Margarine and shortening oils by interesterification of liquid and trisaturated triglycerides

Liquid vegetable oils (VO), including cottonseed, peanut, soybean, corn, and canola, were randomly interesterified with completely hydrogenated soybean or cottonseed hardstocks (vegetable oil trisaturate; VOTS) in ratios of four parts VO and one part VOTS. Analysis of the reaction products by high-performance liquid chromatography showed that at 70°C and vigorous agitation, with 0.5% sodium methoxide catalyst, the reactions were complete after 15 min. Solid-fat index (SFI) measurements made at 50, 70, 80, 92, and 104°F, along with drop melting points, indicated that the interesterified fats possess plasticity curves in the range of commercial soft tub margarine oils prepared by blending hydrogenated stocks. Shortening basestocks were prepared by randomly interesterifying palm or soybean oil with VOTS in ratios of 1:1 or 3:1 or 4:1, respectively. Blending of the interesterified basestocks with additional liquid VO yielded products having SFI curves very similar to commercial all purpose-type shortening oils made by blending hydrogenated stocks. Other studies show that fluid-type shortening oils can be prepared through blending of interesterified basestocks with liquid VO. X-ray diffraction studies showed that the desirable β′ crystal structure is achieved through interesterification and blending. Presented at AOCS Annual Meeting & Expo, Atlanta, Georgia, May 8–12, 1994.     

Über Margarine aus Sojaöl

Margarine from Soybean Oil Fat compositions for the manufacture of margarines of all sorts can be produced from soybean oil alone as the only raw material by indirected interesterification (randomization) of this oil with suitable proportions of hydrogenated soybean fat of definite degree of hardening. The resulting product is then mixed with soybean oil and possibly hardened soybean fat. Especially, the melting behaviour of such compositions has to be adjusted according to the nature of utilization of the individual margarine concerned. The dilatation ranges of household margarine, i. e., for cream-, cake- and pastry-margarine are reported. The keeping properties of a household margarine, which partly contained interesterified fat that consisted of 55% hardened soybean fat and 45% soybean oil, was examined for a longer period, during which its smell, taste structure, consistency, colour as well as autoxidative behaviour were observed. The keeping properties of this margarine were as good as those of high quality vegetable margarines. The same is true for cream-, cake- and pastry-margarines of corresponding compositions.     

Rapeseed oil in a two-component margarine base stock

A two-component margarine base stock with liquid oil as one component allowed for a lowertrans fatty acid content and at the same time provided for a higher essential fatty acid level than a one-component base stock. Transesterification softened a two-component margarine base stock and resulted in a steeper solid fat index curve, but did allow for a lowertrans fatty acid level in a margarine base stock. The high content of erucic acid in rapeseed oil did not change the physical properties of a margarine base stock and provided a good hardstock when this oil was hydrogenated. The use of a hydrogenated rapeseed oil ensured interchangeability of liquid oils in blends and rearranged blends, also seemed superior to soybean hardstocks in this respect.     

Physical and chemical properties of trans-free fats produced by chemical interesterification of vegetable oil blends

Fat blends, formulated by mixing a highly saturated fat (palm stearin or fully hydrogenated soybean oil) with a native vegetable oil (soybean oil) in different ratios from 10:90 to 75:25 (wt%), were subjected to chemical interesterification reactions on laboratory scale (0.2% sodium methoxide catalyst, time=90 min, temperature=90°C). Starting and interesterified blends were investigated for triglyceride composition, solid fat content, free fatty acid content, and trans fatty acid (TFA) levels. Obtained values were compared to those of low- and high-trans commercial food fats. The interesterified blends with 30–50% of hard stock had plasticity curves in the range of commercial shortenings and stick-type margarines, while interesterified blends with 20% hard stock were suitable for use in soft tubtype margarines. Confectionery fat basestocks could be prepared from interesterified fat blends with 40% palm stearin or 25% fully hydrogenated soybean oil. TFA levels of interesterified blends were low (0.1%) compared to 1.3–12.1% in commercial food fats. Presented at the 88th AOCS Annual Meeting and Expo, May 11–14, 1997, Seattle, Washington.     

