Fatty acid methylesters

Quaternized esteramines are usually derived from fat or fatty acid that reacts with an alcoholamine to give an intermediate esteramine. The esteramines are then quaternized. A typical reaction scheme for the preparation of a diester quaternary is shown in equation 9 (210), where R is a fatty alkyl group. Reaction occurs at 75—115°C in the presence of sodium methoxide catalyst. Free fatty acids (230) and glycerides (231) can be used in place of the fatty acid methylester. 

Fatty acid methylester FAME-C18 300 1.20 — 80-85°C 90-95°C Bleaching of acid and... 

PUFA mix accurately weigh each of the fatty acid methylesters and dissolve these in 50 ml chloroform, reaching a concentration level that is identical to that of the internal standard. Add 200 mg BHT to the solution in order to prevent oxidation of the fatty acids. 

First we wanted to avoid the formation of a middle chain monocarboxylic acid (pelargonic acid) as a by-product. Second oleic acid or its methylester are, not industrially available in pure form. Produced by hydrolysis or transesterification of tallow or vegetable oil, they are always contaminated by other C18-fatty acids/methylesters, as for example linoleic acid/methylester, which cannot be separated in an economic manner. 

Table 1. 9-Decenoic acid methylester by metathesis of fatty acid methylesters with ethylene...

Table 9. Dicarboxylic monomethylesters by ruthenium-catalysed oxidative cleavage of co-unsaturated fatty acid methylesters with different types of peracetic acid...

By the same procedure co-unsaturated fatty acid methylesters can be converted to dicarboxylic acid monomethylesters (Table 9). Using distilled peracetic acid, yields of these bifunctional compounds — now isolated by distillation — were 85-90% and purities were about 94%. Using peracetic acid in equilibrium as the oxidant the yields (according to GC) were a little less. 

Fig. 3.21. High-efficiency separation of fatty acid methylesters (standard compounds) on a glass capillary column. Reproduced from [358] with permission of Lipid Research, Inc.

The manufacturing of fatty acids by fat splitting and of fatty acid methylesters by alcoholysis of fets and oils yield approximately 10% to 13% of glycerine (glycerol) as by-product. Established glycerine markets are applications as hydrotrope, humectant, solvent, solubilizer, antifreeze and plasticizer for aqueous systems in cosmetics, pharma, food and industrial markets as humidity stabilizer and preservative for tobacco as raw material for glycerol esters, for polyetherpolyols, for synthetic resins, and nitroglycerine. ... 

Fatty acid methylester can be used directly as a diesel substitute in conventional diesel engines (Table V). Large-scale demonstration projects with FAME based on rape oil (RME) have shown that there are no significant problems, although the more aggressive chemistry of RME compared to conventional diesel fuel requires fuel lines to be made from a more resistant material like Teflon (Heinz et ai, 2000). 

Fatty acids in the form of their methylesters are basic starting materials for the production of surface-active Q -sulfo fatty acid methylesters. While the reaction of fats and oils with concentrated sulfuric acid or oleum was limited to compounds with double bonds or OH-groups in the molecule, saturated fatty acids also became available as feedstock after the introduction of sulfonation with diluted sulfur trioxide gas. The sulfonate group enters in the o -position to the carboxylic group in this process. 

The sodium salts of Q -sulfo fatty acid methylesters are soluble in water and resistant to hydrolysis in the pH range of 3-10. They are also only slightly sensitive to water hardness and offer good detergency in combination with other surfactants. Their foaming ability decreases strongly from the lauric methylester to the stearic methyl ester. 

The preparation of of-sulfo fatty acid methylesters is a two-stage process taking place at two different rates. At first, an addition compound of 1 mol of methylester with 2 mol of SO3 is formed. Then, in the following reaction, 1 mol, of SO3 is split off, to form the final ester. This sulfur trioxide will slowly react further with another methyl ester. Using the fatty acid methylester and SO3 in a molar ratio results in an undesirably long reaction time. Therefore a surplus of sulfur trioxide is used. The reaction mixture then consists of the main product, the a-sulfo fatty acid methylester and also its anhydride with SO3. By neutralization with a solution of caustic soda, on the one hand the desired sodium salt of the required ester is formed, while on the other hand the anhydride is transformed to the corresponding disodium salt and sodium methyl sulfonate. In order to achieve a complete transformation of the fatty acid methylester, a certain amount of the undesired disodium salt has to be expected. 

Figure 18. Simulation of concentration profiles with ASPEN+ in a multistage counter current separation. Separation of fatty acid methylesters with supercritical CO [f 9].

Alpha sulphonated fatty acid methylester sulphonic acid neutralisation and bleaching... 

Adami I. et al., R D Dept., Ballestra SpA, Italy. "Fatty Acid Methylester, a universal raw material for detergent manufacture". 

Fatty acid methylester (FAME) DIN EN 14214 Commercial grade 1.2 1.2 - Causes swelling, [4Z3]... 

Figure 4.3 Surface reaction with preadsorption of fatty acid methylesters on K2CO3, according to Mouloungui, 1987 25.

Chem. Descrip. Polyoxyethylene fatty acid methylester Ionic Nature Nonionic Uses Emulsifier detergent Properties Liq. 92% cone. 

F. are produced by first reacting glucose with methylamine under reductive conditions (Raney Nickel as hydrogenation catalyst). In a subsequent reaction the N-methylglucamine is transferred with - fatty acid methylester into the desired f ... 

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