Transesterified oils

We were successful in producing structured lipids containing the desired ratios of n-6/n-3 in the transesterified oil, and these may be useful in modulation of the biosynthesis of various eicosanoids and possibly preventing certain diseases such as inflammation, coronary heart disease, cancer. 

Polymers obtained from natural products or from their immediate derivatives such as vegetable oil, modified epoxidised oils, transesterified oils, heated oil, monoglyceride and diethanol amide or fatty acids of vegetable oils, cashew nut seed liquid (CNSL) and derivatised polymers, are bioderived polymers. " The details of vegetable oil-based polymers are the subject matter of this book and hence are discussed in detail in subsequent chapters. 

Amine salts of acrylate ester polymers, which are physiologically acceptable and useful as surfactants, are prepared by transesterifying alkyl acrylate polymers with 4-morpholinethanol or alkanolamines and fatty alcohols or alkoxyl-ated alkylphenols and neutralizing with phosphoric acid. This polymer salt (pH of a 10% aqueous solution = 5.1) was used as an emulsifying agent for oils and waxes [70]. 

The important but unusual fatty acid ricinoleic acid, or 12-hydroxyoleic acid, is a major component of castor oil (>87%) and is also found in useful quantities in ergot. The metal salts of the acid find use in dry-cleaning soaps but the majority is converted to aminoundecanoic acid (Scheme 6.6) which is used to make nylon 11. Nylon 11 has very good chemical and shock-resistance properties, which have led to it being used in the automotive industry. Ricinoleic triglyceride is initially transesterified to the methyl ester. This is heated to 300 °C at which temperature it is... 

Several ester-based oils are suitable as lubricants [532,690], as are branched chain carboxylic esters [1588]. Tall oils can be transesterified with glycols [1536] or condensed with monoethanolamine [51]. 

Freedman B, Pryde EH, Mounts TL (1984) Variables affecting the yields of fatty esters from transesterified vegetable oils. J Am Oil Chem Soc 61 1638-1643... 

Esterfip A process for transesterifying vegetable oils to their methyl esters, for use as diesel fuels. Developed by IFP and Sofiproteol, France. 

Demirbas, A. 2003. Biodiesel fuels from vegetable oils via catalytie and non-eatalytie supereritieal aleohol transesterifieations and other methods a survey. Energy Convers Manage 44 2093-2109. 

Alkyds were synthesized by Kienle in the 1920s from trifunctional alcohols and dicar-boxylic acids. Unsaturated oils, called drying oils, were transesterified with the phthalic anhydride in the reaction so that an unsaturated polymer was obtained which could later be reacted producing a cross-linked product. 

Much work has been done on the incorporation of castor oil into polyurethane formulations, including flexible foams [64], rigid foams [65], and elastomers [66]. Castor oil derivatives have also been investigated, by the isolation of methyl ricinoleate from castor oil, in a fashion similar to that used for the preparation of biodiesel. The methyl ricinoleate is then transesterified to a synthetic triol, and the chain simultaneously extended by homo-polymerization to provide polyols of 1,000, 000 molecular weight. Polyurethane elastomers were then prepared by reaction with MDl. It was determined that lower hardness and tensile/elongation properties could be related to the formation of cyclization products that are common to polyester polyols, or could be due to monomer dehydration, which is a known side reaction of ricinoleic acid [67]. Both side reactions limit the growth of polyol molecular weight. 

Gatfield et al. [44] reported in 2001 a method to produce natural ethyl E,Z)-2,4-decadienoate, the impact compound of pear. Immobilised lipase from Candida antarctica is capable of transesterifying Stillingia oil in the presence of ethanol. By this process, a complex mixture of ethyl esters is generated. By fractional distillation, the ethyl ester of ( ,Z)-2,4-decadienoate can be isolated from the mixture in a total yield of about 5% and with a high degree of purity. As only... 

Figure 5 compares the conversion yields of each FAME, transesterified from rapeseed oil, after a 10-min reaction with a 1.0%(w/w) catalyst at a molar ratio of 1 6 and 60°C. In all the catalysts studied, oleic acid was best converted to methyl oleate. 

Figure 5 shows a comparison of the yields of methyl esters between transesterification of triglycerides (rapeseed oil) and methyl esterification of fatty acids by supercritical methanol at various temperatures. At 350°C, both reactions could produce very similar results. At 300°C, transesterification produced about 90% methyl esters at 12 min of treatment, whereas methyl esterification resulted in a complete conversion. When triglycerides were transesterified at 270°C, a plateau was reached at about 40 min of treatment with a yield of about 76%. However, much higher yield could be achieved by methyl esterification at 20 min of treatment. These results, therefore, indicate that the reaction rate in methyl esterification is higher than that in transesterification. 

Dow also developed polyurethane foams from polyols via hydroformylation of fatty acids. The foams have properties which are comparable to foams from petrochemicals in terms of density and flexibility. The advantages of using sustainable feedstocks in viscoelastic foams are increased load bearings and tensile and tear properties [39, 40]. The hydroformylation and consecutive hydrogenation of fatty acids derived from seed oil can also be used to form low viscosity polyester polyols. Therefore, fatty acid methyl esters are transesterified with diols, e.g., glycol (Scheme 12). The polymer contains chemically active hydroxy groups which can be used for polyurethanes in coating applications [41]. 

Raw materials. It is possible to use any fatty acid as a feed material for sulphonation but economic considerations dictate that oleochemical material be preferred. Fatty acids are readily obtained from vegetable and animal oils and fats which are fatty acid triglycerides. These are transesterified to generate glycerol and three moles of a fatty acid ester, normally a methyl ester. The methyl ester can be distilled to give a specific cut and the fatty acid finally isolated by hydrolysis or hydrogenation of the ester. It is common to use animal fats (tallow) in which case the dominant C chains are 16 and 18. 

Dunn, R. O., and Bagby, M. O. 1995. Low-Temperature Properties of Triglyceride-Based Diesel Fuels Transesterified Methyl Esters and Petroleum Middle Distil-late/Ester Blends. J. Am. Oil Chem. Soc., 72, 895-904. 

Freedman, B., Pryde, E. H., and Mounts, T. L. 1984. Variables Affecting the Yields of Fatty Esters from Transesterified Vegetable-Oils. J. Am. Oil Chem. Soc., 61, 1638-1643. 

The individual fatty acid composition of fats and oils are routinely assayed by gas chromatography. Samples are transesterified with methanol to convert the... 

Examples of such developments are sulfation of transesterified rapeseed oil phosphatides (17) and the use of bicontinuous microemulsions obtained by the addition of aliphatic alcohols (18, 19). The stability of these systems promises to be more reliable than those in present use. Oils from wood (tall oil) can be sulfo-nated for self-emulsifying fatliquors (20). Polymerizable oils have been used in fatliquors (21). We expect more progress on the use of high polymers, such as the already commercial alkyl acrylate esters developed by Hodder et al. (22-24), and material based on elastomers (6). We anticipate the development of novel systems to be encouraged by the demand for leather in washable garments and automobile upholstery. 

Fat or fatty acid source Fats and oils or foods containing fats and oils Hydrogenated, transesterified, fractionated fats and oils Hydrolysates thereof... 

In the first stage, the crude castor oil is transesterified, in the presence of excess methanol and traces of sodium methylate acting as a catalyst This takes place at 80 C... 

This reaction is reminiscent of the decarboxylation of / ,y-unsaturated acids. Experimentally, the process is carried out by transesterifying castor oil by methanol and sulfuric acid, dropping the crude methyl ester into a heat-transfer reagent at 500-600°, and fractionating the resulting distillate in a vacuum.75... 

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