Study on the Synthesis and Properties of Novel Branched Fluorinated Surfactants

doi:10.6023/cjoc201806014

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3260-3269.DOI: 10.6023/cjoc201806014 Previous Articles Next Articles

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新型支链型氟碳表面活性剂的合成及性能研究

林超^a,b, 潘仁明^a, 邢萍^b, 姜标^a,b

a 南京理工大学化工学院南京 210094;
b 中国科学院上海有机化学研究所天然产物有机合成化学重点实验室上海 200032

收稿日期:2018-06-11 修回日期:2018-07-17 发布日期:2018-08-22
通讯作者: 姜标 E-mail:jiangb@mail.sioc.ac.cn
基金资助:
国家自然科学基金（No.2167020782）资助项目.

Study on the Synthesis and Properties of Novel Branched Fluorinated Surfactants

Lin Chao^a,b, Pan Renming^a, Xing Ping^b, Jiang Biao^a,b

a School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094;
b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2018-06-11 Revised:2018-07-17 Published:2018-08-22
Contact: 10.6023/cjoc201806014 E-mail:jiangb@mail.sioc.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 2167020782).

1. Study on the Synthesis and Properties of Novel Branched Fluorinated Surfactants.PDF(2186KB)

Abstract

Perfluorooctane sulphonate (PFOS) and perfluorooctanoic acid (PFOA) are one of the most prominent fluorosurfactants and these compounds have the most widely applications. However, such fluorocarbon surfactants have been listed as one of the most difficult to degrade organic pollutants in nature. Perfluoro-2-methyl-2-pentene was used as starting material to introducing fluorinated branch for synthesizing non-bioaccumulable alternatives. Fluorinated surfactants containing CF₃CF₂CF₂C(CF₃)₂ group were successfully synthesized. The surface tension tests showed the hydrophilic groups have a great influence on the surface properties in aqueous solution, and the compound showed the best surface activities when the hydrophilic group was ammonium oxide. The length of the linking group and the size of the hydrophilic group have a general effect on the surface activity, but increasing the rigidity of the two groups can effectively increase the surface activity. The carbonyl group in the surfactant compound and the positively charged nitrogen atom will produce intramolecular interactions, enhance the rigidity of the molecule, and thus increase the surface activity. The critical micelle concentration (cmc) value of the fluorinated surfactant with ammonium oxide as headgroup was about 1.73×10^-2 mol/L and the surface tension in water was 19.93 mN/m at the cmc. A excellent synergism was found when it was mixed with APG0810, the use of fluorocarbon surfactant can be reduced by a factor of 100, whereas the surface tension is basically unchanged.

Key words: perfluoro-2-methyl-2-pentene, branched fluorinated surfactants, surface tension, combined properties

Cite this article

Lin Chao, Pan Renming, Xing Ping, Jiang Biao. Study on the Synthesis and Properties of Novel Branched Fluorinated Surfactants[J]. Chin. J. Org. Chem., 2018, 38(12): 3260-3269.

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References

[1] Kissa, E. Fluorinated Surfactants:Synthesis, Properties, Applica-tions, M. Dekker, New York, 1994.
[2] Rao, N. S.; Baker, B. E. Textile Finishes and Fluorosurfactants, In Organofluorine Chemistry, Springer, Boston, 1994, p. 321.
[3] Renner, R. Environ. Sci. Technol. 2006, 40, 12.
[4] Porter, M. R. Handbook of Surfactants, Springer, Glasgow, 2013.
[5] Kovarova, J.; Svobodova, Z. Neuroendocrinol. Lett. 2008, 29, 599.
[6] Giesy, J. P.; Kannan, K. Environ. Sci. Technol. 2002, 36, 146.
[7] Conder, J. M.; Hoke, R. A.; Wolf, W. d.; Russell, M. H.; Buck, R. C. Environ. Sci. Technol. 2008, 42, 995.
[8] Si, G. Fire Tech. Prod. Inform. 2010, 12, 75(in Chinese). (司戈, 消防技术与产品信息, 2010, 12, 75.)
[9] U. S. Environmental Protection Agency, http://www.epa.gov/oppt/pfoa/pubs/stewardship/index.html.
[10] Krafft, M. P.; Riess, J. G. Curr. Opin. Colloid Interface Sci. 2015, 20, 192.
[11] Venkatesan, A. K.; Halden, R. U. Environ. Res. 2014, 132, 321.
[12] Vierke, L.; Möller, A.; Klitzke, S. Environ. Pollut. 2014, 186, 7.
[13] Guerra, K. H. M. A.; Jurgens, M.; Guerra, M. A. US 0276103, 2007[Chem. Abstr. 2007, 148, 35460].
[14] Boutevin, G.; Tiffes, D.; Loubat, C.; Boutevin, B.; Ameduri, B. J. Fluorine Chem. 2012, 134, 77.
[15] Zana, R.; Benrraou, M.; Rueff, R. Langmuir 1991, 7, 1072.
[16] Jaeger, D. A.; Li, B.; Clark, T. Langmuir 1996, 12, 4314.
[17] Schuster, T.; Krumpfer, J. W.; Schellenberger, S.; Friedrich, R.; Klapper, M.; Müllen, K. J. Colloid Interface Sci. 2014, 428, 276.
[18] Wang, X. Y.; Dai C. J.; Liu, X. Y.; Chen, T.; Wang, J. P. Key Eng. Mater. 2015, 671, 210.
[19] Fisicaro, E.; Contardi, L.; Compari, C.; Bacciottini, F.; Pongiluppi, E.; Viscardi, G.; Barbero, N.; Quagliotto, P.; Rózycka-Roszak, B. Colloids Surf., A 2016, 507, 236.
[20] Sagisaka, M.; Narumi, T.; Niwase, M.; Narita, S.; Ohata, A.; James, C.; Yoshizawa, A.; Taffin de Givenchy, E.; Guittard, F.; Alexander, S.; Eastoe, J. Langmuir 2014, 30, 6057.
[21] Dmowski, W.; Plenkiewicz, H.; Piasecka-Maciejewska, K.; Pres-cher, D.; Schulze, J. Endler, I. J. Fluorine Chem. 1990, 48, 77.
[22] Sha, M.; Pan, R. M.; Zhan, L. W.; Xing, P.; Jiang, B. Chin. J. Chem. 2014, 32, 995.
[23] Sha, M.; Pan, R. M.; Xing, P.; Jiang, B. J. Fluorine Chem. 2015, 169, 61.
[24] Sha, M.; Zhang, D.; Pan, R. M.; Xing, P.; Jiang, B. Acta Chim. Sinica 2015, 73, 395(in Chinese). (沙敏, 张丁, 潘仁明, 邢萍, 姜标, 化学学报, 2015, 73, 395.)
[25] Lin, C.; Pan, R. M.; Xing, P.; Jiang, B. Chin. Chem. Lett. 2018, 29, 1613.
[26] Stähler, K.; Selb, J.; Barthelemy, P.; Pucci, B.; Candau, F. Langmuir 1998, 14, 4765
[27] Tomota, H. JP 07145119, 1995[Chem. Abstr. 1995, 123, 285205].

新型支链型氟碳表面活性剂的合成及性能研究

Study on the Synthesis and Properties of Novel Branched Fluorinated Surfactants

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