Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
  • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
  • C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation

Definitions

• the invention relates to the field of food technology and refers to a process for hydrogenating vegetable and animal oils or fats into products with unique melt profile by means of catalytic hydrogen transfer from an appropriate donor as well as to the products of said hydrogenation.
• Textural characteristics of products which contain hydrogenated oils result from solid content index (SCI) of hydrogenated oils.
• SCI solid content index
• the basic hydrogena­tion process means the conversion of liquid oils into semi-solid substances and partially hydrogenated oils.
• Plastic fats are useful for preparing vegetable fats, margarine and special purpose fats.
• Hydrogenation represents the double bond addition in fat in the presence of a metallic catalyst.
• the purpose of the hydrogenation is the saturation of double bonds of fatty acids in fats.
• the hydrogenation reaction is not simple since it is accompanied by the simultaneous double bond isomerization, which may be a positional or a geometrical one.
• the position of the fatty acid in glycerol (1, 2 and 3) as well as the degree of un­saturation determine the physical properties of the molecule, especially the melting point of the fat, and thence influences on SCI.
• the stepwise conversion of the most un­saturated fatty acid form proceeded to the saturated state, i.e. linolenic to linoleic, then to oleic, and finally to stearic.
• a very narrow melting range or a controlled level of trans acids cannot be achieved by a common hydrogenation.
• European Patent Application 0 246 366 A1 discloses a simplified one-step process with partly deactivated Ni catalyst at a temperature range from 160 to 250 °C and gauge pressure of hydrogen from 0 to 7.105 Pa.
• the hydrogenation is carried on at a temperature fro 20 to 90 °C, usually at room tem­perature and at atmospheric pressure. However, better results are achieved at higher temperatures.
• the batch process is carried out in an organic solvent or in an aqueous emulsion.
• the continuous process is carried out in an organic solvent.
• Oils containing unsaturated fatty acids with at least 12 carbon atoms are hydrogenated.
• products having specific compositions which are the basis for producing margarine, creams, ice-creams etc., with improved edibility and appropriate melting properties as well as oxidation stability.
• the oil acceptor (A) containing double bonds, the hydrogen donor (DHx) and the catalyst are in contact.
• the hydrogen donor may be any organic compound having suffi­ciently low oxidation potential for carrying out the hydrogen transfer at relatively mild conditions.
• the hydrogenation rate depends upon the nature of oil, the nature of hydrogen donor, the activity and the concentration of the catalyst as well as upon the velocity of the ad­sorption and desorption step of the unsaturated oil and the hydrogen donor on the catalyst.
• the compositions and properties of hydrogenated products can vary with regard to the position of the double bonds to be hydrogenated and are due to the in­fluence of the isomerization reactions, which accompany each hydrogenation step. They also largely depends on hydrogenation conditions.
• Vegetable oils or mixture of vegetable oils, which are suitable for hydrogenation are e.g. soya oil, sunflower oil, safflower oil, maize oil, olive oil, bamboo oil, peanut oil, palm oil, rape oil, grape oil, coconut oil, pumpkin oil and castor oil.
• cod-liver-oil or a mixture of cod-liver oil with vegetable oils may be used.
• regenerable catalysts such as 1 - 20% palladium on active carbon (Pd/C), Pd/C/FeCl3, Pd/C/Fe(III) hydroxide or oxide, 0.04 - 10% Pd/Al2O3, 5% Pt/C. 5% Pt/Al2O3, 5% rhodium on active carbon, Raney nickel, ruthenium black and platinum black.
• the hydrogen donor must correspond to the catalyst, therefore formic acid and hypophosphorous acid as well as the salts thereof, such as triethylammonium formate, tri-n-butylammonium formate, sodium formate, potassium formate and ammonium for­mate as well as sodium hypophosphite are used.
• solvents such as ethanol propan-2-ol, formic acid, acetic acid, acetone and ethyl acetate may be selected. Some solvents can also act as the hydrogen donor.
• the reaction may be directed into products, which may be totally or only partly hydrogenated oils.
• the reaction is especially suitable for obtaining partly hydrogenated oils. From soya oil, rape oil or some other vegetable oil, only within a few hours of hydrogenation, an oil containing less than 1 % linolenic acid is obtained.
• cod-liver oils having high contents of poly-unsaturated ⁇ 3 acids (especially C18:3 ⁇ 3, C20:5 ⁇ 3 and C22:6 ⁇ 3), there are obtained fats with lower iodine values and adequate melting properties.
• the continuous process is also very simple since neither mixing nor catalyst removal are necessary.
• the catalyst may also be regenerated in a column and can be used for almost an unlimited period of time.
• one disadvantage of the present process can be present, the solvent and the donor must be removed from the final product before its application.
• weight amounts of oil, catalyst and hydrogen donor, dissolved in an organic solvent or water were agitated mechanically at about 900 rpm in a 150 ml flask which was immersed in a water bath at chosen temperature.
• Iodine value was calculated from fatty acid composition.
• a mixture of sunflower oil (2 ml) having an iodine value of 139.2, acetone (25 ml) and formic acid (2 ml) was eluted through a column filled with celite and with 100 mg of Pd/C.
• the flow rate was 0.5 ml/min. After the removal of the solvent a hydrogenated product having an iodine value of 122.4 and with a fatty acid composition as given in the Table 2 was obtained.
• Example 4 (batch hydrogenation in an aqueous emulsion)

Landscapes

• Chemical & Material Sciences (AREA)
• General Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Fats And Perfumes (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Applications Claiming Priority (2)

Publications (3)

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Family Applications (1)

Country Status (4)

Cited By (21)

Family Cites Families (1)

• 1989
  • 1989-11-20 YU YU220489A patent/YU46273B/sh unknown
  • 1989-11-20 SI SI8912204A patent/SI8912204A8/sl unknown
• 1990
  • 1990-11-16 DE DE1990625553 patent/DE69025553T2/de not_active Expired - Fee Related
  • 1990-11-16 EP EP90121982A patent/EP0429995B1/de not_active Expired - Lifetime

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