Acta Chimica Sinica ›› 2024, Vol. 82 ›› Issue (1): 46-52.DOI: 10.6023/A23090430 Previous Articles     Next Articles

Special Issue: 有机氟化学合集



廖晨宇a,b, 郭山巍a,b, 黄美薇b,*(), 郭勇b,*(), 陈庆云b, 刘超a,*(), 张运文c   

  1. a上海应用技术大学 化学与环境工程学院 上海 201418
    b中国科学院上海有机化学研究所 先进氟氮材料重点实验室 上海 200032
    c三明市海斯福化工有限责任公司 福建三明 365200
  • 投稿日期:2023-09-22 发布日期:2023-12-04
  • 基金资助:
    国家重点研发计划(2021YFF0701700); 上海市科委项目(21010503800); 国家自然科学基金(21871283); 福建省科学技术厅(2023T3066)

Synthesis and Properties of Fluoroether Phosphocholine

Chenyu Liaoa,b, Shanwei Guoa,b, Meiwei Huangb(), Yong Guob(), Qing-Yun Chenb, Chao Liua(), Yunwen Zhangc   

  1. aSchool of Chemical and Environment Engineering, Shanghai Institute of Technology, Shanghai 201418
    bKey Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    cSanming Hexafluo Chemicals Company, Ltd., Sanming, Fujian 365200
  • Received:2023-09-22 Published:2023-12-04
  • Contact: E-mail:;;
  • Supported by:
    National Key Research and Development Program of China(2021YFF0701700); project of Science and Technology Commission of Shanghai Municipality in China(21010503800); National Natural Science Foundation of China(21871283); Science and Technology Department of Fujian Province(2023T3066)

Amphoteric phosphocholine as a family of mild surfactants are widely used in biology due to their phosphate structure related to naturally occurring membrane lipids. Changing its hydrophobic part to the fluorocarbon counterparts, it was found that the interfacial properties of phosphocholine surfactants exhibit significant differences. Currently, the research on fluorinated phosphocholine surfactants is limited and lacks types of fluorinated hydrophobic structures. We found that oxygen atoms exhibit specificity in fluorinated surfactants in our previous works. In this work, a kind of phosphocholine containing a fluoroether hydrophobic chain was synthesized, and its interfacial properties, foam properties, and wetting properties were studied. At the beginning, we conducted a substitution reaction using fluoroether alcohols and 2-chloro-2-oxo-1,3,2-dioxaphospholane as raw materials, triethylamine as a base, and tetrahydrofuran (THF) as a solvent under ice bath. Then, the intermediate C72-P is obtained through distillation, which is a transparent viscous liquid with a yield of 70%. The next step is to dissolve the C72-P with trimethylamine (2 mol/L in THF) in acetonitrile at 70 ℃ for 48 h. Finally, a fluoroether phosphocholine surfactant was obtained and purified through column chromatography to give C72-MPB in 90% yield. Under the same conditions, a fluorinated linear phosphocholine surfactant 6:2-MPB was prepared using perfluorohexyl ethanol, which is a white solid with a overall yield of 60%. The phosphocholine fluorinated surfactants C72-MPB and 6:2-MPB were diluted with distilled water to obtain various concentrations of solutions, the surface properties were measured by surface tension instrument Krüss K100C, and the surface tension was measured by Wilhelmy platinum plate method. On the other hand, the performance of foam under two different concentrations of C72-MPB was tested by bubbling method, and the morphology of foam was observed. C72-MPB solution was dropped onto the surface of polytetrafluoroethylene (PTFE), contact angle on PTFE was measured, and its wettability at different time was recorded. The results show that the new fluoroether phosphocholine surfactant has good solubility, low surface tension, good wettability, good foam stability. Fluoroether phosphocholine surfactants have potential utility value in the field of life sciences and medicine. It is a kind of surfactant with excellent application prospects.

Key words: fluoroether surfactants, phosphocholine, surface tension, critical micelle concentration, foam, contact angle