Epoxidized biodiesel

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. 

Production use F. are mainly produced by sapon-iEcation (alkaline hydrolysis) of natural fats. F. and their derivatives are mainly used in the production of soaps, detergents, lubricants, greases, textile auxiliaries, epoxide and alkyde resins, plastics, paints, softeners, cosmetics, and pharmaceuticals. F. methyl esters are also used as a fuel ( biodiesel ). 

Similar peaks are observed in the H-NMR and C-NMR for the epoxidation of vegetable oils, pure fatty acids, or biodiesel. 

Figure 22.28 and Figure 22.29 show, respectively, the H and C-NMR spectra of the oligoesters prepared from epoxidized sunflower oil methyl esters (methyl biodiesel from sunflower oil) and di-l,2-cyclohexanedicarboxylic anhydride using triethylamine as initiator. These materials are soluble in common organic solvents such as acetone, ethanol, tetrahydrofurane, and chloroform, but insoluble in water. Oligoesters from epoxidized biodiesel can be used as intermediate materials for the synthesis of polyelectrolytes by saponification reactions with aqueous solution of sodium or potassium hydroxide at room temperature (Fig. 22.27). The products obtained after saponification present solubility in water. Amphiphilic materials, such as the polyelectrolytes prepared from epoxidized biodiesel, have hydrophobic and hydrophilic segments. They can spontaneously self-organize in a wide variety of structures in aqueous solution. Understanding the dynamics of the formation and transition between the various self-organized structures is important for technological applications.

FIGURE 22.27 Polymerization of epoxidized biodiesel with subsequent saponification. 

Reiznautt QB, Garcia ITS, Samios D. Oligoesters and polyesters produced by the curing of sunflower oil epoxidized biodiesel with cis-cyclohexane dicarboxylic anhydride synthesis and characterization. Mater Sci Eng C 2009 29 2302-2311. 

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