Hydrogenation for low trans and high conjugated fatty acids

Comprehensive Reviews in Food Science and Food Safety

Volumn 4, Issue 1, 2005, Pages 22-30

  Eun, Seok Jang ^a   Mun, Yhung Jung ^a   Min, David B ^b  

^a Dept of Food Science and Technology ^*  (South Korea)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748756518     PISSN: 15414337     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1541-4337.2005.tb00069.x     Document Type: Review

References (65)

1. Ahmad MM, Priestley TM, Winterbottom JM. 1979. Palladium-catalyzed hydrogenation of soybean oil. J Amer Oil Chem Soc 56:571-7.
2. An W, Hong JK, Pintauro PN, Warner K, Neff W. 1998a. The electrochemical hydrogenation of edible oils in a solid polymer electrolyte reactor. I. Reactor design and operation. J Am Oil Chem Soc 75:917-25.
3. An W, Hong JK, Pintauro PN. 1998b. Current efficiency for soybean oil hydrogenation in a solid polymer electrolyte reactor. J Appl Electrochem 27:947-54.
4. An W, Hong JK, Pintauro PN, Warner K, Neff W. 1999. The electrochemical hydrogenation of edible oils in a solid polymer electrolyte reactor. II. Hydrogenation selectivity studies. J Am Oil Chem Soc 76:215-22.
5. Arkad O, Weiner H, Garti N, Sasson Y. 1987. Catalytic transfer hydrogenation of soybean oil methylester using inorganic formic salts as donors. J Am Oil Chem Soc 64:1529-31.
6. Aro A, Jauhiainen M, Partanem R, Salminen I, Mutanen M. 1997. Stearic acid, trans fatty acids, and dietary fat: Effects on serum and lipoprotein lipids, apolipoproteins, lipoprotein (a), and lipid transfer proteins in healthy subjects. Am J Clin Nutr 65:1419-26.
7. Ascherio A, Hennekens CH, Burring JE, Master C, Smapfet MJ, Willet WC. 1994. Trans fatty acid intake and risk of myocardial infraction. Circulation 89:94-101.
8. Banni S, Day BW, Evans RW, Corongiu FP, Lombardi B. 1994. Liquid-chromatographic-mass spectrometric analysis of conjugated diene fatty acids in a partially hydrogenated fat. J Am Oil Chem Soc 71:1321-5.
9. Basu HN, Chakrabarty MM. 1966. Studies on conjugated hydrogenation: Nickel catalyst with alcohols. J Am Oil Chem Soc 43:119-21.
10. Berben PH, Borninkhof F, Reesink BH, Kuijpers EGM. 2000a. Production of low trans-isomer containing products by hydrogenation. In: Hernandez E, Rhee KC. Practical short course series: Vegetable oils processing and modification techniques. College Station, Texas: Texas A&M Univ.
11. Berben PH, Blom PJW, Sollie JC. 2000b. Palladium and platinum catalyzed oil hydrogenation: Effects of reaction conditions on trans-isomer and saturated fatty acids formation. In: Hernandez E, Rhee KC, editors. Practical short course series: Vegetable oils processing and modification techniques. College Station, Texas: Texas A&M Univ.
12. Boylstone TD, Beitz DC. 2002. Conjugated linoleic acid and fatty acid composition of yogurt produced from milk of cows fed soy oil and conjugated linoleic acid. J Food Sci 67:1973-8.
13. Bulgarella JA, Patton D, Bull AW. 2001. Modulation of prostaglandin H synthesis activity by conjugated linoleic acid (CLA) and specific fatty acids. Lipids 36:407-12.
14. Chakrabarty M, Bhattacharyya D, Basu AK. 1972. Conjugated hydrogenation of triglyceride oil containing conjugated acid. J Am Oil Chem Soc 49:510-4.
15. Chin SF, Liu W, Storkson JM, Ha YL, Pariza MW. 1992. Dietary sources of conjugated dienoic fatty acids of linoleic acid, a newly recognized class of anticarcinogens. J Food Comp Anal 5:185-97.
16. Choi N, Kwon D, Yoon SH, Jung MY, Shin H. 2004. Selectively hydrogenated soybean oil with conjugated linoleic acid modifies body composition and plasma lipids in rats. J Nutrition Biochem 15:411-7.
17. Cook ME, Miller CC, Park Y, Pariza MW. 1993. Immune modulation by altered nutrient metabolism: nutritional control of immune-induced growth depression. Poult Sci 72:1301-5.
18. Cyr A, Huot P, Belot G, Lessard J. 1990. The efficient electrochemical reduction of nirobenzene and azoxybenzene to aniline in neutral and basic aqueous methanolic solutions at Devarda copper and Raney nickel electrodes: Electrocatalytic hydrogenolysis of N-O and N-N bonds. Electrochim Acta 35:147-52.
