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Synthesis and Properties of Some N-Acylethylenediamine Triacetic Acid Chelating Surfactants

  • M. M. A. EL-Sukkary , E. A. Soliman , D. A. Ismail , S. M. El Rayes und M. A. Saad
Veröffentlicht/Copyright: 5. April 2013
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Tenside Surfactants Detergents
Aus der Zeitschrift Tenside Surfactants Detergents Band 48 Heft 1

Abstract

A new kind of surfactants with chelating properties named N-acylethylenediamine triacetate (N-acyl ED3A) of different hydrocarbon chain lengths were synthesized from anhydrous ethylene diamine, fatty acid chlorides (Capryloyl, lauroyl, myristoyl, palmitoyl, stearoyl or oleoyl chloride) and chloroacetic acid. The chemical structures of the prepared compounds were confirmed using different spectroscopic techniques, primarily Fourier transform infrared spectroscopy and nuclear magnetic resonance. The surface properties including surface and interfacial tension, foaming height, emulsification power, calcium ion stability, stability to hydrolysis and critical micelle concentration (CMC) were determined. The trisodium N-acylethylenediamine triacetates have been found to combine the properties of strong surfactancy, extreme mildness with a high tolerance to water hardness, and ability to chelate metal ions, which indicates a promising application prospect in many fields.

Kurzfassung

Ein neuer Typ von Tensiden mit komlexbildenden Eigenschaften, N-Acylethylendiamintriacetat (N-acyl-ED3A) mit unterschiedlichen Kohlenwasserstoffkettenlängen, wurde aus wasserfreiem Ethylendiamin, Fettsäurechloriden (Capryloyl-, Lauroyl-, Myristoyl-, Palmitoyl-, Stearoyl-, Oleoylchlorid) und Chloressigsäure synthetisiert. Die chemische Struktur der hergestellten Verbindungen wurde mit verschiedenen spektroskopischen Verfahren wie Fourier-Transform-Spektroskopie und Kernmagnetische Resonanz untersucht. Es wurden die Oberflächeneigenschaften bestimmt wie Oberflächen- und Grenzflächenspannung, Schaumhöhe, Emulgierfähigkeit, Calciumionenstabilität, Hydrolysestabilität und kritisches Mizellbildungskonzentration (CMC). Die Tri-Natriumacylethylendiamintriacetate besitzen starke tensidische Eigenschaften, sind extrem mild, haben eine hohe Wasserhärtetoleranz und können Metallionen komplexieren, was auf eine vielversprechende Anwendung und unterschiedlichen Feldern hindeutet.

Key words:: N-acylethylenediamine triacetic acid; multifunctional surfactant; chelating surfactants; chelactants
Stichwörter:: N-Acylethylendiamintriessigsäure; multifunktionale Tenside; komplexbildende Tenside; Komplexbildner
∗ M. M. A. El Sukkary, Professor of Petrochemicals, Egyptian Petroleum Research Institute, Nasr City, 11727, Cairo, Egypt. E-Mail:

M. M. A. El-Sukkary, Prof. Dr. of Petrochemicals, Petrochemicals Department, Egyptian Petroleum Research Institute, Cairo, Egypt.

E. A. Soliman, Prof. Dr. of organic chemistry, Faculty of science, Ain Shams University, Cairo, Egypt.

D. A. Ismail, Prof. Dr. of organic chemistry, Applied Surfactant Lab. Petrochemicals Department, Egyptian Petroleum Research Institute, Cairo, Egypt.

