Fatty acids methyl ester process

FAME may in the future become a possible organic feedstock to the sulfonated to fatty acid methyl ester sulfonate (FAMES). This feedstock is naturally renewable as it is produced from oils/fats or fatty acids. There are several possible process routes for the manufacture of FAME. 

D.G.B. Boocock, in Process for production of fatty acid methyl esters from fatty acid triglycerides , US, 2004. 

BASIC PROTOCOL I PREPARATION OF FATTY ACID METHYL ESTERS FROM LIPID SAMPLES CATALYZED WITH BORON TRIFLUORIDE IN METHANOL In this method, lipid samples are first saponified with an excess of NaOH in methanol. Liberated fatty acids are then methylated in the presence of BF3 in methanol. The resulting fatty acid methyl esters (FAMEs) are extracted with an organic solvent (isooctane or hexane), and then sealed in GC sample vials for analysis. Because of the acidic condition and high temperature (100°C) used in the process, isomerization will occur to those fatty acids containing conjugated dienes, such as in dairy and ruminant meat products, that contain conjugated linoleic acids (CLA). If CLA isomers are of interest in the analysis, Basic Protocol 2 or the Alternate Protocol should be used instead. Based on experience, this method underestimates the amount of the naturally occurring cis-9, trans-11 CLA isomer by -10%. The formulas for the chemical reactions involved in this protocol are outlined in Equation D1.2.1 Saponification RCOO-R + NaOH, RCOO-Na + R -OH v 100°C DC Esterification RCOO-Na + CH,OH r 3 v RCOO-CH, + NaOH ioo°c ... 

This unit describes the attenuated total reflection Fourier transform infrared (ATR-FTIR) spectroscopic method (AOCS, 1999a AOAC International, 2000), a novel method for measuring the total amount of fat with isolated trans double bonds. It is applicable to natural fats (ruminant fats) and processed fats and oils (partially hydrogenated fats and oils or refined vegetable oils) consisting of long-chain fatty acid methyl esters or triacylglycerols with trans levels >5%, as percent of total fat (AOAC International, 2000). 

In homogeneous catalysis, the catalyst is in the same phase as the reactants and products. Here we will concentrate on homogeneous catalysis in the liquid phase. In the classic case, the reactant (also called the substrate) molecules and the catalyst are reacted in a solvent. For example, the transesterification of fatty acid triglycerides with methanol (Figure 1.10) is catalyzed by hydroxide (OH-) ions. This is an important process for making fatty acid methyl esters which are then used as biodiesel. 

Fatty acid methyl esters (FAMEs) show large potential applications as diesel substitutes, also known as biodiesel fuel. Biodiesel fuel as renewable energy is an alternative that can reduce energy dependence on petroleum as well as air pollution. Several processes for the production of biodiesel fuel have been developed. Transesterification processes under alkali catalysis with short-chain alcohols give high yields of methyl esters in short reaction times. We investigated transesterification of rapeseed oil to produce the FAMEs. Experimental reaction conditions were molar ratio of oil to alcohol, concentration of catalyst, type of catalyst, reaction time, and temperature. The conversion ratio of rapeseed oil was enhanced by the alcohohoil mixing ratio and the reaction temperature. 

The components of biodiesel are vegetable oils composed of glycerol esters of fatty acids. In the process of transesterification, the glycerol components of the triglyceride molecules are exchanged for methanol. The products are fatty-acid methyl esters consisting of straight saturated and unsaturated hydrocarbon chains, as described under chemical processes. 

In an alcoholysis reaction for production of BDF from vegetable oil, triglyceride (the main component of vegetable oil) is reacted with methanol and fatty acid methyl ester (FAME) and glycerol are formed (Fig. 5.1), and the FAME is used as BDF. In a conventional process for production of BDF, alkaline catalysts such as NaOH and KOH are used to promote the reaction. 

A pilot scale reactor which can produce about 40 L of fatty acid methyl ester in a day by use of superheated methanol vapor bubble method has been constructed (Fig. 5.4). The feasibility of the process will be demonstrated by using the pilot scale reactor. 

These methods are based on lipid (substrate) oxidation and specihc to the analysis of oxidation that occurs in food lipids. The tests employed strongly correlate to the conditions that oils and fats are subjected to during processing, food preparation, and storage. The substrate is a model compound that could be a pure triacylgly-cerol, fatty acid methyl ester, or an actual edible oil/lipid. Favorable conditions for substrate oxidation (e.g., high temperature) are provided to facilitate increased rate of oxidation reactions in a controlled environment. The end point is determined... 

The fatty acids present in fats and oils may be analyzed after their hydrolysis and subsequent conversion by methylation to volatile methyl esters. In this Process, different methylating agents may be used, and these are methanol/sulfuric acid (20) or methanol-BFs (21). The methyl esters so produced are then identified with gas chromatography. Standard fatty acids methyl esters are often used for tentative identification purposes. For determination of fatty acid isomers, including trans-fatty acids, it is necessary to use appropriate columns and conditions for analysis. 

Fatty Alcohols. Fatty alcohol is considered a basic oleochemical manufactured by high-pressure hydrogenation of fatty acids or fatty acid methyl esters. The majority of the fatty alcohol produced is further subjected to various processes, such as sulfation, ethoxylation, amination, phosphatization, sulfitation, and others. 

Fats and oils are renewable products of nature. One can aptly call them oil from the sun where the sun s energy is biochemically converted to valuable oleochemicals via oleochemistry. Natural oleochemicals derived from natural fats and oils by splitting or tran -esterification, such as fatty acids, methyl esters, and glycerine are termed basic oleochemicals. Fatty alcohols and fatty amines may also be counted as basic oleochemicals, because of their importance in the manufacture of derivatives (8). Further processing of the basic oleochemicals by different routes, such as esterification, ethoxylation, sulfation, and amidation (Figure 1), produces other oleochemical products, which are termed oleochemical derivatives. 

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