Journal of the American Oil Chemists' Society

, Volume 88, Issue 12, pp 2023–2034 | Cite as

Physical Properties of Nutritive Shortenings Produced from Regioselective Hardening of Soybean Oil with Pt Containing Zeolite

  • An Philippaerts
  • Annika Breesch
  • Gert De Cremer
  • Pieterjan Kayaert
  • Johan Hofkens
  • Guy Van den Mooter
  • Pierre Jacobs
  • Bert SelsEmail author
Original Paper


Soybean oil was partially hydrogenated using Pt supported in microporous zeolite ZSM-5 and on mesoporous alumina at various IV. Their fatty acid and triacylglycerol composition were determined with GC and HPLC, respectively, and their physical characteristics were monitored by the slip melting point, solid fat content, melting and crystallization thermograms, polymorphism behavior, and the crystal and solid fat network formation. Both the chemical and physical properties were compared with commercial fat samples. Usage of Pt instead of Ni results in a significant reduction in trans fatty acids in the hardened fat. Moreover, the catalyst support of Pt, viz. zeolite ZSM-5 versus γ-alumina, markedly affects the TAG composition. Pt/alumina fats contain large amounts of SSS and polyunsaturates (PUFA), making them unsuitable for shortening application. Because of the (regio)selective hydrogenation property of Pt/ZSM-5, sn-2 unsaturates are hydrogenated faster, yielding an enrichment of intermediately reduced TAG. In addition, this unique fat composition shows a high nutritional added-value (high content of oleate, very low content of trans fatty acids, and low content of cholesterol-raising palmitate and myristate) and high thermal stability (very low in linolenate). Moreover, their melting characteristics perfectly match those of commercial shortenings. Pt/zeolite hardened soybean oil contains spherulitic crystals with orthorhombic β′ molecular packing, arranged in an open, flexible solid network, in accordance with their high plasticity.


Hydrogenation Soybean oil Pt/ZSM-5 catalyst Shortening Hardening Melting behavior Crystallization Solid fat content Polymorphism 



A.P. acknowledges the F.W.O.-Vlaanderen (Research Foundation—Flanders) for a doctoral fellowship and P.K. the Institute for the Promotion of Innovation through Science and Technology in Flanders (IWT—Vlaanderen) for a Ph.D. grant. The authors acknowledge the Flemish government for a long term sponsoring (Methusalem, CASAS). We are grateful to Vandemoortele (Izegem, Belgium) for measuring the solid fat content of the hydrogenated fat samples.

Supplementary material

Supplementary material 1 (WMV 807 kb)

Supplementary material 2 (WMV 869 kb)

Supplementary material 3 (WMV 447 kb)

Supplementary material 4 (WMV 633 kb)


