Development of a Completely New PFOS Alternative with Lower Surface Tension for Minimizing the Environmental Burden

Abstract

Improving the technical performance of related industrial products is an efficient strategy to reducing the application quantities and environmental burden for toxic chemicals. A novel polyfluoroalkyl surfactant potassium 1,1,2,2,3,3,4,4-octafluoro-4-(perfluorobutoxy)butane-1-sulfonate(F404) was synthesized by a commercializable route. It had a surface tension(γ) of 18.2 mN/m at the critical micelle concentration(CMC, 1.04 g/L), significantly lower than that of perfluorooctane sulfonate(PFOS, ca. 33.0 mN/m, 0.72 g/L), and exhibited remarkable suppression of chromium-fog at a dose half that of PFOS. The half maximal inhibitory concentration(IC₅₀) values in HepG2 cells and the lethal concentration of 50%(LC50) in zebrafish embryos after 72 hpf indicated a lower toxicity for F404 in comparison to PFOS. In a UV/sulphite system, 89.3% of F404 were decomposed after 3 h, representing a defluorination efficiency of 43%. The cleavage of the ether C—O bond during the decomposition would be expected to form a short chain·C₄F₉ as the position of the ether C—O in the F404 fluorocarbon chains is C4—O5. The ether unit is introduced in the perfluoroalkyl chain to improve water solubility, biocompatibility and degradation, thereby minimizing the environmental burden.

Keywords

Perfluorooctane sulfonate(PFOS) / Surface tension / Chromium-fog inhibitor / Perfluoropolyether

References

[1] KissaEFluorinated Surfactants and Repellents, Seconded, 2001New YorkMarcel Dekker

[2] LehmlerH-JChemosphere, 2005, 58111471.

[3] ShinodaK, HatoM, HayashiTThe Journal of Physical Chemistry, 1972, 766909.

[4] WangZ, DeWittJ C, HigginsC P, CousinsI TEnvironmental Science & Technology, 2017, 5152508.

[5] ShiL, LiN, YanH, GaoY A, ZhengLLangmuir, 2011, 2751618.

[6] CameronJ AAustralian Dental Journal, 1986, 315364.

[7] ShenJ, BaiY, TaiX, WangW, WangGACS Sustainable Chemistry & Engineering, 2018, 656183.

[8] LindstromA B, StrynarM J, LibeloE LEnvironmental Science & Technology, 2011, 45197954.

[9] Listing of Perfluorooctane Sulfonic Acid, Its Salts and Perfluorooctane Sulfonyl Fluoride, Stockholm Convention on Persistent Organic Pollutants (POPs), Program U. N. E., Ed. UNEP-POPS-COP. 4-SC-4-17, Geneva, Switzerland, 2009

[10] Guan J., Forestry Machinery, 1988, (6), 57

[11] RitterS KChemical & Engineering News, 2010, 88512.

[12] WangZ, CousinsI T, ScheringerM, HungerbühlerKEnvironment International, 2013, 60: 242.

[13] MunozG, LiuJ, Vo DuyS, SauvéSTrends in Environmental Analytical Chemistry, 2019, 23: e00066.

[14] LinY, RuanT, JiangGChinese Science Bulletin, 2017, 62242724.

[15] LuY, LiangY, ZhouZ, WangY, JiangGEnvironmental Science & Technology, 2019, 532414091.

[16] WangZ, CousinsI T, ScheringerM, HungerbuehlerKEnvironment International, 2015, 75: 172.

[17] WangS, HuangJ, YangY, HuiY, GeY, LarssenT, YuG, DengS, WangB, HarmanCEnvironmental Science & Technology, 2013, 471810163.

[18] ShiY, VestergrenR, ZhouZ, SongX, XuL, LiangY, CaiYEnvironmental Science & Technology, 2015, 492414156.

[19] ShiG, CuiQ, PanY, ShengN, SunS, GuoY, DaiJAquatic Toxicology, 2017, 185: 67.

[20] BaoY, HuangJ, CagnettaG, YuGWater Research, 2019, 163: 114907.

[21] AteiaM, MaroliA, TharayilN, KaranfilTChemosphere, 2019, 220: 866.

[22] ZhouZ, LiangY, ShiY, XuL, CaiYEnvironmental Science & Technology, 2013, 47169249.

[23] AhrensL, ShoeibM, HarnerT, LeeS C, GuoR, ReinerE JEnvironmental Science & Technology, 2011, 45198098.

[24] CaporiccioG, BurzioF, CarniselliG, BiancardiVJournal of Colloid and Interface Science, 1984, 981202.

[25] MonduzziM, KnackstedtM A, NinhamB WThe Journal of Physical Chemistry, 1995, 995017772.

[26] Shanghai Guangming Electroplating Plant, Shanghai Institute of Organic Chemistry at Chinese Academy of Science, Jiangsu Taizhou Electrochemical Plant, Mater. Prot.(in Chinese), 1976, 3(3), 27

[27] YinQ, XueW, BaiY, WangW, MaX, DuZ, WangGJournal of Industrial and Engineering Chemistry, 2016, 42: 63.

[28] BentelM J, YuY, XuL, KwonH, LiZ, WongB M, MenY, LiuJEnvironmental Science & Technology, 2020, 5442489.

[29] BrandsmaS H, KoekkoekJ C, van VelzenM J M, de BoerJChemosphere, 2019, 220: 493.

[30] BaoY, DengS, JiangX, QuY, HeY, LiuL, ChaiQ, MumtazM, HuangJ, CagnettaG, YuGEnvironmental Science & Technology, 2018, 522011728

[31] MahamY, MatherA EFluid Phase Equilibria, 2001, 1821325.

[32] LiDFormulation and Production of Electroplating Solution, 2018BeijingChemical Industry Press

[33] CostanzaJ, ArshadiM, AbriolaL M, PennellK DEnvironmental Science & Technology Letters, 2019, 68487.

[34] GenteG, La MesaC, MuzzalupoR, RanieriG ALangmuir, 2000, 16217914.

[35] HuX-Z, HuD-CArchives of Toxicology, 2009, 839851.

[36] YaoX-F, CaoJ, XuL-M, SunX-C, KangJ, YangG, JiangL-P, GengC-Y, GaoC-Z, ZhongL-F, MaY-FFood and Chemical Toxicology, 2014, 67: 96.

[37] GuY, LiuT, WangH, HanH, DongWScience of the Total Environment, 2017, 607: 541.

[38] BentelM J, YuY, XuL, LiZ, WongB M, MenY, LiuJEnvironmental Science & Technology, 2019, 5373718.

[39] PaulA, WannereC S, SchaeferH FThe Journal of Physical Chemistry A, 2004, 108439428.

[40] GuY, DongW, LuoC, LiuTEnvironmental Science & Technology, 2016, 501910554.

[41] NoharaK, TomaM, KutsunaS, TakeuchiK, IbusukiTEnvironmental Science & Technology, 2001, 351114.

RIGHTS & PERMISSIONS

Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH