Synthesis, Characterizations and Multifunctional Activities of New Thiourea-Based Non-Ionic Surfactants

Imdad Ullah; Musharaf Khan; Afzal Shah; Shahan Zeb Khan

doi:10.3139/113.110526

Article

Synthesis, Characterizations and Multifunctional Activities of New Thiourea-Based Non-Ionic Surfactants

Imdad Ullah , Musharaf Khan , Afzal Shah and Shahan Zeb Khan

Published/Copyright: November 13, 2017

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From the journal Tenside Surfactants Detergents Volume 54 Issue 6

Abstract

Six new thiourea-based non-ionic surfactants were prepared from easily existing raw resources in good yield name 1-sec-butyl-3-dodecanoylthiourea, 1-dodecanoyl-3-phenylthiourea, 1,1-dibutyl-3-dodecanoylthiourea, 3-dodecanoyl-1, 1-diphenylthiourea, 1-cyclohexyl-3-dodecanoylthiourea and 1-butyl-3-dodecanoylthiourea. The structural chemistry of these compounds was studied by multinuclear magnetic resonance (¹H, ¹³C), Infrared spectroscopy and UV-Visible spectrophotometry techniques. Their solubility varies according to temperature. They show a low solubility, which increases with the temperature of the water. However, they are not stable. The are soluble in organic solvent like ethanol. These molecules possess a low critical micelle concentration and due to this it shows that they are moderately hydrophobic. These molecules were studied regarding their antimicrobial activities and their antifungal and antibacterial efficiency was tested against five microoganism strains. In all cases, the new compounds show a significant inhibition growth against the tested five bacterial and fungal strains. Due to these behaviors they can be used as future candidates in cleaning as well as in agriculture features. The corrosion inhibition behavior was also studied using chromium and aluminum metals.

Kurzfassung

Sechs neue nichtionische auf Thioharnstoff basierende Tenside wurden aus gut verfügbaren Rohstoffen in guter Ausbeute synthetisiert. Es handelt sich um: 1-sec-Butyl-3-dodecanoylthioharnstoff, 1-Dodecanoyl-3-phenylthioharnstoff, 1,1-Dibutyl-3-dodecanoylthioharnstoff, 3- Dodecanoyl-1, 1-diphenylthioharnstoff, 1-Cyclohexyl-3-dodecanoylthioharnstoff und 1-Butyl-3-dodecanoylthioharnstoff. Die Strukturen dieser Verbindungen wurden mit mehrkerniger Magnetresonanz (¹H, ¹³C), der Infrarotspektroskopie und der UV-Vis-Spektrophotometrie untersucht. Ihre Löslichkeit variiert je nach Temperatur. Sie zeigen in kaltem Wasser eine geringe Löslichkeit, die mit der Temperatur des Wassers steigt, sie sind aber nicht stabil. In organischem Lösungsmittel wie Ethanol sind sie löslich. Diese Moleküle besitzen eine geringe kritische Mizellenbildungskonzentration und zeigen daher, dass sie mäßig hydrophob sind. Diese Moleküle wurden hinsichtlich ihrer antimikrobiellen Aktivitäten untersucht und ihre antimykotische und antibakterielle Effizienz wurde gegen fünf Mikroorganismus-Stämme getestet. Die neuen Verbindungen zeigten immer ein signifikantes Hemmungswachstum gegen den fünf getesteten Bakterien- und Pilzstämmen. Aufgrund dieser Verhaltensweisen können sie als zukünftige Kandidaten sowohl in der Reinigung als auch in der Landwirtschaft genutzt werden. Die Korrosionshemmung der Verbindungen an Chrom und Aluminium wurde auch untersucht.

Key words: Synthesis; thiourea-based surfactants; CMCs; antimicrobial activities; corrosion inhibition

Stichwörter: Synthese; Thioharnstoff-basierte Tenside; CMCs; Antimikrobielle Aktivitäten; Korrosionsinhibierung

*Correspondence address, Dr. Imdad Ullah, Department of Chemistry, Quaid-i-Azam University, Islamabad 45300, Pakistan, E-Mail: hayaimdad@gmail.com, imdadktk70@gmail.com, Alternative:, School of Chemistry, Monash University, Clayton 3800, Melbourne, VIC, Australia, Tel.: +61470231251

Imdad Ullah (Gold medalist in M.Sc) is an assistant professor of Physical Chemistry in the government college of Khyber Pakhtunkhwa, Pakistan. He completed his Ph.D from the Department of Chemistry, Quaid-i-Azam University (QAU), Islamabad, Pakistan. Currently, he is visiting scholar status at the school of chemistry, Monash University Clayton, VIC. Australia. He has synthesized more than fifty new thiourea-based surfactants and working on their environment friendly applications such as extraction of toxic metals and corrosion inhibitions.

Musharaf Khan, lecturer in Biology in Federal college Mardan, Pakistan, received his PhD in biological science from Peshawar University, Pakistan. His research interest includes medicinal plants and taxonomy. He is also working on biosurfactants synthesis and their medicinal use in many drugs and foods.

Afzal Shah is an assistant professor at University of Science and Technology, Bannu, Pakistan. He received his Ph. D. in analytical chemistry from University of Jamshro Sindh in 2008. His research interests include electrochemistry and elucidation of electrode reaction mechanism of biologically important molecules. He is also searching development of new synthetic routes for the preparation of environmental friendly surfactants.

Shahan Zeb Khan got his M. Sc. and M.Phil degrees from QAU. Islamabad. Currently, he is doing PhD from QAU under the supervision of Dr. Zia-ur-Rehman. His research is focused on the synthesis and characterization of surfactants and medicinal applications of metal based compounds.

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Received: 2016-03-31

Accepted: 2016-05-31

Published Online: 2017-11-13

Published in Print: 2017-11-15

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https://doi.org/10.3139/113.110526

Keywords for this article

Synthesis; thiourea-based surfactants; CMCs; antimicrobial activities; corrosion inhibition