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Surface active agents from isopropenyl esters: Acylation of isethionic acid and N‐methyltaurine
Author(s) -
Bistline R. G.,
Rothman E. S.,
Serota S.,
Stirton A. J.,
Wrigley A. N.
Publication year - 1971
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02638512
Subject(s) - stearate , chemistry , organic chemistry , critical micelle concentration , oleic acid , pulmonary surfactant , myristic acid , yield (engineering) , acylation , sodium , acetone , micelle , lauric acid , solubility , fatty acid , nuclear chemistry , palmitic acid , aqueous solution , materials science , biochemistry , metallurgy , catalysis
Acylation of sodium isethionate with isopropenyl stearate at 200 C for 30 min gave a 95% yield of sodium 2‐sulfoethyl stearate, acetone being the only byproduct. Acylation of N‐methyltaurine at 200 C for 90 min gave a 95% yield of N‐methyl‐N‐(2‐sulfoethyl) stearamide sodium salt. Corresponding surface active derivatives were also prepared from pelargonic, lauric, myristic, palmitic, oleic, phenylstearic and hydrogenated tallow fatty acids from their respective isopropenyl esters. Detergency, foam height, wetting time, lime soap dispersing power, critical micelle concentration and other surfactant properties were evaluated. Optimum properties were found at the C 14 −C 18 fatty acid chain length. Unsaturation or branching increased solubility. The 2‐sulfoethyl esters were similar to the N‐methyl‐N‐(2‐sulfoethyl) amides in foam height, wetting ability and lime soap dispersing power, superior to the N‐methyl‐N‐(2‐sulfoethyl) amides in detergency, but inferior in calcium stability and less stable to acid and alkali. Both compounds are readily biodegraded. The fatty isopropenyl ester synthesis has an advantage in yield and purity of the product and could increase the utilization of the 2‐sulfoethyl esters and N‐methyl‐N‐(2‐sulfoethyl) amides in many applications.