Amide surfactants

Also the impact of various reaction parameters on enzymatic synthesis of amide surfactants from ethanolamine and diethanolamine has been studied, although the possibilities of acyl migration are not investigated. However, it was found that the selectivity of the reaction depended on the solubility of the product in the solvent used, and that the choice of solvent was critical to obtain an efficient process [17]. 

The MS analysis using ESI was applied for the determination of an unknown surfactant compound contained in an extract of a shampoo formulation [44]. MS leading to sequential product ions helped to identify the constituents. The MS4 experiments together with other spectral observations confirmed the hypothesis that the unknown compound was a N-( 2-aminoethyl) fatty acid amide with the general formula R-C(0)-NH(CH2-CH2-N)R/R,/. An authentic sample of the proposed laury ampho mono acetate (LAMA) (R = -CH2-CH2-OH and R" = -CH2-CH2-COOH) that was available led to the same [M + H]+ parent ion at m/z 345. The fragmentation that could be observed under ESI-FIA-MS-MS(+) conditions resulted in an intensive examination of amide surfactants. However, only two of them—lauryl diethanol amide ([M + H]+ m/z 288), a non-ionic surfactant and laurylamido-(3-propyl betaine ([M + H]+ m/z 343)—... 

The chemical stability of the amide bond is high. When the surfactant containing an amide bond was subjected to 1 M sodium hydroxide during five days at room temperature, only 5% of the amide surfactant was cleaved. The corresponding experiment performed in 1 M HCl resulted in no hydrolysis. The amide bond was, however, found to be slowly hydrolyzed when lipase from Candida antarctica or peptidase was used as catalyst. Amidase and lipase from Mucor miehei was found to be ineffective. Despite the very high chemical stability, the amide surfactant biodegrades by a similar path in the... 

Fig. 12 Synthesis route for preparation of amide surfactants. MsCl, EtsN, THF and DCM stand for mesyl chloride, triethylamine, tetrahydrofuran and dichloromethane, respectively...

Neoprotex. [Nikko Chem. Co. Ltd.] Methylol amide surfactant softens, water repellent for resin treatmnit... 

Visek KE (1990) Fatty acid amide surfactants In Richmond JM (ed) Cationic surfactants, organic chemistry (Surfactant Science Series 34). Marcel Dekker, New York, Ch l,pp 1-50... 

Antoine J.-R, MarciUoux J., PlusqueUec D., Benvegnu X, Goursaud R, Bituminous aqueous emulsion with glycine betaine ester/amide surfactant for roads coatings, Patent FR 2869910, WO 2005121252, 2005. 

In principle a large number of sulphonated amide surfactants can exist, but only acyl taurates and methyltaurates and sulphosuccinamates are of practical interest. 

Other, even more specialized amide surfactants are known and used in selected products [17]. Sodium cocoyl sarcosinate (CS) and sodium cocoyl tau-rate (CT) are amide-based specialty anionic surfactants closely related to sodium cocoyl isethionate (CIS) structurally (Fig. 13) [18]. All are mild to skin and useful in personal care products. These three surfactants are some-... 

N-alkyl pyrrolidones are a class of amide surfactants made by reacting a primary amine with butyrolactone to give a amide alcohol, then cyclizing to the pyrrolidone (Fig. 17) [21]. 

In studies with acylation of diethanolamine, it was found that direct acylation of diethanolamine to amide is more selective in hexane than in dioxane [50]. As diethanolamine is highly viscous, an increase in temperature was important to reduce the viscosity and promote the reaction. O-acylation does not take place in hexane but is favoured in dioxane rather than A-acylation. Excess of the amine helped to increase the conversion to amide. The transacylation approach resulted in higher reaction rates and selectivities in both the solvents. Lipase-catalysed synthesis of secondary-amide surfactant (A-methyl lauroylethanolamide) in acetonitrile was also favoured in the presence of a molar excess of amine (A-methyl ethanolamine) [51]. 

Fernandez-P ez, M. and Otero, C. (2001) Enzymatic synthesis of amide surfactants from ethanolamine. Enzyme Microb. Technol., 28, 527-536. 

Sharma, J., Batovska, D., Kuwamori, Y. and Asano, Y. (2005) Enzymatic chemoselective synthesis of secondary-amide surfactant from A-methylethanol amine. J. Biosci. Bioeng., 100, 662-666. 

Chem. Descrip. Terpenes/amides/surfactants/solvent blend Uses Paraffin dispersant Features Prevents or removes paraffin Pmperties 40% act. 

Chem. T scrip. Diamines/amides/surfactant blend Uses Paraffin dispersant Features Removes or prevents paraffin Pmperties 100% act. 

Chem. Descrip. Amine/amide surfactant Ionic Nature Anionic... 

Miscellaneous Sulfoester and Amide Surfactants The sulfoesters and amides discussed in the preceding section are those in which the two functionalities were located on adjacent carbon atoms, a situation that imparts some special properties to the resultant surfactant molecules. A second class of related materials is that in which the two groups are more widely separated. General examples of such compounds would be... 

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