19. Desci T, Koletzko B. 1995. Do trans fatty acids impair linolenic metabolism in children? Ann Nutr Metab 39:36-41.
20. Feldman EB, Kris-Etherton PM, Kritchevsky D, Lichtenstein AH. 1996. Position paper on trans fatty acids: ASCN/AIN task force on trans fatty acids. Am J Clin Nutr 63:663-70.
21. Ha YL, Grimm NK, Pariza MW. 1987. Anticarcinogens from fried ground beef: heat-altered derivatives of linoleic acid. Carcinogenesis 8:1881-7.
22. Ha YL, Grimm NK, Pariza MW. 1989. Newly recognized anticarcinogenic fatty acids: Identification and quantification in natural and processed cheeses. J Agric Food Chem 37:75-81.
23. Houseknecht KL, Vanden Heuvel JP, Moya-Camarena SY, Portocarrero CP, Peck LW, Nickel KP, Belury MA. 1998. Dietary conjugated linoleic acid normalizes impaired glucose tolerance in the Zucker diabetic fatty fa/fa rat. Biochem Biophysic Res Communic 244:678-82.
24. Hsu N, Diosady LL, Graydon WF, Rubin LJ. 1986. Heterogeneous catalytic hydrogenation of canola oil using palladium. J Am Oil Chem Soc 63:1036-42.
25. Hsu N, Diosady LL, Rubin LJ. 1988. Catalytic behavior of palladium in the hydrogenation of edible oils. J Am Oil Chem Soc 65:608-88.
26. Ip C, Briggs SP, Haegele AD, Thompson HJ, Storkson J, Scimeca JA. 1996. The efficiency of conjugated linoleic acid in mammary cancer prevention is independent of the level or type of fat in the diet. Carcinogenesis 17:1045-50.
27. Ju JW, Jung MY. 2003. Formation of conjugated linoleic acids during hydrogenation as affected by sulfur addition. J Agric Food Chem 51:3144-9.
28. Ju JW, So WS, Kim JH, Bae BJ, Choi EN, Kown 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 68:1915-22.
29. Judd JT, Clevidence BA, Muesing RA, Wettes J, Sunkin ME, Podczasy JJ. 1994. Dietary trans fatty acids: Effects of plasma lipids and lipoproteins of healthy men and women. Am J Clin Nutr 59:861-8.
30. Jung MY, Ha YL. 1999. Conjugated linoleic acid fatty acids in partially hydrogenated soybean oil obtained during nonselective and selective hydrogenation processes. J Agric Food Chem 47:704-8.
31. Jung MO, Yoon SH, Jung MY. 2001. Effects of temperature and agitation rate on the formation of conjugated linoleic acids in soybean oil during hydrogenation process. J Agric Food Chem 49:3010-6.
32. Jung MO, Ju JW, Choi DS, Yoon SH, Jung MY. 2002. CLA formation in oils during hydrogenation process as affected by catalyst types, catalyst contents, hydrogen pressure, and oil species. J Am Oil Chem Soc 79:501-10.
33. Jung MY, Jung MO. 2002. Identification of conjugated linoleic acids in hydrogenated soybean oil by silver-ion impregnated HPLC and gas chromatography-ion impacted mass spectrometry of their 4,4-dimehyloxazoline derivatives. J Agric Food Chem 50:6188-93.
34. 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 78:107-13.
35. Kim YJ, Liu RH. 2002. Increase of conjugated linoleic acid content in milk by fermentation with lactic acid bacteria. J Food Sci 67:1731-7.
36. Lee KN, Kritchevsky D, Pariza MW. 1994. Conjugated linoleic acid and atherosclerosis in rabbits. Atherosclerosis 108:19-25.
37. Liew C, Schut HAJ, Chin SF, Pariza MW, Dashwood RH. 1995. Protection of conjugated linoleic acids against 2-amino-3-methylimidazo[4,5-f]quinoline- induced colon carcinogenesis in F344 rat; a study of inhibitory mechanisms. Carcinogenesis 16:3037-43.
38. Macher M, Hogberg J, Moller P, Harrod M. 1999. Partial hydrogenation of fatty acid methyl esters at supercritical conditions. Fette/Lipid 8:301-5.
39. Macher M, Holmquivst A. 2001. Hydrogenation of palm oil in near-critical and supercritical propane. Eur J Lipid Sci Technol 101:81-4.
40. Mensink RP, Katan MB. 1990. Effects of trans fatty acids on high-density and low-density lipoprotein cholesterol levels in healthy subjects. N Eng J Med 323:439-45.
41. Miller LL, Christensen L. 1978. Electrocatalytic hydrogenation of aromatic compounds. J Org Chem 43:2059-61.
