新型喹啉类Gemini表面活性剂的合成及界面吸附

Synthesis and Interfacial Adsorption Behavior of Novel Quinoline Gemini Surfactants

以6-氨基喹啉、三光气、三乙胺为原料合成了对称的喹啉脲,其与3种溴代烷进行季铵化反应合成了3种喹啉双季铵盐Gemini表面活性剂,其结构经FTIR、~1HNMR、^(13)CNMR和ESI-MS确证。对中间体喹啉脲及目标产物喹啉Gemini表面活性剂的合成条件进行了优化。合成中间体喹啉脲的最佳反应条件为:二氯甲烷为反应溶剂,n(6-氨基喹啉)∶n(三光气)=5∶1,反应时间为6 h,1,3-二-6-喹啉基脲的收率可达88%。合成喹啉类Gemini表面活性剂的最佳反应条件为:中间体喹啉脲(a)(3.2 g,10.2 mmol),DMF(15 mL)为溶剂,反应温度为110℃,n(1,3-二-6-喹啉基脲)∶n(溴代十二烷)=1∶14,反应时间为8 h,收率可达74%。对目标产物喹啉Gemini表面活性剂在三氯甲烷-水体系中的界面张力进行了测定,结果表明:喹啉Gemini表面活性剂在三氯甲烷溶液内扩散到三氯甲烷-水界面是由纯扩散吸附控制。

1,3-Di-quinolin-6-yl-urea was synthesized from 6-aminoquinoline and triphosgene in the presence of a catalytic amount of triethylamine,and then it reacted respectively with three bromoalkanes to produce three bis-quinolineaternary ammonium bromides,novel Gemini surfactants.Their structures were confirmed by FTIR,1HNMR,13CNMR and ESI-MS.The synthesis conditions of the intermediate and the target quinoline Gemini surfactant were optimized.The optimum reaction conditions for the intermediate were obtained as follows:methylene chloride as reaction solvent,molar ratio of 6-aminoquinoline to triphosgene 5∶1,reaction time 6 h.Under these conditions,the yield of the intermediate,1,3-diquinolin-6-yl-urea was up to 88%.Under the optimum conditions of N,N-dimethylformamide(DMF)as solvent,reaction temperature 110℃,reaction time 8 h,mole ratio of intermediate to 1-bromododecane 1∶14,the yield of target compound reached 74%.The interfacial tensions of the Gemini surfactants were measured in chloroform-water system.The results showed that the diffusion of quinoline Gemini surfactants from chloroform solution into the chloroform-water interface was controlled by pure diffusion adsorption.