Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Perfluorooctanesulfonamide: Difference between pages

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| ImageFile = Perfluoroctansulfonamid.svg

| ImageFile1 = Perfluorooctanesulfonamide-3D-spacefill.png

| ImageSize1 = 230px

| ImageAlt1 = PFOSA molecule

| PIN = 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluorooctane-1-sulfonamide

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 754-91-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 80AM718FML

| InChI = 1/C8H2F17NO2S/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)29(26,27)28/h(H2,26,27,28)

| ChEBI = 138089

}}

|Section2={{Chembox Properties

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|Section7={{Chembox Hazards

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|Section8={{Chembox Related

| OtherFunction_label = compounds

| OtherFunction = [[Perfluorooctanesulfonic acid]] (PFOS), [[Perfluorobutanesulfonic acid]] (PFBS), [[Perfluorooctanoic acid]] (PFOA), [[Perfluorononanoic acid]] (PFNA)

}}

'''Perfluorooctanesulfonamide''' ('''PFOSA''') is a synthetic [[organofluorine compound]]. It is a [[fluorocarbon]] derivative and a [[perfluorinated compound]], having an eight-carbon chain and a terminal [[sulfonamide]] [[functional group]]. PFOSA, a [[persistent organic pollutant]], was an ingredient in [[3M]]'s former [[Scotchgard]] formulation<ref>{{cite journal

| doi=10.1021/cen-v084n049.p037

| author=Stephen K. Ritter

| title=Crystal Ball On The Environment: Detective work and expertise are used to evaluate environmental contaminants of emerging concern

| journal=Chemical & Engineering News

| volume=84 |issue=5 |pages=37–40 |date=January 2006

| url=http://pubs.acs.org/cen/science/84/8405sci1.html| doi-access=free

}} {{webarchive|url=https://web.archive.org/web/20060207134832/http://pubs.acs.org/cen/science/84/8405sci1.html |date=2006-02-07 }}</ref><ref>{{cite journal

|vauthors=Boulanger B, Vargo JD, Schnoor JL, Hornbuckle KC | title=Evaluation of perfluorooctane surfactants in a wastewater treatment system and in a commercial surface protection product

| journal=Environ. Sci. Technol.

| volume=39 |issue=15 |pages=5524–30 |date=August 2005 |pmid=16124283 |doi=10.1021/es050213u| bibcode=2005EnST...39.5524B

}} [http://pubs.acs.org/doi/suppl/10.1021/es050213u/suppl_file/es050213u.pdf Supporting Information] (PDF).</ref> from 1956 until 2003, and the compound was used to repel grease and water in food packaging<ref>{{cite journal

|vauthors=Fromme H, Tittlemier SA, Völkel W, Wilhelm M, Twardella D | title=Perfluorinated compounds &ndash; Exposure assessment for the general population in western countries

| journal=Int. J. Hyg. Environ. Health |volume=212 |issue=3 |pages=239–70 |date=May 2009

| pmid=18565792 |doi=10.1016/j.ijheh.2008.04.007}}</ref> along with other consumer applications.<ref>{{cite journal

|vauthors=Olsen GW, Church TR, Larson EB, van Belle G, Lundberg JK, Hansen KJ, Burris JM, Mandel JH, Zobel LR | title=Serum concentrations of perfluorooctanesulfonate and other fluorochemicals in an elderly population from Seattle, Washington

| journal=Chemosphere |volume=54 |issue=11 |pages=1599–611

| date=March 2004

| pmid=14675839 |doi=10.1016/j.chemosphere.2003.09.025| bibcode=2004Chmsp..54.1599O

}}</ref> It breaks down to form [[perfluorooctanesulfonic acid|perfluorooctane sulfonate]] (PFOS).<ref name=Leh/> The [[perfluorooctanesulfonyl fluoride]]-based chemistry that was used to make sulfonamides like PFOSA was phased out by 3M in the United States (US) during 2000&ndash;2002 but it has grown in China by other producers.

