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第 36 卷第 5 期 精 细 化 工 Vol.36, No.5
201 9 年 5 月 FINE CHEMICALS May 2019

表面活性剂
新型喹啉类 Gemini 表面活性剂的合成及界面吸附

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郝俊生 1,2 ，秦 涛 ，王 攀 ，张 越 1,2 ，张永斌
〔1.山西大学 化学化工学院，山西 太原 030006；2.化学国家级实验教学示范中心（山西大学），山西 太原
030006；3.山西大学 应用化学研究所，山西 太原 030006〕

摘要：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
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种喹啉双季铵盐 Gemini 表面活性剂，其结构经 FTIR、 HNMR、 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。
关键词：Gemini 表面活性剂；喹啉；结构表征；界面吸附
中图分类号：TQ423.12 文献标识码：A 文章编号：1003-5214 (2019) 05-0843-07

Synthesis and Interfacial Adsorption Behavior of
Novel Quinoline Gemini Surfactants

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HAO Jun-sheng , QIN Tao , WANG Pan , ZHANG Yue , ZHANG Yong-bin
（1. College of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, Shanxi, China; 2. National
Demonstration Center for Experimental Chemistry Education, Shanxi University, Taiyuan 030006, Shanxi, China; 3.
Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, Shanxi, China）
Abstract: 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
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confirmed by FTIR, HNMR, CNMR 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-di-
quinolin-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.
Key words: Gemini surfactant; quinoline; structural characterization; interface adsorption
Foundation item: Teaching Reform Project of Colleges and Universities in Shanxi Province (J2017003,
J2012005)

收稿日期：2018-10-25; 定用日期：2019-02-21; DOI: 10.13550/j.jxhg.20180792
基金项目：山西省高等学校教学改革创新项目（J2017003，J2012005）
作者简介：郝俊生（1970—），男，副教授，E-mail：jshao@sxu.edu.cn。