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Synthesis of New Family of Dialkylaryl Disulfonate Gemini Anionic Surfactant

  • Z. Li , R. Yuan und F. Yin
Veröffentlicht/Copyright: 1. März 2013
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Tenside Surfactants Detergents
Aus der Zeitschrift Tenside Surfactants Detergents Band 43 Heft 3

Abstract

A new family of dialkylaryl disulfonate Gemini-type anionic surfactant were synthesized based on the reaction of olefin sulfonic acid (C14AOS acid) with different aromatics. New synthesis route do not require the conventional alkylation unit and strong acid catalysts, and the resulting Gemini-type anionic surfactant differ from existing products by having the sulfonyl group attached to the alkyl chain rather than the aromatic ring. To optimizing reaction condition, a reliable double-wavelength spectrophotometric method and iodine value method were employed for measurement the conversion of the aromatics. The experimental has confirmed that the reaction time and temperature are mainly the factors of the effect of conversion. Under 150°C, C14AOS acid reacts with different aromatics for 4 or 5 hours to form dialkyaryl disulfonic acid, and dialkyaryl disulfonic acid was then neutralized to dialkyaryl disulfonate Gemini-type anionic surfactant. Some surface active property has been investigated too. The critical micelle concentration of ditetradecylbenzene disulfonate, ditetradecylnaphthalene disulfonate, ditetradecylmethylnaphthalene disulfonate, ditetradecylphenanthrene disulfonate, ditetradecyldiphenylether sulfonate, ditetradecyldiphenylmethane sulfonate and ditetradecylbenzophenone sulfonate were 1.7 × 10−4, 8.082 × 10−6, 2 × 10−5, 2.158 × 10−3, 5.0 × 10−6, 1.0 × 10−5 and 1.33 × 10−5 mol l−1. Above datum showed the aromatics of the surfactant may effect on surface active property obviously. Among these, some dialkylaryl disulfonate gemini anionic surfactant have very higher surface active than conventional dodecylbenzene sulfonate and may be widely used in industry and household.

Kurzfassung

Basierend auf der Reaktion von Olefinsulfonsäure (C14AOS-Säure) mit verschiedenen Aromaten wurde eine neue Familie von anionischen Dialkylaryldisulfonat-Gemini-Tensiden synthetisiert. Der neue Syntheseweg erfordert keine Alkylierungsanlage und starke Säurekatalysatoren. Das erhaltene anionische Gemini-Tensid unterscheidet sich von den bisherigen Produkten dadurch, dass die Sulfonylgruppe an der Alkylkette angehängt ist, anstatt am aromatischen Ring. Zur Optimierung der Reaktionsbedingung wurden bewährte Methoden der Doppelwellenlängen-Spektrophotometrie und der Jodzahl eingesetzt, um die Konversion der Aromaten zu messen. Die Versuche haben bestätigt, dass die Reaktionszeit und die Temperatur die hauptsächlichen Faktoren des Konversionseffektes sind. Unter 150°C reagiert C14AOS-Säure mit verschiedenen Aromaten in 4 oder 5 Stunden zu Dialkylaryldisulfonsäure, die dann durch Neutralisation ein anionisches Dialkylaryldisulfonat-Gemini-Tensid bildet. Einige oberflächenaktive Eigenschaften wurden ebenfalls untersucht. Die kritische Mizellbildungskonzentrationen von Ditetradecylbenzendisulfonat, Ditetrade-cylnaphthalendisulfonat, Ditetradecylmethylnaphthalendisulfonat, Ditetradecylphenanthrendisulfonat, Ditetradecyldiphenylethersulfonat, Ditetradecyldiphenylmethansulfonat und Ditetradecylbenzophenonsulfonat waren 1.7 × 10−4, 8.082 × 10−6, 2 × 10−5, 2.158 × 10−3, 5.0 × 10−6, 1.0 × 10−5 and 1.33 × 10−5 mol l−1. Die aufgeführten Messwerte zeigen, daß sich die Aromaten offensichtlich auf die oberflächenaktive Eigenschaften auswirken können. Unter diesen besitzen einige anionische Dialkylaryldisulfonat-Gemini-Tenside eine viel höhere Oberflächenaktivität als konventionelle Dodecylbenzensulfonate und können weitverbreitet in Industrie und Haushalt eingesetzt werden.

Key words:: Gemini-type anionic surfactant; synthesis; critical micelle concentration; dialkyaryl disulfonate
Stichwörter:: Anionische Gemini-Tenside; Synthese; kritische Mizellbildungskonzentration; Dialkylaryldisulfonate
1 Professor Li Zaijun, College of Chemical and Materials Engineering, Southern Yangtze University, 170 Huihe Road, Wuxi, 214036, P.R. China. E-mail:

Dr. Li Zaijun is a graduate of East China Normal University and Southern Yangtze University. He has been involved in organic synthesis and analytical chemistry for over 15 years. He is currently a professor at Southern Yangtze University. Dr. Li Zaijun holds four patents, has edited one book on analytical chemistry, and has published over 80 papers in the fields of organic synthesis and analytical chemistry.

Yuan Rui graduated from Southern Yangtze University and are currently involved in researching various aspects of surfactant application and synthesis as postgraduates at Southern Yangtze University.

Dr. Yin Fushan is a graduate of Peking University in China and Colombia University in the United States. He has worked at Southern Yangtze University and has been involved in various aspects of surfactant application and synthesis. He holds patents in surfactant applications and catalysts and has published articles relating to surfactant applications in agriculture, oilfields, and households. He was previously president of the College of Chemicals and Materials in Southern Yangtze University.

References

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Received: 2005-07-06
Revised: 2006-03-29
Published Online: 2013-03-01
Published in Print: 2006-06-01

© 2006, Carl Hanser Publisher, Munich

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Detergent Ingredient
  6. Hydrolysis of δ-Layered Sodium Disilicate in Ions Binding Process
  7. Novel Surfactants
  8. Polymeric Surfactants from Beechwood Glucuronoxylan
  9. Physical Chemistry
  10. Effect of Aromatic Ring in the Alkyl Chain on Surface Properties of Aryl Alkyl Sulfonate Surfactants
  11. New Family of Trisiloxane Surfactants
  12. Synthesis
  13. Synthesis of New Family of Dialkylaryl Disulfonate Gemini Anionic Surfactant
https://doi.org/10.3139/113.100304
Schlagwörter für diesen Artikel
Gemini-type anionic surfactant; synthesis; critical micelle concentration; dialkyaryl disulfonate

Artikel in diesem Heft

  1. Contents/Inhalt
  2. Contents
  3. Abstracts
  4. Abstracts
  5. Detergent Ingredient
  6. Hydrolysis of δ-Layered Sodium Disilicate in Ions Binding Process
  7. Novel Surfactants
  8. Polymeric Surfactants from Beechwood Glucuronoxylan
  9. Physical Chemistry
  10. Effect of Aromatic Ring in the Alkyl Chain on Surface Properties of Aryl Alkyl Sulfonate Surfactants
  11. New Family of Trisiloxane Surfactants
  12. Synthesis
  13. Synthesis of New Family of Dialkylaryl Disulfonate Gemini Anionic Surfactant
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