Modification of karanja oil (Pongamia glabra) by fractionation,blending, and transesterification

In the present study the modification of detoxified and completely refined karanja oil (Pongamia glabra) was studied by physical and chemical means. Karanja oil was fractionated by the detergent fractionation process at low temperature (3 °C). Astearin fraction was obtained with a yield of 11.0 %. The stearin fraction as such or after bioacidolysis, was found to be suitable as margarine fat bases. Karanja oil was also blended with fats like palm stearin, vanaspati, hydrogenated rice bran oil, and hydrogenated soybean oil in various proportions. The blended products as such or after interesterification were found to be suitable as shortenings, margarine fat bases, or vanaspati substitute.     

Preparation and Characterization of a Zero-trans Margarine

Two new types of margarines were prepared in this study. The first was processed without the traditional milk flavour. The fat phase consists of 40% partially hydrogenated cottonseed oil (m. p. 42.2°C), 40 % cottonseed oil and 20 % olive oil as a source of flavouring and antioxidant materials. The second margarine was based mainly on the interesterified fat formed from lipase interesterification of a mixture of 86.5 % cottonseed oil and 13.5 % fully hydrogenated soybean oil (m. p. 67.2°C). Characterization and evaluation of these new types of margarines in relation to two conventional margarines are reported. The presence of diglycerides in the interesterified fat (free from trans isomers) reduced the amount of crystallized solids and the properties of the product were very close to conventional soft margarines. Margarine with olive oil taste was well accepted.     

Formulation of zero-<Emphasis Type="Italic">trans</Emphasis> acid shortenings and margarines and other food fats with products of the oil palm

The fruit of the oil palm yields two types of oil. The flesh yields 20–22% of palm oil (C16∶0 44%, C18∶1 39%, C18∶2 10%). This represents about 90% of the total oil yield. The other 10%, obtained from the kernel, is a lauric acid oil similar to coconut oil. Palm oil is semisolid, and a large part of the annual Malaysian production of about 14 million tonnes is fractionated to give palm olein, which is widely used for industrial frying, and palm stearin, a valuable hard stock. Various grades of the latter are available. Formulae have been developed by straight blending and by interesterification of palm oil and palm kernel oil to produce shortenings and margarines using hydrogenated fats to give the consistency required. Products that include these formulations are cake shortenings, vanaspati (for the Indian subcontinent), soft and brick margarines, pastry margarines, and reduced fat spreads. Other food uses of palm products in vegetable-fat ice cream and cheese, salad oils, as a peanut butter stabilizer, and in confectioners fats are discussed briefly here.     

Electrochemical hydrogenation of edible oils in a solid polymer electrolyte reactor. Sensory and compositional characteristics of low Trans soybean oils

Soybean oils were hydrogenated either electrochemically with Pd at 50 or 60°C to iodine values (IV) of 104 and 90 or commercially with Ni to iodine values of 94 and 68. To determine the composition and sensory characteristics, oils were evaluated for triacylglycerol (TAG) structure, stereospecific analysis, fatty acids, solid fat index, and odor attributes in room odor tests. Trans fatty acid contents were 17 and 43.5% for the commercially hydrogenated oils and 9.8% for both electrochemically hydrogenated products. Compositional analysis of the oils showed higher levels of stearic and linoleic acids in the electrochemically hydrogenated oils and higher oleic acid levels in the chemically hydrogenated products. TAG analysis confirmed these findings. Monoenes were the predominant species in the commercial oils, whereas dienes and saturates were predominant components of the electrochemically processed samples. Free fatty acid values and peroxide values were low in electrochemically hydrogenated oils, indicating no problems from hydrolysis or oxidation during hydrogenation. The solid fat index profile of a 15∶85 blend of electrochemically hydrogenated soybean oil (IV=90) with a liquid soybean oil was equivalent to that of a commercial stick margarine. In room odor evaluations of oils heated at frying temperature (190°C), chemically hydrogenated soybean oils showed strong intensities of an undesirable characteristic hydrogenation aroma (waxy, sweet, flowery, fruity, and/or crayon-like odors). However, the electrochemically hydrogenated samples showed only weak intensities of this odor, indicating that the hydrogenation aroma/flavor would be much less detectable in foods fried in the electrochemically hydrogenated soybean oils than in chemically hydrogenated soybean oils. Electrochemical hydrogenation produced deodorized oils with lower levels of trans fatty acids, compositions suitable for margarines, and lower intensity levels of off-odors, including hydrogenation aroma, when heated to 190°C than did commercially hydrogenated oil.     

