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Selective Syntheses and Properties of Anionic Surfactants Derived from Isosorbide
Author(s) -
Cho JungEun,
Sim DaeSeon,
Kim YoungWun,
Lim Jongchoo,
Jeong NohHee,
Kang HoCheol
Publication year - 2018
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 - 10.1002/jsde.12182
Subject(s) - chemistry , isosorbide , alkyl , selectivity , yield (engineering) , critical micelle concentration , sulfonic acid , micelle , emulsion , alkylation , organic chemistry , solvent , salt (chemistry) , catalysis , aqueous solution , materials science , metallurgy
Two series of anionic surfactants (endo‐5‐ O ‐alkyl isosorbide‐2‐ O ‐propyl sulfonic acid sodium salt and exo‐2‐ O ‐alkyl isosorbide‐5‐ O ‐propyl sulfonic acid sodium salt) with straight alkyl chains (hexyl, octyl, decyl, and dodecyl) were synthesized from isosorbide derived from biomass, through steps of allylation, alkylation, and sulfonation. The selectivity and efficiency of the reactions were optimized by adjusting the solvent, catalyst, reactant molar ratio, and temperature. The product 2‐ O ‐allyl isosorbide was obtained with a yield of 81% and selectivity of 23:1 (endo:exo), and 2‐ O ‐alkyl isosorbide was obtained with a yield of 72% and selectivity of 24:1 (exo:endo). The synthesized anionic surfactants were characterized using the critical micelle concentration (CMC), surface activity, emulsion stability, foaming height, and the Turbiscan Stability Index. The CMC decreased with increasing alkyl chain length. The properties of endo form and exo form were compared.