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Synthesis and Evaluation of Some Phenol-Based Anionic Gemini Amphiphiles: Studying Their Influence in the Preparation of Cu2O nanoparticles

  • Fawzia I. El-dib , Ammona S. Mohamed , Abdallah A. El-Sawy , Dalia E. Mohamed and Nermeen M. Abdelhalim
Published/Copyright: March 11, 2016
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 53 Issue 2

Abstract

A series of phenol-based anionic gemini amphiphiles called α,ω-bis (m-dodecanoyl benzene sulfonate) with different spacers (C12-En-C12) where n = 1, 2, 3 has been synthesized via three steps of reaction: (1) acylation of phenol by dodecanoic acid using trifluromethane sulfonic acid as a catalyst, (2) tosylation of mono, di and triethylene glycol, then (3) coupling of tosylated ethylene glycols with acylated phenol, followed by sulphonation of the prepared compounds. The chemical structures of the prepared surfactants were confirmed using elementary analysis and different spectroscopic techniques including FTIR and 1H-NMR spectra. Also an evaluation of surface activity for the synthesized compounds has been determined including: surface and interfacial tension, foaming height, emulsification power, critical micelle concentration (CMC), effectiveness and efficiency. The prepared surfactants were used in the synthesis of cuprous oxide nanoparticles. The crystal structure, average particle size and morphology were investigated by X-Ray Diffraction (XRD) and Transmission Electron Microscopy (TEM).

Kurzfassung

Eine Reihe von anionischen Geminitenside auf Phenolbasis (α,ω-Bis(m-dodecanoylbenzenesulfonate mit unterschiedlichen Spacern (C12-En-C12) wobei (n = 1, 2, 3)) wurden in einer Dreistufenreaktion synthetisiert: (1) Acetylierung von Phenol mit Dodecansäure unter Verwendung von Trifluormethansulfonsäure als Katalysator, (2) Tosylierung von Mono, Di- und Triethylenglycol, und (3) Kupplung des tosylierten Ethylenglycols mit dem acylierten Phenol, gefolgt von der Sulfonierung der erzeugten Verbindungen. Die chemische Struktur der synthetisierten Tenside wurde mit Elementaranalyse und verschiedenen spektroskopischen Verfahren wie FTIR und 1H-NMR bestimmt. Außerdem wurde die Oberflächenaktivität analysiert und Größen wie die Oberflächen- und Grenzflächenspannung, die Schaumhöhe, die Emulgierstärke, die kritische Mizellenkonzentration (CMC), die Leistung bestimmt. Die hergestellten Tenside wurden für die Synthese von Kupferoxid-Nanopartikel verwendet. Die Kristallstruktur, die mittlere Größe und die Morphologie der Teilchen wurden mit Hilfe der Röntgenstreuung (XRD) und Transmissionselektronenmikroskopie (TEM) untersucht.

Key words: Phenol; gemini surfactants; surface properties; anionic surfactants; critical micelle concentration (CMC); nano copper particles
Stichwörter: Phenol; Geminitenside; Oberflächeneigenschaften; anionische Tenside; kritische Mizellenkonzentration (CMC); Nano-Kupferpartikel
*Correspondence address, Dr. Dalia E. Mohamed, Petrochemicals Department, Egyptian Petroleum Research Institute, Nasr City, Cairo, Egypt. E-Mail:

Fawzia Ismail El-dib received her Ph. D. in applied and organic chemistry from Al-Azhar University. She is a professor of Applied Organic Chemistry at the (Egyptian Petroleum Research Institute, EPRI) [Applied Surfactants Laboratory]. Her research interests are focused in both environmental and surfactants science and its applications.

Ammona S. Mohamed received her B. Sc. and M. Sc. from the Suez Canal University and her Ph. D. from Ain Shams University (2000). She is presently Professor of Applied Surfactants in the Petrochemicals Department (Egyptian Petroleum Research Institute, EPRI). Her interests are focused on the synthesis and evaluations of surfactants in several fields including, biocidal application, solubilization, and antitumor activity.

Abdallah A. El-Sawy has a Ph. D. in Organic Chemistry, and is currently Professor of Organic Chemistry at Benha University, Benha City, Egypt. His research interests are in surfactants science and applications.

