MXPA98008641A - Soy aceitem with high oxidat stability - Google Patents

Abstract

A high oleic soybean oil having high oxidative stability is exposed. This oil has an induction time greater than 50 hours. Oxidative stability is achieved without the need for hydrogenation or the addition of an antioxidant

Description

SOYBEAN OIL THAT HAS HIGH OXIDATIVE STABILITY FIELD OF THE INVENTION This invention relates to soybean oil and, in particular, higher oleic soybean oil which does not require hydrogenation or the addition of oxidants to achieve high oxidative stability.

- BACKGROUND OF THE INVENTION Soybean oil is currently the predominant vegetable oil in the world. However, soybean oil is relatively unstable to oxidation and therefore its use is limited to applications where a high degree of oxidative stability is not required. Soybean oil contains high levels of polyunsaturated fatty acids and is more prone to oxidation than oils with higher levels of monounsaturated and saturated fatty acids. Increasing the degree of unsaturation in an oil will most likely cause the oil to be pulled out (oxidize). Oxidation leads to the development of flavors and odors in the oil as a result of the degradation process. Oils with high levels of polyunsaturated fatty acids are not commonly used in applications that require a high degree of stability REF .: 28256 oxidative, such as cooking for a long period of time at a high temperature.

Several methods are available to increase the stability of soybean oil. A commonly used method is catalytic hydrogenation, a process that reduces the number of bonds and increases the melting point of fat. Consequently, the hydrogenation also increases the saturated fatty acid content of the oil. Another approach to increase oxidative stability is by the addition of antioxidants.

Each of these approaches suffers from one or more disadvantages, for example, the hydrogenation of the oils has been associated with respect to health, environmental and food quality. A known consequence of the hydrogenation of oils is the production of trans isomers of fatty acids that have been associated with deleterious effects on health including risk of coronary disease. (Food Product Design, November 1994). In the case of antioxidants, some are very expensive to acquire and not all antioxidants resist high temperatures. In addition, in many cases a food manufacturer does not want to use oils with added antioxidants if a label with unadulterated ingredients is desired. Thus, an oil having high oxidative stability under high temperatures without requiring the addition of antioxidants is very desirable.

The U.S. Patent No. 5,260,077, published by Carrick et al. on November 9, 1993, he presents a method to stabilize triglyceride oils with a high content of oleic acid by the addition of tocopherol, a natural antioxidant. The combination of superior oleic oil and tocopherol results in a stable composition for intense frying.

The U.S. Patent No. 4,627,192 discloses a sunflower seed having an oleic acid content of 80% or more. The U.S. Patent No. 4,743,402 discloses a high oleic sunflower oil.

FR 2617675, published on January 13, 1989, exhibits oleaginous seeds with an oleic acid content of 74-84% and a linoleic acid content of approximately 2-8%. The low content of linoleic acid is reported to ensure high storage stability.

World Patent Publication WO91 / 11906, published on August 22, 1991, discloses safflower seeds having an oleic or linoleic acid content of at least 80%.

Oxidative stability is also an important characteristic for industrial oil applications. This problem is particularly acute for triglyceride oils that tend to deteriorate easily due to their high degree of unsaturation. The processes of unsaturation via a mechanism that is initiated by the formation of a free radical and occurs more easily in triglyceride oils due to the high content of active methylene groups adjacent to the double bonds. The overall effect is a high susceptibility of the oil to oxidation, which is more complicated by the contact of the oil with metals, such as iron and copper, present in the equipment or material that acts as a catalyst in the oxidation process and accelerates the degradation of oil.

The U.S. Patent No. 5,580,482, published by Chasan et al. on December 3, 1996, it shows the lubricant compositions stabilized against the effects of heat and oxygen.

The U.S. Patent No. 5,413,725, published by Lal et al. on May 9, 1995, it exhibits the pour point of depressants for monounsaturated vegetable oils and higher monounsaturated vegetable oils / biodegradable base and fluid mixtures.

The U.S. Patent No. 5,399,275, published by Lange et al. on March 21, 1995, he exhibits improved compositions in the environmentally favorable viscosity index.

BRIEF DESCRIPTION OF THE INVENTION The present invention is directed to a high oleic soybean oil having high oxidative stability which comprises a C18: l content greater than 65% of the fatty acid radicals in the oil, a C18: 2 and C18 combined content: 3 less than 20% of the fatty acid radicals in the oil and an induction time of the active oxygen method greater than 50 hours wherein said oxidative stability is achieved without the addition of an antioxidant. The oil of this invention can be used as a mixing source to make a mixed oil product. To be used in the preparation of food.

BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 represents the peroxide values developed during the Active Oxygen Method test for high oleic soybean oil compared to normal soybean oil.

Figure 2A shows the accumulation of polar materials in high oleic and normal soybean oils during heating of the oils.

Figure 2B shows the accumulation of polymeric materials in high oleic and normal soybean oils during heating of the oils.

Figure 3 compares the performance of high oleic soybean oil with normal soybean oil in the Schaal Oven test.

Figure 4 compares the times required to make the equivalent products as indicated by the iodine (IV) value from the hydrogenation of high oleic and normal soybean oils.

Figure 5 presents the Solid Fat Index measurements of a high oleic soybean oil compared to other fats.

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a high oleic soybean oil having high oxidative stability which comprises a C18: l fatty acid content of greater than 65% by weight, combined levels of the content of C18: 2 and C18 fatty acids: 3 less than 20% by weight, and an active oxygen method greater than 50 hours wherein said oxidative stability is achieved without the addition of an antioxidant. A soybean oil with "high oxidative stability" is a soybean oil that is less susceptible to oxidative degradation when compared to normal soybean oil.

A high oleic soybean seed is a soybean seed where the oleic acid is calculated greater than 65 percent of the fatty acid radicals in the oil and, preferably, greater than 75 percent of the fatty acid radicals in the oil . The preferred high oleic soybean oil starting materials are set forth in World Patent Publication W094 / 11516, the disclosure of which is incorporated herein by reference. The soy beans used in the present invention are described later in Example 1.

The high oleic soybean oil of this invention has a C18: 1 content of 65 to 85% of the fatty acid radicals, a C18: 2 and C18: 3 combined content of less than 20% of the fatty acid radicals. Preferably, the oil of the invention has a C18: l content greater than about 70% of the fatty acid radicals, a C18: 2 and C18: 3 combined content of less than 15% fatty acid. More preferably, the oil of the invention has a C18: l content greater than about 75% of the fatty acid radicals, a C18: 2 and-C18: 3 combined content of less than 10% of the fatty acid radicals.-More preferably, the oil of the invention has a C18: l content greater than about 80% of the fatty acid radicals, a C18: 2 and C18: 3 combined content of less than 10% fatty acid.

