Citation: Zhang Ding, Sha Min, Pan Renming, Lin Xiangyang, Xing Ping, Jiang Biao. Design and synthesis of the novel branched fluorinated surfactant intermediates with CF₃CF₂CF₂C(CF₃)₂ group[J]. Chinese Chemical Letters, ;2019, 30(3): 566-568. doi: 10.1016/j.cclet.2018.11.014 shu

Design and synthesis of the novel branched fluorinated surfactant intermediates with CF₃CF₂CF₂C(CF₃)₂ group

Zhang Ding ^a,b ,
Sha Min ^c ,
Pan Renming ^a ,
Lin Xiangyang ^a,*, ,
Xing Ping ^b,*, ,
Jiang Biao ^a,b,*,

a.
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China
b.
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
c.
School of Management Science & Engineering, Nanjing University of Finance & Economics, Nanjing 210046, China

linxiangyang@njust.edu.cn

xingping@mail.sioc.ac.cn

jiangb@mail.sioc.ac.cn

Received Date: 16 September 2018
Revised Date: 5 November 2018
Accepted Date: 13 November 2018
Available Online: 14 March 2018

Figures(3)

Perfluorooctanoic acid (PFOA) or perfluorooctane sulphonate (PFOS) was one of the most prominent fluorosurfactants and applied widely in firefighting and daily chemical, etc. However, these surfactants have recently been identified as toxic and undegradability in the environment. Developing an efficient approach to environment-friendly fluorosurfactants is essential. A fluorocarbon branched chain strategy was adopted to develop /PFOS substitutes. A series of intermediates of novel branched fluorinated surfactants with CF₃CF₂CF₂C(CF₃)₂ group were synthesized from perfluoro-2-methyl-2-pentene. All the steps were mild, easy-handled and cheap. It is expected to be a very significant direction for the development of non-bioaccumulable alternatives of PFOA or PFOS.
- Perfluoro-2-methyl-2-pentene,
- Branched fluorinated surfactants,
- Oxy fluorocarbon chain
1. [1]
  R. Kaplánek, O. Paleta, I. Ferjentsiková, M. Kodícek, J. Fluorine Chem.130(2009) 9308-316.
2. [2]
  P. Krafft Marie, G. Riess Jean, J. Polym. Sci.:Polym. Chem. Ed. 45(2007) 1185-1198. doi: 10.1002/(ISSN)1099-0518
3. [3]
  L. Caillier, E. Taffin de Givenchy, R. Levy, et al., J. Colloid Interf. Sci. 332(2009) 201-207. doi: 10.1016/j.jcis.2008.12.038
4. [4]
  J. Kovarova, Z. Svobodova, Neuro Endocrinol. Lett. 29(2008) 599-608.
5. [5]
  F.G. Drakesmith, D.A. Hughes, J. Appl. Electrochem. 9(1979) 685-697. doi: 10.1007/BF00614962
6. [6]
  P.M. Murphy, C.S. Baldwin, R.C. Buck, J. Fluorine Chem. 138(2012) 3-23. doi: 10.1016/j.jfluchem.2012.03.011
7. [7]
  J. Hutchinson, Fette Seifen Anstrichmittel 76(1974) 158-163. doi: 10.1002/(ISSN)1521-4133
8. [8]
  J.P. Giesy, K. Kannan, Environ. Sci. Technol. 35(2001) 1339-1342. doi: 10.1021/es001834k
9. [9]
  D.J. Luebker, K.J. Hansen, N.M. Bass, J.L. Butenhoff, A.M. Seacat, Toxicology 176(2002) 175-185. doi: 10.1016/S0300-483X(02)00081-1
10. [10]
  M. Sagisaka, T. Narumi, M. Niwase, et al., Langmuir 30(2014) 6057-6063. doi: 10.1021/la501328s
11. [11]
  W. Dmowski, H. Plenkiewicz, K. Piasecka-Maciejewska, et al., J. Fluorine Chem. 48(1990) 77-84. doi: 10.1016/S0022-1139(00)82603-2
12. [12]
  M. Sha, P. Xing, B. Jiang, Chin. Chem. Lett. 26(2015) 491-498. doi: 10.1016/j.cclet.2015.03.038
13. [13]
  M. Sha, R. Pan, P. Xing, B. Jiang, J. Fluorine Chem. 169(2015) 61-65. doi: 10.1016/j.jfluchem.2014.11.005
14. [14]
  M. Sha, R. Pan, L. Zhan, P. Xing, B. Jiang, Chin. J. Chem. 32(2014) 995-998. doi: 10.1002/cjoc.201400377
