Skip to main content
SpringerLink
Log in

Investigation of Conjugated Soybean Oil as Drying Oils and CLA Sources

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

Abstract

Better sources of drying oils for coatings and conjugated linoleic acid (CLA) for potential health benefits are of continuing interest. Iodine under photochemical conditions in hexanesB at reflux temperatures was investigated as a catalyst for conjugating soybean oil (SBO) for use as drying oils and as a potential source of CLA. Variations in catalyst loading, SBO, light source, free radical catalyst, solvent and temperature strongly affected the efficiency of the process. Changes in fatty acid isomer distributions in conjugated SBO (CSBO) influenced drying properties of CSBO. Conjugated dienes formed were predominantly trans-9,trans-11, which contrasts distributions found with catalysts such as strong base and metal compounds. Drying times of some of the CSBOs were superior to that of raw linseed oil. Iodine was partially recovered.

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

Similar content being viewed by others

Abbreviations

SBO:

Soybean oil

CSBO:

Conjugated soybean oil

CLA:

Conjugated linoleic acid

VOCs:

Volatile organic compounds

GC–MS:

Gas chromatography–mass spectrometry

NMR:

Nuclear magnetic resonance spectroscopy

ESI:

Electronic supplementary information

AIBN:

Azobisisobutyronitrile

AICN:

4,4′-Azobis(4-cyanovaleric acid)

LO:

Linseed oil

RBD:

Refined bleached deodorized

References

  1. Krompiec S, Penczek R, Pluta T, Krompiec T, Ignasiak H, Kita A, Michalik S, Matlengiewicz M, Filapek M (2009) Transition metals for conjugation of polyunsaturated acids and their esters. Curr Org Chem 13:896–913

    Article  CAS  Google Scholar 

  2. Pourreau DB, Smyth SE (2004) High-solids alkyds resins with improved properties based on styrene allyl alcohol (SAA) resinous polyols. JCT Coatings Tech 1 (2): 40–47

    Google Scholar 

  3. Akbarinezhad E, Ebrahimi M, Kassiriha SM, Khorasani M (2009) Synthesis and evaluation of water-reducible acrylic-alkyd resins with high hydrolytic stability. Prog Org Coatings 65(2):217–221

    Article  CAS  Google Scholar 

  4. Meier MAR, Metzger JO, Schubert US (2007) Plant oil renewable resources as green alternatives in polymer science. Chem Soc Rev 36:1788–1802

    Article  CAS  Google Scholar 

  5. Wang C, Yang L, Ni B, Shi G (2009) Polyurethane networks from different soy-based polyols by the ring opening of epoxidized soybean oil with methanol, glycol, and 1,2-propanediol. J Appl Polym Sci 114:125–131

    Google Scholar 

  6. Thulasiraman V, Rakesh S, Sarojadevi M (2009) Synthesis and characterization of chlorinated soy oil based epoxy resin/glass fiber composites. Polym Compos 30:49–58

    Article  CAS  Google Scholar 

  7. Henna PH, Andjelkovic DD, Kundu PP, Larock RC (2007) Biobased thermosets from the free-radical copolymerization of conjugated linseed oil. J Appl Polym Sci 104:979–985

    Article  CAS  Google Scholar 

  8. Andjelkovic DD, Li F, Larock RC (2006) Novel polymeric materials from soybean oils: synthesis, properties, and potential applications. In: Bozell JJ, Patel M (eds) Feedstocks for the future: renewables for the production of chemicals and materials. ACS Symposium Series 921, American Chemical Society, Washington, DC, pp 67–81

  9. Pakdeechanuan P, Intarapichet K, Fernando LN, Grün IU (2005) Effects of rhodium heterogeneous catalyst and isomerization conditions on linoleic acid conjugation of soybean oil. J Agric Food Chem 53:923–927

    Article  CAS  Google Scholar 

  10. Simakova OA, Leino A, Campo B, Maki-Arvela P, Kordas K, Mikkola J, Murzin DY (2010) Linoleic acid isomerization over mesoporous carbon supported gold catalysts. Catal Today 150:32–36

    Article  CAS  Google Scholar 

  11. Kapoor R, Reaney M, Westcott ND (2005) Conjugated linoleic acid oils. In: Shahidi F (ed) Bailey’s industrial oil and fat products, 6th edn, Vol 3. Wiley Hoboken, pp 1–36

  12. Banni S, Martin JC (1998) Conjugated linoleic acid and metabolites In: Sébédio J-L, Christie WW(eds) Trans fatty acids in human nutrition. The Oily Press, Dundee, pp 261–302

  13. Gilbert W, Gadang V, Proctor A, Jain V, Devareddy L (2011) Trans–trans conjugated linoleic acid enriched soybean oil reduces fatty liver and lowers serum cholesterol in obese zucker rats. Lipids 46:961–968

    Article  CAS  Google Scholar 

  14. National Research Council (1996) Carcinogens and anticarcinogens in the human diet: a comparison of naturally occurring and synthetic substances. National Academy Press, Washington, DC

    Google Scholar 

  15. Seki K, Kaneko R, Kataoka M (1991) Photoconjugation of methyl linoleate in the presence of iodine compounds. Yukagaku 40:507–510

    CAS  Google Scholar 

  16. Kadamne JV, Castrodale CL, Proctor A (2011) Measurement of conjugated linoleic acid (CLA) in CLA-rich potato chips by ATR–FTIR spectroscopy. J Ag Food Chem 59:2190–2196

