Strategies for synthesizing non-bioaccumulable alternatives to PFOA and PFOS

Min Sha Ping Xing Biao Jiang

Citation:  Min Sha, Ping Xing, Biao Jiang. Strategies for synthesizing non-bioaccumulable alternatives to PFOA and PFOS[J]. Chinese Chemical Letters, 2015, 26(5): 491-498. doi: 10.1016/j.cclet.2015.03.038 shu

Strategies for synthesizing non-bioaccumulable alternatives to PFOA and PFOS

    通讯作者: Biao Jiang,
  • 基金项目:

    This work was supported by the National Natural Science Foundation of China (No. 21102167) (No. 21102167)

    Technology Commission of Shanghai Municipality (No. 12DZ1930902) (No. 12DZ1930902)

摘要: This minireview describes the strategies for synthesis of fluorinated surfactants potentially nonbioaccumulable. Various strategies have been focused on (I) reducing the length of the perfluorocarbon chain, (II) introducing hetero atoms into the fluorocarbon chain, (III) introducing branch (herein and after branch means the fluoro-carbon chain section is not straight). In most cases, the surface tensions versus the surfactant concentrations have been assessed. These above strategies led to various highly fluorinated (perfluorinated or not perfluorinated) surfactants whose chemical changes enabled to obtain novel alternatives to perfluorooctanoic acid (PFOA) and perfluorooctane sulphonate (PFOS).

English

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    1. [1] A.X. Song, S.L. Dong, J.C. Hao, et al., Functions of fluorosurfactants 1: surface activities-improved and vesicle formation of the short-tailed chain sulfonate salt mixed with a fluorosurfactant, J. Fluor. Chem. 126 (2005) 1266-1273.[1] A.X. Song, S.L. Dong, J.C. Hao, et al., Functions of fluorosurfactants 1: surface activities-improved and vesicle formation of the short-tailed chain sulfonate salt mixed with a fluorosurfactant, J. Fluor. Chem. 126 (2005) 1266-1273.

    2. [2] C.Q. Lu, J.H. Kim, D.D. DesMarteau, Synthesis of perfluoro-t-butyl trifluorovinyl ether and its copolymerization with TFE, J. Fluor. Chem. 131 (2010) 17-20.[2] C.Q. Lu, J.H. Kim, D.D. DesMarteau, Synthesis of perfluoro-t-butyl trifluorovinyl ether and its copolymerization with TFE, J. Fluor. Chem. 131 (2010) 17-20.

    3. [3] T. Gramstad, R.N. Haszeldine, Perfluoroalkyl derivatives of sulphur. Part VII. Alkyl trifluoromethanesulphonates as alkylating agents, trifluoromethanesulphonic anhydride as a promoter for esterification, and some reactions of trifluoromethanesulphonic acid, J. Chem. Soc. (1957) 4069-4079.[3] T. Gramstad, R.N. Haszeldine, Perfluoroalkyl derivatives of sulphur. Part VII. Alkyl trifluoromethanesulphonates as alkylating agents, trifluoromethanesulphonic anhydride as a promoter for esterification, and some reactions of trifluoromethanesulphonic acid, J. Chem. Soc. (1957) 4069-4079.

    4. [4] M.P. Krafft, J.G. Riess, Perfluorocarbons: life sciences and biomedical uses dedicated to the memory of Professor Guy Ourisson, a true RENAISSANCE man, J. Polym. Sci. A: Polym. Chem. 45 (2007) 1185-1198.[4] M.P. Krafft, J.G. Riess, Perfluorocarbons: life sciences and biomedical uses dedicated to the memory of Professor Guy Ourisson, a true RENAISSANCE man, J. Polym. Sci. A: Polym. Chem. 45 (2007) 1185-1198.

