Soybean oil derivatives

Soybeans and products thereof, except fully refined soybean oil and natural tocopherols, soybean oils derived phytosterols and phytosterol esters, and stand ester... 

L., Burling, K., and Howell, S. 2002. Effects of Subchronic Inhalation Exposure of Rats to Emissions from a Diesel Engine Burning Soybean Oil-Derived Biodiesel Fuel. Inhalat. Toxicol, 14,1017-1018. 

Soybean oil derivatives epoxidized using 2-hydroxylethyl acrylate in the presence of an acid catalyst result in oligomers applicable in ultraviolet radiation cures. Castor oil consists of ricinoleic acid (12-hydroxy oleic acid) as a major fatty acid, which can be used for the production of polyamide building blocks. 

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. 

Dialkyl esters of 3,3 -thiodipropionic acid (53), cycHc phosphonites such as neopentylphenyl phosphite, derivatives of phosphaphenathrene-lO-oxide (54), secondary aromatic amines, eg, diphenylamine (55), and epoxidi2ed soybean oils (56) are effective stabili2ers for preventing discoloration of cellulose esters during thermal processing. 

Many similar hydrocarbon duids such as kerosene and other paraffinic and naphthenic mineral oils and vegetable oils such as linseed oil [8001-26-17, com oil, soybean oil [8001-22-7] peanut oil, tall oil [8000-26-4] and castor oil are used as defoamers. Liquid fatty alcohols, acids and esters from other sources and poly(alkylene oxide) derivatives of oils such as ethoxylated rosin oil [68140-17-0] are also used. Organic phosphates (6), such as tributyl phosphate, are valuable defoamers and have particular utiHty in latex paint appHcations. Another important class of hydrocarbon-based defoamer is the acetylenic glycols (7), such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol which are widely used in water-based coatings, agricultural chemicals, and other areas where excellent wetting is needed. 

The products of these reactions with maleic anhydride, termed maleated oils, react with polyols to give moderate mol wt derivatives that dry faster than the unmodified oils. For example, maleated, esterified soybean oil is a drying oil with a drying rate comparable to that of a bodied linseed oil with a similar viscosity. Maleated linseed oil can be converted to a water-dilutable form by hydrolysis with aqueous ammonium hydroxide to convert the anhydride groups to ammonium salts of the diacid. Such products have not found significant commercial use, but similar reactions with alkyds and epoxy esters are used on a large scale to make water-dilutable derivatives. 

Soybean oil and tall oil fatty acids are not used in paints without modification. These products, Hsted as used in paints, first must be converted to alkyds or other synthetic drying oils. Presumably significant amounts of the linseed oil Hsted under paints are also converted to alkyds or other derivatives before use. In addition to the numbers given in Table 2, relatively large amounts of the oils are reported to have been consumed by conversion into fatty acids. Some indeterrninate fraction of the fatty acids, especially tall oil fatty acids, are presumably converted into derivatives that are used like drying oils. 

Flaky piecrusts used to contain lard, or at least butter. Solid fats are important in baking, as they separate sheets of dough into thin, independent flakes. Traditional solid fats are animal-derived saturated fats, such as lard and butter. Some vegetable fats, such as coconut and palm kernel oils, are solid, but they are more expensive than some liquid vegetable oils like corn oil, cottonseed oil, or soybean oil. These oils come from plants that are used for more than just the oil they provide. Using several different parts of the plant makes growing them more economical. 

Lycopene was dispersed in medium-chain triglyceride oil derived from esterification of fatty acids and glycerol composition was stable for 3 mo at 25°C, compared with dispersion on soybean oil... 

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. 

The use of oleochemicals in polymers has a long tradition. One can differentiate between the use as polymer materials, such as linseed oil and soybean oil as drying oils, polymer stabilizers and additives, such as epoxidized soybean oil as plasticizer, and building blocks for polymers, such as dicarboxylic acids for polyesters or polyamides (Table 4.2) [7]. Considering the total market for polymers of ca. 150 million tonnes in 1997 the share of oleochemical based products is relatively small - or, in other terms, the potential for these products is very high. Without doubt there is still a trend in the use of naturally derived materials for polymer applications, especially in niche markets. As an example, the demand for linseed oil for the production of linoleum has increased from 10000 tonnes in 1975 to 50 000 tonnes in 1998 (coming from 120000 tonnes in 1960 ) [8a]. Epoxidized soybean oil (ESO) as a plastic additive has a relatively stable market of ca. 100000 tonnes year-1 [8b]. 

In their raw, natural state, these oils exist in the form of a triglyceride or fat. In order to derive the useful oil from the raw material, the triglyceride must be separated from protein bodies and sterols also present within the oil seed. To illustrate this process, soybean oil production will be briefly described. 