15. [15]
  M. Sha, R.M. Pan, B. Jiang, Adv. Mater. Res. 685(2013) 357-361. doi: 10.4028/www.scientific.net/AMR.685
16. [16]
  M. Sha, D. Zhang, R.M. Pan, P. Xin, B. Jiang, Acta Chim. Sinica 73(2015) 395-402. doi: 10.6023/A15030174
17. [17]
  C. Lin, R. Pan, P. Xing, B. Jiang, Chin. J. Org. Chem. (2018), doi: http://dx.doi.org/10.6023/cjoc201806014.
18. [18]
  C. Lin, R. Pan, P. Xin, B. Jiang, Chin. Chem. Lett. 29(2018) 1613-1616. doi: 10.1016/j.cclet.2018.04.017
19. [19]
  C. Lin, R. Pan, P. Xin, B. Jiang, J. Fluorine Chem. 214(2018) 35-41. doi: 10.1016/j.jfluchem.2018.07.015
20. [20]
  G. Kostov, F. Boschet, B. Ameduri, J. Fluorine Chem. 130(2009) 1192-1199. doi: 10.1016/j.jfluchem.2009.08.002
21. [21]
  T. Huo, Y. Huang, W.D. Meng, J. Donghua Univ. (Natural Science) 40(2014) 90-98.
22. [22]
  G. Malinvernoa, I. Colombob, M. Viscab, Regul. Toxicol. Pharmacol. 41(2005) 228-239. doi: 10.1016/j.yrtph.2004.12.003
23. [23]
  K.V. Scherer Jr, T.F. Terranova, J. Org. Chem. 11(1981) 2379-2381.
24. [24]
  X. Zhao, W.Y. Ng, K.C. Lau, A.E.C. Collis, I.T. Horvath, Phys. Chem. Chem. Phys.14(2012) 3909-3914. doi: 10.1039/c2cp23113a
25. [25]
  D. Zhang, M. Sha, R. Pan, et al., J. Fluorine Chem. 219(2019) 62-69. doi: 10.1016/j.jfluchem.2018.11.001
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4. [4]
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5. [5]
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6. [6]
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9. [9]
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10. [10]
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11. [11]
  Ying Chen , Lun Li , Guohao Han , Ren Liu , Guanghui An , Yi Zhu . Macromolecular coumarin sulfonium salt with side chain effect constructed by copolymerization strategy for free radical, cationic, and hybrid photopolymerizations. Chinese Chemical Letters, 2025, 36(7): 110458-. doi: 10.1016/j.cclet.2024.110458
12. [12]
  Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
13. [13]
  Dong-Sheng Deng , Su-Qin Tang , Yong-Tu Yuan , Ding-Xiong Xie , Zhi-Yuan Zhu , Yue-Mei Huang , Yun-Lin Liu . C-F insertion reaction sheds new light on the construction of fluorinated compounds. Chinese Chemical Letters, 2024, 35(8): 109417-. doi: 10.1016/j.cclet.2023.109417
14. [14]
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15. [15]
  Qiuyun Li , Yannan Zhu , Yining Wang , Gang Qi , Wen-Juan Hao , Kelu Yan , Bo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494
16. [16]
  Jianwen Zhao , Shuai Wang , Shanshan Zhao , Liwei Chen , Fangang Meng , Xuelin Tian . A non-fluorinated liquid-like membrane with excellent anti-scaling performance for membrane distillation. Chinese Chemical Letters, 2025, 36(1): 109883-. doi: 10.1016/j.cclet.2024.109883
17. [17]
  Zhen-Zhen Dong , Jin-Hao Zhang , Lin Zhu , Xiao-Zhong Fan , Zhen-Guo Liu , Yi-Bo Yan , Long Kong . Attenuating reductive decomposition of fluorinated electrolytes for high-voltage lithium metal batteries. Chinese Chemical Letters, 2025, 36(4): 109773-. doi: 10.1016/j.cclet.2024.109773
18. [18]
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19. [19]
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20. [20]
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Design and synthesis of the novel branched fluorinated surfactant intermediates with CF₃CF₂CF₂C(CF₃)₂ group