Soybean oils

Soybean oil is the oil produced in largest quantity and is second only to palm oil in traded oil (Table 1.8). There is also a large trade in soybeans but no comparable trade in palm fruits, which are extracted as soon as possible close to the point of collection. The major producers of soybean oil are the US, Brazil, Argentina, China (local beans augmented with imports), and EU-15 (mainly imported beans). Soybean oil is consumed in every country for which details 

Imports 7.44 India 1.20, Iran 0.81, Bangladesh 0.49, Egypt 0.34, Morocco 0.29, former USSR 0.28, Hong Kong 0.27, China 0.24, Venezuela 0.24, Pakistan 0.21, other 3.07 

---

The identity of the moiety (other than glycerol) esterified to the phosphoric group determines the specific phosphoHpid compound. The three most common phosphoHpids in commercial oils are phosphatidylcholine or lecithin [8002-45-5] (3a), phosphatidylethanolamine or cephalin [4537-76-2] (3b), and phosphatidjlinositol [28154-49-7] (3c). These materials are important constituents of plant and animal membranes. The phosphoHpid content of oils varies widely. Laurie oils, such as coconut and palm kernel, contain a few hundredths of a percent. Most oils contain 0.1 to 0.5%. Com and cottonseed oils contain almost 1% whereas soybean oil can vary from 1 to 3% phosphoHpid. Some phosphoHpids, such as dipaLmitoylphosphatidylcholine (R = R = palmitic R" = choline), form bilayer stmetures known as vesicles or Hposomes. The bdayer stmeture can microencapsulate solutes and transport them through systems where they would normally be degraded. This property allows their use in dmg deHvery systems (qv) (8). 

If first-order kinetics are assumed, k /is the linoleic selectivity ratio and k l is the selectivity ratio for reduction of linoleic acid to stearic acid. Figure 2 shows a typical course of hydrogenation for soybean oil the rate constants are = 0.367, = 0.159, and k = 0.013. With a selective nickel catalyst,... 

Fig. 2. Typical products from hydrogenation of soybean oil. Reaction conditions are 175°C, 0.02% Ni, 113 kPa (15 psig), and 600 rpm agitation. O is oleic ...

BHA and BHT, which are both fat soluble, are effective ia protecting animal fat from oxidation, and are often added duting the rendering process. Propyl gallate is also effective, but it has limited fat solubiUty, and turns bluish black ia the presence of iron. It is typically used as a synergist ia combination with BHA or BHT. TBHQ is most effective against oxidation ia polyunsaturated vegetable oils (qv), and is often used ia soybean oil (19). 

Lecithin. Lecithin [8002-43-5] (qv) is a mixture of fat-like compounds that includes phosphatidyl choline, phosphatidyl ethanolamines, inositol phosphatides, and other compounds (37). Commercial lecithin was originally obtained from egg yolks, but is now extracted from soybean oil. Lecithin is used in many products, including margarine, chocolate, ice cream, cake batter, and bread. 

Fig. 2. Flow sheet of lecithin producing unit. Crude soybean oil is heated in the preheater, 1, to 80°C, mixed with 2% water in the proportion control unit, 2, and intensively agitated in 3. The mixture goes to a dweUing container, 4, and is then centrifuged after a residence time of 2—5 min. The degummed oil flows without further drying to the storage tanks. The lecithin sludge is dried in the thin-film evaporator, 6, at 100°C and 6 kPa (60 mbar) for 1—2 min and is discharged after cooling to 50—60°C in the cooler, 8. 9 and 10 are the condenser and vacuum pump, respectively.

Other materials that are often referred to as secondary plasticizers iaclude materials such as epoxidized soybean oil (ESBO) and epoxidized linseed oil (ELO) and similar materials. These can act as lubricants but also as secondary stabilizers to PVC due to thein epoxy content which can remove HCl from the degrading polymer. 

Other Sources. The four oils named above are the most commonly used fats and oils in the soap-making industry in the United States, but other sources are also utilized throughout the world, including lard or hog fat. Babassu oil, rice brand oil, and soybean oil. 

