Fatty acid methyl esters synthesis

Mazzocchia, C. G. Modica A. Kaddouri R. Nannicini. Fatty acid methyl esters synthesis from triglycerides over heterogeneous catalysts in the presence of microwaves. C.R Chimie 2004, 7, 601-605. 

Haas, M. I, Bloomer, S., and Scott, K. 2000. Simple, high-efficiency synthesis of fatty acid methyl esters from soapstock. J. Am. Oil Chem. Soc., 77(4), 373-379. 

Soumanou, M. M., and Bornscheuer, U. T. 2003. Improvement in lipase-catalyzed synthesis of fatty acid methyl esters from sunflower oil. Enzyme and Microb. Technol, 33, 97-103. 

The glycosidation of the reducing sugars obtained from hemicelluloses leads to the alkyl polypentosides surfactants. Glycosylation needs fatty alcohols as raw materials. Natural fatty alcohols derived, for example, from coconut or palm kernel oil are used in the alkyl polyglycoside synthesis to buUd up the hydrophobic part of the surfactants. These alcohols are used as blends obtained after transesterification and fractionation of oils leading to corresponding fatty acid methyl esters, and... 

In the enzymatic process utilized herein for the production of fatty acid methyl ester fixrm rapeseed oil, several factors are known to influence conversion. The initial step of this study involved the identification of factors likely to influence conversion, fri this study, tert-butanol was applied in lipase-catalyzed methanolysis. fert-Butanol has been utilized previously in several enzymatic process, including sorbitan ester synthesis [6, 15]. It has also been confirmed that terf-butanol is inert in the Novozym 435-catalyzed methanolysis of rapeseed oil for the production of biodiesel [12]. 

Chaetomellic acids have been the subject of a number of syntheses. In 1993, we reported the first synthesis of chaetomellic acid A based on the biogenetic type aldol condensation [73]. The aldol reaction of appropriate fatty acid methyl esters with methyl pyruvate yielded two diastereomeric... 

Soares CMF, De Castro HF, Santana MHA et al. (2002) Intensification of lipase performance for long-term operation by immobilization on controlled pore silica in presence of polyethylene glycol. Appl Biochem Biotechnol 98-100 863-874 Soumanou MM, Bornschener UT, Menge U (1997) Synthesis of structured triglycerides firom peanut oil with immobilized lipase. JAOCS 74 427-433 Soumanou MM, Bomscheuer UT (2003) Improvement in Upase-catalyzed synthesis of fatty acid methyl esters from sunflower oil. Enzyme Microb Technol 33(1) 97-103 Straathof AJJ, Panke S, Schmid A (2002) The production of fine chemicals by biotransformations. Curr Opin Biotechnol 13 548-556... 

Kling, M.R., C.J. Easton, and A. Poulos, Synthesis of Very Long Chain Fatty Acid Methyl Esters, J. Chem. Soc. Perkin Trans. 1,1183-1189 (1993). 

Bogaert, P.M.P., F.K.G. Bakker, D. de Wit, T.M. Slaghek, and P. Van der Meeren, New Coupling Method Without Heavy Metals for the Synthesis of a New Class of Fatty Acid Methyl Ester Oligoglycoside Ethers, J. Surfact. Deterg. 1 65-72 (1998). 

Agarwal, R., M.H. Ansari, M.W.Y. Khan, M. Ahmad, and K.D. Sharma, Synthesis and Antimicrobial Activity of Fatty 2-Morpholinones Prepared from Epoxy Fatty Acid Methyl Esters, J. Am. Oil Chem. Soc. 66 825-827 (1989). 

Rojo, J.A., and E.G. Perkins, Chemical Synthesis and Spectroscopic Characteristics of Cjg 1,2-Disubstituted Cyclopentyl Fatty Acid Methyl Esters, Lipids 24 467-476 (1989). 

The principles of biodiesel synthesis are relatively simple oleochemical reactions (see Chapter 9.1) and have been known and applied for many decades (Figure 8.5)." The basic technology consists in a catalyst induced transesterification of a vegetable oil in a batch, semi-batch or continuous process to create a fatty acid methyl ester (FAME). The catalyst used is a strong base,... 

The synthesis of these surfactants involves several steps. The first step is the preparation of a substituted imidazoline, usually l-(hydroxyethyl)-2-alkyl imidazoline, starting from fatty acids or fatty acid methyl esters and aminoethylethanolamine (AEEA) (Figure 15.15). For the production of betaines, the choice of fatty material is in most cases hydrogenated coco fatty acid. The distribution composition of fatty acid chain lengths, given above in Table 15.2, is typical also for cocoam-phoacetates. 

FAME and other fatty acid methyl esters (FAMEs) are endogenous compounds [2, 56], formed via fatty acid ethyl ester synthase (FAEES) [2]. The fatty acid esterification catalyzes an ojg gen atom from the carboxyl group, then condenses the carboxyl group of an acid and the hydroxyl group of an alcohol. FAME synthesis can also be modulated by exogenous methanol and inhibitors of FAEES [2, 57, 58]. 

Figure 7.19 Two-step synthesis of fatty acid glucamides by reductive alkylation of methylamine with glucose using Raney nickel as the hydrogenation catalyst to obtain Al-methyl glucamine, which is acylated by a base-catalyzed reaction with fatty acid methyl ester in a second step.

Rojo, J. A. and Perkins, E. G. (1989a) Chemical synthesis and spectroscopic characteristics of Ci8 1,2-disubstituted cyclopentyl fatty acid methyl esters. Lipids, 24 (6), 467-76. 

To illustrate the recently discovered pathways to functional monomers, Meier and colleagues studied the synthesis of a long-chain diester from a (o-hydroxy fatty acid derived from palmitic acid. The idea was to transform the (0-hydroxyl function into a mesylate, followed by an elimination reaction to prepare the (O-unsaturated fatty acid methyl ester (FAME), which was dimerised by a SM coupling to obtain the desired C30 diester (Scheme 5.5) [14]. This macromonomer was then polymerised with diols and diamines to prepare long-chain polyesters and polyamides (PA) with interesting thermal properties, such as a melting temperature (T ) of 109 °C for the polyester and 166 °C for the PA. 

Synthesis of Oxyethylated Fatty Acid Methyl Esters.275... 

Up to early 1990s, it was assumed that oxyethylation can occur only when the hydrophobic reagent had a labile hydrogen [1-3,5]. Thus, fatty acid methyl esters (FAME) were not considered as a raw material for the direct synthesis of nonionic surfactants with a polyoxyethylene chain. However, esters of fatty acids and PEG monomethyl ethers were known and their properties were described [6]. They were synthesized in a two-step process. Methanol was oxyethylated to PEG monomethyl ether that was then converted into the final product by transesterification with FAME or by esterification with fatty acids, carried out in the presence of an alkaline B or an acid catalyst, respectively. Esters of typical nonionics were synthesized in similar ways and their properties were described [7-9]. 

SYNTHESIS OF OXYETHYLATED FATTY ACID METHYL ESTERS... 

Hreczuch, W., Szymanowski, J., Bekierz, G., Pyralski, K. 1999. Comparison of the synthesis and composition of directly oxyethylated fatty acid methyl esters and oxyethylated alcohols with narrow and broad range distribution of homologues. Proceedings XXIX Joumadas Anuales del CED. Barcelona, 351-358. 

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