Showing papers on "Soybean oil published in 1969"

Selective hydrogenation of soybean oil: IV. Fatty acid isomers formed with copper catalysts

Abstract: Two samples of soybean oil hydrogenated with copper-containing catalysts at 170 and 200 C were analyzed for their natural and isomeric fatty acids. Methyl esters of the hydrogenated oils were separated into saturates, monoenes, dienes and trienes by countercurrent distribution between acetonitrile and pentane-hexane. Monoenes were further separated intocis- andtrans-isomers on a silver-saturated resin column. Double bond location in these fractions was determined by a microozonolysis-pyrolysis technique. The diene fraction was separated with an argentation countercurrent distribution method, and linoleate was identified by infrared, ozonolysis and alkaliisomerization data. The double bonds in thecis-monoenes were located in the 9-position almost exclusively. However, the double bonds in thetrans-monoene were quite scattered with 10- and 11-isomers predominating. About 86% to 92% of the dienes consisted of linoleate as measured by alkali isomerization. Other isomers identified as minor components includecis,trans andtrans, trans conjugated dienes and dienes whose double bonds are separated by more than one methylene group.

Effect of Dietary Fats on Some Chemical and Functional Properties of Eggs

Abstract: SUMMARY —Laying pullets were fed a low fat semipurified diet or the low fat diet supplement with 10% vegetable oil (corn, soybean, olive, safflower or hydrogenated coconut oil). The eggs were analyzed for change in the fatty acid composition of the total yolk lipids with time on the diet and for fatty acid composition of the triglyceride, cephalin and lecithin fractions of lipovitellin and lipovitellenin. Determinations were made for volume of sponge cakes, emulsification, and lipid content of stored eggs. A taste panel was used to assess any difference in flavor and mouth feel of yolk from stored eggs. The fatty acid composition of the total yolk lipids was influenced by all dietary fats. The major change was in the linoleic acid at the expense of oleic acid with corn, soybean and safflower oil. Olive oil increased the oleic acid and hydogenated coconut oil increased lauric, myristic and myristoleic acids. The fatty acid composition of the fractions of the lipoproteins was influenced by the dietary fats and varied between fractions. Differences were noted between sponge cake volume with eggs of low fat, corn oil, soybean oil and hydrogenated coconut oil diets. The dietary fats did not appear to affect emulsification capacity or migration of the yolk. A taste panel was unable to differentiate on the basis of flavor or mouth feel the egg yolk from the several treatments.

High oleic oils by selective hydrogenation of soybean oil

Abstract: High oleic (monoene) oils were obtained from soybean oil by selective hydrogenation with copper catalysts. A mixture of nickel and copper chromite catalyst had activity suitable for producing the high monoene oils. A new catalyst (copper-on-Cab-O-Sil) prepared in the Laboratory was more active than commercial copper catalysts. Hydrogenated oils contained 61–72% monoenoic and 14–24% dienoic acids, and there was essentially no increase in stearic acid. Thetrans-isomer content of these oils varied between 17% to 32%. Double bonds in the monoene were distributed along the molecule from C6 to C15, but were located preferentially in the C9 position for thecis-monoene and in the C10 and C11 positions for thetrans-monoene. When the iodine value of these high monoene oils was about 90–95, they remained liquid above 28 C. Citric acid treatment reduced the copper content of hydrogenated oils to a level that was comparable to that of the original soybean oil.

A dimeric oxidation product of γ-tocopherol in soybean oil

Abstract: A dimeric oxidation product (5-γ-tocopheroxy-γ-tocopherol) has been isolated from soybean oil and identified. The dimer content in extracted oil was increased by elevating the moisture level in raw soybeans. With moisture increase, no change in the quantity of α-tocopherol was observed, but γ- and δ-tocopherol contents were greatly decreased and two kinds of dimer were formed from γ- and δ-tocopherols. When the moisture level in moistened beans was lowered, these dimers reverted to their corresponding original tocopherols. The same results were obtained by treating pulverized soybeans with various reducing agents. γ-Tocopherol added to autoxidizing soybean oil was oxidized more easily in the presence of oxidation products derived from tocopherols and turned into the dimeric product.