  1. 1.
    Ghotra BS, Dyal SD, Narine SS (2002) Lipid shortenings: a review. Food Res Int 35:1015–1048CrossRefGoogle Scholar
  2. 2.
    Albright LF (1963) Mechanism of hydrogenation of triglycerides. J Am Oil Chem Soc 40:16CrossRefGoogle Scholar
  3. 3.
    Clifton PM, Keogh JB, Noakes M (2004) Trans fatty acids in adipose tissue and the food supply are associated with myocardial infarction. J Nutr 134:1848Google Scholar
  4. 4.
    Mozaffarian D, Katan MB, Ascherio A, Stampfer MJ, Willett WC (2006) Medical progress—trans fatty acids and cardiovascular disease. New Engl J Med 354:1601–1613CrossRefGoogle Scholar
  5. 5.
    US Department of Health and Human Services FaDA, 21 CFR Part 101 [Docket No. 94P-0036], Food labeling: trans fatty acids in nutrition labeling, nutrient content claims and health claims, Washington, 2003, p. 254Google Scholar
  6. 6.
    EFSA (2004) Opinion on the scientific panel on dietetic products, nutrition and allergies on the request from the commission related to the presence of trans fatty acids in foods and the effect on human health of the consumption of trans fatty acids (Request No.° EFSA-Q-2003-022). EFSA J 81:1–49Google Scholar
  7. 7.
    Patterson HBW (1994) Hydrogenation of fats and oils: theory and practice. AOCS Press, IllinoisGoogle Scholar
  8. 8.
    Cizmeci M, Musavi A, Kayahan M, Tekin A (2005) Monitoring of hydrogenation with various catalyst ratios. J Am Oil Chem Soc 82:925–929CrossRefGoogle Scholar
  9. 9.
    Berben PH, Borninkhof F, Reesink B, Kuijpers E (1994) Production of low trans-isomer-containing products by hydrogenation. Inform 5:516Google Scholar
  10. 10.
    Beers A, Mangnus G (2004) Hydrogenation of edible oils for reduced trans-fatty acid content. Inform 15:404–405Google Scholar
  11. 11.
    Smidovnik A, Kobe J, Leskovsek S, Koloini T (1994) Kinetics of catalytic transfer hydrogenation of soybean oil. J Am Oil Chem Soc 71:507–511CrossRefGoogle Scholar
  12. 12.
    Ju JW, So WS, Kim JH, Bae BJ, Choi EN, Kwon YH, Chung IM, Yoon SH, Jung MY (2003) Effects of alcohol type and amounts on conjugated linoleic acid formation during catalytic transfer hydrogenation of soybean oil. J Food Sci 68:1915–1922CrossRefGoogle Scholar
  13. 13.
    Yusem GJ, Pintauro PN (1992) The electrocatalytic hydrogenation of soybean oil. J Am Oil Chem Soc 69:399–404CrossRefGoogle Scholar
  14. 14.
    An WD, Hong JK, Pintauro PN, Warner K, Neff W (1998) The electrochemical hydrogenation of edible oils in a solid polymer electrolyte reactor. I. Reactor design and operation. J Am Oil Chem Soc 75:917–925Google Scholar
  15. 15.
    Mondal K, Lalvani SB (2003) Mediator-assisted electrochemical hydrogenation of soybean oil. Chem Eng Sci 58:2643–2656CrossRefGoogle Scholar
  16. 16.
    King JW, Holliday RL, List GR, Snyder JM (2001) Hydrogenation of vegetable oils using mixtures of supercritical carbon dioxide and hydrogen. J Am Oil Chem Soc 78:107–113CrossRefGoogle Scholar
  17. 17.
    Ramirez E, Recasens F, Fernandez M, Larrayoz MA (2004) Sunflower oil hydrogenation on Pd/C in SC propane in a continuous recycle reactor. AIChe J 50:1545–1555CrossRefGoogle Scholar
  18. 18.
    Santana A, Larrayoz MA, Ramirez E, Nistal J, Recasens F (2007) Sunflower oil hydrogenation on Pd in supercritical solvents: Kinetics and selectivities. J Supercrit Fluids 41:391–403CrossRefGoogle Scholar
  19. 19.
    Piqueras CA, Tonetto G, Bottini S, Damiani DE (2008) Sunflower oil hydrogenation on Pt catalysts: comparison between conventional process and homogeneous phase operation using supercritical propane. Catal Today 133:836–841CrossRefGoogle Scholar
  20. 20.
    Khatoon S, Reddy SRY (2005) Plastic fats with zero trans fatty acids by interesterification of mango, mahua and palm oils. Eur J Lipid Sci Technol 107:786–791CrossRefGoogle Scholar