A particularly advantageous feature of the present invention is that no hydrogenation or other fractionation of the oil is necessary to achieve high oxidative stability. In addition, it is not necessary to add antioxidants, such as natural tocopherol-like antioxidants, to the compositions of the invention to increase their stability.

A number of methods are well known to those skilled in the art to determine oxidative stability. The most commonly used method is the Active Oxygen Method (AOM). This is an accelerated oxidation test in which an oil is aerated under a constant high temperature (97.8 ° C) and the degradation is monitored by the peroxide accumulation. The end point, or induction time, is determined by the number of hours required to reach a peroxide value of 100 meq / kg. Thus, at a longer induction time the oil is more stable. Almost all commercial oil samples specify an AOM induction time as a component of the technical results sheet.

The AOM induction time for the high oleic soybean oil of the invention is greater than 50 hours. Preferably, the AOM induction is greater than 75 hours and, more preferably, greater than 100 hours or even greater than 140 hours.

Another standard method now commonly used to evaluate the stability of commercial cooking oils is the Oxidative Stability Index (OSI) which is automatically measured using a machine manufactured by Ominion, Inc. of Rockland, MA, USA.

The OSI machine works by bubbling air through hot oil at 110 ° C. As the oil is oxidized, volatile organic acids, mainly formic acid, are formed which can be collected in distilled water in a cell. The machine constantly measures the conductivity of the distilled water and the induction period is determined as the time it takes for this conductivity to start a rapid increase. Although the results derived from the two methods do not always have a linear correlation, the OSI induction time values for most oils are half the values derived from AOM. The OSI induction time value for the high oleic soybean oil of the invention is greater than 25 hours. Preferably, the OSI induction time value is greater than 50 hours and, more preferably, greater than 75 hours.

Vegetable oils are commonly used in high temperature applications. The oxidation of the oil accelerates in the presence of heat. It is important that an oil allows to resist these conditions for applications such as frying, baking, roasting, etc. In some cases, antioxidants could be added to improve stability but not all antioxidants resist high temperatures. In addition, in many cases a food manufacturer does not want to use oils with added antioxidants if a label with unadulterated ingredients is desired. Therefore, an oil that is stable to oxidation under high temperatures in the absence of any additive or other processing is highly desirable. The overheating of oils often leads to the thermal polymerization of the oil and the oxidation products result in a rubber, similar in composition to varnish in the equipment used for heating and excessive foaming of the oil. As a result of oxidation, a variety of degradation products are formed depending on the conditions under which the oil is exposed. High temperature stability can be evaluated by exposing the oils to high temperature and monitoring the formation of desirable degradation products. These include volatile and non-volatile products and could be hydrocarbons, alcohols, aldehydes, ketones, and acids. The non-volatile components can also be classified into polar and polymerized compounds. The polar and polymerized compounds present in a degraded oil can be analyzed directly by reversed-phase high-performance liquid chromatography as described in Lin, S.S., 1991, Fats and oils oxidation. Introduction to Fats and Oils Technology (Wan, P: J: ed.), Pages 211-232, Am. Oil Chem. Soc.

The oil of this invention can be used in a variety of applications. In general, oxidative stability refers to flavor stability. The oil of this invention can be used in the preparation of food. Examples include, but are not limited to, uses as ingredients, such as coatings, such as salad oils, as spreading oils, as roasting oils, and as frying oils. Foods in which the oil could be used include, but are not limited to, cookies and light food, jam products, syrups and coatings, sauces and juices, soups, blending and baking mixes, bakery mixes and pastas. Foods incorporating oil of this invention could retain better flavor for long periods of time due to the improved stability against oxidation imparted by this oil.

The oils of this invention can also be used as a mixing source to make a mixed oil product. By a mixing source, it is understood that the oil of this invention can be mixed with other vegetable oils to improve the characteristics, such as fatty acid composition, taste, and oxidative stability, of the other oils. The amount of oil of this invention that can be used will depend on the desired properties sought to achieve in the oil product of the resulting final mixture. Examples of mixed oil products include, but are not limited to, margarines, shortenings, frying oils, salad oils, etc.

In another aspect, the oils of this invention can be subjected to further processing such as hydrogenation, fractionation, interesterification of cut fat (hydrolysis).

In yet another aspect, this invention relates to by-products formed during the production of oils of this invention.

The methods for the extraction and processing of soybeans to produce soybean oil and food are well known throughout the soy processing industry. In general, soybean oil is produced using a series of steps that perform the extraction and purification of an edible oil product from the seed that has the oil.

Soybean oils and soybean byproducts are produced using the generalized steps shown in the following diagram.

Process Impurities Removed / Byproducts Obtained Soybean Seed 1 Extraction of Deaceated Soy Flakes Oil (Food, Protein Products) I Degumization Lecithin and Alkali or Refining Gums, Free Fatty Acids, Physics Pigments I Water Washing Soap and Bleached Color, Soap, Metal I (Hydrogenation) I ( Insulators) Stearin and Deodorization FFA, Tocopherols, Sterols, Volatiles Oil products Soybeans are cleaned, tempered, peeled, and flaked, which increases the efficiency of oil extraction. Oil extraction is usually done by solvent extraction (hexane) but can also be achieved by a combination of physical pressure and / or solvent extraction. The resulting oil is called crude oil. The crude oil could be degummed by hydrating phospholipids and other polar and neutral lipid complexes that facilitate their separation from the non-hydrating triglyceride fraction (soybean oil). The resulting lecithin gums could be processed further to make commercially important lecithin products used in a variety of foods and industrial products as emulsification and release (anti-stick) agents. The degummed oil could be further refined for the removal of impurities; mainly free fatty acids, pigments, and residual gums. The refining is carried out by means of the addition of caustic soda which reacts with free fatty acid to form soap and phosphatides and hydrated proteins in the crude oil. The water is used to wash traces of soap formed during refining. The byproduct of existing soap could be used directly in animal feed or acidified to recover free fatty acids. The color is removed by adsorption with a bleaching earth that removes most of the chlorophyll and carotenoid compounds. The refined oil can be hydrogenated resulting in fats with various melting properties and textures. The insulation (fractionation) could be used to remove stearin from the hydrogenated oil by crystallization under carefully controlled cooling conditions. Deodorization, which is mainly steam distillation under vacuum, is the last step and is designed to remove compounds that impart oil odor and taste. Other valuable by-products such as tocopherol and sterols could be removed during the deodorization process. The deodorized distillate containing these by-products could be sold for the production of natural vitamin E and other high-value pharmaceuticals. Refined, bleached (hydrogenated, fractionated) and deodorized oils and fats could be packaged and sold directly or further processed into more specialized products. A more detailed reference for soybean processing, soybean oil production and by-product utilization can be found in Erickson, 1995, Practical Handbook of Soybean Processing and Utilization, The American Oil Chemists' Society and United Soybean Board.