Trans-18:1 acids in french tub margarines and shortenings: Recent trends

The fatty acid composition of twelve French tub margarines and three industrial shortenings was established with particular attention to theirtrans-18:1 acid content. Four of the twelve margarines (including two major brands, with 60% of market share) were devoid oftrans isomers, one contained less than 2%trans-18:1 acids, whereas the seven others had a mean content of 13.5 ± 3.6%trans isomers. Four years ago, no margarines with 0%trans-18:1 acids could be found. It is deduced that the recent Dutch and American studies on possible effects oftrans acids on human health (serum cholesterol, heart disease risks) may have had some influence on French margarine manufacturers. Presently, an average French tub margarine contains only 3.8% oftrans-18:1 acids instead of 13% four years ago. To protect brand names, some manufacturers have replaced partially hydrogenated oils with tropical fats or fully hydrogenated oils. On the other hand, two of the three shortenings had high levels oftrans-18:1 acids: 53.5 and 62.5%. This last value, obtained for a sample of hydrogenated arachis oil, seems to be one of the highest values ever reported for edible hydrogenated oils. In this sample,trans-18:1 plus saturated acids accounted for 85% of total fatty acids. This would indicate that shortening producers and users are not yet aware of recent dietary recommendations, probably because these products are not easily identifiable by consumers in food items, in contrast to margarines.     

Trans-free bakery shortenings from mango kernel and mahua fats by fractionation and blending

Bakery shortenings prepared by hydrogenation contain high levels of trans fatty acids, which are considered to be risk factors for cardiovascular disease. The shortenings prepared from maogo kernel and mahua fats have no trans fatty acids. Mahua fat was fractionated by dry fractionation to obtain a high-melting fraction (10% yield, Mh1). Mango fat was fractionated by two-stage solvent fractionation, separating about 15% high-melting fraction (Mk1) in the first stage, followed by 40% stearin (Mk2) in the second stage. The formulation containing 80% Mh1 and 20% of mango middle stearin fraction (Mk2) showed melting characteristics and onset and enthalpy of crystallization similar to those of commercial hydrogenated shortenings designed for cakes and biscuits. The formulation suitable for puff pastry shortening was prepared by blending 50% mango 1st stearin (Mk1) and 50% mahua fat with addition of 5–7% of fully hydrogenated vegetable oil. The formulations having melting characteristics similar to those of commercial cake and biscuit shortenings were also prepared by blending 40% mango fat and 60% mahua fat with 5–7% incorporation of fully hydrogenated peanut oil. However, these formulations showed delayed transition to the stable forms compared to those of commercial samples. Fatty acid composition revealed that commercial hydrogenated shortenings consisted of 18–29% trans oleic acid, whereas the formulations we prepared did not contain any trans acids. The iodine values of commercial samples were 57–58, whereas the value for the formulations prepared were 47–53. The consistency of the prepared samples as measured by cone penetrometer was slightly harder than commercial samples. These studies showed that it is possible to prepare bakery shortenings with no trans fatty acids by using mango and mahua fats and their fractions.     

Vegetable oils: Effects of processing,storage and use on nutritional values

At the present time, vegetable oils are the source of most of the visible fat in the U.S. diet. They are used as salad and cooking oils, in salad dressing, margarine and shortening. Processing methods include extraction, refining, hydrogenation and interesterification. During storage and use, the products are exposed to oxygen and/or heat, particularly during frying. Processing, storage and use are related to changes in composition, nutritive value and physical characteristics of vegetable oils. Refining removes undesirable minor components present in crude oils. Refined polyunsaturated vegetable oils are the primary dietary source of tocopherols. Hydrogenation modifies physical characteristics and improves sensory and oxidative stability. This process converts some of the polyunsaturated fatty acids to new fatty acid isomers. Although the biochemical effects of these isomers are still being studied, long-term animal feeding trials and human experience have demonstrated that the partially hydrogenated oils in margarines and shortenings are wholesome foodstuffs. Abusive overheating of fat in air sharply decreases its palatability and nutritive value and may create minor amounts of carcinogenic materials. However, long-term animal feeding studies with properly used frying fats have revealed little, if any, effect on life span and incidence of pathological conditions.     

Measurement of the consistency of plastic vegetable fats

Summary 1. An improved micropenetrometer is described, by means of which it is possible to measure the consistency of fats with a high degree of precision. 2. The intelligent use of a micropenetration method requires some consideration of the theory of plasticity in fats. This theory is briefly discussed. 3. The influence of various factors on the consistency of solidified fats has been investigated, and as a result of this investigation a standard technique for making micropenetration tests is proposed. 4. Micropenetration data are recorded on cottonseed, peanut, and soybean oils hydrogenated to different degrees, on cottonseed oil blended with various proportions of highly hydrogenated oil, and on various commercial samples of shortening and margarine. 5. A quick micropenetration method, applicable as a control in the hydrogenation of fat products, is described.     

A comparison of nuclear magnetic resonance and dilatometry for estimating solids content of fats and shortenings

The percent solids values of fats and shortenings using nuclear magnetic resonance (NMR) and solid fat index (SFI) have been compared. The samples used were: blends of hard fat and safflower oil, safflower oil hydrogenated to varying degrees, and different types of shortenings. This investigation demonstrated the empirical nature of the SFI technique and shows the nature of the deviations from the solids content determined by the NMR method. The magnitude of the deviation of SFI from the NMR solids content increased with the level of the solids. The SFI values and the NMR solids content were similar at the lower levels (SFI values of 10) but at the upper limit for the SFI method (SFI values of 50) the solids content by the NMR method can be 80% or more, a difference of 30 units. Although the determination of solids content by NMR is reliable, the relationship between SFI values and NMR values for different types of samples is so variable that the calculation of the SFI value from percent solids by NMR, or percent solids from SFI values from prediction equations is not very reliable. Since NMR measures the solids content more accurately than SFI and is applicable over the entire range of solids, 0 to 100%, it will be very useful in fat and oil research and control.     

Low-<Emphasis Type="Italic">trans</Emphasis> Shortening and Spread Fats Produced by Electrochemical Hydrogenation

Partially hydrogenated soybean oils (90–110 IV) were prepared by electrochemical hydrogenation at a palladium/cobalt or palladium/iron cathode, moderate temperature (70–90 °C) and atmospheric pressure. The trans fatty acid (TFA) contents of 90–110 IV products ranged from 6.4 to13.8% and the amounts of stearic acid ranged from 8.8 to 15.4% (the higher stearic acid contents indicated that some reaction selectivity had been lost). The solid fat values and melting point data indicated that electrochemical hydrogenation provides a route to low-trans spreads and baking shortenings. Shortenings produced by conventional hydrogenation contain 12–25% trans fatty acids and up to 37% saturates, whereas shortening fats produced electrochemically had reduced TFA and saturate content. Electrochemical hydrogenation is also a promising route to low-trans spread and liquid margarine oils. Compared to commercial margarine/spread oils containing 8–12% TFA, the use of electrochemical hydrogenation results in about 4% TFA. Names are necessary to report factually an available data: the USDA neither guarantees nor warrants the standard of the product, and the use of the name USDA implies no approval of the product to the exclusion of others that may also be suitable.     

Evaluation of Transesterified Hardened and Liquid Soybean Oils as Raw Materials for Margarine Oils

Margarine oils have been prepared by transesterification of blends of hardened and liquid soybean oils or by blending of transesterified hardened oils with liquid soybean oil. The dilatometric characteristics of those oils and their nutritional values (as characterized by the L/S ratio of linoleic acid to total saturated acids) have been compared with the same parameters of margarine oils from local and foreign table margarines. It was concluded that margarine oils of suitable melting characteristics and of an average nutritional value (L/S ratio of about 0.70) can be prepared from blends of soybean oils alone, using transesterification process.     

CLA‐Rich Soy Oil Shortening Production and Characterization

Conjugated linoleic acid‐rich soy oil (CLARSO) has been shown to have numerous health benefits, including anti‐obesity and anti‐carcinogenic properties. This oil was previously used to produce CLA‐rich margarine that showed physical characteristics similar to commercially available margarine. The objective of this study was to produce CLA‐rich shortening and analyze its physical properties relative to commercially available shortenings and soy oil control shortenings. The shortenings were prepared and their rheology, thermal behavior, and solid fat content (SFC) were determined and compared to the commercial samples. The CLA‐rich shortening samples showed similar rheological properties to the commercial samples and showed a better consistency (more solid‐like behavior) compared to the soy oil control samples. In addition, the CLA‐rich shortenings also have a higher SFC (% SFC) as well as higher latent heat of crystallization and melting than the soy oil controls indicating a comparatively higher crystalline fraction. Thus, CLARSO produced firmer shortenings than did conventional soy oil by interacting with the crystallizing stearin fraction and consequently increasing the crystalline mass fraction without significantly altering the microstructure kinetics of solid fat crystallization.     

