Fatty alcohols esterification

Eucarol AGE/EC, ET and SS ionic surfactants have been developed recently by Cesalpinia Chemicals for different applications, for example, cosmetic and pharmaceutical purposes. These surfactants are anionic ester derivatives of alkylpolyglucosides they do not contain a polyoxyethylene chain, the hydrophilic moiety includes glucose units instead of ethylene oxide, and during their production no ethoxylation is carried out. They do not have an irritating effect as they are free from contaminating components such as dioxane consequently no irritating effect is expected. After the glucosidation of fatty alcohol, esterification proceeds in order to obtain anionic derivatives. On the basis of the favourable properties listed, they can be used for medicinal purposes. 

Esters of ether carboxylic acids (propylated and/or ethoxylated) and fatty alcohols or ethoxylated fatty alcohols are described [40], prepared by esterification of the ether carboxylic acid and the alcohol with an acid catalyst like H2S04 or p-toluenesulfonic acid under vacuum and at a temperature of about 130°C. The purpose of these esters is to mainly use them in cremes and lotions with better conditioning and moisture controlling properties. 

Highly concentrated ether carboxylic acids with a low degree of ethoxylation even at room temperature can give an esterification reaction with the non-converted nonionic, especially with the fatty alcohol, to several percentage points. The result may be that a too low value is found for the ether carboxylate content. This mistake in analysis can be avoided by saponification of the formed ester [238]. Two hundred to 300 mg matter and ca 100 mg NaOH were weighed in a 50-ml Erlenmeyer glass, heated with 20 ml ethanol under reflux, and after cooling supplied with water to 100 ml. Afterward a two-phase titration was carried out. 

How the aliphatic monomers are incorporated into the suberin polymer is not known. Presumably, activated co-hydroxy acids and dicarboxylic acids are ester-ified to the hydroxyl groups as found in cutin biosynthesis. The long chain fatty alcohols might be incorporated into suberin via esterification with phenylpro-panoic acids such as ferulic acid, followed by peroxidase-catalyzed polymerization of the phenolic derivative. This suggestion is based on the finding that ferulic acid esters of very long chain fatty alcohols are frequently found in sub-erin-associated waxes. The recently cloned hydroxycinnamoyl-CoA tyramine N-(hydroxycinnamoyl) transferase [77] may produce a tyramide derivative of the phenolic compound that may then be incorporated into the polymer by a peroxidase. The glycerol triester composed of a fatty acid, caffeic acid and a>-hydroxy acid found in the suberin associated wax [40] may also be incorporated into the polymer by a peroxidase. 

Fatty Acid Esters and Fatty Alcohols Fatty acid esters are obtained by transesterification of triglycerides (vegetable oils) or by esterification of fatty acid with alcohol or polyols. Fatty alcohols are obtained by hydrogenation of esters on metal catalysts. Fatty acid esters and fatty alcohols are useful platform molecules to prepare surfactants, emulsifier, lubricants and polymers. 

Despite the fact that glycolic acid has been successfully used as an acyl donor in esterification reactions with fatty alcohols, there are few reports dealing with the enzymatic ROP of glycolide [139], On the other hand, cyclic diesters based on ethylene glycol have been polymerized successfully by lipase catalysis and afford AA-BB-typepolyesters [140, 141],... 

For a number of processes, reactive distillation is not possible, as some of the reactants are destroyed or degraded in side reactions by heating them up to boiling temperature. Examples of such processes are the Knoevenagel-condensation of aldehydes or ketones with components of high CH-acidity, the production of enam-ines or carbonic acid amides, or the esterification of fatty acids with fatty alcohols to fatty esters [7]. 

To obtain substantial yields of surfactant hydrophobes, especially in the most useful C12— 14 range, the choice is restricted to coconut, palm and palm kernel oils. In the C16-18 range, the same oils are also used but animal (normally beef) tallow can be used. The use of animal fats raises some ethical issues but these are not commonly used to produce anionic surfactants. The oils may be converted to methyl esters by transesterification which allows easier distillation to remove heavy/light fractions and the esters are finally hydrogenated to fatty alcohols. Alternatively, the fat or oil can be hydrolysed to fatty acid prior to esterification... 

Fatty alcohol can be fractionated to separate the C8-C10 fraction, known as plasticizer range alcohol, and the C12-C18, known as the detergent range alcohol. The plasticizer range alcohol is a liquid with good dissolving power. It can be used in a limited way as a solvent for printing inks and lacquers. Esterification with a polycarboxylic acid, such as phthalic anhydride, yields an excellent plasticizer especially for PVC. 

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. 

The fatty acids are introduced into a large volume of circulating fatty alcohols, more than 250 times the volume of the acids, so that the esterification is effected rapidly without the damaging effect of the fatty acids on the catalyst (17). 