S. M. El Rayes, Lecturer Prof. of organic chemistry, Faculty of science, Suez Canal University, Ismailia, Egypt.

M. A. Saad, Research student, Faculty of science, Suez Canal University, Ismailia, Egypt.

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Received: 2010-05-05
Published Online: 2013-04-05
Published in Print: 2011-01-01

© 2011, Carl Hanser Publisher, Munich

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Editorial
  6. Rückblick auf zwei erfolgreiche Jahre 2009/2010
  7. Application
  8. Surface Activity and Adsorption Properties of New Perfluorinated Carbohydrate Surfactants
  9. Novel Surfactants
  10. Study of Glycerol Residue as a Carbon Source for Production of Rhamnolipids by Pseudomonas aeruginosa (ATCC 10145)
  11. Study of CLSI-M44-A Disk Diffusion Method for Determining the Susceptibility of Candida Species against Novel Complexes Derived from Copper Stearate with 2-Amino Benzothiazoles
  12. European Detergents Conference
  13. Bicontinuous Microemulsion as Reaction Medium for ω-Transaminase Catalysed Biotransformations
  14. Physical Chemistry
  15. SAXS Study on Azithromycin Loaded Nonionic Microemulsions
  16. Effects of Alkaline Cations on Self-assembly of Cetylpyridinium Surfactants
  17. Influence of Surfactants on Release of Chlorhexidine from Hydrogels
  18. Environmental Chemistry
  19. Influence of Surfactants on the Performance of Calcium Phosphate Scale Inhibitors
  20. Technical Chemistry
  21. Preparation and Characterization of a Phosphorous Free and Non-Nitrogen Antiscalant in Industrial Cooling Systems
  22. Preparation and Characterization of Pillared Derivatives from δ-Layered Sodium Disilicate and their Tribological Properties in Liquid Paraffin
  23. Synthesis
  24. An Efficient and Mild Procedure for the Preparation of Aldonic Acids via Oxidation of D-Sucrose by Employing N-Bromophthalimide Oxidant and Micellar System
  25. Synthesis and Properties of Some N-Acylethylenediamine Triacetic Acid Chelating Surfactants
  26. Conference and Meeting Report
  27. Sixth European Detergents Conference Report
  28. GDCh-Intensive Course Surfactants: Detergents, Cosmetics, Technical Applications
https://doi.org/10.3139/113.110108
Schlagwörter für diesen Artikel
N-acylethylenediamine triacetic acid; multifunctional surfactant; chelating surfactants; chelactants

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Editorial
  6. Rückblick auf zwei erfolgreiche Jahre 2009/2010
  7. Application
  8. Surface Activity and Adsorption Properties of New Perfluorinated Carbohydrate Surfactants
  9. Novel Surfactants
  10. Study of Glycerol Residue as a Carbon Source for Production of Rhamnolipids by Pseudomonas aeruginosa (ATCC 10145)
  11. Study of CLSI-M44-A Disk Diffusion Method for Determining the Susceptibility of Candida Species against Novel Complexes Derived from Copper Stearate with 2-Amino Benzothiazoles
  12. European Detergents Conference
  13. Bicontinuous Microemulsion as Reaction Medium for ω-Transaminase Catalysed Biotransformations
  14. Physical Chemistry
  15. SAXS Study on Azithromycin Loaded Nonionic Microemulsions
  16. Effects of Alkaline Cations on Self-assembly of Cetylpyridinium Surfactants
  17. Influence of Surfactants on Release of Chlorhexidine from Hydrogels
  18. Environmental Chemistry
  19. Influence of Surfactants on the Performance of Calcium Phosphate Scale Inhibitors
  20. Technical Chemistry
  21. Preparation and Characterization of a Phosphorous Free and Non-Nitrogen Antiscalant in Industrial Cooling Systems
  22. Preparation and Characterization of Pillared Derivatives from δ-Layered Sodium Disilicate and their Tribological Properties in Liquid Paraffin
  23. Synthesis
  24. An Efficient and Mild Procedure for the Preparation of Aldonic Acids via Oxidation of D-Sucrose by Employing N-Bromophthalimide Oxidant and Micellar System
  25. Synthesis and Properties of Some N-Acylethylenediamine Triacetic Acid Chelating Surfactants
  26. Conference and Meeting Report
  27. Sixth European Detergents Conference Report
  28. GDCh-Intensive Course Surfactants: Detergents, Cosmetics, Technical Applications
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