Page 83 - 精细化工2019年第12期

第 36 卷第 12 期 精 细 化 工 Vol.36, No.12
2019 年 12 月 FINE CHEMICALS Dec. 2019

表面活性剂
氟化季铵盐表面活性剂的合成及其表面活性

郭 睿 1,2 ，刘雪艳 1,2* ，高弯弯 1,2 ，冯文佩 1,2 ，李秀环 1,2 ，霍文生 1,2

（1. 陕西科技大学 化学与化工学院，陕西 西安 710021；2. 教育部轻化工助剂化学与技术重点实验室，
陕西 西安 710021）

摘要：以三氟乙酸乙酯和 N，N-二甲基乙二胺为原料，经酰化反应制得中间体 NDAET；然后将 NDAET 与
溴代十二烷发生季铵化反应得到氟化季铵盐表面活性剂 N,N-二甲基-N-{2-[(2,2,2-三氟乙酰基)氨基]乙基}-1-
1
13
十二烷基铵溴化物（NDAET-12）。通过 FTIR、 CNMR、 HNMR 对其结构进行了表征。考察了反应物物
质的量比、反应时间、反应温度、溶剂用量对 NDAET-12 产率的影响。在单因素实验的基础上，采用正交
实验对 NDAET-12 的合成工艺进行了优化。NDAET-12 的最佳合成工艺条件为：n(NDAET)∶n(溴代十二
烷)=1.0∶1.3，NDAET 质量为 2.76 g，反应时间 12 h，反应温度 90 ℃，溶剂用量为 20 mL。在该条件下
进行平行验证实验，得到 NDAET-12 的平均产率为 86.75%。热重分析表明，NDAET-12 是一种热稳定性较
好的表面活性剂。对 NDAET-12 的临界胶束浓度（CMC）、表面活性和乳化性能进行了测定。NDAET-12
的 CMC 为 0.8 g/L，γ CMC =25.15 mN/m，表面活性较好。与十二烷基三甲基溴化铵（DTAB）和十六烷基三
甲基溴化铵（CTMAB）相比，NDAET-12 从乳化体系中分出 10 mL 所需要的时间最长，为 473 s，具有优
异的乳化性能。
关键词：含氟酰胺；氟化季铵盐；乳化性能；表面活性剂
中图分类号：TQ423 文献标识码：A 文章编号：1003-5214 (2019) 12-2411-07

Synthesis and Surface Activity of a Fluorinated
Quaternary Ammonium Salt Surfactant

1,2
1,2
1,2
GUO Rui , LIU Xue-yan 1,2* , Gao Wan-wan , FENG Wen-pei ,
1,2
1,2
LI Xiu-huan , HUO Wen-sheng
（1. College of Chemistry and Chemical Engineering, Shaanxi University of Science & Technology, Xi'an 710021,
Shaanxi, China; 2. Key Laboratory of Auxiliary Chemistry & Technology for Chemical Industry of the Ministry of
Education, Shaanxi University of Science & Technology, Xi'an 710021, Shaanxi, China）
Abstract: N-[2-(Dimethylamino)ethyl]-2,2,2-trifluoroacetamide (NDAET) was synthesized by acylation
between ethyl trifluoroacetate and N,N-dimethylethylenediamine. Then, it reacted with 1-bromododecane to
obtain a fluorinated quaternary ammonium salt surfactant, 1-dodecyl ammonium NDAET-12. The structure
13
1
of the product was characterized by FTIR, CNMR and HNMR. The effects of raw material molar ratio,
reaction time, reaction temperature and solvent dosage on the yield of NDAET-12 were investigated by
single factor experiments. Subsequently, the synthesis process of NDAET-12 was optimized by orthogonal
test. The optimal synthesis conditions of NDAET-12 were obtained as follows: n(NDAET) ∶
n(bromododecane) = 1.0∶1.3, 2.76 g NDAET, reaction time 12 h, reaction temperature 90 ℃, solvent
dosage 20 mL. A parallel verification experiment was carried out under the above-mentioned conditions and
NDAET-12 achieved an average yield of 86.75%. Thermogravimetric analysis showed that NDAET-12 was
a surfactant with good thermal stability. The critical micelle concentration (CMC), surface activity and
emulsifying properties of NDAET-12 were measured. The CMC of NDAET-12 solution was 0.8 g/L and the
surface tension γ CMC was 25.15 mN/m. Moreover, NDAET-12 exhibited good surface activity. Compared

收稿日期：2018-12-04; 定用日期：2019-05-10; DOI: 10.13550/j.jxhg.20180884
基金项目：陕西省重点研发计划——重点项目（2017ZDXM-GY-087）；陕西省重点研发计划项目——一般项目（2017GY-185）；西安
市科技计划项目[CXY1701（3）]
作者简介：郭 睿（1959—），男，硕士，教授。联系人：刘雪艳（1994—），女，硕士生，E-mail：863736528@ qq.com。