Supplermentary Date to IEAM vol 7. no. 4, pp SUPPLEMENTAL DATA

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1 SUPPLEMENTAL DATA PERFLUOROALKYL AND POLYFLUOROALKYL SUBSTANCES IN THE ENVIRONMENT: TERMINOLOGY, CLASSIFICATION, AND ORIGINS Robert C. Buck, James Franklin*, Urs Berger, Jason M. Conder, Ian T. Cousins, Pim de Voogt#, Allan Astrup Jensen, Kurunthachalam Kannan, Scott A. Mabury, and Stefan P. J. van Leeuwen E.I. du Pont de Nemours & Co. Inc., DuPont Chemicals and Fluoroproducts, 4417 Lancaster Pike, CRP B, Wilmington, DE USA CLFChem Consulting SPRL, 3 Clos du Châtaignier, BE1390 GrezDoiceau, Belgium (james.franklin@skynet.be) Department of Applied Environmental Science (ITM), Stockholm University, Svante Arrhenius väg 8, SE10691 Stockholm, Sweden (urs.berger@itm.su.se; ian.cousins@itm.su.se) ENVIRON International Corporation, Von Karman Avenue, Suite 600, Irvine, CA 92612, USA (jconder@environcorp.com) #Institute for Biodiversity and Ecosystem Dynamics, University of Amsterdam, PO Box 94248, NL1090 GE Amsterdam, The Netherlands (w.p.devoogt@uva.nl) Nordic Institute for Product Sustainability, Environmental Chemistry and Toxicology (NIPSECT), 1 Dalgas Boulevard, DK2000 Frederiksberg, Denmark (allan.astrup.jensen@gmail.com) Wadsworth Center, New York State Department of Health, and Department of Environmental Health Sciences, School of Public Health, State University of New York at Albany, Empire State Plaza, P.O. Box 509, Albany, NY , USA (kkannan@wadsworth.org) Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada (smabury@chem.utoronto.ca) RIKILT Institute of Food Safety, PO Box 230, 6700 AE Wageningen, The Netherlands (Stefan.van.Leeuwen@WUR.nl) *To whom correspondence may be addressed: james.franklin@skynet.be, Phone/Fax

2 Table of Contents PART 1 FAMILIES OF SUBSTANCES (NON POLYMERS)...4 PART 2 SELECTED INDIVIDUAL COMPOUNDS (NON POLYMERS)...7 Perfluoroalkyl carboxylic acids (and selected salts)...7 Perfluoroalkyl carboxylate anions...8 Perfluoroalkane sulfonic acids (and selected anions and salts)...10 Perfluoroalkane sulfinic acids...11 Perfluoroalkyl phosphonic acids...12 Perfluoroalkyl phosphinic acids...12 Perfluoroalkyl iodides...12 (n:2) Fluorotelomer iodides...13 (n:2) Fluorotelomer olefins...13 (n:2) Fluorotelomer alcohols...14 (n:2) Fluorotelomer acrylates...14 (n:2) Fluorotelomer methacrylates...15 Polyfluoroalkyl phosphoric acid monoesters...16 Polyfluoroalkyl phosphoric acid diesters...16 Semifluorinated n alkanes...17 Semifluorinated n alkenes...17 (n:2) Fluorotelomer (saturated) aldehydes...18 (n:2) Fluorotelomer unsaturated aldehydes...18 Perfluoroalkyl aldehydes...19 Perfluoroalkyl aldehyde hydrates...19 (n:2) Fluorotelomer (saturated) carboxylic acids...20 (n:2) Fluorotelomer unsaturated carboxylic acids

3 Other biotransformation products of n:2 FTOHs...21 (n:2) Fluorotelomer sulfonic acids...21 (n:2) Fluorotelomer sulfonate anions...22 Perfluoroalkane sulfonyl fluorides...22 Perfluoroalkane sulfonamides...23 N Methyl perfluoroalkane sulfonamides...23 N Ethyl perfluoroalkane sulfonamides...23 N,N Dialkyl perfluoroalkane sulfonamides...24 Perfluoroalkane sulfonamido ethanols...24 Perfluoroalkane sulfonamidoacetic acids...25 N Methyl perfluoroalkane sulfonamidoethanols...25 N Ethyl perfluoroalkane sulfonamidoethanols...26 N Methyl perfluoroalkane sulfonamidoacetic acids and salts...26 N Ethyl perfluoroalkane sulfonamidoacetic acids and salts...27 N Methyl perfluoroalkane sulfonamidoethyl acrylates...27 N Ethyl perfluoroalkane sulfonamidoethyl acrylates...28 N Methyl perfluoroalkane sulfonamidoethyl methacrylates...28 N Ethyl perfluoroalkane sulfonamidoethyl methacrylates...29 Figure S1. Terminology Decision Flowcharts...30 Example #1 8:2 Fluorotelomer alcohol...32 Example #2 Perfluorobutane sulfonamide...33 Example #3 Perfluorohexyl phosphonic acid...34 Example #4 Side chain Fluorinated Acrylate Polymer (Fluorotelomer origin)