Hydrogenation is a chemical reaction in which hydrogen is added to the double bonds of the unsaturated fatty acid with the aid of a catalyst such as nickel. High oleic soybean oil contains oleic, linoleic, and linolenic fatty acids and each of these can be hydrogenated. Hydrogenation has two main effects. First, the oxidative stability of the oil increases as a result of the reduction of the unsaturated fatty acid content. Second, the physical properties of the oil are changed because the fatty acid modification increases the melting point resulting in a semi-liquid or solid fat at room temperature.

There are many variables that affect the hydrogenation reaction that at the same time alters the composition of the final product. Operating conditions include pressure, temperature, type and concentration of the catalyst, agitation and reactor design are among the most important parameters that can be controlled. The selective hydrogenation conditions can be used to hydrogenate the more unsaturated fatty acids in preference to the less unsaturated fatty acids. Very light or mild hydrogenation is often used to increase the stability of liquid oils. The additional hydrogenation converts a liquid oil to a solid fat physically. The degree of hydrogenation depends on the desired performance and the melting characteristics designed for the particular final product. Liquid shortenings, used in the manufacture of bakery products, fats and solid shortenings used for commercial frying and roasting operations, and the base reserve for the production of margarine are among a large number of possible oil and fat products achieved through of hydrogenation. A more detailed description of hydrogenation and hydrogenated products can be found in Patterson, H.B. ., 1994, Hydrogenation of Fats and Oils: Theory and Practice. The American Oil Chemists' Society.

"Interesterification" refers to the exchange of the fatty acid radical between an ester and an acid (acidolysis), an ester and an alcohol (alcoholysis) or an ester and an ester (transesterification). The interesterification reactions are achieved using chemical or enzymatic processes. Random or directed transesterification processes rearrange the fatty acids in the triglyceride molecule without changing the fatty acid composition. The modified triglyceride structure could result in a fat with altered physical properties. Targeted interesterification reactions using lipases are becoming increasingly interesting for specialty products * high value similar to cocoa butter substitutes. Products that are commercially produced using interesterification reactions include but are not limited to shortenings, margarines, cocoa butter substitutes and structured lipids containing medium chain fatty acids and polyunsaturated fatty acids. Interesterification is discussed further in Hui, Y.H., 1996, Bailey's Industrial Oil and Fat Products, Volume 4, John Wiley & Sons.

Fatty fatty acid methyl esters are two of the most important oleochemical derivatives of vegetable oils. Fatty acids are used for the production of many products such as soaps, medium chain triglycerides, polyol esters, alkanolamides, etc. Vegetable oils can be hydrolyzed or divided into their corresponding fatty acids and glycerin. Fatty acids produced from various fat separation processes could be used raw or more often purified in fractions or individual fatty acids by distillation and fractionation. The purified fatty acids and the fractions thereof are converted into a wide variety of oleochemicals, such as dimers and trimers acids, diacids, alcohols, amines, amides and esters. Methyl esters of fatty acid increasingly replace fatty acids as starting materials for many oleochemicals such as fatty alcohols, alkanolamides, a-sulfonated methyl esters, diesel oil components, etc. Glycerin is also obtained by cutting triglycerides using division or hydrolysis of vegetable oils. Additional references in the commercial use of fatty acids and oleochemicals could be found in Erickson, D.R., 1995, Practical Handbook of Soybean Processing and Utilization, The American Oil Chemists' Society, and United Soybean Board: Pryde, E.H., 1979, -Fatty Acids. The American Oil Chemists' Society; and Hui, Y.H., 1996, Bailey's Industrial Oil and Fat Products, Volume 4, John Wiley & Sons.

In another aspect, this invention relates to the industrial use of the soybean oil of this invention for industrial applications such as an industrial lubricant for a variety of end uses, such as a hydraulic fluid, etc. The industrial use of vegetable oils as a base fluid for lubricants has been known for many years. However, the interest has intensified due to environmental interests in the use of petroleum oils in environmentally sensitive areas. Vegetable oils are easily biodegradable, have low toxicity and have good lubricating characteristics. However, high pour points and rapid oxidation at high temperatures limit its use. Since the soybean oil of this invention is low in polyunsaturates, as discussed herein, and has high oxidative stability and high temperature stability, these characteristics also make the soybean oil of this invention desirable for industrial applications such as an industrial fluid. , p. ex. , as an industrial lubricant or as a hydraulic fluid, .etc. The additives that can be used to make industrial lubricants and hydraulic fluids are commercially available. In fact, some additives have been specially formulated for use with high oleic vegetable oils. The additives generally contain antioxidants and materials that retard the formation of foam, wear, rust, etc.

A common method for measuring the oxidative stability of industrial fluids is the rotary pump oxidation test (ASTM D-2272). The operation of the oil of this invention when compared to commercially available products using the rotary pump oxidation test is established in the following example.

EXAMPLES The present invention is further defined in the following examples, in which all parts are by weight, percents are by weight (to volume), and degrees are Celcius, unless otherwise stated. It should be understood that these Examples, while indicating the preferred embodiments of the invention, are given by way of illustration only. From the foregoing discussion and these Examples, one skilled in the art can ascertain the essential characteristics of this invention, and without deviating from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various uses and conditions.

EXAMPLE 1 Soybeans with High Oleic Content The production of a soybean oil in linoleic acid and low in polyunsaturated fatty acids, without the need for chemical processing of the oil, requires the availability of soybeans that have a high content of oleic acid in the fatty acid fraction. High oleic soybeans were prepared by recombinant manipulation of the oleoyl 12-desaturase activity. In soybean (Glycine max) there are two genes for this activity, one of which (GmFad 2-1) is expressed only in the developed seed (Heppard et al. (1996) Plant Physiol. 110: 311- 319). The expression of this gene increases during the period of oil deposition that starts about 10 days after flowering, and its gene product is responsible for the synthesis of the polyunsaturated fatty acids found in soybean oil. GmFad 2-1 is described in detail by Okuley, J. et al. (1994) Plant Cell 6: 147-158 and in W094 / 11516. It is available from the ATCC in the form of plasmid pSF2-169K (ATCC accession number 69092). The other gene (GmFad 2-2) is expressed in the seed, leaf, root and stem of the soybean plant at a constant level and is the "housekeeping" 12-desaturase gene. The product of the Fad 2-2 gene is responsible for the synthesis of polyunsaturated fatty acids for cell membranes.

