Synthesis, urfactant Properties and Catalytic Action of CroWn Ethers Bearing Aminimide Group

Abstract

Higher homologueso f (2-hydroxyalkydl)i m ethylammonio-N-acylimin(aems inimidesb) earing a macrocyclicp o lyetherg roup (Cn-AIC(m), n: 12 and 18, 7 12: 5 and 6) were synthesizedin the yields of 30∼ 40% from 1, 2-epoxyalkaneN, , N-dimethylhydrazinaen d 4 '- ( ethoxycarbonyl)benzo-crowne thers by the Slagel methodf or preparinga minimides( Scheme1 ).
Some surface a ctivep ropeitiesa nd effectivenessin phase transfer catalys is of Cn-AIC(m)werd examineda nd: comparedw ith those of several r eference compounds( Scheme2 ). The obtainedC nTAIC(m)w ere all solublei n water. While they had much lower critical micelle concentration( CMC)c omparedt o the correspondinga minimidest, heir cloud points (Cp) and CMCsw ere rather higher t han. that of the other crown ethers ( [3], [8] and [9]) hav ing the same allyl chain ( Figsi 1, 2 ). The CMC of Cn-AIC(m)d ecreasedm arkedly with, t he increaseo f n just in surface active aminimidesb, ut dependenceb oth on n and m was not apprbciablef or the Cp of C, MIC(m) (Table2 ).
With respectt o the catalytica, ction, Cn-AI C(m) were far more activet han t heir respective functionalm oieties ([2] and [4]). In comparisonw ith the referencec rown ethers, Cn-AIC (m) were most effective( eqiivalentt o [7] on reductiono f 2-octanonew ith aqueou sN aBH4(Table3 ), but their effectivehesws as rather moderate( closet o that of [9] in the substitution reactiono f 1-bromooctanwe ith aqueousa lkali metal iodide (Table4 ). On both the reaction, the efficiencyo f -en-AIC(m) increasedw ith the increasingn. These results were interpreted in terms of concertedc omplexationw ith two ligands ( aminimideand polyether ring) in.Cn-AIC(m) and of suitabilityo f the hydrophile-lipophilbea lance of the catalyst to the reaction phase.