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Preparation, surface‐active properties and acid decomposition profiles of a new “soap” bearing a 1,3‐dioxolane ring
Author(s) -
Ono Daisuke,
Masuyama Araki,
Nakatsuji Yohji,
Okahara Mitsuo,
Yamamura Shingo,
Takeda Tokuji
Publication year - 1993
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/bf02545363
Subject(s) - dioxolane , chemistry , alkaline hydrolysis , pulmonary surfactant , reagent , hydrolysis , ring (chemistry) , alkyl , decomposition , condensation , micelle , critical micelle concentration , alkali metal , organic chemistry , biochemistry , physics , aqueous solution , thermodynamics
New soap‐type surfactants bearing a 1,3‐dioxolane ring were prepared in good yields by the acid‐catalyzed condensation of 1‐ O ‐alkylglycerols (alkyl: decyl, dodecyl, tetradecyl, heptadecyl, octadecyl, or cis ‐9‐octadecenyl) with oxocarboxylic acid esters, followed by alkaline hydrolysis without any expensive reagent and special equipment. These surfactants were soluble in alkaline water at room temperature. Their critical micelle concentrations were much smaller than that of sodium dodecanoate. An alkaline solution of the octadecyl homologue was nonfoaming, but the other homologues, including the cis ‐9‐octadecenyl derivative, showed high foaming ability in alkaline solutions. The structural effect of these compounds on the area per molecule at the surface is also discussed. Because these surfactants contain a 1,3‐dioxolane ring, they can be utilized as a new acid‐decomposable type of cleavable surfactant. At pH 1, they decompose almost completely into nonsurface‐active species after 80 min.