Fatty acid isethionate

As an example, the cM data of the binary mixtures dependent on the mixture composition were experimentally determined for the systems alkanesul-fonate/fatty acid isethionate, alkanesulfonate/betaine, and fatty acid isethionate/ betaine. In Fig. 31 the calculated ternary cM area of state is depicted for the mixture alkanesulfonate/fatty acid isethionate/betaine [58]. Interestingly, the... 

Description. Fatty acid isethionates are usually prepared by the reaction of a fatty acid chloride with sodium isethionate (HO-CHz-CHz-SOs-Na), itself resulting from the addition of sodium bisulfite to ethylene oxide. Like other esters, they are sensitive to hydrolysis. These surfactants are insensitive to water hardness and show good wetting, foaming, and emulsifying properties. In addition, they have excellent compatibility with the skin. 

Taurides (or taurates) are acylamino alkane sulfonates which have chemical structures close to isethionates. They are prepared by the reaction of a fatty acid chloride with N-methyl taurine (CH3-NH-CH2-CH2-S03-Na). Oleic acid chloride or coconut fatty add chloride are suitable reactants. At variance with the above fatty acid isethionates, taurides are less prone to hydrolysis. Taurides have good foaming and emulsifying properties and are insensitive to water hardness. 

A.gllsethionates. These are among the oldest of the synthetic detergents and were developed ia Germany to overcome problems of hard water. They are prepared by reaction of fatty acid chlorides with a salt of isethionic acid, ie, 2-hydroxyethanesulfonic acid [107-36-8]. These detergents have moderate foaming properties and have seen only limited use ia shampoos. 

The viscous fatty acid chloride is mixed with soHd sodium isothionate and is heated under vacuum and agitation without water or solvent HCl is evolved, leaving the product as a finely divided powder. The direct esterification of fatty acid and sodium isethionate has been patented (69). 

The solubihty characteristics of sodium acyl isethionates allow them to be used in synthetic detergent (syndet) bars. Complex blends of an isethionate and various soaps, free fatty acids, and small amounts of other surfactants reportedly are essentially nonirritant skin cleansers (66). As a rule, the more detersive surfactants, for example alkyl sulfates, a-olefin sulfonates, and alkylaryl sulfonates, are used in limited amounts in skin cleansers. Most skin cleansers are compounded to leave an emollient residue on the skin after rinsing with water. Free fatty acids, alkyl betaines, and some compatible cationic or quaternary compounds have been found to be especially useful. A mildly acidic environment on the skin helps control the growth of resident microbial species. Detergent-based skin cleansers can be formulated with abrasives to remove scaly or hard-to-remove materials from the skin. 

In addition to the soaps and fatty acids, some bars contain cocamidopropyl betaine, a mild amphoteric detergent that is added to control irritation without decreasing suds or cleaning power, and benzine sulfonate detergents such as sodium dode-cylbenzinesulfonate. Other detergents, such as sodium isethion-ate and sodium cocoyl isethionate, are also common. 

As a historical note, SAI for Dove was made by this acyl chloride process until a commercial process for direct esterification of fatty acid and sodium isethionate was developed by Lever Brothers Co. in the late 1950 s. The SAI made by direct esterification is generally termed DEFI, an acronym for directly esterified fatty isethionate . The DEFI reaction is follows ... 

Typical weight per cent chain length distributions based on 20 80 tallow coconut fatty acid chain distribution specified for sodium acyl isethionate specified for the Monsavon bar [9], and the purely coconut fatty acid source for SCI. 

Irciniasulfonic acid (629) was obtained from Ircinia sp. from Japanese waters. Spectroscopic and chemical analyses revealed it to consist of three different kinds of acids common fatty acids, a novel unsaturated branched CIO fatty acid and an isethionic acid. Irciniasulfonic acid (629) reverses multidrug resistance in human carcinoma cells caused by overexpression of membrane glycoprotein [498]. 

Chemistry and general properties. Sodium isethionate is 2-hydroxyethane sulphonate, sodium salt and will form an ester with a fatty acid halide, normally an acyl chloride (Figure 4.26). 

Raw materials. Sodium isethionate is produced by the reaction of ethylene oxide with sodium bisulphite. The most common commercially available isethionates are based on coconut fatty acid. 

Fatty acid chlorides have been discussed in Section 4.4.3. As with isethionates and sar-cosinates, the cocoyl derivative is predominant. 

New fatty acid ester compounds of polyoxyalkylene isethionate salts — are mild surfactants with good calcium tolerance for use in liquid and solid detergent compositions and personal care products... 

U.S. 6013616 (2000) Fabry et al. (Henkel) Monoglyceride (ether) sulfate fatty acid condensations (isethionates, taurates, or sacrosinates) Mild detergent mixtures... 

Fenopon . [Rhone-Poulenc Surf.] Ethoxy sulfates, cocoyl isethionates, or fatty acid taurates surfactants. 

Coconut fatty acid, 2-sulfoethyl ester, sodium salt EINECS 263-052-5 Fatty acids, coco, 2-sutfoe1hyl esters, sodium salts Fatty acids, coconut oil, sulfoethyl esters, sodium salts Igepon AC-78 Jordapon Cl Sodium cocoyl isethionate. 

Definition Ammonium salt of the coconut fatty acid ester of isethionic acid... 

Fatty acids, coco, 2-sulfoethyl esters, sodium salts. See Sodium cocoyl isethionate Fatty acids, coco, tridecyl esters. See Tridecyl cocoate... 

In a similar way, the fatty acid can be attached to 2-hydroxyethanesulfonic acid, thus forming an ester instead of an amide. The sodium salt is the so-called sodium isethionate (2). 

Alkyl isethionates such as sodium cocoyl isethionate are used mainly in creams, toilet bars, shower gels, bath foams, and baby products. These derivatives are obtained from sodium 2-hydroxyethane-sulfonate, which can react either by esterification with fatty acids or condensation with fatty acid chlorides as follows ... 

Acid. Conversion to carboxylic acid and alcohol takes place. The sulphonate group may be on either of these. Thus acyl isethionates yield a fatty acid and isethionate ions, mono- and di-alkyl sulphosuccinates yield fatty alcohols and sulphosuccinic acid, and a-sulphonated fatty esters yield the a-sulphonated fatty acid and a low-molecular-weight alcohol. 

The active content of acyl isethionates in raw materials and products is determined either by titration with benzethonium chloride or by saponification. The fatty acid may be extracted after acidification for molecular-... 

Extraction of fatty acid (acyl isethionates) or of fatty alcohol (sulpho-succinates)... 

Extraction of fatty acid gives the acyl isethionate plus the acyl methyltaurate. 

Description. Sarcosinates (or salts of acyl amino acids) are the condensation products of fatty acids with iV-methylglycine (CH3-NH-CH2-COOH) (or sarcosine). The properties of sarcosinates are similar to those of isethionates. The TEA salts are more soluble than sodium salts around neutral pH. Because of the internal amide chemical function, sarcosinates undergo hydrolysis at extreme pH ranges. 

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