Fluorotelomer alcohol

Commonly, an individual fluorotelomer alcohol molecule is named by the number of carbons that are fluorinated versus the number that are hydrocarbon-based. For example, 8:2 fluorotelomer alcohol would represent a molecule with 8 fluorinated carbons and a 2 carbon ethyl alcohol group. The structure of a fluorotelomer alcohol is most commonly F(CF₂)_nCH₂CH₂OH, where n is an even number.

The synthesis of fluorotelomer alcohols requires a varying number of tetrafluoroethylene monomers that form an oligomer with a pentafluoroethyl iodide telogen. The fluorinated iodide then undergoes an addition with ethylene to form an organoiodine compound with increased synthesis possibilities.{{cite journal |author=Lehmler HJ |title=Synthesis of environmentally relevant fluorinated surfactants—a review |journal=Chemosphere |volume=58 |issue=11 |pages=1471–96 |date=March 2005 |pmid=15694468 |doi=10.1016/j.chemosphere.2004.11.078 |bibcode=2005Chmsp..58.1471L }} The terminal iodine is replaced by a hydroxyl group to yield the fluorotelomer alcohol. The fluorotelomer alcohol can then be used to produce acrylate polymers with the fluorotelomer alcohols attached via ester functional groups.{{cite journal |last=Renner |first=Rebecca |title=Do perfluoropolymers biodegrade into PFOA? |journal=Environ. Sci. Technol. |volume=42 |issue=3 |pages=648–50 |date=February 2008 |doi=10.1021/es087093l |pmid=18323078 |bibcode=2008EnST...42..648R |doi-access= }}

Fluorotelomer alcohols are volatile and widely detected in air.{{cite journal |vauthors=Oono S, Harada KH, Mahmoud MA, Inoue K, Koizumi A |title=Current levels of airborne polyfluorinated telomers in Japan |journal=Chemosphere |volume=73 |issue=6 |pages=932–7 |date=October 2008 |pmid=18701130 |doi=10.1016/j.chemosphere.2008.06.069 |bibcode=2008Chmsp..73..932O }}{{cite journal |vauthors=Piekarz AM, Primbs T, Field JA, Barofsky DF, Simonich S |title=Semivolatile fluorinated organic compounds in Asian and western U.S. air masses |journal=Environ. Sci. Technol. |volume=41 |issue=24 |pages=8248–55 |date=December 2007 |pmid=18200847 |doi=10.1021/es0713678 |bibcode=2007EnST...41.8248P }}

Acrylate polymers with fluorotelomer substituents are under investigation for their potential to degrade into environmental contaminants." The USEPA has carried out environmental degradation studies with two DuPont acrylate polymers in four soils and water.{{Cite journal |last1=Washington |first1=John W. |last2=Jenkins |first2=Thomas M. |last3=Rankin |first3=Keegan |last4=Naile |first4=Jonathan E. |date=2015-01-20 |title=Decades-Scale Degradation of Commercial, Side-Chain, Fluorotelomer-Based Polymers in Soils and Water |url=https://pubs.acs.org/doi/10.1021/es504347u |journal=Environmental Science & Technology |language=en |volume=49 |issue=2 |pages=915–923 |doi=10.1021/es504347u |issn=0013-936X}}{{Cite journal |last1=Washington |first1=John W. |last2=Jenkins |first2=Thomas M. |date=2015-12-15 |title=Abiotic Hydrolysis of Fluorotelomer-Based Polymers as a Source of Perfluorocarboxylates at the Global Scale |url=https://pubs.acs.org/doi/10.1021/acs.est.5b03686 |journal=Environmental Science & Technology |language=en |volume=49 |issue=24 |pages=14129–14135 |doi=10.1021/acs.est.5b03686 |pmid=26526296 |issn=0013-936X}} These studies reported environmental degradation half-life ranges for these commercial fluorotelomer-based polymers of 33 to 112 years. FTOHs can also be used as intermediates in the production of surfactants.{{cite journal

|vauthors=Martin JW, Chan K, Mabury SA, O'Brien PJ |title=Bioactivation of fluorotelomer alcohols in isolated rat hepatocytes

|journal=Chem. Biol. Interact. |volume=177 |issue=3 |pages=196–203 |date=February 2009

