Journal of Surfactants and Detergents

, Volume 12, Issue 4, pp 337–344 | Cite as

Anionic Surfactants Synthesised from Replenishable Phenolic Lipids

  • Ian E. Bruce
  • Lina Mehta
  • Michael J. Porter
  • Bridget K. Stein
  • John H. P. Tyman
Original Article

Abstract

The oligomers (m = 1,2,3,4 and 5) in the profile of compounds obtained in the ethoxylation of saturated cardanol with ethylene oxide have been synthesised. The first member which occurs only in traces in the reaction has now been synthesised by an improved method. This monoethoxylate of 3-pentadecylphenol and a diethoxylate of 5-pentadecylresorcinol (2-hydroxyethyl derivatives) have been synthesised by the base-catalysed reaction with ethylene carbonate. Cardanol and cardol separated from technical cashew nut-shell liquid (CNSL) have been similarly reacted as have saturated cardanol and saturated cardol obtained by reduction of the side-chain. Reaction of the anhydrous potassium salt of 3-pentadecylphenol in dichloromethane with ethylene sulfate has afforded a derivatives having a sulfate group in place of the terminal hydroxyl group and avoiding the use of sulfuric acid. Similarly CNSL and saturated CNSL reacted with ethylene sulfate gave sulfo derivatives which possess excellent surfactancy. By contrast, with sulfuric acid, 3-pentadecyl phenol monoethoxylate gave a trisulfo product comprising a terminal side-chain sulfate and a ring disulfonic acid. 3-Pentadecylphenol reacted with sulfuric acid in carbon tetrachloride to give 4-hydroxy-6-pentadecylphenol-1,3-disulfonic acid.

Keywords

Monoethoxylates 3-Pentadecylphenol 5-Pentadecylresorcinol Cardanol Cardol Saturated(15:0)-cardanol Saturated(15:0)-cardol Ethylene carbonate Ethylene sulfate Surfactancy 

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Copyright information

© AOCS 2009

Authors and Affiliations

  • Ian E. Bruce
    • 1
  • Lina Mehta
    • 2
  • Michael J. Porter
    • 3
  • Bridget K. Stein
    • 4
  • John H. P. Tyman
    • 1
    • 2
  1. 1.Department of ChemistryBrunel UniversityMiddlesexUK
  2. 2.Institute for the EnvironmentBrunel UniversityUxbridgeUK
  3. 3.Department of ChemistryUniversity College LondonLondonUK
  4. 4.Department of Chemistry, EPSRC National Mass Spectrometry CentreUniversity of WalesSwanseaUK

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