Synthesis, Surfactant Properties and C6talytic Action of Macrocyclic Polyethers Possessing 4-Alkyl-1, 3, 5-triazine Subunit

Abstract

2, 6-Dichloro-4-alkyl(or alkoxy) -1, 3, 5-triazines derived from cyanuric chloride were treated with equimolar tetra- and hexaethylene glycol dianions in toluene to give two series of 1 : 1 macrocyclic polyethers, (1) and (2), respectively. Cloud point, critical micelle concentration (CMC), surface tension at CMC (γcmc) and cata-lytic action on the reaction of octyl bromide with saturated aqueous potassium salts were examined for these macrocycles. The data were compared with those of known crown ethers ((3), (4), (5) and (6) and of linear poly (oxyethylene) surfactants ((7), (8)) and poly-ethylene glycol monoalkyl ethers). Higher homologes of (2) were soluble in water. Their cloud point, CMC and γcmc decre ased with the increasing alkyl chain length. With respect to these properties, (2) seemed to be equivalent to (3) and (4) having the same alkyl chain (Table 2). The CMC of (2) was rather higher than that of linear polyethers (7), although (2) had, much lower cloud point compared to (7) (Figs. 3, 4). The catalytic efficiency of (2) increased with the increasing alkyl chain length. When the catalytic action was compared among all series examined, the efficiency appeared to increase in the order : (1)<(5)<<(2)<(7)<(8)≤(6) (Tables 3, 4). The role of crown compounds in surfactant properties and the relation of surface activity to cataivtin antinn were discussed on the basis of the results obtained here.