GmFad 2-1 is placed under the control of a strong seed-specific promoter derived from the oi subunit of the β-conglycinin gene (Glycine max). This promoter allows high level of specific expression of the seed of the gene being treated. It extends over 606 bp upstream of the initiation codon of the a subunit of the β-conglycinin storage protein of Glycine max. The β-conglycinin promoter sequence represents an allele of the published β-conglycinin gene (Doyle et al., (1986) J. Biol. Chem. 261: 9228-9238) having differences in the 27 nucleotide positions. It has been shown to maintain seed-specific expression patterns in transgenic plants (Barker et al., (1988) Proc. Nati, Acad. Sci. 85: 458-462 and Beachy et al., (1985) EMBO J. 4 : 3048-3053). The reading frame was terminated with a 3 'fragment of the phaseolin gene of the bean (Phaseolus v? Lgaris). This is an 1174 bp extension of 3 'sequences of the Phaseolus vulgaris phaseolin gene from the stop codon (originated from the clone described in Doyle et al., 1986).

The open reading frame of GmFad 2-1 (ORF) was in a nonsense orientation with respect to the promoter to produce a silent gene of the antisense cDNA of GmFad 2-1 and the endogenous GmFad 2-1 gene. This phenomenon, known as "sense suppression" is an effective method for deliberately shutting down genes in plants and is described in U.S. Pat. No. 5,034,323.

For the maintenance and replication of the plasmid in E. coli the GmFad 2-1 transcriptional unit described above was cloned into the plasmid pGem-9z (-) (Promega Biotech, Madison Wl, USA).

The ß-glucuronidase (GUS) gene from E. coli was used for the identification of the transformed soybean plants. The cassette used consisted of three modules; the 35S promoter of the Cauliflower Mosaic Virus, the ß-glucuronidase (GUS) gene from E. coli and a 0.77 kb fragment containing the nopaline synthetase (NOS) gene terminator of the Ti plasmid of Agrobacterium tumefasciens. The 35S promoter is a 1.4 kb promoter region of CaMV for constitutive expression of the gene in most plant tissues (Odell et al. (985) Nature 303: 810-812), the GUS gene a fragment encoding the enzyme β-glucuronidase (Jefferson et al (1986) PNAS USA 83: 8447-8451) and the terminator NOS a portion of the 3 'end of the region encoding nopaline synthetase (Fraley et al., (1983) PNAS USA 80: 4803 -4807). The GUS cassette was cloned and cloned into the GmFad 2-l / pGEM-9z (-) construct and designated pBS43.

Plasmid pBS43 was transformed into meristems of the elite soybean line, by the particle bombardment method (Christou et al., (1990) Trends Biotechnol., 8: 145-151). The fertile plants were regenerated using methods well known in the art.

From the initial population of transformed plants, a plant was selected that was expressing GUS activity and that was also positive for the GmFad 2-1 gene (Event 206-05) when evaluated by PCR. Small fragments of a number of Rl seeds were taken from plants 260-05 and screened for the fatty acid composition. The fragmented seed was planted and germinated later. The genomic DNA was extracted from the leaves of the resulting plants and cost with the restriction enzyme Bam Hl. The spots are tested with a phaseolin test.

From the pattern of DNA hybridization it is clear that in the original transformation event the GmFad 2-1 construct has been integrated into two different loci in the soybean genome. At a locus (Locus A) the GmFad 2-1 construct was causing a quenching of the endogenous GmFad 2-1 gene, which resulted in a relative oleic acid content of approximately 85% (compared to approximately 20% in elite soybean varieties) . At locus A there were two copies of pBS43. In the DNA hybridization spot this was seen as two cosegregant bands. At the other integration locus (Locus B) the GmFad 2-1 was overexpressed, thus lowering the oleic acid content to approximately 4%.

The segregant lines of the fourth generation (plants R4), generated from the original transformant, were allowed to grow until mature. The seeds of R4, which contained only the silent Locus A (eg, G94-1), did not contain any detectable mRNA of GmFad 2-1 (when measured with Northern blot) in samples recovered 20 days after flowering. The mRNA of GmFad 2-1, although somewhat reduced compared to the controls, was not suppressed. Thus the sense construction of GmFad 2-1 had the desired effect of preventing the expression of the GmFad 2-1 gene and thus increasing the oleic acid content of the seed. All plants homozygous for the silent locus of GmFad 2-1 had an identical Southern blot profile for a number of generations. This indicates that the insertion was stable and in the same position of the genome for at least four generations. A summary of the content of oleic acid found in the different generations of recombinant soybean plants and seeds is presented in Table 1.

TABLE 1 Plant ID Generation Seed Oleic Acid Plant2 Analyzed3 total. { %) G253 R0: 1 Rl: 2 84.1% G276 R0: 1 Rl: 2 84.2% G296 R0: 1 Rl: 2 84.1% G313 R0: 1 Rl: 2 83.8% G328 R0: 1 Rl: 2 84.0% 6168-187 Rl: 2 R2: 3 84.4% G168-171 Rl: 2 R2: 3 85.2% G168-59--4 R2: 3 R3: 4 84.0% G168-72--1 R2: 3 R3: 4 84.1% G168-72--2 R2: 3 R3: 4 84.5% G168-72--3 R2: 3 R3: 4 84.3% G168-72--4 R2: 3 R3: 4 83.3% aR0: l indicates the seed and the grown plant of the seed after unifying the first transforming generation. Rl: 2 indicates the seed and the plant grown from the seed after uniforming the second transforming generation. R2: 3 indicates the seed and the plant grown from the seed after unifying the third transforming generation. R3: 4 indicates the seed and the plant grown from the seed after unifying the fourth transforming generation.

EXAMPLE 2 Extraction v Processing of high oleic oil sova High oleic and normal soybean oils are each produced on the laboratory table or in a - Commercial pilot plant using industry standard methods as described below. Commercial samples of other high stability oils and shortening used for comparison were obtained from the manufacturers and stored cold under nitrogen. These samples include soy frying oil, clear liquid lard, heavy lard, low linoleic soybean oil, and high oleic hemp oil. High oleic corn oil was produced using standard conditions similar to those described above.