    Article  CAS  Google Scholar 

  17. Jain VP, Proctor A, Lall R (2008) Pilot-scale production of conjugated linoleic acid-rich soy oil by photoirradiation. J Food Sci 73:E183–E192

    Article  CAS  Google Scholar 

  18. Robyt JF, Choe J-Y, Fox JD, Hahn RS, Fuchs EB (1996) Acid modification of starch granules in alcohols: reactions in mixtures of two alcohols combined in different ratios. Carbohydr Res 283:141–150

    Article  CAS  Google Scholar 

  19. Nonaka Y, Hamada K (1981) The effects of BF2- and B(C2H5)2-substitution for bridging hydrogen atoms in the cobalt(II), nickel(II), and copper(II) complexes with some oximate ligands. Bull Chem Soc Jpn 54:3185–3190

    Article  CAS  Google Scholar 

  20. Bailey AE (1950) Melting and solidification of fats Interscience Publishers, New York, 117–237

  21. Wicks ZW, Jones FN, Pappas SP, Wicks DA (2007) Organic Coatings: Science and Technology, 3rd edn. Wiley Interscience, Hoboken, pp 296–304

    Book  Google Scholar 

  22. Bahatia SK, Liu F, Arvind G (2000) Effect of pore blockage on adsorption isotherms and dynamics: anomalous adsorption of iodine on activated carbon. Langmuir 16:4001–4008

    Article  Google Scholar 

  23. Teitelbaum RC, Ruby SL, Marks TJ (1980) A resonance Raman/iodine Mössbauer investigation of the starch-iodine structure. Aqueous solution and iodine vapor preparations. J Am Chem Soc 102:3322–3328

    Article  CAS  Google Scholar 

  24. Rendleman JA (2003) The reaction of starch with iodine vapor. Determination of iodide-ion content of starch–iodine complexes. Carbohydr Polymers 51:191–202

    Article  CAS  Google Scholar 

  25. Smith WT, Smith GT (1969) Solvent effects on formation of the starch-iodine complex. Carbohydr Res 10:598–600

    Article  CAS  Google Scholar 

  26. Rai Choudhury AK (1947) The starch-iodide complex. Sci Cult 13:40–41

    CAS  Google Scholar 

  27. US Energy Information Administration, Average Electricity Consumption (Industrial): http://www.eia.gov/electricity/data.cfm

  28. USDA Economics, Statistics and Market Information, Oil Crops Yearbook (89002) http://usda.mannlib.cornell.edu/MannUsda/viewDocumentInfo.do?documentID=1290

  29. Iodine: Global industry markets and outlook 10th edn 2010, Roskill http://www.roskill.com/reports/industrial-minerals/iodine

  30. Gray N (2009) Using charcoal to fix the price of carbon emissions. sustainability: practice and policy 5, p 1 http://www.google.com/search?hl=en&source=hp&biw=1449&bih=811&q=Using+Charcoal+to+Fix+the+Price+of+Carbon+Emissions.+Sustainability%3A+Practice+%26+Policy+5&btnG=Google+Search&oq=Using+Charcoal+to+Fix+the+Price+of+Carbon+Emissions.+Sustainability%3A+Practice+%26+Policy+5&aq=f&aqi=&aql=&gs_sm=s&gs_upl=819l819l0l2059l1l1l0l0l0l0l129l129l0.1l1l0

  31. ICIS chemicals pricing for Europe 2011 http://www.icispricing.com/

  32. Martin J (2011) Omnitech International New York Mercantile Exchange average trading price 2010 ($3.0935/gal, 116.6¢/kg)

  33. Kumar R, Bhatia A, Arora D (2009) Health benefits of conjugated linoleic acid: a review. J Clinical Diagnostic Res 3:1953–1967

    CAS  Google Scholar 

  34. Goncalves DC, Lira FS, Carnevali LC Jr, Rosa JC, Pimentel GD Seelaender M (2010) Conjugated linoleic acid: good or bad nutrient Diabetology and Metabolic Syndrome 2

Download references

Acknowledgments

The authors thank the United Soybean Board and the United States Department of Agriculture (USDA) for support. RBD soybean oil was kindly provided by REG and Cargill. We are grateful for the SEM photographs provided by Professor Victor S.-Y. Lin before his untimely death.

Author information

Authors and Affiliations

  1. Department of Chemistry, Gilman Hall, Iowa State University, Ames, IA, 50011, USA

    Venkat Reddy Chintareddy, Reed E. Oshel, Zhengkun Yu, Wei Wu, Guangtao Zhang & John G. Verkade

  2. USDA/NCAUR/ARS, Bio-Oil Research, 1815 N. University Street, Peoria, IL, 61604, USA

    Kenneth M. Doll

Authors
  1. Venkat Reddy Chintareddy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Reed E. Oshel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kenneth M. Doll
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhengkun Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wei Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Guangtao Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. John G. Verkade
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to John G. Verkade.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 4.56 mb)

About this article

Cite this article

Chintareddy, V.R., Oshel, R.E., Doll, K.M. et al. Investigation of Conjugated Soybean Oil as Drying Oils and CLA Sources. J Am Oil Chem Soc 89, 1749–1762 (2012). https://doi.org/10.1007/s11746-012-2072-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-012-2072-4

Keywords

Search

Navigation