    5. [5] R. Kaplánek, O. Paleta, I. Ferjentsiková, M. Kodíček, Novel perfluoroalkylated oligo(oxyethylene) methyl ethers with high hemocompatibility and excellent co-emulsifying properties for potential biomedical uses, J. Fluor. Chem. 130 (2009) 308-316.[5] R. Kaplánek, O. Paleta, I. Ferjentsiková, M. Kodíček, Novel perfluoroalkylated oligo(oxyethylene) methyl ethers with high hemocompatibility and excellent co-emulsifying properties for potential biomedical uses, J. Fluor. Chem. 130 (2009) 308-316.

    6. [6] L. Caillier, E.T. de Givenchy, R. Levy, et al., Polymerizable semi-fluorinated gemini surfactants designed for antimicrobial materials, J. Colloid Interface Sci. 332 (2009) 201-207.[6] L. Caillier, E.T. de Givenchy, R. Levy, et al., Polymerizable semi-fluorinated gemini surfactants designed for antimicrobial materials, J. Colloid Interface Sci. 332 (2009) 201-207.

    7. [7] J. Kovarova, Z. Svobodova, Perfluorinated compounds: occurrence and risk profile, Neuro Endocrinol. Lett. 29 (2008) 599-608.[7] J. Kovarova, Z. Svobodova, Perfluorinated compounds: occurrence and risk profile, Neuro Endocrinol. Lett. 29 (2008) 599-608.

    8. [8] D. Prescher, U. Gross, J. Wotzka, M. Tscheu-Schlü ter, W. Stark, Environmental behavior of fluoro surfactants. Part 2. Study on biochemical degradability, Acta Hydrochim. Hydrobiol. 13 (1985) 17-24.[8] D. Prescher, U. Gross, J. Wotzka, M. Tscheu-Schlü ter, W. Stark, Environmental behavior of fluoro surfactants. Part 2. Study on biochemical degradability, Acta Hydrochim. Hydrobiol. 13 (1985) 17-24.

    9. [9] B.D. Key, R.D. Howell, C.S. Criddle, Fluorinated organics in the biosphere, Environ. Sci. Technol. 31 (1997) 2445-2454.[9] B.D. Key, R.D. Howell, C.S. Criddle, Fluorinated organics in the biosphere, Environ. Sci. Technol. 31 (1997) 2445-2454.

    10. [10] B.D. Key, R.D. Howell, C.S. Criddle, Defluorination of organofluorine sulfur compounds by Pseudomonas Sp. Strain D2, Environ. Sci. Technol. 32 (1998) 2283-2287.[10] B.D. Key, R.D. Howell, C.S. Criddle, Defluorination of organofluorine sulfur compounds by Pseudomonas Sp. Strain D2, Environ. Sci. Technol. 32 (1998) 2283-2287.

    11. [11] M. Houde, J.W. Martin, R.J. Letcher, K.R. Solomon, D.C.G. Muir, Biological monitoring of polyfluoroalkyl substances: a review, Environ. Sci. Technol. 40 (2006) 3463-3473.[11] M. Houde, J.W. Martin, R.J. Letcher, K.R. Solomon, D.C.G. Muir, Biological monitoring of polyfluoroalkyl substances: a review, Environ. Sci. Technol. 40 (2006) 3463-3473.

    12. [12] C. Lu, Y.L. Shi, Z. Zhou, et al., Perfluorinated compounds in blood of textile workers and barbers, Chin. Chem. Lett. 25 (2014) 1145-1148.[12] C. Lu, Y.L. Shi, Z. Zhou, et al., Perfluorinated compounds in blood of textile workers and barbers, Chin. Chem. Lett. 25 (2014) 1145-1148.

    13. [13] K. Kannan, S. Corsolini, J. Falandysz, et al., Perfluorooctanesulfonate and related fluorochemicals in human blood from several countries, Environ. Sci. Technol. 38 (2004) 4489-4495.[13] K. Kannan, S. Corsolini, J. Falandysz, et al., Perfluorooctanesulfonate and related fluorochemicals in human blood from several countries, Environ. Sci. Technol. 38 (2004) 4489-4495.

