Monoglyceride production

Ferreira-Dias et al. (15) tested Lipozyme IM-20 for the glycerolysis of olive oil residue in n-hexane aimed at the production of monoglycerides and diglycerides. The highest monoglyceride production was in the range of 43-45% (w/w), on the basis of total fat, with about 26% Lipozyme IM-20. 

A comparison of these methods shows that the development of monoglyceride production by enzymatic method could be considered as compared to the chemical process, since milder reaction conditions are utilized and less energy is consumed in a shorter time. 

Hayes, D. G. and Gulari, E., 1-Monoglyceride production from lipase-catalyzed esterification of glycerol and fatty acid in reverse micelles, Biotechnol. Bioeng., 38, 507-517, 1991. 

Freitas, L. Bueno, T Perez, VH Castro, HF. Monoglycerides production by enzymatic route and applications. Quimica Nova, 2008, v. 31 (6), 1514-1521. 

Fats and Oils. Fats and oils (6) are traditionally sulfated using concentrated sulfuric acid. These are produced by the sulfation of hydroxyl groups and/or double bonds on the fatty acid portion of the triglyceride. Reactions across a double bond are very fast, whereas sulfation of the hydroxyl group is much slower. Yet 12-hydroxyoleic acid sulfates almost exclusively at the hydroxyl group. The product is generally a complex mixture of sulfated di-and monoglycerides, and even free fatty acids. Other feeds are castor oil, fish oil, tallow, and sperm oil. 

Fig. 3. Schematic process flow diagram for an imitation cheese product having the following formulation dry ingredients, calcium caseinate (or rennet casein), 24.5 wt % tapioca flour, 3.0 wt % salt, 2.16 wt % adipic acid, 0.6 wt % vitamins and minerals, 0.1 wt % sorbic acid (mold inhibitor), 0.5 wt % fat—color blend, soybean oil hydrogenated to a Wiley melting point of 36°C, 21.3 wt % lactylated monoglycerides, 0.05 wt % red-orange coloring, 0.01 wt...

Monoglycerides are used as emulsifying agents in many products, such as baked goods, whipped cream, and ice cream. 

Alkyd resin synthesis. This synthesis consists of two steps. In the first step, a triglyceride oil is reacted at ca. 250°C with polyols, such as glycerol or pentaery-thritol, in tire presence of a basic catalyst to form a monoglyceride. In the second step, phthalic anhydride, with or without another dibasic acid such as maleic anhydride, is added to the reaction medium and reacted at high temperature. The resulting product is a branched polyester (Scheme 2.56). 

Figures 2 and 3 illustrate the reactant and intermediate product profiles at different reaction times for Mg0-Al203 and Ti02-S04 catalysts, respectively. The results in Fig. 2 show that over 95% triglyceride (TG) is converted to methyl ester and intermediate products within 3 h and the intermediate products of monoglyceride (MG) and diglyceride (DG) remain at a very low concentration level of 1.5% and 4%, respectively.

Chemoenzymatic synthesis of alkyds (oil-based polyester resins) was demonstrated. PPL-catalyzed transesterification of triglycerides with an excess of 1,4-cyclohexanedimethanol mainly produced 2-monoglycerides, followed by thermal polymerization with phthalic anhydride to give the alkyd resins with molecular weight of several thousands. The reaction of the enzymatically obtained alcoholysis product with toluene diisocyanate produced the alkyd-urethane. 

Figure 5.15 GALDI mass spectra of (a) linseed oil (35 years airtight storage from THF solution) and (b) linseed oil as in (a) after 2 weeks of natural ageing (from THF solution). Signal groups of free fatty acids, their oxidation products, and monoglycerides (m/z <500) can be distinguished from diglycerides (m/z 500 800), and triglycerides (m/z 800 1000) (see Table 5.7)...

Alcoholysis Process In alcoholysis process the oil is heated with polyol at 240°C in presence of a base like calcium hydroxide. The principal product formed is a monoglyceride. The dibasic acid is then added and further esterification done ... 

Monoglyceride (MG) is one of the most important emulsifiers in food and pharmaceutical industries [280], MG is industrially produced by trans-esterification of fats and oils at high temperature with alkaline catalyst. The synthesis of MG by hydrolysis or glycerolysis of triglyceride (TG) with immobilized lipase attracted attention recently, because it has mild reaction conditions and avoids formation of side products. Silica and celite are often used as immobilization carriers [281], But the immobilized lipase particles are difficult to reuse due to adsorption of glycerol on this carriers [282], PVA/chitosan composite membrane reactor can be used for enzymatic processing of fats and oils. The immobilized activity of lipase was 2.64 IU/cm2 with a recovery of 24%. The membrane reactor was used in a two-phase system reaction to synthesize monoglyceride (MG) by hydrolysis of palm oil, which was reused for at least nine batches with yield of 32-50%. 

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