Physical and textural evaluation of some shortenings and margarines

Solid fat content of shortening and margarine was estimated by pulsed NMR. These values were compared with those of the melted fats using different cooling methods. Solid fat content of shortenings measured at 10 and 20 C followed the same trend as those measured on the melted fat tempered at 30 C. Solid fat content of margarines followed the same trend as those measured on the nontempered fats. Softening points of the products were similar to the dropping points of the fats, as were the temperatures of the DSC major melting peaks. Compression tests of cylindrical samples provided more information about textural characteristics of the products than one penetration tests.     

Palm oil in margarines and shortenings

Palm oil has become used increasingly as a raw material in soaps, edible fat-based products and confectionary. This paper deals specifically with applications in margarines and shortenings. Properties of palm oil are described, indicating both the special characteristics that make it suitable for such applications and its limitations. Modification techniques which can minimize or eliminate the disadvantages and hence broaden the scope of application include hydrogenation, fractionation and interesterification. Various applications of palm oil, both modified and unmodified, in margarines and shortenings for use in both tropical and temperate climatic conditions are described.     

Baking performance of palm diacylglycerol bakery fats and sensory evaluation of baked products

Baking performance of palm diacylglycerol (PDG)‐enriched fats was evaluated and compared with that of commercial bakery fats. PDG‐enriched shortenings were found to produce cakes with significantly (p<0.05) higher mean values for specific volume than that produced from commercial shortening. As for PDG‐enriched margarines, cookies prepared from PDG‐enriched margarines were found to have reduction in cookies spread as compared to that of commercial shortening. Nevertheless, this reduction was not statistically significant. Sensory evaluation of the baked products was also conducted. Both trained and untrained panelists rated cakes prepared from PDG‐enriched shortenings as having higher moistness, softer, and airier texture than that of commercial shortening. This is in agreement with findings from principal component analysis (PCA). As for cookies, both trained and untrained panelists rated cookies prepared from PDG‐enriched margarines as having softer texture and compactness compared to that prepared from commercial margarine.     

Essential fatty acid contents of various fats: Interpretations of values by physico-chemical tests

Biological assays of oil and fat products, free from isomers of the naturally-occurringcis-9,cis-12 linoleic acid, have been shown to provide estimates of essential fatty acid content which agree well with values obtained by spectrophoto-metric analysis. However, when partially hydrogenated fats, such as those used in margarines, are bio-assayed the estimates obtained are only about 60% of those derived by spectro-photometric tests. In a blended corn oil margarine, good agreement was obtained for linoleic acid content by using biological assay or spectrophotometry, thio-cyanometric procedure, column chromatography for saturates plus iodine value, and gas liquid partition (GLP) chromatography. This margarine fat contained about 29% of the essential form of linoleic acid, and had a ratio to saturated fatty acids of 1.6:1. The hydrogenated corn oil margarine is unlike conventional margarines in providing high amounts of the isomeric forms of linoleic acid which lack essential fatty acid activity. For this reason, poor agreement was obtained between biological assay results and those by physico-chemical measurements of linoleic acid content. Such fat contains only about 6% of the essential form of linoleic acid, with a ratio to saturated fatty acids of ca. 0.3.1. From this study it is now possible to characterize, even without bio-assay data, the fatty acid composition of a highly isomerized fat, such as is found in hydrogenated corn oil margarine. The characterization groups the fatty acids into saturates and total linoleic acids, with the latter including estimates of the positional isomers of linoleic acid with widely spaced double bonds,trans forms of linoleic acid with methylene-in-terrupted double bonds, linoleic acids with the double bonds in conjugated position, andcis-9,cis-12 linoleic acid. The combined use of the spectrophotometric and thiocyanometric procedures makes it possible to estimate the essential fatty acid content of hydrogenated fats containing residual dienes.