Synthesis and Properties of a Series of CO2 Switchable Gemini Imidazolium Surfactants

Hongsheng Lu; Yu He; Zhiyu Huang

doi:10.3139/113.110323

Article

Synthesis and Properties of a Series of CO₂ Switchable Gemini Imidazolium Surfactants

Hongsheng Lu , Yu He and Zhiyu Huang

Published/Copyright: September 25, 2014

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From the journal Tenside Surfactants Detergents Volume 51 Issue 5

Abstract

Novel switchable gemini imidazolium surfactants with different carbon atoms in hydrophobic group were successfully synthesized by condensation of fatty acid with triethylene tetramine, then the intermediates were reacted with CO₂ to give the imidazolinium bicarbonates. The structures of intermediates and products were identified by IR and ¹H-NMR spectra. As the results show, the structures of the products obtained correspond to the target compounds designed. By surface tension measurements, these Gemini surfactants have excellent surface activity with low cmc and surface tension. The conductivity and surface tension cycles show that these surfactants could be switched from imidazoline (neutral form) to imidazolium bicarbonate (charged form) reversibly and repeatedly.

Kurzfassung

Es wurden neue schaltbare Gemini-Imidazolintenside mit unterschiedlicher Anzahl an Kohlenstoffatomen in der hydrophoben Gruppe durch Kondensation von Fettsäuren mit Triethylentetramin und anschließender Reaktion der Zwischenprodukte mit CO₂ zu den Imidazoliumbicarbonaten synthetisiert. Die Struktur der Zwischen- und Endprodukte wurden mittels IR- und ¹H-NMR-Spektren festgestellt. Die Ergebnisse zeigen, dass die Strukturen der erhaltenen Produkte denen der erwünschten Zielprodukte entsprechen. Messungen der Oberflächenspannung zeigen, dass die Gemini-Tenside eine hervorragende Oberflächenaktivität mit einer geringen cmc und Oberflächenspannung bei der cmc aufweisen. Die Leitfähigkeit und die Oberflächenspannungszyklen zeigen, dass die Tenside zwischen ihrer Imidazolin-Form (ohne Ladung) und ihrer Imidazoliumbicarbonat-Form (geladene Form) hin und her geschaltet werden können.

Key words: Synthesis; CO2-Switchable; gemini surfactant; imidazolium; bicarbonate

Stichwörter: Synthese; CO2-schaltbar; Gemini-Tensid; Imidazoliumbicarbonat

* Correspondence address Dr. Hongsheng Lu, School of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu, P. R. China. Tel.: +8628 83037305, Fax: +8628 83037305, E-Mail: hshlu@swpu.edu.cn

Dr Hongsheng Lu is currently associate professor at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. He received his Ph.D. in Chengdu Institute of Organic Chemistry of Chinese Academy of Science. His research interests include synthesis and application of oil chamicals.

Mr. Yu He is currently a M.D. candidate at the College of Chemistry and Chemical Engineering, Southwest Petroleum University. His main research is synthesis and application of novel CO₂ switchable surfactants.

Prof. Zhiyu Huang is currently the director of Gradate School, Southwest Petroleum University. He received his Ph.D. in Applied Chemistry at the college of Chemistry and Chemical Engineering, Southwest Petroleum University. His research interests include synthesis and application of oil chamicals.

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Received: 2013-10-10

Revised: 2014-04-08

Published Online: 2014-09-25

Published in Print: 2014-09-15

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Articles in the same Issue

https://doi.org/10.3139/113.110323

Keywords for this article

Synthesis; CO2-Switchable; gemini surfactant; imidazolium; bicarbonate