Abstract
A series of quaternary alkylammonium sulfobetaines of general
formula RN+ (CH3 )2 (CH2 )n SO3
- ,
where n = 2-4, have been synthesised
by reacting the corresponding N,N- dimethylamines with
either sodium 2-chloroethanesulfonate (n = 2),
1,3-propanesultone (n = 3), or 1,4-butanesultone
(n = 4). Full details of the preparation
of the required N ,N- dimethylamines
are reported.
Key words
Mannich bases - Friedel-Crafts reactions - zwitterions - sultones - surfactants
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