Part A: Oil processing at scale (pilot plant) The harvested soybeans (97.5 kg) were tempered by sucking the seed with water to increase the moisture to 8.7%. The water and the seed were mixed for about 10 minutes and allowed to equilibrate for about 21 hours. The tempered seeds were cracked using a Ferrell-Ross Cracking Roll equipment at 3.5 on the scale of the shell roller. The husks were separated in a Kice Multi-aspirator Model 6F6 using an air differential pressure of 0.8-1.2 inches of water. The soaked soy substances were cooked in a Simon-Rosedowns two-dish cooker at approximately 40 ° C for 10-30 minutes the heated soy substances were dropped into the second dish and heated to 60-75 ° C for 15- 25 minutes. The cooked soy substances were made flakes with a thickness of approximately 0.4 mm in an E.R. Flake Roller. and F. Turner. The resulting soy flakes were extracted with hexane in a Crown Iron Works Cycle Extractor (Type II) using a total residence time of 60 minutes and a solvent to solids ratio of approximately 1.5: 1 (p: p). The temperature of the solvent was 50-60 ° C. The micelle (hexane / oil mixture) was desolventized using a Tetra-Laval Scraped Surface Heat Exchanger followed by complete desolventization in the laboratory using a rotary evaporator. The crude oil was collected and kept under nitrogen until further processing.

The crude oil was degummed in water in the following manner. The oil was heated to 60-70 ° C and a volume of water at 90 ° C equivalent to 2% of the oil volume was added and mixed for 15 minutes at 75-80 ° C; the solids were then separated by centrifugation. The degummed oil was refined by heating to 70-80 ° C.

The crude oil was degummed water in the following manner. The oil was heated to 60-70 ° C and a volume of water at 90 ° C equivalent to 2% of the oil volume was added and mixed for 15 minutes at 75-80 ° C; the solids were then separated by centrifugation. The degummed oil was refined by heating to 70-80 ° C. A volume of an 85% phosphoric acid solution equivalent to 0.1% of the volume of degummed oil was added and the solution was mixed for 30 minutes. Sufficient NaOH was added to reach 16 Bé to neutralize free fatty acids; an additional excess of 0.08% w / w NaOH was added and the solution was mixed for 30 minutes while heating to 80-85 ° C. The solids were separated by centrifugation. The oil was washed with water by heating to 75-80 ° C and adding water at 95 ° C to 10% (v / v), mixed for 10 minutes at 80-90 ° C, and centrifuged. The oil washed with water was bleached by charging 1200 g of oil in a Parr reactor of 2L and adding a bleaching clay (Clarion 470 SA, American Colloid Co.) up to 0.5% (w / w) in vacuum and heating to 110 ° C. for 30 minutes before cooling to 65 ° C. The oil was removed and 30 g of "filter aid" was added and the oil was filtered. These steps were repeated until all the oil was blanched. The oil was deodorized by charging 2200 g in the 5L glass deodorizer under vacuum and heated to 100 ° C. Steam was added at 3% (w / w) / h and the oil was brought to 240 ° C with continuous dispersion during lh at the temperature. The oil was then cooled to 70 ° C and the oil was removed from the deodorizer. Thirty ppm of citric acid were added to simulate industrial standards during deodorization. The deodorized oil was stored frozen in nitrogen.

Part B: Small scale oil processing (laboratory) The harvested soybeans were heated in the microwave to 180 ° F, cooled to room temperature and cracked using a Roskamp TRC 650-6 Crack and Roll. The soy husks were removed using a Kice Aspirator and the remaining substances were heated to 180 ° F and flaked on a Roskamp TRC 912 Flake and Roll. The crude oil was extracted in a glass extraction vessel with a water jacket heated to 60 ° C for 45 minutes using a solids to solids ratio of about 4: 1. The hexane / oil micelle was collected and the extraction repeated. The micelle was desolventized using a rotary evaporator leaving the crude oil.

A volume of an 85% phosphoric acid solution equal to 0.1% (v / v) of the crude oil was added and the solution was heated to 65-70 ° C for 10 minutes while stirring. NaOH (8% aqueous solution) hot (60 ° C) was added dropwise to the oil to neutralize the free fatty acids H3P04 with an additional excess of 0.2% w / w. The solution was stirred for five minutes and the solids were separated by centrifugation. The oil was washed with water adding hot water up to 20% (v / v) as the sample was heated to 90 ° C with rapid stirring. The oil and water were allowed to cool to room temperature for 10 minutes and then separated by centrifugation. The oil was dehydrated using very rapid stirring under vacuum at 85-95 ° C for 30 minutes or until all the moisture (bubbles, condensation) had been removed. The vacuum was then broken with nitrogen. The oil was bleached by adding 2% (w / w) of Activated Bleaching Earth (AOCS # Z1077) and the solution was mixed under vacuum for 30 minutes at 85-95 ° C before cooling to 80 ° C. The vacuum was broken with nitrogen and 1% (w / w) of diatomaceous earth was added and the mixture was filtered through a bed prepared from diatomaceous earth.

The citric acid was added to about 50 ppm, and the oil was deodorized at 240 ° C with steam (4 mL of water per 100 g of oil) in a glass deodorizer for about 1 hour. The oil was cooled to 80 ° C with dissipation, and further cooled to 40 ° C under nitrogen. The refined, bleached, and deodorized oil was stored frozen in a nitrogen atmosphere.

EXAMPLE 3 Composition Analysis The oils produced in Example 2 were analyzed for the composition as described below. The composition results for the oils are given in Table 2.

Crassus acid composition: The fatty acid composition was determined essentially by the methods described in AOCS Ce lc-89. The methyl esters of fatty acid were prepared as follows. Ten μL of oil were mixed with 1 mL of hexane and 0.25 mL of a 3% sodium methoxide solution for 30 minutes'. Acetic acid (0.1 mL of a 10% solution) was added, the sample was mixed and the layers separated by centrifugation. The resulting fatty acid methyl esters extracted in the hexane layer were resolved by gas chromatography (GC). Hewlett Packard 5890GC (Wilmington, DE) equipped with an SP2340 column (60 m, 0.25 mm ID, 0.20 micron film thickness) (Supelco, Bellefonte, PA). the temperature of the column was 150 ° C at the injection and the temperature set from 150 ° C to 200 ° C at 2 ° C / min for 40 minutes. The temperatures of the injector and detector were 215 ° C and 230 ° C, respectively.

Peroxide value, free fatty acid, and color: The peroxide values were determined essentially by titration by the AOCS method Cd 8-53 and the data were expressed as milliequivalents peroxide / kg of oil. The free fatty acid values were determined by the AOCS method Ca 5a-40 and the data were expressed as% free fatty acids (such as oleic acid). The color was measured using a Lovibond Tinturometer and a 5-1 / 4"tube according to the AOCS Ccl3b-45 method.