Lipids. Representative fatty acid compositions of the unprocessed triglyceride oils found in the four oilseeds are given in Table 4 (see Fats and FATTY oils). Cottonseed, peanut, and sundower oils are classified as oleic—linoleic acid oils because of the high (>50%) content of these fatty acids. Although the oleic and linoleic acid content of soybean oils is high, it is distinguished from the others by a content of 4—10% of linolenic acid, and hence is called a linolenic acid oil. 

In addition to the triglycerides, the four oilseeds also contain phosphatides. For example, soybean oil containing 1.47% phosphatides consists of 48.9% phosphatidylcholine, 27.0% phosphatidylethanolamine, 21.9% phosphatidjlinositol and 2.2% phosphatidic acid (24). Total phosphatides of cottonseed and peanut kernels are estimated to be 1.5—1.9 and 0.8%, respectively (25). 

Although soybeans contribute about one-half of the world production of oilseeds, they supply less than one-third of the total edible vegetable fats and oils (Table 11) because of their relatively low oil content. Nonetheless, production of soybean oil exceeds the combined production of cottonseed, peanut, and sunflower seed oils. 

Industrial, ie, nonfood, utilization of vegetable oils is much smaller than food usage. Soybean oil usage in the United States for industrial purposes was ca 2% of total production in 1993. Quantities are given in Table 13 (55). 

Edible Oil. For edible uses, oilseed oils are processed into salad and cooking oils, shortenings, margarines, and confectionery fats such as for candy, toppings, icings, and coatings (73). These products are prepared by a series of steps, as outlined for soybean oil in Figure 6. 

Fig. 6. Schematic outline for manufacture of edible soybean oil products, where D = deodorization, W = winterization, and S = solidification (73).

Polyunsaturated fatty acids in vegetable oils, particularly finolenic esters in soybean oil, are especially sensitive to oxidation. Even a slight degree of oxidation, commonly referred to as flavor reversion, results in undesirable flavors, eg, beany, grassy, painty, or fishy. Oxidation is controlled by the exclusion of metal contaminants, eg, iron and copper addition of metal inactivators such as citric acid minimum exposure to air, protection from light, and selective hydrogenation to decrease the finolenate content to ca 3% (74). Careful quality control is essential for the production of acceptable edible soybean oil products (75). 

Nonfood Uses. Vegetable oils are utilized in a variety of nonedible applications, but only a few percent of the U.S. soybean oil production is used for such products (see Table 13). Soybean oil is converted into alkyd resins (qv) for protective coatings, plasticizers, dimer acids, surfactants (qv), printing inks, SoyDiesel fuel (methyl esters used to replace petroleum-based diesel fuel) and other products (76). 

In addition to the mono- and dialkylamines, representative stmctures of this class of surfactants include /V-alkyltrimethylene diamine, RNH(CH2)3NH2, where the alkyl group is derived from coconut, tallow, and soybean oils or is 9-octadecenyl, 2-aLkyl-2-imidazoline (3), where R is heptadecyl, heptadecenyl, or mixed alkyl, and l-(2-aniinoethyl)-2-aLk5l-2-imidazoline (4), where R is heptadecyl, 8-heptadecenyl, or mixed alkyl. 

Abamectin is also used to control the imported red fine ant Soknopsis invicta. For this use abamectin is formulated as a bait together with soybean oil and com grits. Worker ants transport the bait to the colony, the queen becomes sterile, and the colony is eliminated after 12 to 21 weeks. Similar effects on the fecundity of other female insects at nonlethal doses have been reported (16,17). 

Ammonium acetate and sodium methoxide are effective catalysts for the ammonolysis of soybean oil (49). Polyfunctional amines and amino alcohols such as ethylenediamine, ethanolamine, and diethanolamine react to give useful intermediates. Ethylenediamine can form either a monoamide or a diamide depending on the mole ratio of reactants. With an equimolar ratio of reactants and a temperature of >250° C, a cyclization reaction occurs to give imidazolines with ethylenediamine (48) ... 

The composition of common fats and oils are found in Table 1. The most predominant feedstocks for the manufacture of fatty acids are tallow and grease, coconut oil, palm oil, palm kernel oil, soybean oil, rapeseed oil, and cottonseed oil. Another large source of fatty acids comes from the distillation of cmde tall oil obtained as a by-product from the Kraft pulping process (see Tall oil Carboxylic acids, fatty acids from tall oil). 

---