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Licensed Unlicensed Requires Authentication Published by De Gruyter April 11, 2013

A Novel Synthesis of Anionic Heterogemini Surfactants Containing COOH, SO3H and PO(OH)2 Headgroups from Corynomicolic Acid and its Derivatives

Eine neue Synthese anionischer Hetero-Geminitenside mit COOH, SO3H und PO(OH)2-Kopfgruppen aus Corynomycolsäure und deren Derivaten
  • T. Kawase , T. Aisaka and T. Oida
From the journal Tenside Surfactants Detergents
https://doi.org/10.3139/113.110154

Abstract

Anionic heterogemini surfactants with –COOH, –SO3H and –PO(OH)2 headgroups in combination were synthesized from Corynomicolic acid derivatives having R = C11H23. The –SO3H headgroup was obtained by the successive conversion of OH → OMs → SCN → SH → –SO3H. The PO(OH)2 headgroup was introduced by the conjugate-addition to E-isomer of α,β-unsaturated ester derived from Corynomycolic acid ester. Heterogemini surfactant with –SO3H and –PO(OH)2 headgroups was also synthesized from phosphonate analog of Corynomycolic acid. The stereoisomers (syn- and anti-isomers) of heterogemini surfactants were separately prepared except for heterogemini surfactants with –COOH and –PO(OH)2 headgroups. Effects of variation and stereochemistry of two anionic headgroups on their surfactant properties were also studied on the basis of surface tension measurements.

Kurzfassung

Anionische Hetero-Geminitenside mit –COOH, –SO3H und –PO(OH)2-Kopfgruppen wurden aus Derivaten der Corynomycolsäure mit R = C11H23 synthetisiert. Die –SO3H-Kopfgruppe wurde aus der schrittweisen Umwandlung von OH → OMs → SCN → SH → –SO3H erhalten. Die PO(OH)2 –Kopfgruppe wurde eingeführt über die konjugate Addition zum E-Isomer des α,β-ungesättigen Esters, der aus dem Ester der Corynomycolsäure erhalten wurde. Die Hetero-Geminitenside mit –SO3H and –PO(OH)2-Kopfgruppen wurden synthetisiert aus dem Phosphonat analog zur Corynomycolsäure. Die Stereoisomere (syn- und anti-Isomere) der Hetero-Geminitenside wurden getrennt hergestellt. Ausnahmen waren die Hetereo-Geminitenside mit –COOH- und –PO(OH)2-Kopfgruppen. Die Effekte der Variation und der Stereochemie der zwei anionischen Kopfgruppen auf die Tensideigenschaften wurden mit Hilfe von Messungen der Oberflächenspannung studiert.

Key words:: Anionic heterogemini surfactants; Corynomycolic acid; stereoisomer; surface tension
Stichwörter:: anionische Hetero-Geminitenside; Corynomycolsäure; Stereoisomer; Oberflächenspannung
∗ Prof. Tokuzo Kawase, Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Hashigamicho 1, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan, Tel.: +81-75-724-7515, Fax: +81-75-724-7515. E-Mail:

Tokuzo Kawase was born in 1951. He is a Professor of chemistry at Kyoto Institute of Technology. He received his D. Engineering from Kyoto University in 1979 and another Ph. D. from Osaka City University in 1995. His current scientific interests are focused on the synthesis of novel surfactants including fluorinated surfactants.

Tsunetomo Aisaka completed his M. Sc. in applied chemistry from Kyoto Institute of Technology. Presently he is working at Nissha Co. Ltd.

Tatsuo Oida is an Associate Professor at Kyoto Institute of Technology. His current scientific interests are focused on the synthesis of novel surfactants and their structure-related surfacant properties.

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Received: 2011-05-18
Published Online: 2013-04-11
Published in Print: 2011-11-01

© 2011, Carl Hanser Publisher, Munich

From the journal
Tenside Surfactants Detergents
Tenside Surfactants Detergents
Volume 48 Issue 6

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