Environmentally benign perfluorooctanesulfonate alternatives using a Zn/CuI mediated Michael-type addition in imidazolium ionic liquids

Vijaykumar, B.V.D.; Premkumar, B.; Jang, Kiwan; Choi, Bong In; Falck, John R.; Sheldrake, Gary N.; Shin, Dong Soo

doi:10.1039/c3gc42642d

Cited by 15 publications

(8 citation statements)

References 22 publications

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“…10,12 In continuation of our efforts towards the synthesis of PFOS alternatives, we embarked on the design and synthesis of cyclic type semi-fluorinated disodium sulfonate, another fascinating target. As described earlier, it is evident that the introduction of bio-degradable perfluorobutyl group as hydrophobic chain in surfactant is our foremost priority.…”

Section: Resultsmentioning

confidence: 99%

“…The solvent was removed under reduced pressure. The crude cyclic diester product in THF (10 mL) was added dropwise to a stirred solution of LiAlH 4 (80 mg, 5.63 mmol) in dry THF (10 mL 3,3,4,4,5,5,6,6-octafluorocycloheptane-1,1-diyl)-bis(methylene))bis(oxy))bis(propane-1-sulfonate) (10) Diol (8, 0.1 g, 0.33 mmol) pre-dissolved in dry THF (10 mL) solution was added to suspension of sodium hydride (60% in mineral oil, 0.03 g, 0.72 mmol) at 60 o C. Another dry THF solution (5 mL) containing propane sultone (9, 0.11 g, 0.82 mmol) was then added to the reaction mixture at the same temperature. After 16 h of stirring under reflux conditions, 20 mL of methanol was added at ambient temperature to deactivate any excess of sodium hydride.…”

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confidence: 99%

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Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate

Chirumarry¹,

Ko²,

Jang³

et al. 2016

Journal of the Korean Chemical Society

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ABSTRACT. A new perfluorobutyl substituted cyclic type disodium alkanesulfonate is designed, synthesized and characterized as alternative substance to perfluorooctane sulfonic acid (PFOS, 1), a well-known surfactant. Cylic type sulfonate was accomplished from commercially available 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol in four steps. Bio-degradable perfluorobutyl moiety was introduced from fluorous diol, which is symmetrically substituted amphiphile via installation of an intermediate trifluoromethanesulfonyl ester and easily manipulated by double displacement of triflate using potassium malonate and further reduction followed by nucleophilic ring opening are key reactions to get target disodium alkanesulfonate. The efficiency and simplicity in the synthesis of this material offer a new strategy to design PFOS alternatives.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate

Chirumarry¹,

Ko²,

Jang³

et al. 2016

Journal of the Korean Chemical Society

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“…Therefore, it is of great importance to find environmentally-benign solvents. In this context, ionic liquids (ILs) are considered as environmentally-benign solvents compared to the conventional solvents because of their negligible vapor pressure, high dissolving power, and high thermal stability and recyclability [ 13 , 14 , 15 ]. At present, ILs have found applications in diverse areas such as the conversion of biomass [ 15 ] and biocatalysis [ 16 , 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition

et al. 2018

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Recently, ionic liquids (ILs) have been regarded as ideal media for non-aqueous bio-catalysis. In this work, the synthesis of warfarin by the lipase-catalyzed Michael addition in IL media and the parameters that affected the warfarin yield were investigated. Experimental results demonstrated that the chemical structures of the ILs were a major factor for influencing the warfarin yield. The ILs containing the NTf2– anion were suitable reaction media due to the high chemical stability of this anion. The incorporation of the hydroxyl group on the IL cation significantly improved the lipase activity due to the H2O-mimicking property of this group. The lipase activity decreased by increasing the alkyl chain length on the IL cation due to the non-polar domain formation of the IL cation at the active site entrance of lipase. The ILs and lipase could be reused no less than five times without reduction in the warfarin yield.

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“…Although 3M volutariliy suspended its PFOS production in 2002 and developed alternatives including perfluorobutanesulfonate with a reduced number of carbon chains, a fully replacable material for PFOS has not been developed. The present study investigated the biodegradation features of 4 types of PFOS alternatives developed by Vijaykumar et al [ 4 ] and compared these molceules to PFOS.…”

Section: Introductionmentioning

confidence: 99%

Study on the biodegradation of perfluorooctanesulfonate (PFOS) and PFOS alternatives

Choi¹,

Son²,

Shin³

et al. 2016

Environ Health Toxicol

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ObjectivesIn this study, we investigated the biodegradation features of 4 perfluorooctanesulfonate (PFOS) alternatives developed at Changwon National University compared to those of PFOS.MethodsBiodegradation testing was performed with microorganisms cultured in the good laboratory practice laboratory of the Korea Environment Corporation for 28 days following the Organization for Economic Cooperation and Development guidelines for the testing of chemicals (Test No. 301 C).ResultsWhile C8F17SO3Na, PFOS sodium salt was not degraded after 28 days, the 4 alternatives were biodegraded at the rates of 20.9% for C15F9H21S2O8Na2, 8.4% for C17F9H 25S2O8Na2, 22.6% for C23F18H28S2O8Na2, and 23.6% for C25F17H32O13S3Na3.ConclusionsC25F17H32S3O13Na3, C23F18H28S2O8Na2, and C15F9H21S2O8Na2 were superior to PFOS in terms of biodegradation rates and surface tension, and thus they were considered highly applicable as PFOS alternatives. Environmental toxicity, human toxicity, and economic feasibility of these compounds should be investigated prior to their commercialization.

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Environmentally benign perfluorooctanesulfonate alternatives using a Zn/CuI mediated Michael-type addition in imidazolium ionic liquids

Abstract: Michael-type addition in imidazolium ionic liquids for the synthesis of bio-degradable and efficient alternatives to perfluorooctanesulfonic acid.

Cited by 15 publications

References 22 publications

Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate

Synthesis of Cyclic Type Semi-Fluorinated Disodium Alkanesulfonate

Ionic Liquids: Efficient Media for the Lipase-Catalyzed Michael Addition

Study on the biodegradation of perfluorooctanesulfonate (PFOS) and PFOS alternatives

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