Anionic Surfactants Synthesised from Replenishable Phenolic Lipids

• Published in: Journal of surfactants and detergents Vol. 12; no. 4; pp. 337 - 344
• Main Authors: Bruce, Ian E., Mehta, Lina, Porter, Michael J., Stein, Bridget K., Tyman, John H. P.
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer-Verlag 01.10.2009; Springer Nature B.V
• Subjects: 3‐Pentadecylphenol; 5‐Pentadecylresorcinol; Aquatic Pollution; Cardanol; Cardol; Chemical synthesis; Chemistry; Chemistry and Materials Science; Ethylene carbonate; Ethylene sulfate; Hydrogenation; Industrial Chemistry/Chemical Engineering; Lipids; Monoethoxylates; Original Article; Phenols; Physical Chemistry; Polymer Sciences; Saturated(15:0)‐cardanol; Saturated(15:0)‐cardol; Sulfates; Sulfuric acid; Surfaces and Interfaces; Surfactancy; Surfactants; Thin Films; Waste Water Technology; Water Management; Water Pollution Control; 5-Pentadecylresorcinol; Monoethoxylates; Cardanol; Ethylene carbonate; Saturated(15:0)-cardol; Surfactancy; 3-Pentadecylphenol; Saturated(15:0)-cardanol; Ethylene sulfate; Cardol
• ISSN: 1097-3958; 1558-9293
• DOI: 10.1007/s11743-009-1116-8

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.