Skip to main content
SpringerLink
Log in

Counter-Current Carbon Dioxide Purification of Partially Deacylated Sunflower Oil

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

Abstract

A liquid carbon dioxide counter-current fractionation method was developed to remove by-product fatty acid propyl esters (FAPEs) from the reaction mixture after the partial deacylation of sunflower oil. The fractionation column was 1.2 m long and separations were done at 25 °C and 8.27 MPa. Several solvent to feed ratios (S:FR) (i.e., 7.6, 15.2, 30.3 and 60.6 g/g) and feed rates (FR) (i.e., 1, 2, 2.5, 3 and 4 mL/min) at a constant S:FR of 15.2 were examined. Raffinate purity (i.e., percentage glycerides) and extract purity (i.e., percentage FAPEs) were both monitored. Percentage glycerides in both the raffinate and the extract increased with S:FR. The raffinate contained ca. 83, 97, 100 and 100% glycerides at S:FRs of 7.6, 15.2, 30.3 and 60.6, respectively. The percentage glycerides in the extracts were ca. 3, 4, 8 and 17%, respectively. With the S:FR held constant at 15.2, the raffinate purity peaked at ca. 99% glycerides at a FR of 2.5 mL/min and the extract at this FR contained ca. 96% FAPEs. The optimal S:FR and FR determined from the experimental assays was applied to large batches in both a semi-continuous feed mode, and later in a continuous feed mode, which gave raffinates of 99.3 and 98.1% glycerides, respectively, and extracts of 97.3 and 97.2% FAPEs, respectively.

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. Compton DL, Laszlo JA, Berhow MA (2000) Lipase-catalyzed synthesis of ferulate esters. J Am Oil Chem Soc 77:513–519

    Article  CAS  Google Scholar 

  2. Compton DL, King JW (2001) Lipase-catalyzed synthesis of triolein-based sunscreens in supercritical CO2. J Am Oil Chem Soc 78:43–47

    Article  CAS  Google Scholar 

  3. Laszlo JA, Compton DL, Eller FJ, Taylor SL, Isbell TA (2003) Packed-bed bioreactor synthesis of feruloylated monoacyl- and diacylglycerols: clean production of a “green” sunscreen. Green Chem 5:382–386

    Article  CAS  Google Scholar 

  4. Compton DL, Laszlo JA (2000) Sunscreens from vegetable oil and plant phenols. US Patent 6346236

  5. Warner K, Laszlo JA (2005) Addition of ferulic acid, ethyl ferulate, and feruloylated monoacyl- and diacylglycerols to salad oils and frying oils. J Am Oil Chem Soc 82:647–652

    Article  CAS  Google Scholar 

  6. Laszlo JA, Compton DL (2006) Enzymatic glycerolysis and transesterification of soybean oil for enhanced production of feruloylated mono- and diacylglycerols. J Am Oil Chem Soc 83:765–770

    Article  CAS  Google Scholar 

  7. Compton DL, Laszlo JA, Eller FJ, Taylor SL (2008) Purification of 1,2-diacylglycerols from vegetable oils: comparison of molecular distillation and CO2 extraction. Ind Crops Prod 28:113–121

    Article  CAS  Google Scholar 

  8. Brunner G (1998) Industrial process development: countercurrent multistage gas extraction (SFE) processes. J Supercrit Fluids 13:283–301

    Article  CAS  Google Scholar 

  9. Nilsson WB, Gauglitz EJ Jr, Hudson JK, Stout VF, Spinelli J (1988) Fractionation of menhaden oil ethyl esters using supercritical fluid CO2. J Am Oil Chem Soc 65:109–117

    Article  CAS  Google Scholar 

  10. Perretti G, Motori A, Bravi E, Favati F, Montanari L, Fantozzi P (2007) Supercritical carbon dioxide fractionation of fish oil fatty acid ethyl esters. J Supercrit Fluids 40:349–353

    Article  CAS  Google Scholar 

  11. Vazquez L, Torres CF, Fornari T, Senorans FJ, Reglero G (2007) Recovery of squalene from vegetable oil sources using countercurrent supercritical carbon dioxide extraction. J Supercrit Fluids 40:59–66

    Article  CAS  Google Scholar 

  12. Vazquez L, Fornari T, Senorans FJ, Reglero G, Torres CF (2008) Supercritical carbon dioxide fractionation of nonesterified alkoxyglycerols obtained from shark liver oil. J Agric Food Chem 56:1078–1083

    Article  CAS  Google Scholar 

  13. King JW, Sahle-Demessie E, Temelli F, Teel JA (1997) Thermal gradient fractionation of glyceride mixtures under supercritical fluid conditions. J Supercrit Fluids 10:127–137

    Article  CAS  Google Scholar 

  14. Dunford NT, Teel JA, King JW (2003) A continuous countercurrent supercritical fluid deacidification process for phytosterol ester fortification in rice bran oil. Food Res Inter 36:175–181

    Article  CAS  Google Scholar 

  15. Ruivo R, Couto R, Simoes PC (2008) Supercritical carbon dioxide fractionation of the model mixture squalene/oleic acid in a membrane contactor. Sep Purif Technol 59:231–237

    Article  CAS  Google Scholar 

  16. Ruivo R, Cebola MJ, Simoes PC, Nunes da Ponte M (2001) Fractionation of edible oil model mixtures by supercritical carbon dioxide in a packed column. Part I. Experimental results. Ind Eng Chem Res 40:1706–1711

    Article  CAS  Google Scholar 

  17. Nilsson WB, Gauglitz E Jr, Hudson JK (1988) Solubilities of methyl oleate, oleic acid, oleyl glycerols, and oleyl glycerol mixtures in supercritical carbon dioxide. J Am Oil Chem Soc 68:1087–1091

    Google Scholar 

  18. Eller FJ, Taylor SL, Compton DL, Laszlo JA, Palmquist DE (2008) Counter-current liquid carbon dioxide purification of a model reaction mixture. J Supercrit Fluids 43:510–514

    Article  CAS  Google Scholar 

  19. Compton DL, Vermillion KE, Laszlo JA (2007) Acyl migration kinetics of 2-monoacylglycerols from soybean oil via 1H NMR. J Am Oil Chem Soc 84:343–348

    Article  CAS  Google Scholar 

  20. Laszlo JA, Compton DL, Vermillion KE (2008) Acyl migration kinetics of vegetable oil 1,2-diacylglycerols. J Am Oil Chem Soc 85:307–312

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. New Crops & Processing Technology Research, National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture, 1815 North University Street, Peoria, IL, 61604, USA

    F. J. Eller, S. L. Taylor, J. A. Laszlo, D. L. Compton & J. A. Teel

Authors
  1. F. J. Eller
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. L. Taylor
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. J. A. Laszlo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. L. Compton
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. J. A. Teel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to F. J. Eller.

Additional information

Names are necessary to report factually on available data; however, the USDA neither guarantees nor warrants the standard of the product, and the use of the name USDA implies no approval of the product to the exclusion of others that may also be suitable.

About this article

Cite this article

Eller, F.J., Taylor, S.L., Laszlo, J.A. et al. Counter-Current Carbon Dioxide Purification of Partially Deacylated Sunflower Oil. J Am Oil Chem Soc 86, 277–282 (2009). https://doi.org/10.1007/s11746-008-1340-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-008-1340-9

Keywords

Search

Navigation