Pilot‐plant selective hydrogenation of soybean oil: Activation and evaluation of copper‐containing catalysts

Abstract: In pilot-plant tests, the linolenate content of soybean oil was reduced to less than 1% without increasing the saturates, by hydrogenation to an IV of about 115 with an active copper-chromite catalyst The linolenate-linoleate selectivity ratio (KLe/KLo) was from 9 to 12 Several commercial copper-chromite catalysts were used in hydrogenation tests The activities of four of five commercial catalysts tested were improved to various degrees by heating in air at 350 C (one was inactive both before and after heating) Examination by differential thermal analysis (DTA) of each catalyst, just as received and then after being heated at 350 C, demonstrated that heating greatly diminished or removed peak areas from the DTA curve Studies made with one commerical copper-chromium-barium catalyst showed that heating the catalyst was also necessary to gain maximum linolenate-linoleate selectivity in hydrogenating soybean oil

Removal of copper from hydrogenated soybean oil

Abstract: Hydrogenation with a copper-chromite catalyst at 170 C, 30 psi, increased the copper content of a refined, bleached soybean oil from 0.02 to as much as 3.8 ppm. Removing residual copper from soybean oil is essential to the successful use of copper catalysts for selective hydrogenation. Various methods were examined to remove this copper, including alkali refining, bleaching, acid washing, citric acid treatment and cation-exchange resin treatment. Properly conducted, each of the methods except alkali refining gives 95% or higher removal of copper introduced during hydrogenation. Ion exchange appears to be the most economical, but addition of about 0.01% citric acid during deodorization may be needed to inactivate traces of unremoved copper. Soybean oil hydrogenated with a copper-chromite catalyst, bleached or treated with an ion-exchange resin and deodorized with 0.01% citric acid added had low AOM peroxide values and acceptable flavor scores after eight days at 60 C which indicate that removal of residual copper from the oil should be adequate for the production of stable oils low in linolenic acid content.

Some radiochemical experiments on minor constitutents in soybean oil

Abstract: A14C-labeled high molecular weight hydrocarbon and an insecticidal compound were added as minor constituents in soybean oil samples. Liquid scintillation counting was used to assay the radioactivity of the oil preceding and after laboratory simulations of commercial processing procedures (bleaching and deodorization). Radiochemical techniques were found to be highly sensitive and quantitative and detection was unaffected by chemical modification or decomposition of the parent compound. Labeled (14C) benzo(a)pyrene was retained primarily by the oil during extraction, filtering, solvent stripping, deodorization and treatment with AOCS bleaching earths. Treatment of the oil with activated charcoal effected removal of this hydrocarbon. Bleaching was ineffective in removing added14C-endrin from the oil but a deodorization using specific conditions of temperature (250 C), time (2 hr), and pressure (4.5 mm) removed this constituent.

Lipids of defatted soybean flakes: extraction and characterization

Abstract: SUMMARY Dehulled soybean flakes, defatted with pentane-hexane, were further extracted with various nonpolar and polar solvents to remove free and bound lipids with the object of deter­ mining sources of flavor in these flakes and their products. The flakes con­ tain 0.10% residual oil as determined by official test methods. They contain about 3% crude lipids extractable with an azeotropic mixture of hexane: ethanol. Phospholipids, including phos­ phatidic acid, account for about 60% of the crude lipids. Sterols, triglycer­ ides, sugars and amino acids, together with lesser amounts of the isoflavones, daidzein and genistein and their glu­ coside derivatives, are also present. Palmitic acid content of the phospho­ lipids is nearly three times higher than that in typical soybean oil. The higher content of palmitic acid is bal­ anced bv decreases in oleic and lino­ leic acids. The hexane-ethanol azeotrope and hot 95% ethyl alcohol are effective solvents in removing the more intense flavors of defatted soybean flakes and the extracted flakes are much reduced in flavor. Fractionation of the crude lipids by silicic acid column chroma­ tography is an effective method for concentrating the soybean flavors.

An automated method for determining tocopherol in deodorized soybean oil.

Abstract: A method has been developed, utilizing the Technicon AutoAnalyzer, to determine the tocopherol content of deodorized oil. The chemistry of the Emmerie-Engel method, based upon the reduction of ferric chloride, is utilized in the development of this automated method. The tocopherol content of soybean oil is measured relative to a standard sample of d-α-tocopherol. The tocopherol content as measured by this method will include any other reducing substances present in the sample to be analyzed. The standard deviation, as derived from a pooling of the variances of four deodorized soybean oil samples is ± 0.0023% at the 0.1% level.

