Esterification of glycerol

Esterification of glycerol 3-phosphate with a long-chain fatty acid produces a strongly amphipathic lysophosphatidate (enzyme glycerol-3-phosphate acyltransferase 2.3.1.15). In this reaction, an acyl residue is transferred from the activated precursor acyl-CoA to the hydroxy group at C-1. 

Easter gum, a cross-linked ester, is obtained by the esterification of glycerol or pentaerythritol with rosin. 

Esterification of glycerol with acids 324a-324e provided a series of mono-, di- and trisubstituted triacylglycerols (325) in 70-99% radiochemical yields labelled with 125I, Cholesteryl-c< -(3-amino-2,4,6-triiodophenyl)alkanoates have been 125I-labelled in pivalic acid, also in high 94-98% yields. 

Again, it can be concluded that the system used in our work, without solvent, is a less costly and more selective process to produce mono- and diglycerides by direct esterification of glycerol and fatty acid. Such a system avoids the problems of separation, toxicity, and flammability of organic solvents, permitting recovery of product without further complex purification or evaporation steps and lowering the cost of the final product. 

Another focal point for glycerol utilization has been in the synthesis of condensation polymers by esterification of glycerol with difunctional comonomers such as aliphatic dicarboxylic acids. In the past, monomers such as glycidol (Sunder et al, 1999), which is a highly reactive epoxide, or cis-1,3-0-benzylideneglycerol (Carnahan and Grinstaff,2001) were used as the glycerol-... 

Succinylated Monoglycerides occur as waxy solids having an off white color. They are a mixture of succinic acid esters of mono- and diglycerides produced by the succinylation of a product obtained by the glycerolysis of edible fats and oils, or by the direct esterification of glycerol with edible fatforming fatty acids. They melt at about 60°. They are soluble in warm methanol, in ethanol, and in n-propanol. 

Lipase-mediated esterification of glycerol and fatty acids is also an equilibrium reaction. The extent of esterification depends on the water content of the medium. The accumulation of water during esterification is a concern because it enhances the hydrolysis of the resultant esters. The water, which is produced during this reaction, may be continuously removed and this is usually accomplished by carrying out the reaction in the presence of molecular sieves (17). A small amount of water, however, is needed in the reaction medium to maintain the activity of the enzyme. The ester concentration at equilibrium is dependent on various medium properties, i.e., the water activity of the reaction system. Usually, a low water activity is necessary to obtain a high ester concentration. Water activity, however, is not the only parameter that determines the equilibrium position. The thermodynamic activities of other reaction variables also are important. 

When inclusion of PUFA are concerned, direct esterification of glycerol with individual free fatty acids, including EPA and DHA, had been carried out by employing CV- and CC-lipases (128). Several researchers have reported that this method affords a high degree of incorporation of targeted fatty acids into the TAG molecule, which has been observed with microbial lipases for marine oils (128-130) and plant oils (131-133). All these studies have pointed out that the water content in the reaction medium is a crucial factor determining the extent of the esterification... 

Glyceryl monooleate is prepared by the esterification of glycerol with fatty acids, chiefly oleic acid. As the fatty acids are not pure substances, but rather a mixture of fatty acids, the product obtained from the esterification will contain a mixture of esters, including stearic and palmitic. Di- and tri-esters may also be present. The composition and, therefore, the physical properties of glyceryl monooleate may thus vary considerably from manufacturer to manufacturer e.g., the melting point may vary from 10-35°C. 

Janssen, A. E. M., van der Padt, A., and van t Riet, K., Solvent effects on lipase-catalyzed esterification of glycerol and fatty acids, Biotechnol. Bioeng., 42, 953-962, 1993. 

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. 

As for the direct esterification of glycerol, previous works have shown that numerous solid and acid oxides could be used as catalysts (6, 8-11). 

The aim of our work is to find a new type of solid catalysts in order to be able to control the selectivity. We present in this paper some results obtained with crosslinked porous polymers. Also, we compare the behaviour of different catalysts, in particular, ion-exchange resins, in the esterification of glycerol with oleic acid. The influence of the nature of the resin as well as its swelling properties are discussed. 

In the first part of our study, the esterification of glycerol with oleic acid in the presence of different acid solids with a controlled porosity (zeolite, clay, ion-exchange resin) was studied (Table 1). 

As the K 1481 resin for the esterification of glycerol with oleic acid was the most active solid catalyst of the series, we compared different cationic resins whose characteristics are presented in Table 2. 

Esterification of glycerol with oleic acid in the presence of ion exchange resins. Influence of the resin structure. 

Pseudomonas cepacia and Rhizopus oryzae lipase Phyllosilicate sol-gel matrix Esterification of glycerol [55]... 

The esterification of glycerol with a fatty acid produces a neutral glyceride. Esterification may occur at one, two, or all three positions, producing monoglycerides, diglycerides, or triglycerides. You will also see these referred to as mom-, di-, or triacylglycerols. 

Write a general equation for the esterification of glycerol and one fatty acid. Solution... 

Using condensed formulas, draw the mono-, di-, and triglycerides that would result from the esterification of glycerol with each of the following acids. 

Esterification of glycerol with three molecules of myristic acid... 

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