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Synthesis and Characterization of N-alkyl-N′-glucosylhexanediamine Surfactant

  • Fu Han , Ya-di Gao , Yi-lang Liu , Yin-lian Liang , Ya-wen Zhou and Bao-cai Xu
Published/Copyright: November 17, 2014
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Tenside Surfactants Detergents
From the journal Tenside Surfactants Detergents Volume 51 Issue 6

Abstract

The synthesis and structural analysis of glucosamide surfactants of the general formula CnH2n+1NH(CH2)6NHCO(CHOH)4CH2OH (n = 8, 10, 12) were described, and the surface activity properties of the surfactants were studied, and the interfacial tensions between n-octane and the aqueous surfactant solution were measured. N-alkylhexanediamines were synthesized by the alkylation of the 1,6-hexanediamine with alkyl bromide. The glucosamide surfactants, N-alkyl-N′-glucosylhexanediamine (CnGA), were prepared by amidation of the precursor diamine with D-gluconic acid δ-lactone. They were structurally characterized by IR, 1H NMR and MS. They reduced the surface tension of water to approximately 28–33 mN · m−1 at concentration levels of (0.2–1.0) × 10−3 mol · L−1, and reduced the interfacial tensions between n-octane and the aqueous surfactant solution to approximately 1–2 mN · m−1 at concentration levels of (0.3–4.2) × 10−3 mol · L−1.

Kurzfassung

Es wurde die Synthese und Strukturanalyse von Glucosamiden mit der allgemeinen Formel CnH2n+1NH(CH2)6 · NHCO(CHOH)4CH2OH (n = 8, 10, 12) beschrieben. Ihre Oberflächenaktivitäten wurden untersucht und die Grenzflächenspannungen zwischen n-Octan und den wässrigen Tensidlösungen wurden gemessen. Die N-Alkylhexandiamine wurden durch Alkylierung von 1,6-Hexandiamin mit Alkylbromid synthetisiert. Die Glycosamide, N-Alkyl-N′-glucosylhexandiamine (CnGA) wurden durch Amidierung des Precursors Diamin mit D-Glucono-1,5-lacton (Glucono-δ-lacton, GDL) präpariert. Sie wurden mittels IR, 1H-NMR und MS charakterisiert. Sie reduzierten die Oberflächenspannung zu Wasser auf etwa 28–33 mN · m−1, wobei die Tensidkonzentration in der Größenordnung von (0.2–1.0) × 10−3 mol · L−1 lag. Die Grenzflächenspannung zwischen den wässrigen Tensidlösungen und n-Octan betrug etwa 1–2 mN · m−1, wobei die Tensidkonzentration (0.3–4.2) × 10−3 mol · L−1 betrug.

Key words: Synthesis; characterization; glucosamide; alkylation; amidation
Stichwörter: Synthese; Charakterisierung; Glucosamide; Alkylierung; Amidierung
* Correspondence address, Mr. Dr. Bao-cai Xu, School of Food Science and Chemical Engineering, Beijing Technology and Business University, No. 11, Fucheng Road, Haidian District, Beijing 100048, P. R. China. E-Mail:

Fu Han received a B. Sc. in Chemical Engineering from East China University of Technology, a M. Sc. in Physicochemistry from China Research Institute of Daily Chemical Industry, and a Ph. D. in Physicochemistry from Wuhan University. His research interests are synthesis and properties of novel surfactants.

Ya-di Gao is currently working on his B. Sc. in Applied Chemistry at Beijing Technology and Business University. His research interests are synthesis and properties of surfactants.

Yi-lang Liu is currently working on his B. Sc. in Applied Chemistry at Beijing Technology and Business University. His research interests are synthesis and properties of surfactants.

Yin-lian Liang is currently working on her B. Sc. in Applied Chemistry at Beijing Technology and Business University. Her research interests are synthesis and properties of surfactants.

Ya-wen Zhou received a B. Sc. in Organic Chemistry from Yaiyuan University of Technology, a M. Sc. in Applied Chemistry from China Research Institute of Daily Chemical Industry. Her research interests are synthesis and properties of surfactants.

Bao-cai Xu received a B. Sc. and M. Sc. in Applied Chemistry from Beijing Technology and Business University, and a Ph. D. in Applied Chemistry from Beijing Institute of Technology. His research interests are synthesis and properties of novel surfactants.

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Received: 2014-01-05
Accepted: 2014-04-28
Published Online: 2014-11-17
Published in Print: 2014-11-17

© 2014, Carl Hanser Publisher, Munich

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https://doi.org/10.3139/113.110336
Keywords for this article
Synthesis; characterization; glucosamide; alkylation; amidation

Articles in the same Issue

  1. Contents/Inhalt
  2. Contents
  3. Application
  4. Rapid Assessment of Glass Etching/Corrosion using the Quartz Crystal Microbalance with Dissipation Monitoring, QCM-D
  5. Micelle Based Spectrofluorimetric Determination of Chloroquine Phosphate in Commercial Formulation and Human Plasma
  6. Novel Surfactants
  7. Synthesis of Rice Bran Fatty Acids (RBFAs) Based Cationic Surfactants and Evaluation of Their Performance Properties in Combination with Nonionic Surfactant
  8. Synthesis and Properties of Guerbet Hexadecyl Sulfate
  9. Synthesis and Characterization of N-alkyl-N′-glucosylhexanediamine Surfactant
  10. Mizellar Catalysis
  11. Methanesulfonic Acid as a More Efficient Catalyst for the Synthesis of Lauraldehyde Glycerol Acetal
  12. Surfactant Assisted Enhancement of Bioremediation Rate for Hexavalent Chromium by Water Extract of Siris (Albizia lebbeck) Sawdust
  13. Physical Chemistry
  14. Synergistic Interactions in Mixed W/O Microemulsions of Cationic Gemini and Anionic Surfactants
  15. Percolative Behavior Models Based on Artificial Neural Networks for Electrical Percolation of AOT Microemulsions in the Presence of Crown Ethers as Additives
  16. Junction Characteristics System Based on Composite Organic Semiconductors: Polystyrene/Polyaniline Doped by [BMIM] [BF4] Ionic Liquid
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