收稿日期: 2023-09-22
网络出版日期: 2023-12-07
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
Received date: 2023-09-22
Online published: 2023-12-07
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)
廖晨宇 , 郭山巍 , 黄美薇 , 郭勇 , 陈庆云 , 刘超 , 张运文 . 氟醚磷酸胆碱的合成及性能研究[J]. 化学学报, 2024 , 82(1) : 46 -52 . DOI: 10.6023/A23090430
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.
[1] | (a) Xu, Y.; Takai, M.; Ishihara, K. Ann. Biomed. Eng. 2010, 38, 1938. |
[1] | (b) Cheng, Y.-Q.; Du, T.-T.; Niu, C.-R.; Xue, L.-N.; Jin, Z.-W.; Feng, Z. Fine Chemicals 2019, 36, 190. (in Chinese) |
[1] | (程玉桥, 杜婷婷, 牛春荣, 薛莉娜, 晋战稳, 冯喆, 精细化工, 2019, 36, 190.) |
[1] | (c) Zheng, Y.; Yang, Y.-F.; Li, H.; Tan, G.-H. Electronics Process Technology 2015, 36, 89. (in Chinese) |
[1] | (郑毅, 杨艺峰, 李华, 谭国华, 电子工艺技术, 2015, 36, 89.) |
[1] | (d) Wu, W.-B.; Zhao, L.; Zhang, H.-T.; Xu, B.-C. China Surfactant Detergent & Cosmetics 2016, 46, 75. (in Chinese) |
[1] | (吴望波, 赵莉, 张华涛, 徐宝财, 日用化学工业, 2016, 46, 75.) |
[1] | (e) Kashgary, A.; Sontrop, J. M.; Li, L. H.; Al-Jaishi, A. A.; Habibullah, Z. N.; Alsolaimani, A. R.; Clark, W. F. BMC Nephrol. 2016, 17, 104. |
[1] | (f) Han, G. S.; He, C.; Zhao, J. F.; Liao, X. C.; Wu, X. L. Chin. J. Org. Chem. 2011, 31, 1848. (in Chinese) |
[1] | (韩国胜, 何成, 赵军峰, 廖新成, 武现丽, 有机化学, 2011, 31, 1848.) |
[1] | (g) Liu?, S.; Cheng, Q.; Wei?, T.; Yu, X. L.; Johnson, L. T.; Farbiak1, L.; Siegwart, D. J. Nat. Mater. 2021, 20, 701. |
[2] | Kissa, E. Fluorinated Surfactants and Repellents, Marcel Dekker Inc., New York, 2001, pp. 1-21. |
[3] | Baba, T.; Takagi, T.; Sumaru, K.; Kanamori, T. Chem. Phys. Lipids 2020, 227, 104870. |
[4] | (a) Krafft, M.-P.; Rolland, J.-P.; Vierling, P.; Riess, J. G. New J. Chem. 1990, 14, 869. |
[4] | (b) Krafft, M.-P. Biochimie 2012, 94, 11. |
[5] | Zhou, L.; Triozzi, A.; Figueiredo, M.; Emrick, T. ACS Macro Lett. 2021, 10, 1204. |
[6] | Wang, X.; Huang, M. W.; Su, Z. B.; Qian, L. B.; Guo, Y.; Chen, Q.-Y.; Wu, C. Y.; Lv, T.; Su, Q.; Shen, Q.; Ma, J. Chin. Chem. Lett. 2023, 34, 107961. |
[7] | Dai, L. H.; Guo, Y.; Su, Z. B.; Huang, M. W.; Chen, Q.-Y.; Zhao, Z.-G.; Wu, C. Y.; Su, Q.; Shen, Q. J. Fluorine Chem. 2021, 246, 109793. |
[8] | Krafft, M. P.; Riess, J. G. Curr. Opin. Colloid Interface Sci. 2015, 20, 192. |
[9] | (a) Pan, Y. T.; Zhang, H. X.; Cui, Q. Q.; Sheng, N.; Yeung, L.; Guo, Y.; Sun, Y.; Dai, J. Y.. Environ. Sci. Technol. 2017, 51, 9553. |
[9] | (b) Cui, Q.-Q.; Pan, Y. T.; Zhang, H. X.; Sheng, N.; Wang, J. S. Guo, Y.; Dai, J. Y.. Environ. Sci. Technol. 2018, 52, 982. |
[9] | (c) Pan, Y. T.; Zhang, H. X.; Cui, Q. Q.; Sheng, N.; Yeung, L.; Guo, Y.; Sun, Y.; Dai, J. Y. Environ. Sci. Technol. 2018, 52, 7261. |
[10] | Sakai, T.; Kaneko, Y. J. Surfactants Deterg. 2004, 7, 291. |
[11] | Liu, J. J.; Xu, H. J. China Surfactant Detergent & Cosmetics. 2020, 7, 446. (in Chinese) |
[11] | (刘佳佳, 许虎君, 日用化学工业, 2020, 7, 446.) |
[12] | Kovalchuk, N. M.; Trybala, A.; Starov, V.; Matar, O.; Ivanova, N. Adv. Colloid Interface Sci. 2014, 210, 65. |
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