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Synthesis of cationic surfactants with alkenyl group
Author(s) -
Okahara Mitsuo,
Ohashi Yoko,
Nishimura Fujio,
Ohashi Takehisa,
Komori Saburo
Publication year - 1973
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02671102
Subject(s) - chemistry , allylic rearrangement , cationic polymerization , chloride , ammonium , amine gas treating , ammonium chloride , alkyl , medicinal chemistry , critical micelle concentration , organic chemistry , micelle , catalysis , aqueous solution
Quaternary ammonium chlorides with long chain alkenyl groups were synthesized by the reaction of tert‐amines with alkylallyl chloride which, in turn, were obtained by the allylic chlorination of 1‐olefins with N‐tert‐butyl‐ or N‐cyclohexyl‐N‐chloro‐ethanesulfonamides. Of the two kinds of alkylallyl chlorides prepared by the allylic chlorination of 1‐olefins, the γ‐alkylallyl chlorides(I), were found to be reactive with tert‐amines, while the secondary chlorides, α‐alkylallyl chlorides(II), were not so reactive and, when the allylic chloride mixture was reacted with tert‐amine under suitable reaction conditions, the γ‐alkylallyl chloride could be selectively converted to a quaternary ammonium chloride while the α‐alkylallyl chloride was recovered unreacted. The quaternary ammonium chlorides thus obtained were identified as γ‐alkylallyl ammonium chlorides from their spectra, and they were shown to possess almost the same surface tension lowering ability as their saturated homologs, although larger critical micelle concentration values and greater water solubilities were observed.