4 PART 1 FAMILIES OF SUBSTANCES (NONPOLYMERS) NAME OF FAMILY Perfluoroalkyl substances Generic name: See main paper PFASs Perfluoroalkyl acids Includes perfluoroalkyl carboxylic, sulfonic, sulfinic, phosphonic and phosphinic acids PFAAs Perfluoroalkyl carboxylic acids C n F 2n+1 COOH PFCAs Perfluoroalkane sulfonic acids C n F 2n+1 SO 3 H PFSAs Perfluoroalkane sulfinic acids C n F 2n+1 SO 2 H PFSIAs Perfluoroalkyl phosphonic acids O=P(OH) 2 C n F 2n+1 PFPAs Perfluoroalkyl phosphinic acids O=P(OH)(C n F 2n+1 )(C m F 2m+1 ) PFPIAs NAME OF FAMILY Perfluoroalkyl iodides C n F 2n+1 I PFAIs (n:2) Fluorotelomer iodides C n F 2n+1 CH 2 CH 2 I (n:2) FTIs (n:2) Fluorotelomer olefins C n F 2n+1 CH=CH 2 (n:2) FTOs (n:2) Fluorotelomer alcohols C n F 2n+1 CH 2 CH 2 OH (n:2) FTOHs (n:2) Fluorotelomer acrylates C n F 2n+1 CH 2 CH 2 OC(O)CH=CH 2 (n:2) FTACs (n:2) Fluorotelomer methacrylates C n F 2n+1 CH 2 CH 2 OC(O)C(CH 3 )=CH 2 (n:2) FTMACs 4

5 Polyfluoroalkyl phosphoric acid esters / Polyfluoroalkyl phosphates / (n:2) Fluorotelomer phosphates (O)P(OH) 3x (OCH 2 CH 2 C n F 2n+1 ) x PAPs Polyfluoroalkyl phosphoric acid monoesters (O)P(OH) 2 (OCH 2 CH 2 C n F 2n+1 ) monopaps Polyfluoroalkyl phosphoric acid diesters (O)P(OH)(OCH 2 CH 2 C n F 2n+1 )(OCH 2 CH 2 C m F 2m+1 ) dipaps Semifluorinated nalkanes F(CF 2 ) n (CH 2 ) m H SFAs Semifluorinated nalkenes F(CF 2 ) n CH=CH(CH 2 ) m2 H SFAenes (n:2) Fluorotelomer (saturated) aldehydes C n F 2n+1 CH 2 CHO (n:2) FTALs (n:2) Fluorotelomer unsaturated aldehydes C n1 F 2n1 CF=CHCHO (n:2) FTUALs Perfluoroalkyl aldehydes C n F 2n+1 CHO PFALs Perfluoroalkyl aldehyde hydrates C n F 2n+1 CH(OH) 2 PFAL.H 2 Os (n:2) Fluorotelomer (saturated) carboxylic acids C n F 2n+1 CH 2 COOH (n:2) FTCAs (n:2) Fluorotelomer unsaturated carboxylic acids C n1 F 2n1 CF=CHCOOH (n:2) FTUCAs [Biotransformation product of (n+1):2 FTOH] C n F 2n+1 CH 2 CH 2 COOH n:3 Acid [Biotransformation product of (n+1):2 FTOH] C n F 2n+1 CH=CHCOOH n:3 UAcid (n:2) Fluorotelomer sulfonic acids C n F 2n+1 CH 2 CH 2 SO 3 H (n:2) FTSAs 5