|pmid=19041856 |doi=10.1016/j.cbi.2008.11.001 }}

Fluorotelomer alcohols can biodegrade to perfluorinated carboxylic acids, which persist in the environment and are found in the blood serum of populations and wildlife, such as the toxic PFOA and PFNA.{{cite journal |vauthors=Henderson WM, Smith MA |title=Perfluorooctanoic acid and perfluorononanoic acid in fetal and neonatal mice following in utero exposure to 8-2 fluorotelomer alcohol |journal=Toxicol. Sci. |volume=95 |issue=2 |pages=452–61 |date=February 2007 |pmid=17093205 |doi=10.1093/toxsci/kfl162 |doi-access=free }}{{cite journal |vauthors=Fang X, Zhang L, Feng Y, Zhao Y, Dai J |title=Immunotoxic effects of perfluorononanoic acid on BALB/c mice |journal=Toxicol. Sci. |volume=105 |issue=2 |pages=312–21 |date=October 2008 |pmid=18583369 |doi=10.1093/toxsci/kfn127 |doi-access=free }}

File:Aerobic biotransformation 8-2 FTOH soil labeled.svg

The fluorotelomer alcohols 6:2 FTOH and 8:2 FTOH have been found to be estrogenic.{{cite journal |vauthors=Maras M, Vanparys C, Muylle F |title=Estrogen-like properties of fluorotelomer alcohols as revealed by mcf-7 breast cancer cell proliferation |journal=Environ. Health Perspect. |volume=114 |issue=1 |pages=100–5 |date=January 2006 |pmid=16393665 |pmc=1332663 |doi=10.1289/ehp.8149 |url=http://ehpnet1.niehs.nih.gov/members/2005/8149/8149.html |display-authors=etal |url-status=dead |archive-url=https://archive.today/20120712032551/http://ehpnet1.niehs.nih.gov/members/2005/8149/8149.html |archive-date=2012-07-12 }}

File:10-2 FTOH.svg alcohol (10:2 FTOH)]]

The atmospheric oxidation of fluorotelomer alcohols can also result in anthropogenic perfluorinated carboxylic acids.{{cite journal |vauthors=Sulbaek Andersen MP, Nielsen OJ, Hurley MD |title=Atmospheric chemistry of 4:2 fluorotelomer alcohol (n-C4F9CH2CH2OH): products and mechanism of Cl atom initiated oxidation in the presence of NOx |journal=J Phys Chem A |volume=109 |issue=9 |pages=1849–56 |date=March 2005 |pmid=16833516 |doi=10.1021/jp045672g |url=http://pubs.acs.org/doi/abs/10.1021/jp0493576|display-authors=etal|bibcode=2005JPCA..109.1849S }} In addition to perfluorinated carboxylic acids, fluorotelomer alcohols can degrade to form unsaturated carboxylic acids which have been detected in bottlenose dolphins.{{cite journal |vauthors=Houde M, Wells RS, Fair PA |title=Polyfluoroalkyl compounds in free-ranging bottlenose dolphins (Tursiops truncatus) from the Gulf of Mexico and the Atlantic Ocean |journal=Environ. Sci. Technol. |volume=39 |issue=17 |pages=6591–8 |date=September 2005 |pmid=16190216 |doi=10.1021/es0506556 |display-authors=etal|bibcode=2005EnST...39.6591H }}

Fluorotelomer alcohols such as 4:2 FTOH, 6:2 FTOH, 8:2 FTOH, and 10:2 FTOH, have been identified as residuals in consumer products such as stain repellents, Zonyl FSE, and windshield wash, among others.{{cite journal |author=Renner R |title=Leftovers may explain perfluorinated compound puzzle |journal=Environ. Sci. Technol. |volume=40 |issue=5 |pages=1376–7 |date=March 2006 |pmid=16568742 |doi=10.1021/es0626436 |last2=Eichenseher |first2=Tasha |last3=Thrall |first3=Lizz|bibcode=2006EnST...40.1376R |doi-access= }} The United States Environmental Protection Agency has asked eight chemical companies to reduce the amount of residuals, including fluorotelomer alcohols, from products.

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Category:Alcohols

Category:Organofluorides

Category:Pollutants