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Preparation, surface‐active properties and acid decomposition profiles of a new “soap” bearing a 1,3‐dioxolane ring

1993; Wiley; Volume: 70; Issue: 1 Linguagem: Inglês

10.1007/bf02545363

1558-9331

Daisuke Ono, Araki Masuyama, Yohji Nakatsuji, Mitsuo Okahara, Shingo Yamamura, Tokuji Takeda,

Chemical Synthesis and Reactions

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.