Tocopherol content: The tocopherol content was determined by normal phase HPLC using a Dynamax HPLC Rainin Instrument and a data acquisition system equipped with a Milton Roy spectromonitor UV detector. HPLC conditions were: Waters silica column μPorasil 3.9 x 300 mm (unbound, irregularly), a system of solvent hexane / isopropyl alcohol (98.5 / 1.5) with a flow rate of 1.5 mL / min. Total run time for each sample was 7.0 minutes. Samples for HPLC analysis were prepared by adding 900 μL of hexane / isopropyl alcohol (98.5 / 1.5) to 100 μL of refined, bleached and deodorized oil. 40 μL was injected into the HPLC. The absorbance was monitored at 295 nm. The results were expressed as mg of tocopherol / 100 g of oil.

These results show the analysis of the composition of the soybean oil of the invention and the vegetable oils with which it was compared. The operation of these oils was then evaluated in the examples as discussed below.

TABLE 2 Composition and Chemical Analysis of Oils Composition of Fatty Acid Tocopherol C18: l C18: l Oil Tested ci6: 0 C18.0 cis trans C18.2 C18: 3 PV FFA Color Additives mg / 100G of oil oya high in oleic 6.4 3.3 85.6 1.6 2.2 0.01 0.01 0.5Y 0.5R 160.4 oya normal 10.4 4.1 22.9 52.9 7.5 0.00 0.00 1.0Y 0.2R 160.9 high oleic sunflower 3.6 4.3 82.2 9.9 0.0 0.14 0.02 6.0Y 0.4R 46.0 S3 high oleic acid 9.0 2.3 64.8 22.2 0.5 0.04 0.01 1.7Y 0.3R 72.8 oya low in linoleic 10.0 5.1 27.6 54.1 2.8 0.0 0.02 2.0Y 0.4R 89.3 high oleic acid 3.6 2.3 '78.8 5.1 5.2 0.01 0.07 2.0Y 0.3R soybean meal 11.4 4.5 25.1 53.0 6.0 0.08 0.04 3.0Y 0.5R TBHQ, silicone 112.8 clear liquid antennas 11.4 4.7 40.4 8.8 34.7 0.0 0.09 0.04 2.0Y 0.3R TBHQ, silicone 112.2 heavy weights 10.5 10.2 42.5 31.7 3.8 0.0 0.06 0.06 2.0Y 0.4R TBHQ, silicone 110.0 EXAMPLE 4 Oxidative Stability The high oleic and normal soybean oils produced in Example 2 were evaluated for oxidative stability by means of AOM and OSI. The other commercial oils used for comparison were evaluated only by OSI. The OSI determinations were made at 110 ° C using the Oxidative Stability Instrument (Omnion, Inc., Rockland, MA) using the official AOCS methods (AOCS Method Cd 12b-92). The samples were run in duplicate and the results presented are the average values for each sample. The AOM determinations were made using the official AOCS methods (Cd 12-57). The tests were run at 97.8 ° C and the induction times given represent the number of hours required to reach 100 milliequivalents of peroxide per kg of oil tested.

Figure 1 shows a graph comparing the AOM results of soybean oil with high oleic and normal content. The average AOM induction time for high oleic soybean oil was 145 hours compared to 15 hours for normal soybean oil. The untreated results used to make the graph are given in Table 3. The values obtained from the OSI determinations are given in Table 4. The high oleic soybean oil had an OSI induction time of 80.7 hours compared to 6.9 hours for normal soybean oil.

TABLE 3 AOM values for normal and high oleic soybean oils Time (hours) Soybean Oil Normal Soy Oil High Oleic Content 0 0 0 7 9.77 1.93 15 97.06 11.68 17 141.04 15.2 23 18.76 31 20.83 46.5 36.48 54.5 31.1 70 34.97 94 41.75 108 46.85 147.5 86.84 171.5 279.54 TABLE 4a OSI induction times for various vegetable oils Oil Time (hours) Induction OSI Soybean high oleic 80.7 +/- 3.2 normal soy 6.9 +/- 0.4 high oleic sunflower 18.2 +/- 0.1 high oleic corn 15.4 +/- 0.2 soybean low in linolenic 6.5 +/- 0.3 hemp high in oleic 20.9 +/- 1.0 soy frying oil 21.2 +/- 1.0 clear liquid butter 31.8 +/- 0.9 heavy butter 84.8 +/- 1.2 The compositions of these oils are given in Table 2 EXAMPLE 5 Stability at High Temperature of Sova Oil with High Oleic Content The high temperature stability of refined, bleached, and deodorized high oleic soybean oil produced in Example 2 was compared to the stability of normal soybean oil and other commercial oil samples. Stability was determined by heating the oils to frying temperature and monitoring the formation of polar products and polymer degradation by HPLC. High oleic soybean oil developed polar materials and polymers to a lesser degree than normal soybean oil as shown in Figure 2A and 2B.

Sample Preparation: The oil samples (5 mL) were heated in glass tubes in an aluminum block on a hot plate controlled with a temperature controller and PMC Dataplate 520 timer. The oils were heated at 190 ° C for 10 minutes. hours each day and allowed to cool before reheating. Fifty μL samples were collected for HPLC analysis after 10, 20, 30, 40, 50, and 60 hours of heating. The samples were stored at -20 ° C until they could be tested.

Reverse Phase High Resolution Liquid Chromatography: The methods used for reverse phase HPLC analysis of heated oils are similar to those of Lin (1991). Before the HPLC analysis, 50 μL samples were brought to room temperature and 950 μL of an isopropyl alcohol / hexane solution (20:80, v / v) were added and the samples were vortexed. The HPLC system consisted of a Dynamax Rainin Instrument HPLC and data acquisition system, two Rabbit-HP solvent delivery pumps, Spectra Physics SP8880 / 8875 Autosampler, and Milton Roy spectromonitor 254 nm UV detector. The column was a Beckman Ultrasphere 4.6 x 25 cm. The gradient conditions changed from 40:60 to 90:10 isopropanol: methanol for 37 minutes. The resulting chromatographs were integrated and the areas below the peaks corresponding to polar and polymeric materials were identified. The results were expressed as area units of the total polar peak and total polymer.

EXAMPLE 6 Schaal Oven Test The oxidative stability of soybean oil with high oleic content today was also determined in an accelerated aging test known as the Schaal Oven Test. The oils used in this test were those produced in Example 2.