6 NAME OF FAMILY Perfluoroalkane sulfonyl fluorides C n F 2n+1 SO 2 F PASFs Perfluoroalkane sulfonamides C n F 2n+1 SO 2 NH 2 FASAs NMethyl perfluoroalkane sulfonamides C n F 2n+1 SO 2 NH(CH 3 ) MeFASAs NEthyl perfluoroalkane sulfonamides C n F 2n+1 SO 2 NH(C 2 H 5 ) EtFASAs N,NDialkyl perfluoroalkane sulfonamides C n F 2n+1 SO 2 N(C m H 2m+1 )(C p H 2p+1 ), with m, p = 1 or 2 Me 2 FASAs, Et 2 FASAs, MeEtFASAs Perfluoroalkane sulfonamidoethanols C n F 2n+1 SO 2 NHCH 2 CH 2 OH FASEs Perfluoroalkane sulfonamidoacetic acids C n F 2n+1 SO 2 NHCH 2 COOH FASAAs NMethyl perfluoroalkane sulfonamidoethanols C n F 2n+1 SO 2 N(CH 3 )CH 2 CH 2 OH MeFASEs NEthyl perfluoroalkane sulfonamidoethanols C n F 2n+1 SO 2 N(C 2 H 5 )CH 2 CH 2 OH EtFASEs NMethyl perfluoroalkane sulfonamidoacetic acids C n F 2n+1 SO 2 N(CH 3 )CH 2 COOH MeFASAAs NEthyl perfluoroalkane sulfonamidoacetic acids C n F 2n+1 SO 2 N(C 2 H 5 )CH 2 COOH EtFASAAs NMethyl perfluoroalkane sulfonamidoethyl acrylates C n F 2n+1 SO 2 N(CH 3 )CH 2 CH 2 OC(O)CH=CH 2 MeFASACs NEthyl perfluoroalkane sulfonamidoethyl acrylates C n F 2n+1 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)CH=CH 2 EtFASACs NMethyl perfluoroalkane sulfonamidoethyl methacrylates C n F 2n+1 SO 2 N(CH 3 )CH 2 CH 2 OC(O)C(CH 3 )=CH 2 MeFASMACs NEthyl perfluoroalkane sulfonamidoethyl methacrylates C n F 2n+1 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)C(CH 3 )=CH 2 EtFASMACs 6

7 PART 2 SELECTED INDIVIDUAL COMPOUNDS (NONPOLYMERS) Perfluoroalkyl carboxylic acids (and selected salts) Trifluoroacetic acid CF 3 COOH TFAA Perfluoropropanoic acid C 2 F 5 COOH PFPrA Perfluorobutanoic acid C 3 F 7 COOH PFBA Ammonium perfluorobutanoate NH + 4 C 3 F 7 COO NH 4 PFBA Sodium perfluorobutanoate Na + C 3 F 7 COO NaPFBA Perfluoropentanoic acid C 4 F 9 COOH PFPeA Ammonium perfluoropentanoate NH + 4 C 4 F 9 COO NH 4 PFPeA Perfluorohexanoic acid C 5 F 11 COOH PFHxA Ammonium perfluorohexanoate NH + 4 C 5 F 11 COO NH 4 PFHxA Sodium perfluorohexanoate Na + C 5 F 11 COO NaPFHxA Perfluoroheptanoic acid C 6 F 13 COOH PFHpA Ammonium perfluoroheptanoate NH + 4 C 6 F 13 COO NH 4 PFHpA Sodium perfluoroheptanoate Na + C 6 F 13 COO NaPFHpA Perfluorooctanoic acid C 7 F 15 COOH PFOA Ammonium perfluorooctanoate NH 4 + C 7 F 15 COO APFO (or NH 4 PFOA) 7

8 Sodium perfluorooctanoate ²²²Na + C 7 F 15 COO NaPFOA Potassium perfluorooctanoate K + C 7 F 15 COO KPFOA Perfluorononanoic acid C 8 F 17 COOH PFNA Ammonium perfluorononanoate NH 4 + C 8 F 17 COO APFN (or NH 4 PFNA) Sodium perfluorononanoate Na + C 8 F 17 COO NaPFNA Perfluorodecanoic acid C 9 F 19 COOH PFDA Ammonium perfluorodecanoate NH 4 + C 9 F 19 COO NH 4 PFDA Perfluoroundecanoic acid C 10 F 21 COOH PFUnDA Ammonium perfluoroundecanoate NH 4 + C 10 F 21 COO NH 4 PFUnDA Perfluorododecanoic acid C 11 F 23 COOH PFDoDA Perfluorotridecanoic acid C 12 F 25 COOH PFTrDA Perfluorotetradecanoic acid C 13 F 27 COOH PFTeDA Perfluoropentadecanoic acid C 14 F 29 COOH PFPeDA Perfluorohexadecanoic acid C 15 F 31 COOH PFHxDA Perfluoroheptadecanoic acid C 16 F 33 COOH PFHpDA Perfluorooctadecanoic acid C 17 F 35 COOH PFODA Perfluoroalkyl carboxylate anions TFA Trifluoroacetate CF 3 COO 8