    14. [14] U.S. Environmental Protection Agency, http://www.epa.gov/oppt/pfoa/pubs/stewardship/index.html.[14] U.S. Environmental Protection Agency, http://www.epa.gov/oppt/pfoa/pubs/stewardship/index.html.

    15. [15] J.R. Parsons, M. Sáez, J. Dolfing, P. de Voogt, Biodegradation of Perfluorinated Compounds, Reviews of Environmental Contamination and Toxicology, vol. 196, Springer, New York, 2008, pp. 53-71.[15] J.R. Parsons, M. Sáez, J. Dolfing, P. de Voogt, Biodegradation of Perfluorinated Compounds, Reviews of Environmental Contamination and Toxicology, vol. 196, Springer, New York, 2008, pp. 53-71.

    16. [16] K.A. Kennedy, G.W. Roberts, J.M. Desimone, Heterogeneous Polymerization of Fluoroolefins in Supercritical Carbon Dioxide, Polymer Particles, Advances in Polymer Science, vol. 175, Springer-Verlag, Berlin, 2005, pp. 329-346.[16] K.A. Kennedy, G.W. Roberts, J.M. Desimone, Heterogeneous Polymerization of Fluoroolefins in Supercritical Carbon Dioxide, Polymer Particles, Advances in Polymer Science, vol. 175, Springer-Verlag, Berlin, 2005, pp. 329-346.

    17. [17] W.Y. Gu, D.D. Feng, X.L. Su, Progress of alternatives for PFOA, Organo-Fluor. Ind. 3 (2009) 28-30.[17] W.Y. Gu, D.D. Feng, X.L. Su, Progress of alternatives for PFOA, Organo-Fluor. Ind. 3 (2009) 28-30.

    18. [18] M.G. Wang, M.Y. Wang, Y.B. Tan, et al., Short fluorocarbon chain-based environment- friendly cationic fluorosurfactant and its preparation method, CN 102,814,144 A, 2012.[18] M.G. Wang, M.Y. Wang, Y.B. Tan, et al., Short fluorocarbon chain-based environment- friendly cationic fluorosurfactant and its preparation method, CN 102,814,144 A, 2012.

    19. [19] L. Wang, Synthesis and Properties of Perfluorobutylamide Fluorinated Surfactants, M.S. thesis, Shanxi University of Science and Technology, 2014.[19] L. Wang, Synthesis and Properties of Perfluorobutylamide Fluorinated Surfactants, M.S. thesis, Shanxi University of Science and Technology, 2014.

    20. [20] G.D. Long, S. Xiao, D.M. Fu, J. Gulmira, X.S. Li, Synthesis and surface properties of perfluorobutyl cationic surfactant, Organo-Fluor. Ind. 3 (2012) 1-4.[20] G.D. Long, S. Xiao, D.M. Fu, J. Gulmira, X.S. Li, Synthesis and surface properties of perfluorobutyl cationic surfactant, Organo-Fluor. Ind. 3 (2012) 1-4.

    21. [21] G.D. Long, S. Xiao, J. Gulmira, et al., Synthesis and surface properties of N'- 3(dimethyl)-propyl-(N-perfluorobutyl sulfonyl-N-alkylsulfonyl)-amine oxide, Organo-Fluor. Ind. 4 (2012) 1-4.[21] G.D. Long, S. Xiao, J. Gulmira, et al., Synthesis and surface properties of N'- 3(dimethyl)-propyl-(N-perfluorobutyl sulfonyl-N-alkylsulfonyl)-amine oxide, Organo-Fluor. Ind. 4 (2012) 1-4.

    22. [22] B.Q. Yang, K. Chen, H. Xing, J.X. Xiao, Perfluorobutyl-based fluorinated surfactant with high surface activity, Acta Phys. Chim. Sin. 25 (2009) 2409-2412.[22] B.Q. Yang, K. Chen, H. Xing, J.X. Xiao, Perfluorobutyl-based fluorinated surfactant with high surface activity, Acta Phys. Chim. Sin. 25 (2009) 2409-2412.

