Methyl soyate

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. 

Dunn, R. O. 1998. Effect of Winterization on Fuel Properties of Methyl Soyate. In Peterson, C. L. (Ed.), Proc., Commercialization of Biodiesel Producing a Quality Fuel (pp. 164-186). Moscow University of Idaho. 

Dunn, R. 0.2000. Analysis of Oxidative Stability of Methyl Soyate by Pressurized-Dif-ferential Scanning Calorimetry. Trans. ASAE, 43,1203-1208. 

Dunn, R. 0.2002. Effect of Oxidation Under Accelerated Conditions on Fuel Properties of Methyl Soyate (Biodiesel). J. Am. Oil Chem. Soc., 79, 915-920. 

Stavinoha, L. L., and Kline, K. S. 2001. Oxidation Stability of Methyl Soyates—Modified ASTM D5304 and D 6186 for Biodiesel B100. In Report, Oxidation Stability of Methyl Soyates—Modified ASTM D 5304 and D 6186 for Biodiesel B100. Warren MI U.S. Army, TACOM, TARDEC, National Automotive Center. 

The heat of combustion of various vegetable oils is nearly 90 percent that of No. 2 diesel fuel, but engine viscosity is 10 to 20 times greater. Conversion of soybean oil to methyl soyate reduces fuel viscosity to... 

Biosolvents or green solvents —as they are sometimes called—are derived from agrochemicals (see Figure 12.24). Some of the better known biosolvents are limonene (derived from citrus fruits), methyl soyate (produced from soy), and ethyl lactate (produced mainly from com). 

In particular, methyl soyate (the biodiesel formed from soybean oil and methanol) is finding industrial applications including cleaning and degreasing technologies (Table 5.5). In industry, solvents are needed to dissolve a material for its removal or transport and then are often evaporated to restore the original material. Therefore, two important parameters are solvent power and evaporation rate. One way to measure solvent power is the kauri-butanol value (KBV), which is a measure of the solubility of kauri gum in the solvent. A high... 

Table 5.4 Summary of advantageous properties of biodiesels including methyl soyate as solvents ...

Table 5.5 Market applications of methyl soyate as a solvent.

Typical commodity soybean oil is rich in polyunsaturated FA (linoleic, 18 2 and lino-lenic acid, 18 3), with some contributions from saturated and monounsaturated FA (Table 7.2). The oil is suitable for many industrial and food uses. For industrial use, soybean oils with the typical FA composition noted are successfully used in the production of inks, lubricants, fuels, etcetera (United Soybean Board, 2005). They can be epoxidized to make plasticizers and coatings or interesterified to produce methyl soyate, which is used in solvent production. Soybean oil or methyl soyate also can be derivatized to produce soap, polyurethanes, composites, and paints, among other products (United Soybean Board, 2005). 

Biodiesel made with commodity soybean oil tends to crystallize when used at low temperature (-2°C). Biodiesel made from soybean oil with a low content of 16 0, together with branched chain alcohols, has a decreased crystallization temperature (-7°C) (Lee et al., 1995). In the same way, when methyl soyate made from low-l6 0 soybean oil was winterized to decrease its saturation, and thus its crystallization temperature, the yield of the process was better than that from winterization of methyl soyate from commodity soybean oil (Lee et al., 1996). 

Dunn, R.O. Effect of oxidation under accelerated conditions on fuel properties of methyl soyate (biodiesel)./ Am. Oil Chem. Soc. 2002, 79, 915—920. 

Dunn, R.O. Analysis of oxidative stability of methyl soyate by pressurized-differential scanning calorimetry. Trans. ASAE 2000, 43, 1203—1208. 

Wildes, S. Methyl soyate a new green alternative solvent. Chemical Health Safety 2002, 9 24-26. 

One of the current active research areas is green chemistry and sustainability. As part of this thrust, there has been a fair amount of research interest in soybean oil and its derivatives. Soybean oil (SBO) (/) is cheap, easily available, renewable, and environmentally friendly. Some examples of SBO derivatives are epoxidized oil (2), SBO methyl ester (methyl soyate) (5), maleated products (4), SBO polymers (5), and others (5). This area of research has been reviewed 5a, 7). 

For fuel applications, a popular SBO derivative is methyl soyate (SBO methyl ester, also known as Soy Gold) (J). This biodiesel has several advantages over diesel fuel from petroleum sources because it is biodegradable, has a high flash combustion temperature, contains negligible amount of sulfur, is neutral with respect to carbon dioxide emission, and can potentially reduce many harmful exhaust emissions. Methyl soyate is also an increasingly useful industrial solvent for grease removal. 

Currently methyl soyate is made commercially via an alkaline transesterification reaction involving soybean oil. methanol, sodium methoxide at 60-66 C, sometimes under pressure. In this work, we have used an enzyme to carry out a similar reaction with the SBO-DEAD adduct (Figure 4). 

In a mixture of SBO, methanol, and water, a lipase can carry out the transesterification reaction at high yields. The end product is similar to methyl soyate, except for the added aza-carboxylate ester. Since methanol is in excess, dimethyl esters are formed. The reaction can be conducted at a low temperature (35°C). Several lipases have been attempted, and the reaction is relatively straightforward. The use of an immobilized lipase (e.g., Novozym 435) is particularly beneficial because it allows enzyme recycling and cost reduction. 

Figure 4. Enzymatic reaction of structure 2 to form methyl soyate containing dimethyl azadicarboxylate (5)...

The production of methyl soyate for environmentally friendly solvents and for biodiesel fuel (in the USA) is becoming a significant outlet for soy oil in non-food applications. Further progress in the demand for soy biodiesel will result in additional soybean meal supphes, which will considerably increase soy meal competitiveness as feedstock for hvestock farming and aquaculture. 

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