Of soybean oil

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 ...

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. 

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. 

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) ... 

FIG. 23-34 Effeot of reaction pressure and temperature on tLe rate of hydrogenation of soybean oil. (Swern, ed., Baileys Industrial Oil and Fat Products, ijol 2, Wiley, 1979. )... 

This material was made up with distilled water to provide 41 g per liter, and the mixture was adjusted to pH 7.0 with potassium hydroxide solution. To the mixture were added per liter 5.0 g of calcium carbonate and 7.5 ml of soybean oil. 2,000 ml portions of this medium were then added to fermentation vessels, equipped with stirrers and aeration spargers, and sterilized at 121°C for 60 minutes. After cooling the flasks were inoculated with a suspension of strain No. ATCC 11924 of Streptomyces lavendulae, obtained from the surface of agar slants. The flasks were stirred for 4 days at 28°C at approximately 1,700 rpm. At the end of this period the broth was found to contain cycloserine in the amount of about 250 C.D.U./ml of broth. The mycelium was separated from the broth by filtration. The broth had a pH of about 7.5. Tests showed it to be highly active against a variety of microorganisms. 

After the pH had been adjusted, 5 g of calcium carbonate, 5 ml of soybean oil antifoam and... 

Production costs for biodiesel from soybean oil exceeds 2.00 per gal ( 0.53 per 1), compared to 0.55 to 0.65 per gal ( 0.15 to 0.17 per 1) for conventional diesel. The main cost in biodiesel is in the raw material. It takes about 7.7 lb (3.5 kg) of soybean oil valued at about 0.25 per lb (0.36 per kg) to make 1 gal (3.81) of biodiesel. Waste oils, valued at 1 per gal ( 3.79 per 1) or less, have the potential to provide low feedstock cost. However, much waste oil" is currently collected, reprocessed as yellow and white greases, and used for industrial purposes and as an animal feed supplement. Production of biodiesel... 

The homogeneous hydrogenation of soybean oil methyl ester Olefin disproportionation... 

The Chinese are also counting on petrochemical feedstock to promote synthetic substitutes for the huge quantities of edible oils used industrially (i.e., in the paint industry). Edible oil supply is still deficient in China (China imported 36 million worth of soybean oil from the U.S. in 1979 to help alleviate the shortage), and is rationed. The use of petrochemical derivatives should help boost the per-capita edible oil consumption (less than one-quarter kg/month), and correct some dietary deficiencies. 

Also for this reaction, namely esterification plus transesterification, mixed oxides, this time acidic in nature, appear to be the most promising alternative. Tungstated zirconia-alumina (WZA), sulfated zirconia-alumina and sulfated tin oxide were shown to be active in the transesterification of soybean oil with methanol at 200-300 °C and in the esterification of n-octanoic acid with methanol at 175-200 °C. Although the order of activities is different for the two reactions, WZA gives high conversions in both readions and it is stable under the reaction conditions [31]. Titania on zirconia, alumina on zirconia and zirconia on alumina also showed good performances [32, 6]. 

Ti alkoxides are well-known transesterification catalysts. Grafting of these alkoxides on to a silica surface in a nitrogen atmosphere, followed by steam hydrolysis and calcination, gives stable catalysts for the transesterification of soybean oil at... 

Fig. 23 Idealized structure of the soybean oil polyol top) and GPC trace of soybean oil polyol used in the study bottom). Reproduced from [164] by permission of Elsevier Press...

For current information on the commercial uses of triglyceride oils, readers are directed to follow the periodic communications from the New Uses Committee of the United Soybean Board [191], which is staffed with informative professionals who remain current in the alternative applications of soybean oil, and who support the efforts of industry to develop alternative sources of feedstocks to reduce dependence on petroleum. 

Seppanen, C. M. and Csallany, A. (2006). The effect of Intermittent and continuous heating of soybean oil at frying temperature on the formation of 4-hydroxy-2-(rans-nonenal and other a-, p-unsaturated hydroxyaldehydes. J. Am. Oils Chem. Soc. 83,121-127. 

The correlation between the TEARS assay and MDA dnring oxidation of edible oils may be complicated by the presence of tocopherols (e.g. Vitamin E, 21) . An evaluation was carried of MDA, determined by an independent method , and TEARS as indices for direct oxygen uptake of edible oils and unsatnrated fatty acids. The linear increase of MDA and TEARS with oxygen consumption of soybean oil, in a closed vessel at 170 °C, stops when the latter value reaches 500 p.molL, when both MDA and TEARS start to decrease on further O2 consumption. The same process carried out at 40 °C, using 2,2 -azobis(2,4-dimethylvaleronitrile) (171) as initiator, shows linearity up to 1500 p,molL O2 consumption . A similar behavior is observed for nnsatnrated fatty acids snch as oleic, linoleic and linolenic acids . On the other hand, depletion of Vitamin E (a-tocopherol, 21) and its analogs y- and 5-tocopherol (172, 173) present in the oil show a linear dependence on O2 consumption of the oil, np to 1800 p,molL . This points to the consumption of these antioxidants, and especially 21, as a good index for the O2 uptake in oils at high temperature. The determination of the tocopherols is carried ont by HPLC-FLD (Xex = 295 nm, Ah = 325 nm) . ... 