By late 1996, Monsanto had planned to divide itself into two entities Monsanto Life Sciences and a chemical entity (later given the name Solutia) (Reisch). This occurred within a year, during which Monsanto purchased a plant biotechnology company (Calgene) that held patents for improved fresh produce, cotton seeds, specialty industrial and edible oils (derived from seeds) and plant varieties (Anonymous, 1997). Based on analysis of 1995 sales, the life sciences products accounted for annual sales of S5.3 billion based on the major products of Round-up herbicide, Roundup-resistant soybeans, Bollguard insect-protected cotton, Nutrasweet sweetner, and prescription drugs for arthritis and insomnia. 

The IUPAC Commission on Oils, Fats and Derivatives undertook the development of a method and collaborative study for the determination of triglycerides in vegetable oils by liquid chromatography. Three collaborative studies were conducted from 1985 to 1987. Refinements were made in the method after the first collaborative study, and the second and third collaborative studies demonstrated that the method produces acceptable results. Materials studied were soybean oil, almond oil, sunflower oil, olive oil, rapeseed oil, and blends of palm and sunflower oils and almond and sunflower oils. Six test samples were analyzed by 18 laboratories from 11 countries in the second study 4 test samples were analyzed by 16 laboratories from 12 countries in the third study. The method for the determination of triglycerides (by partition numbers) in vegetable oils by liquid chromatography was the first action adopted by AOAC INTERNATIONAL as an IUPAC-AOC-AOAC method (103). 

In commercial formulations, phospholipids are not available as pure products. Mostly they are obtained as a by-product of the process of refining vegetable oils, during the so-called degum-ming step (3,4), from which a liquid-to-pasty product is obtained that is referred to as lecithin. Lecithin contains about 65% phospholipids plus about 30% residual neutral lipids and minor amounts of glycolipids. For historical reasons, most commercially available lecithins are derived from soybean oil, but lecithins of other oils could be used as well. From this discussion it follows that the determination and quantification of phospholipids is of importance both to control how efficiently the phospholipids have been removed from vegetable oils and to control the quality of the lecithin. For this purpose it is important to know not only the total amount of phospholipids but also the amount of the different types of phospholipids present, because it is well known that the functional properties of the various phospholipids differ widely (2-8). 

Ethyl lactate is another lactic acid derivative that has recently been commercialized. An environmentally benign solvent with properties superior to many conventional petroleum-based solvents, it can be blended with methyl soyate derived from soybean oil to create custom-tailored solvents for various applications. 

These fatty acids and oils, as well as their derivatives, are applied in a broad range of products such as surfactants, lubricants and coatings, and, obviously, biodiesel. Upon epoxidation of the double bonds of the unsaturated fatty acids, very important compounds for the polymer industry are produced, which are used as plasticizers and stabilizers for a broad range of polymers such as polyvinyl chloride (PVC), polyesters, and polyurethanes [71]. Another interesting application has been found in the conversion of epoxidized soybean oil to carbonated soybean oil that can be reacted with ethylene diamine to obtain a polyurethane with interesting properties [72], Traditionally, stoichiometric reagents are used for the epoxidation of these oils and fats, albeit in some cases, with limited results. Therefore, the MTO/H2O2 system has been explored to epoxidize unsaturated fatty acids and oils. 

In an effort to observe this proposed transfer of hydrogen, a mixture of cellulose (1), soybean oil, and an acid catalyst was pyrolyzed at 300°C using the procedure described by Morin.4 Analysis of the products showed no new significant products derived from the biomass but the yield of levoglucosenone (2), the major small organic compound produced under these conditions, was increased significantly. 

Epoxidised oils (with isolated double bonds), such as epoxidised soybean are used as plasticisers. The natural occurrence of epoxidised fatty acids could be exploited to reduce processing costs on the pathway to polymerisation. For example, seed oils derived from Vernonia galamensis and Euphorbia lagascae both contain significant proportions (60-80%) of the epoxy acid vemolic acid, with interesting applications in greases and polyurethane applications (Turley et al., 2000). 

Corredig, M., Dalgleish, D.G. 1998a. Buttermilk properties in emulsions with soybean oil as affected by fat globule membrane-derived proteins. J. Food Sci. 63, 476 180. 

Plant oils or their derived fatty acids are inexpensive renewable carbon sources. In addition, the theoretical yield coefficient of bioproducts (PHA) from plant oil and fatty acid is considerably higher than that from sugars. High cell density fed-batch cultures produced value-added products from soybean oil or oleic acid as the carbon source. PHAs with high yield were produced by fed-batch culture of R. eutropha or its recombinant strain from soybean oil. High cell concentrations obtained by fed-batch cultures from oleic acid improved lipase activity by C. cylindracea and 10-KSA by Flavobacterium, sp. DS5, compared with those of flask cultures. There are still many industrially important value-added products that can be produced from inexpensive substrates such as soybean oil. 

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