1. PFCs
In the Environment

2. What are PFCs? Anthropogenic or “man-made”
Fully fluorinated carbon chains
Perfluorochemicals, Perfluorinated Compounds
Polyfluorinated Compounds
Used in many commercial and household products
(Gao et. al. 2015)

3. Fluorine Most Electronegative element on the Periodic Table
Typically exists in nature as an insoluble compound
Very Pretty but dangerous
(Okazoe 2009)

4. Carbon Not as pretty as Fluorine unless it’s a diamond
Not as dangerous as Fluorine
Basis for organic chemistry, as it occurs in all living organisms.
(Dr. Nalley, C.U. 2015)

5. The Carbon-Fluorine Bond
The C-F bond is the strongest in organochemistry
This high-energy bond give PFCs extreme thermal and chemical stability
Resists degradation
Bioaccumulates

6. The Family is Large… Groups of PFCs: PASs – perfluoroalkyl surfactants
PFCAs – perfluorocarboxylic acid
PFSAs – polyfluorinated alkyl substances
FTOH – fluorotelomer alcohols
PFAAs – perfluoroalkyl acids
Minnesota Pollution Control Agency (2008)

7. Individual PFCs PFBA – perfluorobutanoic acid
PFBS – perfluorobutane sulfonate
PFPeA – perfluoropentanoic acid
PFHxA – perfluorohexanoic acid
PFHxS – perfluorohexane sulfonate
PFHpA – perfluoroheptanoic acid
PFOA – perfluorooctanoic acid
PFOS – perfluorooctane sulfonate
PFOSA – perfluorooctane sulfonamide
PFNA – perfluorononanoic acid
PFDA – perfluorodecanoic acid
PFUnA – perfluoroundecanoic acid
PFDoA – perfluorododecanoic acid
Minnesota Pollution Control Agency (2008)

8. The Two Most Studied PFCs are:
PFOA – perfluorooctanoic acid
PFOS – perfluorooctane sulfonate

9. These same qualities, allow them to persist in nature
The unique qualities of PFCs make them very attractive in many industrial and manufacturing uses
These same qualities, allow them to persist in nature
They are resistant to biodegradation and have been shown to bioaccumulate
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

10. How is a PFC made? Two main processes use to produce PFCs…
Electrochemical Fluorination (ECF)
-uses electrolysis to produce a linear or branched isomer.
Telomerization
-chemical reaction to produce longer chains adding a hydrophyllic and hydrophobic end to the chain.
Telomerized chains are useful as surfactants.
(Jahnke et. al. 2007)

11. PFCs are most well noted for their use as Polymers and Surfactants…
Polymer: a substance that has a molecular structure consisting chiefly or entirely of a large number of similar units bonded together, e.g., many synthetic organic materials used as plastics and resins.

12. Surfactant: a substance, such as a detergent that can reduce the surface tension of a liquid, thus allowing it to foam or penetrate solids; a wetting agent.
Collins English Dictionary - Complete & Unabridged 2012 Digital Edition © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009, 2012

13. PFCs are found in 98% of Humans Worldwide
PFCs are found in 98% of Humans Worldwide. How are PFCs getting into our bodies?
Food
Water
Air
Soil
Products

14. Microwave Popcorn Bags Non-stick Cookware
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

15. Household products…
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

16. Personal Care Products & Cosmetics
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

17. Textiles: Fabrics & Carpeting
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

18. Waterproofing…
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

19. Paints & Adhesives
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

20. Fire Foams and Flame Retardants…
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

21. And many other products...
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

22. Waste Sludge, Effluent Wastewater, Landfill Leaching…
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

23. Where they end up…
(Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

24. (Domingo et. al. 2012; Ding et. al. 2012; Mao et. al. 2015)

25. PFCs have been found in ALL biological and environmental matrices…
Air (indoor and outdoor)
Water (surface and groundwater)
Arctic Ice
Soils
Birds (avian species)
Polar Bears (nonhuman mammals)
Humans (mammals)
Marine Organisms
(Wen et. al. 2013)

26. Brief History of the PFC
By accident, Roy J. Plunkett makes the discovery of what would become, the first PFCs (1938)
(Lindstrom et. al. 2011)

27. The First of Many of Uses…WWII
(Lindstrom et. al. 2011)

28. Timeline… 1949 - DuPont introduces Teflon® brand
FDA approves a Zonyl® for use in food packaging
Organic fluorine found in human serum
M reports PFOA found in blood of workers
PFOA found in local drinking water near Washington Works plant, WV
Adapted from:(Lindstrom et. al. 2011)

29. 1998 - 3M reports EPS fluoro-chemicals widespread in human blood bank
M announces phase out of C8 based chemistry
EPA begins review of data linking C8 to health problems
EPA and 8 major companies launch 2010/2015 PFOA Stewardship Program
PFOS and related compounds are listed under Annex B of the Stockholm Convention on Persistent Organic Pollutants
Adapted from: (Lindstrom et. al. 2011)

30. PFCs are globally ubiquitous…
Research was conducted to see how PFCs travel
Observed: Tibetan Mountain Snow
Readings taken from
Temporal Trends show a decrease, most likely due to the decrease in manufacturing
Study done by Wang et. al. 2013