Compositions of matter

Abstract: IMPROVED FATTY ACID PRODUCTS OF ENHANCED FLAVOR CHARACTERISTICS HAVE INCORPORATED AUTOXIDATION FLAVOR COUNTERACTANTS OF THE FORMULA RCH:CHCH:CHZ WHERE R IS AN ALKYL GROUP CONTAINING UP TO 9 CARBON ATOMS AND Z IS AN ORGANOLEPTICALLY ACCEPTABLE POLAR GROUP. THE FATTY ACID PRODUCTS INCLUDE EDIBLE FATS AND OILS PARTICULARLY TALLOW AND SOYBEAN OIL, AND THEIR PRODUCTS SUCH AS MARGARINE. THE COUNTERACTANTS MAY BE FREE OF COMBINED FATTY ACIDS OR ALDEHYDES, WHICH ARE EFFECTIVE IN MINUTE AMOUNTS, AND THEY MAY BE INCORPORATED AT LEAST IN PARTY BY PRECURSORS ADDED TO CONVERT TO THE COUNTERACTANT IN THE FATTY ACID PRODUCT DURING STORAGE.

Melting Pent of Edible Solid Fats. IV.

Abstract: The samples used for this experiment were liquid soybean oil (I. V. 136.2) mixed with fully hardened soybean oil (I.V. 0.4) or fully hardened beef tallow (I.V. 0.3) by 10, 20, 40, 60 or 80%, The open capillary melting point was measured, as in the previous work, after standing at 0°, 10°, 20°, 40° or 50°C for 1, 5, 24, 120 and 1, 440 hr (2 months). At the same time, its correlation to polymorphism was examined, and the softening point (ring-ball type), Wiley melting point and slipping point were also investigated.1) The open capillary melting point showed a great difference according to the temperature of standing when mixed with 10 or 20% of fully hardened oil, but the difference became smaller withincrease in the amount of hardened oil present.2) The sample mixed with hardened soybean oil showed rapid transition, all becoming β-type after lhr, and there was no difference by the time and temperature of standing. Samples mixed with 1040% of hardened beef tallow became β-type in 1 hr, and were β′-3 type with 6080% mixture, : showing far more rapid transition than the solitary hardened beef tallow.3) In all the samples, presence of a large amount of liquid oil resulted in indistinct pattern in X-ray diffraction because of the segregation. Since there was a difference in the melting point by the temperature of standing in spite of the absence of difference in polymorphism it was considered that in such a mixture of oppositely different substances progress of crystallization resulted in segregation, with separation of the solid and liquid parts, and the difference of crystal growth in the solid portion created a difference in the melting point.4) Both the Wiley melting point and slipping point were higher than the open capillary melting point, and the difference was greater with increase in the amount of liquid oil present. In contrast, the softening point became lower with increase in the amount of liquid oil, but became higher than the open capillary melting point with increase in the amount of hardened oil and there was no definite correlation between them.5) In general, the lower the temperature of standing and the greater the amount of liquid oil present the measured values became scattered. The scattering of the measured values became greater in the order of the Wiley melting point, softening point and open capillary melting point.

Determination of the Δ15 double bond in fatty acids of hydrogenated soybean oil

Abstract: A method was developed to determine the extent of hydrogenation of the Δ15 double bond which occurs during partial catalytic hydrogenation of soybean oil. A linear relationship was found to exist between the linolenate content of commonly occurring C18 unhydrogenated oils (containing no tetraene) and the propanal resulting from their ozonization reduction. The amount of propanal so produced is directly related to the amount of Δ15 double bond in these oils, as well as in hydrogenated soybean oils. Soybean oil was treated with ozone in carbon tetrachloride at —20 C and then reduced with triphenylphosphine. The ozonized-reduced sample was injected into a gas chromatograph, operated at 170C and equipped with a 12 ft × 1/4 in. column of 100/ 120 mesh porous polymer beads. The propanal peak was identified and its area used as a measure of the fatty acids containing Δ15 double bonds in unhydrogenated soybean and other oils of known linolenate content. A nearly stoichiometric amount of propanal results from ozonizing, reducing and chromatographing soybean oil as shown by comparison with a standard mixture of propanal and carbon tetrachloride. The relative standard deviation for the method is ±4.4%. We have also found this method applicable to other oils containing the omega-3 double bond.