The process involves reacting the degummed oil with an excess of methyl alcohol in the presence of an alkaline catalyst such as sodium or potassium methoxide, reaction products between sodium or potassium hydroxide and methyl alcohol. The reaction is carried out at approximately 150°F under pressure of 20 psi and continues until trans-esterification is complete. Glycerol, free fatty acids and unreacted methyl alcohol are separated from the methyl ester product. The methyl ester is purified by removal of residual methyl alcohol and any other low-boiling-point compounds before its use as biodiesel fuel. From 7.3 lb of soybean oil, 1 gallon of biodiesel fuel can be produced. See FIGURE 12-5. 

Table 7 Average reaction rate constants and activation energies at 50°C for the methanolysis of soybean oil using NaOH ...

Compared to the base-catalyzed synthesis of biodiesel, fewer studies have dealt with the subject of acid-catalyzed transesterification of lipid feedstocks. Among acid catalysts, sulfuric acid has been the most widely studied. In the previously mentioned work of Freedman et al., the authors examined the transesterification kinetics of soybean oil with butanol using sulfuric acid. The three reaction regimes observed (in accordance with reaction rate) for base-catalyzed reactions were also observed here. A large molar ratio of alcohol-to-oil, 30 1, was required in this system in order to carry out the reaction in a reasonable time. As expected, transesterification followed pseudo-first-order kinetics for the forward reactions (Figure 2), while reverse reactions showed second-order kinetics. 

Most industrial reactors and high pressure laboratory equipment are built using metal alloys. Some of these same metals have been shown to be effective catalysts for a variety of organic reactions. In an effort to establish the influence of metal surfaces on the transesterification reactions of TGs, Suppes et collected data on the catalytic activity of two metals (nickel, palladium) and two alloys (cast iron and stainless steel) for the transesterification of soybean oil with methanol. These authors found that the nature of the reactor s surface does play a role in reaction performance. Even though all metallic materials were tested without pretreatment, they showed substantial activity at conditions normally used to study transesterification reactions with solid catalysts. Nickel and palladium were particularly reactive, with nickel showing the highest activity. The authors concluded that academic studies on transesterification reactions must be conducted with reactor vessels where there is no metallic surface exposed. Otherwise, results about catalyst reactivity could be misleading. 

Furuta et al. tested a series of strong solid acids (alumina promoted sulfated zirconia, alumina promoted tungstated zirconia and sulfated tin oxide) for the transesterification of soybean oil with methanol at 200-300°C. Reaction yields over 90% were obtained for the alumina promoted tungstated zirconia at reaction times of 20 h using a flow reactor T = 250°C). The activity of the same catalyst was maintained for up to 100 h. 

The solubilities of soybean oil in neat supercritical carbon dioxide (SC-C02) and CO2 with entrained helium were measured (King et al., 1995). 

Odorants that cause aroma changes, e.g. olf-flavours, may be detected by a comparative AEDA of fresh and deteriorated samples. Studies on storage defects of soybean oil [22, 51], buttermilk [52], boiled cod [53], dry parsley [54] and black and white pepper [55] are examples. 

As an example, we will illustrate the technology with oils/propane/hydrogen. The oils are triglycerides and fatty-acid methyl esters. The phase behaviour of soybean oil/propane/H2 has... 

Shimada, K., Fujikawa, K., Yahara, K., and Nakamura, T. 1992. Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion. J. Agric. Food Chem. 40 945-948. 

Herslof and Kindmark (105) report the use of the mass detector (light-scattering detector) in this sense. The column used (250 X 4.6-mm ID) was packed with LICHROSPHER RP 100 and thermostated at 22°C. The mass detector oven temperature was 40°C, and the inlet gas pressure was 15 psi. The mobile phase consisted of mixtures of acetonitrile, ethanol, and hexane. Gradients from 0 to 100 of ternary premixtures of the three solvents were used at a flow rate of 1 ml/ min. The sample was dissolved in hexane-isopropanol (1 1), and 12 /A were injected (approx. 150 fj.g total sample). The chromatogram of the standard mixture of TGs is shown in Fig. 35. The separations of soybean oil and a mixture of soybean and coconut oils illustrate the resolution of vegetable oils into TG species (Fig. 36). 

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