The oil samples (15 mL) were placed in a 30 mL beaker with a watch glass cover and stored in a forced draft oven at 63 ° C. Oxidative degradation was measured as titrable peroxide equivalents according to AOCS Method Cd 8-53. Samples for analysis were collected at various times during heating of the oil. Figure 3 presents the results of this test.

EXAMPLE 7 The Effects of the Presence or Absence of Tocopherol in Oxidative Stability Test A: Comparison of Normal Sova and High Oleic Oils Tocopherols are antioxidants that occur naturally and are present at different levels in different oil seeds. The tocopherol content of the extracted oils could also vary depending on the conditions used to make the oil.

Specifically, more or less tocopherol can be maintained in the oil depending on the time and temperature conditions used during the deodorization. The content of tocopherol for soybean oil of high oleic and normal content was measured to determine if varying the levels could affect the stability of the two oils. These results are included in Table 2. High oleic and normal soybean oil does not differ the total tocopherol content or in the ratio of individual tocopherols. While typical for the deodorization conditions used herein, the values are somewhat higher than the values obtained for commercially produced oils which are generally about 100 mg total tocopherol / 100 g oil, depending on the supplement. High oleic sunflower oil, high oleic corn oil and high oleic hemp oil were all subjected to somewhat lower contents of tocopherol than soybean oils; these values were in the range of 46 mg (sunflower) to 73 mg (corn) per 100 g of oil.

The high oleic oil oil and the high oleic sunflower oil of Table 5 have similar fatty acid compositions with respect to potential oxidation. The difference between the OSI induction time for high oleic soybean (80.7) and high oleic sunflower (34.3 hours) suggests other factors except that the fatty acid composition alone is affecting the oxidation rate. Tocopherols are known to exert a strong antioxidant affectation that is concentration dependent. Soybean and sunflower oils differ in the total tocopherol content and the individual tocopherols present. To determine if the tocopherols were responsible for the difference in OSI, individual tocopherols were added to achieve the relative ratios and total amount of tocopherol (Table 4) present in the high oleic soybean oil. As shown in Table 5, the OSI of the high oleic sunflower was increased to that of the high oleic soybean by equalizing the individual and total tocopherols present in high oleic soybean oil.

TABLE 5 The effect on the OSI induction time to add tocopherols to oils with high oleic content to equalize the content present in high oleic soybean oil Sunflower Oil Soy Oil High Content High Oleic Oleic Content Fatty Acid Composition C16: 0 6.4 3.0 C18: 0 3.3 4.3 C18: 85.6 87.0 C18: 2 1.6 4.1 C18: 3 2.2 0.0 PV 0.02 0.01 FFA 0.3 0.01 total tocopherol 160.4 46.7 (initial) p% (initial) Alpha 5.1 95.1 range 71.5 4.9 delta 23.4 0.0 OSI (initial) 80.7 34.3 total tocopherol 193.0 (final) p% (initial) Alpha 25.1 58.0 range delta 17.0 OSI (final) 74.6 The effect of tocopherols was also examined by producing high oleic soybean oils with lower tocopherol content (equal to the concentrations found in high oleic sunflower) and measuring stability by means of AOM. The oils were produced by varying the time and temperature during the deodorization of soybean oil with high refined, bleached oleic content. The temperatures used were 240 ° C and 265 ° C. The deodorization times were in the range of 0 to 360 hours. Table 6 shows the deodorization conditions, the resulting oil compositions and the stability of AOM.

TABLE 6 Deodorization of High Oleic Soybean Oil Condition 1 2 3 4 5 6 7 nes temperat 240 240 240 240 240 265 265 ura ° C time at 0 30 60 120 240 240 360 the temperature, min. tocofero 192.3 177.9 177.5 161.4 138.5 32.5 28.1 les, total, mg / 100 g AOM 122.0 111.3 111.0 107.5 105.8 94.8 94.5 (hours) While the content of tocopherol was significantly reduced in high oleic soybean oil, it can be seen in Table 6 that its oxidative stability, as measured by the time of AOM induction, was not reduced by more than 25% in the sample with the lowest tocopherol content. An induction time of 94 hours is significantly longer than comparable OSI values for any other oil listed in Table 4.

EXAMPLE 8 Hidrocenación of Soybean Oils Normal v of High Oleic Content This example illustrates the advantages of hydrogenating the high oleic soybean oil of this invention.

The high oleic and normal soybean oils were hydrogenated using industry standard methods as described below. The hydrogenation reactions were carried out using 0.04% nickel catalyst (Nysosel 325, Engelhard Corp), 75 ml oil, 104 ° C, under 90 psi hydrogen, stirred at 750 rpm in a reactor made by Autoclave Engineer, Inc., (EZE-Seal Reactor). Changes in the fatty acid composition of the oil during the reaction were monitored by refractive index. The oil samples were collected with iodine values (IVs) in the range of about 95 to 45. The oils were filtered through celite and deodorized using the conditions described above. The hydrogenated oil samples were evaluated for free fatty acids, peroxides, fatty acid composition, and OSI induction time using the method described above. The solid fat index of each oil sample was determined using AOCS Method Cd 10-57. The solid fat index is a measure of the solids content at a given temperature, and is an important test in characterizing the physical properties of a fat.

TABLE 7 Properties of High Hydrogenated Soybean Oil Oleic Content Solid Fat Index Acids Sample- IV IV 50 (° F) 70 (° F) 80 (° F) 92 (° F) 104 (° F) OSI (130 ° C) OSI (! 10 ° C) Calculated Fat Time AOM (97.8 ° C) Trans * (minutes) high in oleic-78 78 6.2 4.9 5 4.6 4.3 33.8 134.6 325.6 3.7 19 high in oleic-71 71 13.1 8.2 8.1 7.6 6.2 52.6 209.9 508.0 7.3 30 high in oleic-59 59 32 23.8 21.3 18.6 13.7 64.4 256.9 622.0 12.4 45 high in oleic-46 46 57.3 50.7 49.5 46 36.6 95.1 379.1 918.0 17.2 65 normal soy 95 9.3 6 6 4.4 2.9 5.1 20.4 49.0 11.9 45 normal soy 92 1 1.9 8.1 7.3 5.3 3.2 4.8 18.9 45.4 14.8 55 normal soy 83 14.4 8.6 8.2 5.5 3.2 9.1 36.3 87.3 14.2 130 normal soy 72 27.6 17.5 16.5 10.1 6 19.2 76.7 185.3 17.0 145 normal soy 63 50 40.3 38.7 28.3 18 47.2 188.3 455.7 17.8 185 normal soy 49 59.6 52.9 51.2 41 29.6 63.4 252.9 612.3 17.5 245 a As a percentage of the total fatty acids Using high oleic soybean oil as the base oil for hydrogenation reactions has advantages over using normal soybean oil. Significantly, less time is required to achieve any given product, as represented by IV, of high oleic soybean oil when compared to normal soybean oil (Figure 4). The resulting hydrogenated products also have several advantages including lower trans fatty acids and substantially larger OSI induction times. Figure 5 presents the solid fat index values for one of the high hydrogenated oleic soybean oil products compared to the products of normal hydrogenated soybean oil and a variety of commercial fats.