Dalia E. Mohamed received her B. Sc. and M. Sc. from Cairo University and Ph. D. from Ain Shams University. She is currently associate professor of organic chemistry at the Egyptian Petroleum Research Institute (Surfactants Laboratory). Her research interests are in synthesis, properties and applications of new surfactants.

Nermeen M. Abdelhalim was received her B. Sc. from Benha University (2006), Researcher assistant at Egyptian Petroleum Research Institute (Surfactants Laboratory). Her interests are focused on synthesis, properties and applications of new surfactants in several fields.

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Received: 2015-04-29
Accepted: 2015-09-08
Published Online: 2016-03-11
Published in Print: 2016-03-16

© 2016, Carl Hanser Publisher, Munich

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Application
  4. Qualitative and Quantitative Analysis of Microbial Communities in Household Dishwashers in Germany
  5. Molecular Dynamics
  6. Mesoscopic Simulations on the Aggregate Behavior of Oligomeric Adamantane Surfactants in Aqueous Solutions
  7. Novel Surfactants
  8. Synthesis, Surface Activity and Application Properties of a Novel Ethoxylated Gemini Trisiloxane Surfactant
  9. Synthesis and Surface Active Properties of Novel Oligomer Betaine Surfactants
  10. Synthesis and Evaluation of Some Phenol-Based Anionic Gemini Amphiphiles: Studying Their Influence in the Preparation of Cu2O nanoparticles
  11. Scale Inhibition
  12. Preparation of a Multifunctional Terpolymer Inhibitor for CaCO3 and BaSO4 in Oil Fields
  13. Experimental and Theoretical Study on Corrosion Inhibition of Mild steel in 20 % Formic Acid Solution Using Schiff Base-Based Cationic Gemini Surfactant
  14. Physical Chemistry
  15. Dipeptide Glycyl-Glycine (Gly-Gly)–Ninhydrin Reaction: Effect of Alkanediyl-α,ω-bis(dimethylcetylammonium bromide) (16-s-16, s = 4, 5, 6) Gemini Surfactants on the Reaction Rate
  16. Interactions of Cellulase and Oleic Acid Solution Mixtures
  17. Effect of Surfactants on Hydrolysis of Mono-N-ethyl-o-toluidine Phosphate
  18. Thermodynamic Solution Properties of Benzalkonium Chloride in Aqueous and Ethanolic Media and its Interactions with Organized Assemblies of Anionic Surfactant Sodium Dodecyl Sulphate and Amino Acids
https://doi.org/10.3139/113.110419
Keywords for this article
Phenol; gemini surfactants; surface properties; anionic surfactants; critical micelle concentration (CMC); nano copper particles

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Application
  4. Qualitative and Quantitative Analysis of Microbial Communities in Household Dishwashers in Germany
  5. Molecular Dynamics
  6. Mesoscopic Simulations on the Aggregate Behavior of Oligomeric Adamantane Surfactants in Aqueous Solutions
  7. Novel Surfactants
  8. Synthesis, Surface Activity and Application Properties of a Novel Ethoxylated Gemini Trisiloxane Surfactant
  9. Synthesis and Surface Active Properties of Novel Oligomer Betaine Surfactants
  10. Synthesis and Evaluation of Some Phenol-Based Anionic Gemini Amphiphiles: Studying Their Influence in the Preparation of Cu2O nanoparticles
  11. Scale Inhibition
  12. Preparation of a Multifunctional Terpolymer Inhibitor for CaCO3 and BaSO4 in Oil Fields
  13. Experimental and Theoretical Study on Corrosion Inhibition of Mild steel in 20 % Formic Acid Solution Using Schiff Base-Based Cationic Gemini Surfactant
  14. Physical Chemistry
  15. Dipeptide Glycyl-Glycine (Gly-Gly)–Ninhydrin Reaction: Effect of Alkanediyl-α,ω-bis(dimethylcetylammonium bromide) (16-s-16, s = 4, 5, 6) Gemini Surfactants on the Reaction Rate
  16. Interactions of Cellulase and Oleic Acid Solution Mixtures
  17. Effect of Surfactants on Hydrolysis of Mono-N-ethyl-o-toluidine Phosphate
  18. Thermodynamic Solution Properties of Benzalkonium Chloride in Aqueous and Ethanolic Media and its Interactions with Organized Assemblies of Anionic Surfactant Sodium Dodecyl Sulphate and Amino Acids
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