PFOSA can be synthesized from perfluorooctane[[sulfonyl halide]]s by reaction with liquid [[ammonia]]<ref name=Leh>{{cite journal

| last=Lehmler |first=HJ

| title=Synthesis of environmentally relevant fluorinated surfactants—a review

| journal=Chemosphere |volume=58 |issue=11 |pages=1471–96 |date=March 2005

| doi=10.1016/j.chemosphere.2004.11.078 |pmid=15694468|bibcode=2005Chmsp..58.1471L

}}</ref> or by a two step reaction via an [[azide]] followed by [[reduction (chemistry)|reduction]] with [[Zinc|Zn]] and [[hydrochloric acid|HCl]].<ref>{{cite journal

|vauthors=Lehmler HJ, Rama Rao VV, Nauduri D, Vargo JD, Parkin S | title=Synthesis and Structure of Environmentally Relevant Perfluorinated Sulfonamides

| journal=J. Fluorine Chem.

| volume=128 |issue=6 |pages=595–607 |date=June 2007

| pmid=18516235 |pmc=2394736 |doi=10.1016/j.jfluchem.2007.01.013}}</ref> PFOSA is also a metabolic by-product of ''N''-alkylated perfluorooctanesulfonamides.<ref name=Leh/> For example, ''N''-ethyl perfluorooctanesulfonamidoethanol (''N''-EtFOSE), which was primarily used on paper,<ref>{{cite journal

| author=Renner R

| title=Perfluorinated sources outside and inside

| journal=Environ. Sci. Technol.

| volume=38 |issue=5 |pages=80A |date=March 2004

| pmid=15046317 |doi=10.1021/es040387w| bibcode=2004EnST...38...80R

| doi-access=free}}</ref>

and ''N''-methyl perfluorooctanesulfonamidoethanol (''N''-MeFOSE), which was primarily used on carpets and textiles, both metabolize via [[acetate]]s to PFOSA.<ref>{{cite journal |vauthors=Olsen GW, Church TR, Miller JP, etal |title=Perfluorooctanesulfonate and other fluorochemicals in the serum of American Red Cross adult blood donors |journal=Environ. Health Perspect. |volume=111 |issue=16 |pages=1892–901 |date=December 2003 |pmid=14644663 |pmc=1241763 |doi=10.1289/ehp.6316 }}</ref>

In addition, PFOSA is thought to be the biologically active form of the [[insecticide]] [[Sulfluramid]] (''N''-ethyl perfluorooctanesulfonamide)<ref>{{cite journal

|vauthors=Grossman MR, Mispagel ME, Bowen JM | title=Distribution and tissue elimination in rats during and after prolonged dietary exposure to a highly fluorinated sulfonamide pesticide

| journal=J. Agric. Food Chem. |volume=40 |issue=12 |pages=2505–9 |date=December 1992

| doi=10.1021/jf00024a033}}</ref><ref name=Sta>{{cite journal

|vauthors=Starkov AA, Wallace KB | title=Structural determinants of fluorochemical-induced mitochondrial dysfunction

| journal=Toxicol. Sci.

| volume=66 |issue=2 |pages=244–52 |date=April 2002

| pmid=11896291 |doi= 10.1093/toxsci/66.2.244}}</ref>

as it is an extremely potent [[uncoupler]] of [[oxidative phosphorylation]]<ref name=Sta/><ref>{{cite journal

|vauthors=Schnellmann RG, Manning RO | title=Perfluorooctane sulfonamide: a structurally novel uncoupler of oxidative phosphorylation

| journal=Biochim. Biophys. Acta

| volume=1016 |issue=3 |pages=344–8 |date=April 1990

| pmid=2331477 |doi= 10.1016/0005-2728(90)90167-3}}</ref>

with an [[IC50|IC₅₀]] of about 1 [[micromolar]]<ref name=Leh/> (≈500 [[nanogram]]s per [[milliliter]] or [[parts per billion]]). PFOSA was the most toxic perfluorinated compound in a study with [[PC12 cells]].<ref name=Fie>{{cite journal

| author=Fields S

| title=Brain Effects Stick Around: PFCs and Neural Cell Development

| journal=Environ. Health Perspect. |volume=116 |issue=6 |pages=A258 |date=June 2008

|pmc=2430260 |doi=10.1289/ehp.116-a258b}}</ref><ref>{{cite journal

|vauthors=Slotkin TA, MacKillop EA, Melnick RL, Thayer KA, Seidler FJ | title=Developmental Neurotoxicity of Perfluorinated Chemicals Modeled in Vitro

| journal=Environ. Health Perspect. |volume=116 |issue=6 |pages=716–22 |date=June 2008

| pmid=18560525 |pmc=2430225 |doi=10.1289/ehp.11253}}</ref> Concentrations ranged from 10 to 250 micromolar in the study (or 5000 to 125,000 parts per billion).