EXAMPLE 9 Stability of high oleic soybean oil as a function of composition The high oleic soybean oil oil grown during the subsequent growing seasons was harvested and the oil was extracted and processed by the conditions set forth in Example 2. The results of the composition were obtained using the methods described in the Example 3. The high oleic soybean oils of these productions varied slightly in the fatty acid composition, tocopherol content, and AOM / OSI induction times as shown in Table 8.

TABLE 8 Composition and stability of sova oils IA, 95 PR, 95 IA, 96 (Control) Composition is Fatty Acid C16: 0 6.3 7.1 6.4 10.1 C18 3.7 3.7 3.1 3.5 C18: 84.0 81.7 82.6 17.9 C18: 2 1.6 2.0 2.3 58.6 C18: 3 2.4 3.6 3.7 8.2 • Quality PV 0.0 0.0 0.06 FFA 0.01 0.01 0.01 color 1.5Y 0.3R 0.9Y 0.1R 1.8Y 0.2R AOM, hr 141 107 82 14 OSI, hr 52-80 56-63 43 6 tocopherols 137 170 87.9 (mg / lOOg) range 101.0 115.0 54.9 delta 25.5 43.5 29.6 alpha 10.1 11.0 3.4 EXAMPLE 10 High oleic soya oil as a source of the mixture Part A: Mix with normal sova oil The high oleic soybean oil produced in Example 2 was mixed with normal soybean oil to vary the percentages and the oxidative stability of the mixed oils was evaluated by OSI. Table 9 shows the effect of increased oxidative stability of normal soybean oil when mixed with high oleic soybean oil.

TABLE 9 The effect on the oxidative stability of normal soybean oil when mixed with high oleic soybean oil.

Fatty Acid Compositions % of OSI C16: 0 C18: 0 C18: l C18: 2 C18: 3 oil (normal soy hrs in mixture 76.4 6.3 3.7 84.6 1.7 2.3 2. 5 63.9 6.6 3.6 82.9 2.5 46. 3 6.7 3.4 80.9 4.6 2.6 38.4 6.9 3.7 78.4 6.9 2.8 30.5 7 3.7 75.8 9.1 3.1 25.7 7.4 3.8 72.9 11.5 3.3 100 6.0 10.1 3.5 17.9 58.6 8.2 Part B: Mixture with soybean oil with low linolenic acid content The high oleic soybean oil produced in Example 2 was mixed with a soybean oil of low linolenic content and the resulting mixture was evaluated for oxidative stability by OSI. Table 10 shows the composition and oxidative stability of the mixture.

TABLE 1.0 The effect on oxidative stability in low linolenic soybean oil when mixed with high oleic soybean oil % of C16: 0 C18: 0 C18: l C18: 2 C18: 3 Soybean Induction Oil Time of OS I low (hours) linolenic content in the mixture 6.4 3.7 84.4 1.0 2.2 72.7 50 7.3 4.0 61.2 23.2 2.6 18.6 100 .3 4.3 37.7 44.4 3.4 10.9 EXAMPLE 11 Evaluation of the use of oil of sova of high oleic content in applications of industrial fluid and hydraulic fluid Operation of the use of the oil of this invention in industrial fluid and hydraulic fluid applications was compared with commercially available industrial oil products using the Rotatory Test Oxidation Test (RBOT) (ASTM D-2272). This test was used to evaluate the oxidation characteristics of the hydraulic turbine transformer and tool oils. The test apparatus consists of a pressurization pump that rotates axially at an angle of 30 ° with respect to the horizontal in a bath at 150 ° C 50 grams of the test oil with or without commercial additive and 5 grams of water were charged to the pump that contained a roll of copper catalyst. The pump was initially pressurized with oxygen at 90 psi at room temperature. The temperature bath at 150 ° C causes this pressure to increase to approximately 200 psi. As oxidation occurs, the pressure drops, and the point of failure is taken as a 25 psi drop from the maximum pressure achieved at 150 ° C. The results are reported as the number of minutes for the 20 psi loss, as shown in Table 11 below.

TABLE 11 Operation of oils in the Rotary Pump Oxidation test RBOT Oil Minutes soybean oil high 22 oleic content, without additive high soy oil 250 oleic content + 4.5% Lubrizol 7653 Control soybean oil, without 18 additive control soybean oil + 49 4.5% Lubrizol 7653 Mobil hydraulic fluid EAL 29 224H (hemp base) Mobile DTE 13M (base of 216 oil) Pep Boys ATF (base of 135 oil) These results show the superior performance of the oil of the present invention in industrial fluid and hydraulic fluid applications that require high oxidative stability.

It is noted that in relation to this date, the best method known by the applicant to carry out the aforementioned invention, is the conventional one for the manufacture of the objects to which it relates.

Having described the invention as above, the content of the following is claimed as property.

Claims (9)

1. A high oleic soybean oil having high oxidative stability, characterized in that it comprises a content of C18: l greater than 65% of the fatty acid radicals in the oil, a combined content C18: 2 and C18: 3 less than 20% of the fatty acid radicals in the oil, and an active induction time by the active oxygen method greater than 50 hours wherein said oxidative stability is achieved without the addition of an antioxidant.

2. High oleic soybean oil having high oxidative stability according to Claim 1, characterized in that said oil is useful as a mixing source to make a mixed oil product.

3. The high oleic soybean oil having high oxidative stability according to claim 1, characterized in that said oil is useful in the preparation of food.

4. The high oleic soybean oil having high oxidative stability according to Claim 1, characterized in that said oil is further processed, said processing being selected from the group consisting of hydrogenation, fractionation, interesterification, and hydrolysis.

5. A food having improved stability against oxidation, characterized in that the oil of Claim 1 has been incorporated therein.

6. Products made from the hydrogenation, fractionation, interesterification or hydrolysis of the oil of Claim 1.

7. A mixed oil product, characterized in that it is made with the oil of Claim 1.

8. Byproducts, characterized in that they are made during the production of the oil of Claim 1.

9. The by-product of Claim 8, characterized in that said by-product is a deodorized distillate containing an increased level of tocopherol wherein the oxidative stability of the oil of Claim 1 is maintained.