    23. [23] S. Xiao, Synthesis and Application on Substituting Fluorine Containing Surfactant for PFOS, M.S. thesis, Central China Normal University, 2013.[23] S. Xiao, Synthesis and Application on Substituting Fluorine Containing Surfactant for PFOS, M.S. thesis, Central China Normal University, 2013.

    24. [24] J. Gulimire, Synthesis and Application of Fluorinated Surfactants, M.S. thesis, Central China Normal University, 2014.[24] J. Gulimire, Synthesis and Application of Fluorinated Surfactants, M.S. thesis, Central China Normal University, 2014.

    25. [25] L. Peng, G.D. Long, S.L. Wang, et al., Synthesis and surface properties of N-3- (dimethylamino)-propyl perfluorohexylsulfonyl compounds, Fire Sci. Technol. 30 (2011) 937-939.[25] L. Peng, G.D. Long, S.L. Wang, et al., Synthesis and surface properties of N-3- (dimethylamino)-propyl perfluorohexylsulfonyl compounds, Fire Sci. Technol. 30 (2011) 937-939.

    26. [26] H.X. Shi, X.L. Qiu, H.K. Wu, L.J. Chen, J.P. Xiang, Synthesis and properties of ammonium salts of perfluorohexylsulfonamides, Fine Chem. 29 (2012) 438-442.[26] H.X. Shi, X.L. Qiu, H.K. Wu, L.J. Chen, J.P. Xiang, Synthesis and properties of ammonium salts of perfluorohexylsulfonamides, Fine Chem. 29 (2012) 438-442.

    27. [27] M.M. Yao, Y. Yang, M.Y. Xue, M. Lin, Synthesis and properties of novel fluorinated surfactant, N. Chem. Mater. 41 (2013) 73-75.[27] M.M. Yao, Y. Yang, M.Y. Xue, M. Lin, Synthesis and properties of novel fluorinated surfactant, N. Chem. Mater. 41 (2013) 73-75.

    28. [28] C. Zhang, Study on Synthesis and Properties of Fluorocarbon, M.S. thesis, Hubei University, 2013.[28] C. Zhang, Study on Synthesis and Properties of Fluorocarbon, M.S. thesis, Hubei University, 2013.

    29. [29] F.G. Drakesmith, D.A. Hughes, The electrochemical fluorination of octanoyl chloride, J. Appl. Electrochem. 9 (1979) 685-697.[29] F.G. Drakesmith, D.A. Hughes, The electrochemical fluorination of octanoyl chloride, J. Appl. Electrochem. 9 (1979) 685-697.

    30. [30] R.N. Haszeldine, Synthesis of fluorocarbons, perfluoroalkyl iodides, bromides, and chlorides, and perfluoroalkyl Grignard reagents, Nature 167 (1951) 139-140.[30] R.N. Haszeldine, Synthesis of fluorocarbons, perfluoroalkyl iodides, bromides, and chlorides, and perfluoroalkyl Grignard reagents, Nature 167 (1951) 139-140.

    31. [31] H.J. Emeléus, R.N. Haszeldine, The reactions of fluorocarbon radicals. I. The reaction of iodotrifluoromethane with ethylene and tetrafluoroethylene, J. Chem. Soc. (1949) 2856-2861.[31] H.J. Emeléus, R.N. Haszeldine, The reactions of fluorocarbon radicals. I. The reaction of iodotrifluoromethane with ethylene and tetrafluoroethylene, J. Chem. Soc. (1949) 2856-2861.

    32. [32] P.M. Murphy, C.S. Baldwin, R.C. Buck, Synthesis utilizing n-perfluoroalkyl iodides[RFI, CnF2n+1-I] 2000-2010, J. Fluor. Chem. 138 (2012) 3-23.[32] P.M. Murphy, C.S. Baldwin, R.C. Buck, Synthesis utilizing n-perfluoroalkyl iodides[RFI, CnF2n+1-I] 2000-2010, J. Fluor. Chem. 138 (2012) 3-23.