31. s 1. Mt. Muztagata, 2. Namco Lake, 3. Mt. Zuoqiupu.
Adapted from:
(Wang et. al. 2013)

32. (Wang et. al. 2013)

33. He compared three sites, with Arctic Ice.
The purpose of Wang’s study was to determine, if possible, how PFCs were showing up in remote locations.
He compared three sites, with Arctic Ice.
His study also shows, that PFCs travel via the atmosphere, not just through oceans.
The trend shows that PFC concentrations decreased as the manufacturing of PFCs decreased.
(Wang et. al. 2013)

34. Air
In a research study done by Fraser et. al. (2011), air samples were tested in office buildings. The findings were that the highest levels of PFCs were found in the newest building constructed, the second highest levels were recorded from an older building that was newly renovated, and the lowest levels were found to be in an older building with no renovations.

35. Health Concerns… Long half-lives of PFCs in Humans
years (Fraser et. al. 2011)
Due to hydrophilicity and lipophobicity, it binds to proteins
Proteins are the building blocks of our bodies
Toxicity has been demonstrated in rodent, avian, reptilian, mammalian and nonmammalian wildlife.
Immunotoxicity in Children
(DeWitt et. al. 2012; Dixon et. al. 2012; Grandjean et. al. 2013)

36. Worth mentioning….
Standardization, although better now was not so evident in earlier studies
Since PFCs are in so many products used in the laboratory, experiment results may/could have been compromised by the use of these items
The general concensus is, more research is needed!

37. The Future Alternative compounds Remediation Efforts
So prevalent, will be living with them a long, long, long time

38. DeWitt, Jamie C. , Margie M. Peden-Adams, Jennifer M
DeWitt, Jamie C., Margie M. Peden-Adams, Jennifer M. Keller, and Dori R. Germolec. Immunotoxicity of Perfluorinated Compounds: Recent Developments. Toxicologic Pathology. 2012, 40,
Ding, Guanghui, Jing Zhang, Yihong Chen, Luyan Wang, Man Wang, Deqi Xiong, and Yeqing Sun. Combined Effects of PFOS and PFOA on Zebrafish (Danio rerio) Embryos. Archives of Environmental Contamination and Toxicology , 64,

39. Dixon, Darlene, Casey E. Reed, Alicia B. Moore, Eugene A
Dixon, Darlene, Casey E. Reed, Alicia B. Moore, Eugene A. Gibbs-Flournoy, Erin P. Hines, Elizabeth A. Wallace, Jason P. Stanko, Yi Lu, Wendy N. Jefferson, Retha R. Newbold, and Suzanne E. Fenton. Histopathologic Changes in the Uterus, Cervix and Vagina of Immature CD-1 Mice Exposed to Low Doses of Pefluorooctanoic Acid (PFOA) in a Uterotrophic Assay.
Reproductive Toxicology. 2012, 33 (4),
Domingo, José L., Ingrid Ericson-Jogsten, Gemma Perelló, Martί Nadal, Bert Van Bavel, and Anna Kärrman. Journal of Agricultural and Food Chemistry , 60,

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41. Gao, Yan, Jianjie Fu, Huiming Cao, Yawei Wang, Aiqian Zhang, Yong Liang, Thanh Wang, Chunyan Zhao, and Guibin Jiang. Differential Accumulation and Elimination Behavior of Perfluoroalkyl Acid Isomers in Occupational Workers in a Manufactory in China. Environmental Science and Technology. 2015, 49,
Grandjean, Philippe, Esben Budtz-Jørgensen. Immunotoxicity of perfluorinated alkylates: calculation of benchmark doses based on serum concentrations in children. Environmental Health. 2013, 12, 35.

42. Jahnke, Annika, Lutz Ahrens, Ralf Ebinghaus, Urs Berger, Jonathan L
Jahnke, Annika, Lutz Ahrens, Ralf Ebinghaus, Urs Berger, Jonathan L. Barber, and Christian Temme. An improved method for the analysis of volatile polyfluorinated alkyl substances in environmental air samples. Analytical and Bioanalytical Chemistry. 2007, 387,
Lindstrom, Andrew B., Mark J. Strynar, and E. Laurence Libelo. Polyfluorinated Compounds: Past, Present, and Future. Environmental Science and Technology. 2011, 45,

43. Mao, Pan, and Daohing Wang. Biomonitoring of Perfluorinated
Mao, Pan, and Daohing Wang. Biomonitoring of Perfluorinated Compounds in a Drop of Blood. Environmental Science and Technology. 2015, 49,
PFCs in Minnesota’s Ambient Environment: 2008 Progress Report (online)

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Wen, Bei, Longfei Li, Yu Liu, Hongna Zhang, Xiaoyu Hu, Xiao-quan Shan, and Shuzhen Zhang. Mechanistic studies of perfluorooctane sulfonate, perfluorooctanoic acid uptake by maize (Zea mays L. cv. TY2). Plant and Soil: An International Journal on Plant-Soil Relationships ,