42. Mondal K, Lalvani S. 2000. A second-order model for catalytic transfer hydrogenation of edible oils. J Am Oil Chem Soc 77:1-8.
43. Mondal K, Lalvani SB. 2003. Electrochemical hydrogenation of canola oil using hydrogen transfer agent. J Am Oil Chem Soc 80:1135-41.
44. Naglic M, Smidovnik A, Koloini T. 1998. Kinetics of catalytic transfer hydrogenation of some vegetable oils. J Am Oil Chem Soc 75:629-33.
45. Ogumi Z, Inaba M, Ohashi SI, Uchida M, Takehara ZI. 1988. Application of the SPE method to organic electrochemistry. VII. The reduction of nirobenzene on a modified Pt-Nafion. Electrochim Acta 33:365-9.
46. Ogumi Z, Nishio K, Yoshizawa S. 1981. Application of the SPE method to organic electrochemistry. II. Electrochemical hydrogenation of olefinic double bonds. Electrochim Acta 26:1779-82.
47. Park K, Pintauro PN, Baizer MM, Nobe K. 1985. Flow reactor studies of the paired electro-oxidation and electroreduction of glucose. J Electrochem Soc 182:1850-5.
48. Park K, Pintauro PN, Baizer MM, Nobe K. 1986. Current efficiencies and regeneration of poisoned Raney nickel in the electrohydrogenation of glucose to sorbitol. J Applicat Electrochem 16:941-6.
49. Park Y, Storkson JM, Albright KJ, Liu W, Pariza MW. 1999. Evidence that the trans-10,cis-12 isomer of conjugated linoleic acid induces body composition changes in mice. Lipids 34:235-41.
50. Pintauro PN, Bontha J. 1991. The role of supporting electrolytes during the electrocatalytic hydrogenation of aromatic compounds. J Appl Electrochem 21:799-804.
51. Ray JD. 1985. Behavior of hydrogenation catalysts. I. Hydrogenation of soybean oil with palladium. J Am Oil Chem Soc 62:1213-7.
52. Riserus U, Berglund L, Vessby B. 2001. Conjugated linoleic acid (CLA) reduced abdominal adipose tissue in obese middle-aged men with signs of metabolic syndrome: a randomized controlled trial. Int J Obesity 25:1129-35.
53. Riesz CH, Weber HS. 1970. Catalysts for selective hydrogenation of soybean oil. II. Commercial catalysts. J Am Oil Chem Soc 41:400-06.
54. Robin D, Comtois M, Martel A, Lemieux R, Cheong AK, Belot G, Lessard J. 1990. The electrocatalytic hydrogenation of fused polycyclic aromatic compounds at Raney nickel electrodes: The influence of catalyst activation and electrolysis conditions. Can J Chem 68:1218-27.
55. Shantha NC, Decker EA, Ustunol Z. 1992. Conjugated linoleic acid concentration in processed cheese. J Am Oil Chem Soc. 69:425-8.
56. Song Y, Pintauro PN. 1991. The electrochemical synthesis of aminonitriles. I. H-Cell studies with adiponitiles and azelanitrile. J Appl Electrochem 21:21-7.
57. Tagawa T, Nishiguchi T, Fukuzumi K. 1978. Transfer hydrogenation and transfer hydrogenolysis: XII. Selective hydrogenation of fatty acid methyl esters by various hydrogen donors. J Am Oil Chem Soc 55:332-6.
58. Troisi R, Willett WC, Weiss ST. 1992. Trans-fatty acid intake in relation to serum lipid concentrations in adult men. Am J Clin Nutr 56:1019-24.
59. Warner K, Neff WE, List GR, Pintauro P. 2000. Electrochemical hydrogenation of edible oils in a solid polymer electrolyte reactor. Sensory and compositional characteristics of low trans soybean oils. J Am Oil Chem Soc 77:1113-7.
60. Willet WC, Stampfer MJ, Manson JE. 1993. Intake of trans fatty acids and risk of coronary heart disease among women. Lancet 341:581-5.
61. Wright AJ, Wong A, Diosady LL. 2003. Ni catalyst promotion of a cis-selective Pd catalyst for canola oil hydrogenation. Food Res Intl 36:1069-72.
62. Yusem G, Pintauro PN. 1992. The electrocatalytic hydrogenation of soybean oil. J Am Oil Chem Soc 69:399-404.
63. Yusem G, Pintauro PN, Cheng PC, An W. 1996. Electrocatalytic hydrogenation of soybean oil in a radial flow-through Raney nickel powder reactor. J Appl Electrochem 26:989-97.
64. Yusem G, Pintauro PN. 1997. Computer-aided electrochemical process design: Simulation and economic analysis of an electrocatalytic soybean oil hydrogenation plant. J Appl Electrochem 27:1157-71.
65. Zajcew M. 1960. The hydrogenation of fatty oils with palladium catalyst. III. Hydrogenation of fatty oils for shortening stock. J Am Oil Chem Soc 37:11-4.