    33. [33] M.A. Guerra, K. Hintzer, M. Jurgens, et al., Fluorinated surfactants with low toxicity and/or little bioaccumulation, their manufacture and use, US 20,070,276,103 A1, 2007.[33] M.A. Guerra, K. Hintzer, M. Jurgens, et al., Fluorinated surfactants with low toxicity and/or little bioaccumulation, their manufacture and use, US 20,070,276,103 A1, 2007.

    34. [34] D.S. Slinn, S.W. Green, Fluorocarbon fluids for the use in the electronic industry, in: R.E. Banks (Ed.), Preparation, Properties and Industrial Applications of Organofluoride Compounds, vol. 2, Ellis Horwood, Chichester, 1982, pp. 45-82.[34] D.S. Slinn, S.W. Green, Fluorocarbon fluids for the use in the electronic industry, in: R.E. Banks (Ed.), Preparation, Properties and Industrial Applications of Organofluoride Compounds, vol. 2, Ellis Horwood, Chichester, 1982, pp. 45-82.

    35. [35] D. Sianesi, G. Marchionni, R.J. De Pasquale, Perfluoropolyethers from perfluoroolefin photooxidation, in: R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry: Principles and Commercial Applications, Plenum Press, New York, 1994, pp. 431-460.[35] D. Sianesi, G. Marchionni, R.J. De Pasquale, Perfluoropolyethers from perfluoroolefin photooxidation, in: R.E. Banks, B.E. Smart, J.C. Tatlow (Eds.), Organofluorine Chemistry: Principles and Commercial Applications, Plenum Press, New York, 1994, pp. 431-460.

    36. [36] J. Scheirs, Perfluoropolyethers: synthesis, characterization and application, in: J. Scheirs (Ed.), Modern Fluoropolymers, Wiley, New York, 1997, pp. 435-486.[36] J. Scheirs, Perfluoropolyethers: synthesis, characterization and application, in: J. Scheirs (Ed.), Modern Fluoropolymers, Wiley, New York, 1997, pp. 435-486.

    37. [37] S.V. Kostjuk, E. Ortega, F. Ganachaud, B. Améduri, B. Boutevin, Anionic ringopening polymerization of hexafluoropropylene oxide using alkali metal fluorides as catalysts: a mechanistic study, Macromolecules 42 (2009) 612-619.[37] S.V. Kostjuk, E. Ortega, F. Ganachaud, B. Améduri, B. Boutevin, Anionic ringopening polymerization of hexafluoropropylene oxide using alkali metal fluorides as catalysts: a mechanistic study, Macromolecules 42 (2009) 612-619.

    38. [38] J.L. Howell, E.W. Perez, Perfluoropolyoxyalkylenes and perfluoropolyethers as lubricating oils and greases for magnetic recording devices, US 20,030,073,588 A1, 2003.[38] J.L. Howell, E.W. Perez, Perfluoropolyoxyalkylenes and perfluoropolyethers as lubricating oils and greases for magnetic recording devices, US 20,030,073,588 A1, 2003.

    39. [39] P. Kappler, M.J. Lina, Process for manufacture of fluoropolymers and surfactant for use in the process, FR 2,871,460 A1, 2005.[39] P. Kappler, M.J. Lina, Process for manufacture of fluoropolymers and surfactant for use in the process, FR 2,871,460 A1, 2005.

    40. [40] G. Boutevin, D. Tiffes, C. Loubat, B. Boutevin, B.Ameduri,Newfluorinated surfactants based on vinylidene fluoride telomers, J. Fluor. Chem. 134 (2012) 7-84.[40] G. Boutevin, D. Tiffes, C. Loubat, B. Boutevin, B.Ameduri,Newfluorinated surfactants based on vinylidene fluoride telomers, J. Fluor. Chem. 134 (2012) 7-84.

