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Synthesis and surface properties of chemodegradable anionic surfactants: Diastereomeric (2‐ n ‐alkyl‐1,3‐dioxan‐5‐yl) sulfates with monovalent counter‐ions
Author(s) -
Piasecki Andrzej,
Mayhew Alexandra
Publication year - 2000
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-000-0114-3
Subject(s) - chemistry , alkyl , critical micelle concentration , pyridine , surface tension , aqueous solution , diastereomer , inorganic chemistry , sulfur trioxide , aggregation number , medicinal chemistry , micelle , organic chemistry , sulfuric acid , physics , quantum mechanics
Sodium, potassium and ammonium cis ‐ and trans ‐(2‐ n ‐alkyl‐1,3‐dioxan‐5‐yl) sulfates 6–8 (alkyl: n ‐C 9 H 19 , 6a–8a , and n ‐C 11 H 23 , 6b–8b ) were synthesized in a reaction of aliphatic aldehydes 1a,b with glycerol 2 followed by separation in high yields of individual geometric isomers of cis ‐and trans ‐2‐ n ‐alkyl‐5‐hydroxy‐1,3‐dioxanes, cis ‐ 3a,b and trans ‐ 3a,b , followed by sulfation with sulfur trioxide‐pyridine complex, and finally neutralization with NaOH, KOH, and NH 4 OH, respectively. Physical data of the compounds and some surface properties of 2‐ n ‐nonyl derivatives, such as critical micelle concentration (CMC), effectiveness of aqueous surface tension reduction (Π CMC ), surface excess concentration Γ CMC , and the surface area demand per molecule (A CMC ), were determined. It was shown that the surface activity of these compounds is influenced both by their geometric structure and by the monovalent counter‐ion.