Abstract
Several new series of aminimides [(3ac, e), (4ah), (5d) and (6a, b) in Scheme-1] were synthesized by Slagel method1). Some surface active properties and the effectiveness on phase transfer catalysis were examined for these compounds. The results were compared with those of several reference compounds.
Surface active properties of aminimides (1ae)5) and (2ag)2), and bis(aminimides) (5ac)3) have been reported previously. Substitution of an aromatic group, especially pyridyl group, for an alkyl group (C23) on imino nitrogen of aminimides caused a decrease in cloud point (Cp) and critical micelle concentration (cmc), but an increase in melting point, Krafft point (Kp) and γcmc (surface tension above cmc). Melting point, Cp and γcmc increased with increasing the number of hydroxyl group in an amineimide molecule regardless of the relative position (Table-2). In the case of bis(aminimides), (6a) was similar to (5d), but differed from (6b) regarding to the dissolution behavior (Kp and Cp) (Table-3).
It was found that the efficiency of aminimides as phase transfer catalysts in the substitution reaction of 1-bromooctane with aqueous potassium iodide depended on the following structural factors: a) HLB (hydrophilic-lipophilic balance) of aminimides, b) the position on which long chain placed (_??_+N- and/or -N-), c) the number of hydroxyl groups, d) introduction of pyridyl group, and e) the chain length and the steric structure of the linking group between two aminimide groups in bis(aminimides). The series (1) were the most effective among the series examined, and some of (1) had a high efficiency close to that of “Dicyclohexyl-18-crown-6” (Table-4).
