Residual Alkaline Catalysts from Biodiesel Production. J Am Oil Chem Soc 88, 551–557 (2011). https://doi.org/10.1007/s11746-010-1688-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-010-1688-5

Keywords

Search

Navigation