    41. [41] T.T. Vasil’eva, V.A. Kochetkova, B.V. Nelyubin, et al., Radical telomerization of 3,3,3-trifluoro-1-propene with tetbromomethane. Individual chain transfer constants, Izv. Akad. Nauk SSSR, Ser. Khim. (1987) 808-811.[41] T.T. Vasil’eva, V.A. Kochetkova, B.V. Nelyubin, et al., Radical telomerization of 3,3,3-trifluoro-1-propene with tetbromomethane. Individual chain transfer constants, Izv. Akad. Nauk SSSR, Ser. Khim. (1987) 808-811.

    42. [42] T.T. Vasil’eva, V.A. Kochetkova, V.I. Dostovalova, et al., Reaction of 3,3,3-trifluoro- 1-propene with bromoform and methylene bromide, Izv. Akad. Nauk SSSR, Ser. Khim. (1989) 2558-2562.[42] T.T. Vasil’eva, V.A. Kochetkova, V.I. Dostovalova, et al., Reaction of 3,3,3-trifluoro- 1-propene with bromoform and methylene bromide, Izv. Akad. Nauk SSSR, Ser. Khim. (1989) 2558-2562.

    43. [43] T.T. Vasil’eva, I.A. Fokina, S.V. Vitt, et al., Radical telomerization of 3,3,3-trifluoropropene- 1 with CCl4, Izv. Akad. Nauk SSSR, Ser. Khim. (1990) 1807-1811.[43] T.T. Vasil’eva, I.A. Fokina, S.V. Vitt, et al., Radical telomerization of 3,3,3-trifluoropropene- 1 with CCl4, Izv. Akad. Nauk SSSR, Ser. Khim. (1990) 1807-1811.

    44. [44] T.T. Vasil’eva, I.A. Fokina, S.V. Vitt, Reaction of benzyl chloride with propylene and trifluoropropene under metal complex initiation conditions, Izv. Akad. Nauk SSSR, Ser. Khim. (1991) 1384-1388.[44] T.T. Vasil’eva, I.A. Fokina, S.V. Vitt, Reaction of benzyl chloride with propylene and trifluoropropene under metal complex initiation conditions, Izv. Akad. Nauk SSSR, Ser. Khim. (1991) 1384-1388.

    45. [45] R.A. Zamyslov, A.G. Shostenko, I.V. Dobrov, V.E. Myshkin, Radical telomerization of 3,3,3-trifluoro-1-propene with 2-propanol, Zh. Org. Khim. 16 (1980) 897-901.[45] R.A. Zamyslov, A.G. Shostenko, I.V. Dobrov, V.E. Myshkin, Radical telomerization of 3,3,3-trifluoro-1-propene with 2-propanol, Zh. Org. Khim. 16 (1980) 897-901.

    46. [46] R.A. Zamyslov, Reactivity of C1-C4 aliphatic alcohols in radical telomerization with 3,3,3-trifluoropropylene, Zh. Vses. Khim. Obsh. 31 (1986) 589-591.[46] R.A. Zamyslov, Reactivity of C1-C4 aliphatic alcohols in radical telomerization with 3,3,3-trifluoropropylene, Zh. Vses. Khim. Obsh. 31 (1986) 589-591.

    47. [47] R.N. Haszeldine, Reactions of fluorocarbon radicals. V. Alternative synthesis for (trifluoromethyl)acetylene (3,3,3-trifluoropropyne) and the influence of polyfluoro groups on adjacent hydrogen and halogen atoms, J. Chem. Soc. (1951) 2495-2504.[47] R.N. Haszeldine, Reactions of fluorocarbon radicals. V. Alternative synthesis for (trifluoromethyl)acetylene (3,3,3-trifluoropropyne) and the influence of polyfluoro groups on adjacent hydrogen and halogen atoms, J. Chem. Soc. (1951) 2495-2504.

    48. [48] R.N. Haszeldine, The addition of free radicals to unsaturated systems. I. The direction of radical addition to 3,3,3-trifluoropropene, J. Chem. Soc. (1952) 2504-2513.[48] R.N. Haszeldine, The addition of free radicals to unsaturated systems. I. The direction of radical addition to 3,3,3-trifluoropropene, J. Chem. Soc. (1952) 2504-2513.