  21. 21.
    Siew WL, Cheah KY, Tang WL (2007) Physical properties of lipase-catalyzed interesterification of palm stearin with canola oil blends. Eur J Lipid Sci Technol 109:97–106CrossRefGoogle Scholar
  22. 22.
    Chu BS, Ghazali HM, Lai OM, Man YBC, Yusof S, Tee SB, Yusoff MSA (2001) Comparison of lipase-transesterified blend with some commercial solid frying shortenings in Malaysia. J Am Oil Chem Soc 78:1213–1219CrossRefGoogle Scholar
  23. 23.
    Lee JH, Akoh CC, Lee KT (2008) Physical properties of trans-free bakery shortening produced by lipase-catalyzed interesterification. J Am Oil Chem Soc 85:1–11CrossRefGoogle Scholar
  24. 24.
    Katan MB, Zock PL, Mensink RP (1994) Effects of fats and fatty-acids on blood-lipids in humans - an overview. Am J Clin Nutr 60:S1017–S1022Google Scholar
  25. 25.
    Philippaerts A, Paulussen S, Beersch A, Turner S, Lebedev OI, Van Tendeloo G, Sels B, Jacobs P (2011) Unprecedented shape selectivity in hydrogenation of triacylglycerol molecules with Pt/ZSM-5 zeolite. Angew Chem Int Ed 50:3947–3949CrossRefGoogle Scholar
  26. 26.
    Philippaerts A, Paulussen S, Turner S, Lebedev OI, Van Tendeloo G, Poelman H, Bulut M, De Clippel F, Smeets P, Sels B, Jacobs P (2010) Selectivity in sorption and hydrogenation of methyl oleate and elaidate on MFI zeolites. J Catal 270:172–184CrossRefGoogle Scholar
  27. 27.
    Kris-Etherton PM, Pearson TA, Wan Y, Hargrove RL, Moriarty K, Fishell V, Etherton T (1999) High-monounsaturated fatty acid diets lower both plasma cholesterol and triacylglycerol concentrations. Am J Clin Nutr 70:1009–1015Google Scholar
  28. 28.
    Kelly FD, Sinclair AJ, Mann NJ, Turner AH, Abedin L, Li D (2001) A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. Eur J Clin Nutr 55:88–96CrossRefGoogle Scholar
  29. 29.
    Luddy FE, Magidman P, Herb SF, Riemenschneider RW, Barford RA (1964) Pancreatic lipase hydrolysis of triglycerides by semimicro technique. J Am Oil Chem Soc 41:693CrossRefGoogle Scholar
  30. 30.
    Hastert RC (1996) Hydrogenation. In: Hui YH (ed) Bailey’s Industrial Oil & Fat Products. Wiley, New York, p 679Google Scholar
  31. 31.
    Chu YH, Lin LH (1991) An evaluation of commercial nickel-catalysts during hydrogenation of soybean oil. J Am Oil Chem Soc 68:680–683CrossRefGoogle Scholar
  32. 32.
    Linderborg KM, Kallio HPT (2005) Triacylglycerol fatty acid positional distribution and postprandial lipid metabolism. Food Rev Int 21:331–355CrossRefGoogle Scholar
  33. 33.
    Hernqvist L (1984) Polymorphism of fats. Lund University, LundGoogle Scholar
  34. 34.
    Dsouza V, Deman JM, Deman L (1990) Short spacings and polymorphic forms of natural and commercial solid fats—a review. J Am Oil Chem Soc 67:835–843CrossRefGoogle Scholar
  35. 35.
    Watanabe A, Tashima I, Matsuzaki N, Kurashige J, Sato K (1992) On the formation of granular crystals in fat blends containing palm oil. J Am Oil Chem Soc 69:1077–1080CrossRefGoogle Scholar
  36. 36.
    List GR, Jackson M, Eller F, Adlof RO (2007) Low trans spread and shortening oils via hydrogenation of soybean oil. J Am Oil Chem Soc 84:609–612CrossRefGoogle Scholar

Copyright information

© AOCS 2011

Authors and Affiliations

  • An Philippaerts
    • 1
  • Annika Breesch
    • 1
  • Gert De Cremer
    • 1
  • Pieterjan Kayaert
    • 2
  • Johan Hofkens
    • 3
  • Guy Van den Mooter
    • 2
  • Pierre Jacobs
    • 1
  • Bert Sels
    • 1
    Email author
  1. 1.Department of M2SK.U.LeuvenHeverlee, LeuvenBelgium
  2. 2.Laboratory Farmacotechnology and BiopharmacyK.U.LeuvenLeuvenBelgium
  3. 3.Department of ChemistryK.U.LeuvenHeverlee, LeuvenBelgium

Personalised recommendations