Phosphate esters are prepared by the partial esterification of fatty alcohol with phosphorous oxychloride followed by hydrolysis (20). This method yields a product that is a mixture of monoalkyl, dialkyl, and trialkyl phosphates. 

Cetyl esters wax is prepared by the direct esterification of the appropriate mixtures of fatty alcohols and fatty acids. 

By esterification of fatty alcohols with dicarboxylic acids, highly polar lubricants such as adipic acid distearylate or distearyl phthalate with excellent compatibility are obtained. 

Soybean oil may be hydrolyzed into glycerol and fatty acids, or soybean oil soap-stocks (foots) may be acidified to produce fatty acids. Crude soybean fatty acids are used to make adhesive tape, shaving compounds, textile water repellents, carbon paper, and typewriter ribbons. Consumption of fatty acids in the United States, Western Europe, and Japan was 2.3 MMT (2.5 million t) in 2001. These soybean fatty acids can be separated into various fractions by distillation, and are used in candles, crayons, cosmetics, polishes, buffing compounds, and mold lubricants. These fatty acids can be converted to FAME by esterification, alkyl epoxy esters by epoxidation, fatty alcohols by hydrogenation (Kreutzer, 1983 Voeste Buchold, 1983), and dimer and trimer acids by conjugation or amines and amides as shown in Fig. 17.7 (Maag, 1983). 

Linko et al. 1998). Lipases have been extensively used in the production of surfactants of different chemical nature by esterification of alkyl glycosides and fatty acids, by transesterification of natural oils and alcohols, by transesterification of phospholipids and alcohols, and also by esterification of amino acids and amides (Saxena et al. 1999). Personal care products, hke isopropyl myristate and isopropyl palmitate, have been produced in solvent-free media with immobilized lipase and wax esters (esters from long-chain fatty acids and fatty alcohols) are also being produced with lipases (Hasan et al. 2006). 

Fats and Oils The Raw Materials of Oleochemistry. Fats and oils are triglycerides (i.e., fatty acid esters of glycerol). They are the starting materials for the production of fatty acid methyl esters, which are important intermediates in the production of fatty alcohols and surfactants [198] by the oleochemical route, which has great ecological benefits [199]. The fatty acid methyl esters are produced either by the esterification of fatty acids after hydrolysis of the triglycerides or by direct transesterification with methanol. The overall transesterification reaction is as follows ... 

Fatty acid esters of mono- and polyfunctional alcohols are the workhorses of oleochemistry. In many fields of application fatty acid methyl esters replace fatty adds because they are less corrosive. Chemical reactions can often be carried out under milder conditions. They have lower boiling points and require less energy to distil and to fractionate than the corresponding fatty acids. The elimination of methanol from the reaction products can be more easily achieved than that of water. Therefore fatty acid methyl esters are primarily used for the production of saturated and unsaturated fatty alcohols. Methyl esters are manufactured by acid catalyzed esterification of fatty acids in counter-current reaction columns or by alkaline transesterification starting directly from the triglyceride oils in a batch, semi-batch or continuous process (Figure 9.1.37> ° ° ... 

Over the last two decades, there has been an increasing interest in the industrial use of plant proteins for non-food applications because of their renewabiUty or biodegradability Plant proteins ve thus been used for the fabrication of materials such as films and coatings, adhesives, thermoplastics and surfactants. However, for many applications, it is necessary to confer and/or to improve some specific properties by chemical modification of the native proteins. Particularly, the esterification of their carboxyl and amide groups by a fatty alcohol (Fig 1) could lead to a protein-derivative with improved functional properties. Such modification would result into a lower water sensitivity of the protein-based products and it would therefore offer... 

EsterificaticMi with a fatty alcohol modified the functional properties of proteins, particularly their solubility in alkaline water. For wheat gluten and sunflower esterified proteins, solubility at basic pH decreased compared to native proteins, indicating thus a hydrophobation effect Fig 4 shows the effect of esterification on solubility of sunflower proteins. The solubility of unmodified sunflower proteins increased significantly in alkaline media and... 

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]. 

Phenolic resins have been developed to a highly versatile degree as lacquer and paint bases. Pure Novolak is only soluble in polar solvents such as acetone, alcohol, low esters, etc. However, the market potential of alcohol-based lacquers is limited, and such lacquers are too brittle for many uses. For this reason, so-called plasticized and elasticized phenolic resins ( substituted phenolics ) were developed. Plastification is achieved either by partial etherification (e.g., with t-butyl alcohol), esterification (e.g., with fatty acids), or both etherification and esterification (e.g., with adipic acid and trimethylol propanol). These plasticized phenolic resins have increased elasticity, are soluble in aromatics, are compatible with polyvinyl compounds and fatty acids, and are suitable for use as stoving enamels. 

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