Engle Lab Group Meeting 05/18/17 Miriam L. O Duill
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1 Engle Lab Group Meeting 05/18/17 Miriam L. O Duill
2 What are PFASs? Fluorosurfactants: fluorinated tail, hydrophilic head; lipophobic, hydrophobic Uses - Emulsifier in Teflon production - Textile impregnating agents - Fire-fighting foams - Insulation of electric wires - Semiconductor coatings - Hydraulic fluids in aircrafts 2
3 What are PFASs? Fluorosurfactants: fluorinated tail, hydrophilic head; lipophobic, hydrophobic Current Remediation - Barriers - Pump-and-treat technologies (e.g. ex-situ filtration through activated carbon) - Chemical oxidation (activation necessary) Uses - Emulsifier in Teflon production - Textile impregnating agents - Fire-fighting foams - Insulation of electric wires - Semiconductor coatings - Hydraulic fluids in aircrafts Challenge - PFCs (Perfluorinated Compounds) very stable towards oxidation (C F BDE 552 kj/mol) - Activation required Opportunity - Chemical depolymerisation of PFASs to small fluorinated building blocks: recycling Disadvantages - Stable, non-biodegradable (half-life >97 years) - Persistent organic pollutants: bioaccumulative, toxic - Health implications: carcinogens, brain, immune system, hormone levels, fertility - Now listed under the Stockholm Convention on Persistent Organic Chemicals, US (EPA): voluntary phase-out since 2006 California Environmental Contaminant Biomonitoring Program, March 2015 Meeting of the Scientific Guidance Panel; Z. Wang, J. C. DeWitt, C. P. Higgins, I. T. Cousins, Environ. Sci. Technol. 2017, 51, 2508; N. Törneman, Remedial methods and strategies for PFOS and PFOA. Presentation at 4th 3 Joint Nordic Meeting on Remediation of Contaminated Sites, September 2012, in Oslo, Norway.
4 Proposed Radical Decomposition Mechanism: Activation Modes - Persulfate radicals - Photocatalysis/UV - Heat/Plasma - Electrochemistry - Utrasound - Microbial J. Niu, H. Lin, C. Gong, X. Sun, Environ. Sci. Technol. 2013, 47, 14341; R. R. Giri, H. Ozaki, X. Guo, R. Takanami, S. Taniguchi, Int. J. Environ. Sci. Tech. 2014, 11, 1277; Y. Bo, L. Yingying, Y. Gang, D. Shubo, Z. Qiongfang, Z. Hong, Progress in Chem. 2014, 26,
5 Persulfate Activation Electrochemical Activation Photocatalytic Activation Other anodes used: SnO 2, PbO 2, boron-doped diamond, Ti/SnO 2 Sn-Bi, Ti/SnO 2 Sb, Ti/SnO 2 Sb/PbO 2, Ti/SnO 2 Sb/MnO 2 Ultrasound Activation Other photocatalysts used: ZnO, InO 2 H, Plasma Activation Lower ph (acid catalysis) increases efficiency Effect of atmosphere: N 2 > air > O 2 Effect of added anions: Br > none Cl > SO 4 2 C. S. Liu, C. P. Higgins, F. Wang, K. Shih, Separation and Purification Technology 2012, 91, 46; Y. Qian, X. Guo, Y. Zhang, Y. Peng, P. Sun, C.- H. Huang, J. Niu, X. Zhou, J. C. Crittenden, Environ. Sci. Technol. 2016, 50, 772; R. Dillert, D. Bahnemann, H. Hidaka, Chemosphere 2007, 67, 785; K. Yasuoka, K. Sasaki, R. Hayashi, Plasma Sources Sci. Technol. 2011, 20, ; J. Niu, H. Lin, C. Gong, X. Sun, Environ. Sci. Technol. 2013, 47, 14341; Y.-C. Lee, M.-J. Chen, C.-P. Huang, J. Kuo, S.-L. Lo, Ultrasonics Sonochemistry 2016, 31,
6 Y. Bo, L. Yingying, Y. Gang, D. Shubo, Z. Qiongfang, Z. Hong, Progress in Chem. 2014, 26,
7 Experimental Set-ups: Microbial Cultures, Activated Sludge, Soil and Sediment Laccase-catalysed degradation of PFOA Laccases: Copper-based oxidase enzymes; Laccase from Pleurotus ostreatus (Oyster mushroom): degradation/depolymerisation of lignin Tricopper site found in many laccases Source: Wikipedia J. Liu, S. M. Avandano, Environment International 2013, 61, 98; Q. Luo, J. Lu, H. Zhang, Z. Wang, M. Feng, S.-Y. D. Chiang, D. Woodward, Q. Huang, Environ. Sci. Technol. Lett. 2015, 2, 198; ; and references therein. 7
8 Question: Would it be possible to degrade PFCs into synthetically useful fluorinated building-blocks by transition-metal catalysis? Two aims: (1) recycle resistant organic pollutant, (2) cheap source of fluorinated reagents. R. N. Perutz, T. Braun, Transition Metal-mediated C F Bond Activation in: Comprehensive Organometallic Chemistry III, 2007, ; M. F. Kuehnel, D. Lentz, T. Braun, Angew. Chem. Int. Ed. 2013, 52, 3328; M. K. Whittlesey, E. Peris, ACS Catal. 2014, 4, 3152; T. A. Unzner, T. Magauer, Tet. Lett. 2015, 56, 877; T. Ahrens, J. Kohlmann, M. Ahrens, T. Braun, Chem. Rev. 2015, 115,
9 ! Engle Lab: Mark Boulous Joe Derosa John Gurak Matt Holcomb Zhen Liu Kin Yang, Ph.D Keary Engle, Ph.D! Carrie Gabaldon! NMR Facilities Staff: Laura Pasternack, Ph.D Dee-Hua Huang, Ph.D! Other labs at TSRI for support and supplies: Yu Lab Baran Lab Shenvi Lab Boger Lab! DAAD for funding 9
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