    49. [49] G.K. Kostov, B. Ameduri, S.M. Brandstadter, Telomerization of 3,3,3-trifluoroprop- 1-ene and functionalization of its telomers, Collect. Czechoslov. Chem. Commun. 73 (2008) 1747-1763.[49] G.K. Kostov, B. Ameduri, S.M. Brandstadter, Telomerization of 3,3,3-trifluoroprop- 1-ene and functionalization of its telomers, Collect. Czechoslov. Chem. Commun. 73 (2008) 1747-1763.

    50. [50] G. Kostov, B. Améduri, S.M. Brandstadter, Radical telomerization of 3,3,3-trifluoropropene with diethyl hydrogen phosphonate: characterization of the first telomeric adducts and assessment of the transfer constants, J. Fluor. Chem. 128 (2007) 910-918.[50] G. Kostov, B. Améduri, S.M. Brandstadter, Radical telomerization of 3,3,3-trifluoropropene with diethyl hydrogen phosphonate: characterization of the first telomeric adducts and assessment of the transfer constants, J. Fluor. Chem. 128 (2007) 910-918.

    51. [51] W. Dmowski, H. Plenkiewicz, K. Piasecka-Maciejewska, Synthetic utility of 3- (perfluoro-1,1-dimethylbutyl)-1-propene. Part III. Synthesis and properties of (perfluoro-1,1-dimethylbutyl) acetic and propionic acids and their salts, J. Fluor. Chem. 48 (1990) 77-84.[51] W. Dmowski, H. Plenkiewicz, K. Piasecka-Maciejewska, Synthetic utility of 3- (perfluoro-1,1-dimethylbutyl)-1-propene. Part III. Synthesis and properties of (perfluoro-1,1-dimethylbutyl) acetic and propionic acids and their salts, J. Fluor. Chem. 48 (1990) 77-84.

    52. [52] G. Kostov, F. Boschet, B. Ameduri, Original fluorinated surfactants potentially nonbioaccumulable, J. Fluor. Chem. 130 (2009) 1192-1199.[52] G. Kostov, F. Boschet, B. Ameduri, Original fluorinated surfactants potentially nonbioaccumulable, J. Fluor. Chem. 130 (2009) 1192-1199.

    53. [53] Z.M. Liu, C.M. Tan, J.F. Wu, et al., Synthesis of fluoro-tertiary and quaternary ammonium cationic surfactants, Dyest. Color. 43 (2006) 31-33.[53] Z.M. Liu, C.M. Tan, J.F. Wu, et al., Synthesis of fluoro-tertiary and quaternary ammonium cationic surfactants, Dyest. Color. 43 (2006) 31-33.

    54. [54] Q.S. Zhang, Z.Y. Luo, D.P. Curran, Separation of "light fluorous" reagents and catalysts by fluorous solid-phase extraction: synthesis and study of a family of triarylphosphines bearing linear and branched fluorous tags, J. Org. Chem. 65 (2000) 8866-8873.[54] Q.S. Zhang, Z.Y. Luo, D.P. Curran, Separation of "light fluorous" reagents and catalysts by fluorous solid-phase extraction: synthesis and study of a family of triarylphosphines bearing linear and branched fluorous tags, J. Org. Chem. 65 (2000) 8866-8873.

    55. [55] S.Q. Mao, M.F. Tang, C. Gu, Synthesis, surface activities and oil collecting performance of different ionic fluorinated surfactants derived from hexafluoropropylene trimer, Organo-Fluor. Ind. 1 (1996) 1-5.[55] S.Q. Mao, M.F. Tang, C. Gu, Synthesis, surface activities and oil collecting performance of different ionic fluorinated surfactants derived from hexafluoropropylene trimer, Organo-Fluor. Ind. 1 (1996) 1-5.

    56. [56] I. Ikeda, M. Tsuji, M. Okahara, Fluoro surfactants, tenside, surfactants, Detergents 24 (1987) 272-274.[56] I. Ikeda, M. Tsuji, M. Okahara, Fluoro surfactants, tenside, surfactants, Detergents 24 (1987) 272-274.

    57. [57] H. Tomota, N. Nakayama, Preparation of fluorine-containing aromatic carboxylic acids as intermediates for surfactants and polymers, JP 03,093,744 A, 1991.[57] H. Tomota, N. Nakayama, Preparation of fluorine-containing aromatic carboxylic acids as intermediates for surfactants and polymers, JP 03,093,744 A, 1991.

    58. [58] Z.M. Liu, J.F. Wu, L.M. Tan, et al., Synthesis and properties of cationic surfactant from hexafluoropropene dimer, Fine Chem. 22 (2005) 53-55.[58] Z.M. Liu, J.F. Wu, L.M. Tan, et al., Synthesis and properties of cationic surfactant from hexafluoropropene dimer, Fine Chem. 22 (2005) 53-55.

    59. [59] B.Q. Yang, L. Wang, J. Yang, J. Liu, Synthesis and properties of fluorinated surfactants based on hexafuoropropene dimmer, Chem. Res. Appl. 25 (2013) 1523-1527.[59] B.Q. Yang, L. Wang, J. Yang, J. Liu, Synthesis and properties of fluorinated surfactants based on hexafuoropropene dimmer, Chem. Res. Appl. 25 (2013) 1523-1527.

    60. [60] T.C. Zheng, Y.J. Zhao, Z.G. Lei, Q. Zhou, S.H. Wang, Research progress on performance and synthesis of surfactants based on hexafluoroprpene oligomers, Chem. Prod. Technol. 19 (2012) 6-11.[60] T.C. Zheng, Y.J. Zhao, Z.G. Lei, Q. Zhou, S.H. Wang, Research progress on performance and synthesis of surfactants based on hexafluoroprpene oligomers, Chem. Prod. Technol. 19 (2012) 6-11.

    61. [61] H. Qi, W.G. Xu, W.J. Zhao, et al., Hexafluoropropylene dimer and its applications, Organo-Fluor. Ind. 4 (2012) 18-22.[61] H. Qi, W.G. Xu, W.J. Zhao, et al., Hexafluoropropylene dimer and its applications, Organo-Fluor. Ind. 4 (2012) 18-22.

    62. [62] J.H. Xu, Z.J. Chen, W.B. Zhang, Hexafluoropropylene dimers and derivatives thereof, Organo-Fluor. Ind. 3 (2007) 29-32.[62] J.H. Xu, Z.J. Chen, W.B. Zhang, Hexafluoropropylene dimers and derivatives thereof, Organo-Fluor. Ind. 3 (2007) 29-32.

    63. [63] M. Sha, R.M. Pan, L.W. Zhan, P. Xing, B. Jiang, Synthesis and surface activity study of a novel branched fluorinated anion surfactant with CF3CF2CF2C(CF3)2 group, Chin. J. Chem. 32 (2014) 995-998.[63] M. Sha, R.M. Pan, L.W. Zhan, P. Xing, B. Jiang, Synthesis and surface activity study of a novel branched fluorinated anion surfactant with CF3CF2CF2C(CF3)2 group, Chin. J. Chem. 32 (2014) 995-998.

    64. [64] M. Sha, R.M. Pan, P. Xing, B. Jiang, Synthesis and surface activity study of branched fluorinated cationic (FCS), gemini (FGS) and amphoteric (FAS) surfactants with CF3CF2CF2C(CF3)2 group, J. Fluor. Chem. 169 (2015) 61-65.[64] M. Sha, R.M. Pan, P. Xing, B. Jiang, Synthesis and surface activity study of branched fluorinated cationic (FCS), gemini (FGS) and amphoteric (FAS) surfactants with CF3CF2CF2C(CF3)2 group, J. Fluor. Chem. 169 (2015) 61-65.

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  • 发布日期:  2015-04-07
  • 收稿日期:  2015-02-04
  • 网络出版日期:  2015-03-13
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