Wildlife [[biomonitoring]] studies have found the highest level of PFOSA in the [[liver]] of [[common dolphin]] ([[Mediterranean Sea]], Italy) with a concentration of 878 [[parts per billion]]; the liver of [[mink]] from [[Illinois]], US, contained 590 parts per billion.<ref name=hou>{{cite journal

|vauthors=Houde M, Martin JW, Letcher RJ, Solomon KR, Muir DC | title=Biological monitoring of polyfluoroalkyl substances: A review

| journal=Environ. Sci. Technol.

| volume=40 |issue=11 |pages=3463–73 |date=June 2006

| pmid=16786681 |doi=10.1021/es052580b| bibcode=2006EnST...40.3463H

}} [http://pubs.acs.org/doi/suppl/10.1021/es052580b/suppl_file/es052580bsi20060303_021408.pdf Supporting Information] (PDF).</ref> In fish, the highest levels detected were in the liver of Norway [[Esox|Pike]] (91 parts per billion) and [[homogenization (biology)|homogenate]]s of [[slimy sculpin]] (150 parts per billion) from [[Lake Ontario]].<ref name=hou/> Differences in biotransformation across species could explain some of its presence.<ref name=hou/> In humans, PFOSA has been detected in sub- to low-parts per billion levels;<ref name=hou/> for example, in 1999–2000 US serum samples, the 95th [[percentile]] (or value where only 5% of the population was higher) was 1.4 parts per billion<ref>{{cite journal

|vauthors=Calafat AM, Kuklenyik Z, Reidy JA, Caudill SP, Tully JS, Needham LL | title=Serum concentrations of 11 polyfluoroalkyl compounds in the U.S. population: data from the National Health and Nutrition Examination Survey (NHANES)

| journal=Environ. Sci. Technol.

| volume=41 |issue=7 |pages=2237–42 |date=April 2007

| pmid=17438769 |doi=10.1021/es062686m| url=https://figshare.com/articles/Serum_Concentrations_of_11_Polyfluoroalkyl_Compounds_in_the_U_S_Population_Data_from_the_National_Health_and_Nutrition_Examination_Survey_NHANES_1999_2000/3015763

}}</ref> while in 2003–2004 the 95th percentile fell to 0.2 parts per billion.<ref name=Calafat2007>{{cite journal

|vauthors=Calafat AM, Wong LY, Kuklenyik Z, Reidy JA, Needham LL | title=Polyfluoroalkyl Chemicals in the U.S. Population: Data from the National Health and Nutrition Examination Survey (NHANES) 2003–2004 and Comparisons with NHANES 1999–2000

| journal=Environ. Health Perspect. |volume=115 |issue=11 |pages=1596–602 |date=November 2007

| pmid=18007991 |pmc=2072821 |doi=10.1289/ehp.10598}} [http://www.ehponline.org/members/2007/10598/suppl.pdf Supplemental Material] {{webarchive|url=https://web.archive.org/web/20081102231515/http://www.ehponline.org/members/2007/10598/suppl.pdf |date=2008-11-02 }} (PDF).</ref> However, whole-blood concentrations are about five times higher than those in [[blood plasma|blood plasma or serum]].<ref>{{cite journal

|vauthors=Kärrman A, Ericson I, van Bavel B, Darnerud PO, Aune M, Glynn A, Lignell S, Lindström G | title=Exposure of Perfluorinated Chemicals through Lactation: Levels of Matched Human Milk and Serum and a Temporal Trend, 1996–2004, in Sweden

| journal=Environ. Health Perspect. |volume=115 |issue=2 |pages=226–30 |date=February 2007

| pmid=17384769 |pmc=1831521 |doi=10.1289/ehp.9491}}</ref>

==See also==

*[[Fluorosurfactant]]

*[[Ionophore]]

==References==

{{reflist|2}}

==External links==

*[https://www.nilu.no/publikasjon/6492/ Perfluorinated Alkylated Substances (PFAS) in the European Nordic Environment]

[[Category:Perfluorinated compounds]]

[[Category:Sulfonamides]]