Monoglyceride synthesis

Cauvel, A., Renard, G. and Brunei, D. Monoglyceride synthesis by heterogeneous catalysis using mcm-41 type silicas functionalized with amino groups. J. Org. Chem., 1997, 62, 749-751. 

Bellot, J.C., Choisnard, L., Castillo, E., and Marty, A. 2001. Combining solvent engineering and thermodynamic modebng to enhance selectivity during monoglyceride synthesis by lipase-catalyzed esterification. Enz. Microb. Technol. 28 362-369. 

Figure 2.. Monoglyceride synthesis by nucleophilic ring opening of epoxides (a) or (iransksicrificalion reactions tb. ...

Ferretti CA, Puente S, Ferullo R, Castellan N, Apesteguia CR, Di Cosimo JI. Monoglyceride synthesis by glycerolysis of methyl oleate on MgO catalytic and DFT study of the active site. Appl Catal A Gen 2012 413-414 322-331. 

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). 

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. 

Membrane reactor Synthesis of monoglycerides Lipase from Candida rugosa 75... 

Scheme 3.5, and carotenoids have been previously incorporated into vesicles of phospholipids, Figure 3.1 (Milon et al. 1986, Britton 1998). It was therefore reasonable to connect carotenoids with a phosphate group, above all because hydrophobic phosphate esters had previously been synthesized (Sliwka 1997). The C30-monoglyceride, 3.12, was therefore used as an educt for the synthesis of the zwitterionic, hydrophobic C30-lysophosphocholine, 3.15, via aminolyse of the bromo phosphoester,... 

PVA/chitosan blend membranes can be applied for the synthesis of monoglyceride, when used as a membrane enzyme reactor [277]. 

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%. 

Hydrolases, which catalyze the hydrolysis of various bonds. The best-known subcategory of hydrolases are the lipases, which hydrolyze ester bonds. In the example of human pancreatic lipase, which is the main enzyme responsible for breaking down fats in the human digestive system, a lipase acts to convert triglyceride substrates found in oils from food to monoglycerides and free fatty acids. In the chemical industry, lipases are also used, for instance, to catalyze the —C N —CONH2 reaction, for the synthesis of acrylamide from acrylonitril, or nicotinic acid from 3-pyridylnitrile. 

The reader should also be aware that some information provided in this section and in the sections below does not directly address the subject of biodiesel synthesis. Some discussions, for instance, are about the transesterification of simple esters or the production of monoglycerides by transesterification of vegetable oils nevertheless, the information provided is relevant to the topic of biodiesel synthesis since knowledge of catalyst reactivity in these systems is directly applicable to reactions involving TGs and FFAs. 

Glycerol for milk lipid synthesis is obtained in part from hydrolysed blood lipids (free glycerol and monoglycerides), partly from glucose and a little from free blood glycerol. Synthesis of triglycerides within the cell is catalysed by enzymes located on the endoplasmic reticulum, as shown in Figure 3.13. 

LPL is synthesized in the mammary gland secretory cells and most is transported to the capillary endothelium where it hydrolyzes triglycerides in circulating lipoproteins to FFAs and 2-monoglycerides. These products are absorbed by the mammary gland and used for the synthesis of milk fat. The LPL in milk appears to be identical with the enzyme in the mammary gland (Askew et al., 1970) and to be the result of a spillover. Its level in milk is low at parturition but increases rapidly during the first few days of lactation and remains almost constant for the remainder of the lactation (Saito and Kim, 1995). 

Osman, F., Ashour, A. E., and Gad, A. M. 1968. Monoglycerides I. Synthesis by direct esterification of fatty acids and glycerol. Fette Seifen Anstrichmittel, 70(5), 331-333. 

An acetal of benzaldehyde may become a protective group of polyhydroxy compounds. The hydroxyl groups in the 1 and 3 positions of glycerol may form a cyclic acetal with benzaldehyde. The secondary hydroxyl group left intact is available for esterification. Hydrogenolytic removal of the benzal group allows the synthesis of the P-monoglyceride (eq. 13.21).46... 

It is in this class of compounds that the practice of semi-synthesis particularly in the industrial sphere of single or two-step operations is pre-eminent and traditional. The preparation of soap, monoglycerides, or their sulphates, the fatty alcohols, amides and numerous other functional compounds many of which are examples of nucleophilic substitution almost entirely devolve on the reactions of glycerides many of which are examples of nucleophilic substitution. The range of these tranformations particularly with reference to recent developments in surfactant chemistry has been summarised (ref. 100) and discussed with regard to edible applications (ref.101). 

Synthesis of 2-monoglycerides. Boric acid is recommended for removal of the 1,3-benzylidene group from l,3-benzyUdene-2-acyl glycerols. The derivative is heated in triethyl borate with finely powdered boric acid until conversion to the diborate ester is complete and this is then hydrolyzed with water, for example to 2-monoolein. 

SyMhuti of glyctridts, Trifluoruauetiu anhydride has been used for the direct synthesis of a glyceride from glycerol and a fatty add monoglycerides (1 - and 2-) can... 

In some instances, water may not be necessary at all for the solubilization of the enzyme in a hydrocarbon solvent. A striking example has been provided by Okahata and coworkers [78] who solubilized lipase in benzene or n-hexane by coating the enzyme with the nonionic surfactant (24) or 2Ci6Br. The lipid-coated lipase showed activity for the synthesis of di- and triglycerides from monoglycerides and aliphatic acids. 

Birkhahn R, McCombs C, Clemens R, Hubbs J. Potential of the monoglyceride and triglyceride of DL-3-hydroxybutyrate for paienteral nutrition synthesis and preliminary biological testing in the rat. Nutrition 1997 13 213-219. 

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