9 PFPrA Perfluoropropanoate C 2 F 5 COO PFBA Perfluorobutanoate C 3 F 7 COO PFPeA Perfluoropentanoate C 4 F 9 COO PFHxA Perfluorohexanoate C 5 F 11 COO PFHpA Perfluorohepanoate C 6 F 13 COO PFOA Perfluorooctanoate C 7 F 15 COO PFNA Perfluorononanoate C 8 F 17 COO PFDA Perfluorodecanoate C 9 F 19 COO PFUnDA Perfluoroundecanoate C 10 F 21 COO PFDoDA Perfluorododecanoate C 11 F 23 COO PFTrDA Perfluorotridecanoate C 12 F 25 COO PFTeDA Perfluorotetradecanoate C 13 F 27 COO PFPeDA Perfluoropentadecanoate C 14 F 29 COO PFHxDA Perfluorohexadecanoate C 15 F 31 COO None available PFHpDA Perfluoroheptadecanoate C 16 F 33 COO PFODA Perfluorooctadecanoate C 17 F 35 COO 9

10 Perfluoroalkane sulfonic acids (and selected anions and salts) Trifluoromethane sulfonic (or triflic) acid CF 3 SO 3 H TFMS Perfluoroethane sulfonic acid C 2 F 5 SO 3 H PFEtS Perfluoropropane sulfonic acid C 3 F 7 SO 3 H PFPrS Perfluorobutane sulfonic acid C 4 F 9 SO 3 H or PFBS Perfluorobutane sulfonate anion C 4 F 9 SO 3 Potassium perfluorobutane sulfonate K + C 4 F 9 SO PFBS KPFBS Perfluoropentane sulfonic acid C 5 F 11 SO 3 H PFPeS Potassium perfluopentane sulfonate K + C 5 F 11 SO KPFPeS Perfluorohexane sulfonic acid C 6 F 13 SO 3 H PFHxS Perfluorohexane sulfonate anion C 6 F 13 SO 3 Potassium perfluorohexane sulfonate K + C 6 F 13 SO PFHxS KPFHxS Perfluoroheptane sulfonic acid C 7 F 15 SO 3 H PFHpS Ammonium perfluoroheptane sulfonate NH 4 + C 7 F 15 SO 3 Potassium perfluoroheptane sulfonate K + C 7 F 15 SO NH 4 PFHpS KPFHpS Perfluorooctane sulfonic acid C 8 F 17 SO 3 H PFOS Perfluorooctane sulfonate anion C 8 F 17 SO PFOS 10

11 Ammonium perfluorooctane sulfonate NH + 4 C 8 F 17 SO 3 Sodium perfluorooctane sulfonate Na + C 8 F 17 SO 3 Potassium perfluorooctane sulfonate K + C 8 F 17 SO 3 Lithium perfluorooctane sulfonate Li + C 8 F 17 SO NH 4 PFOS NaPFOS KPFOS LiPFOS Tetraethylammonium perfluorooctane sulfonate Diethanolammonium perfluorooctane sulfonate N(C 2 H 5 ) 4 + C 8 F 17 SO 3 NH 2 (CH 2 CH 2 OH) 2 + C 8 F 17 SO NEt 4 PFOS Perfluorononane sulfonic acid C 9 F 19 SO 3 H PFNS Ammonium perfluorononane sulfonate NH 4 + C 9 F 19 SO NH 4 PFNS Perfluorodecane sulfonic acid C 10 F 21 SO 3 H PFDS Perfluorodecane sulfonate anion C 10 F 21 SO 3 Ammonium perfluorodecane sulfonate NH 4 + C 10 F 21 SO 3 Potassium perfluorodecane sulfonate K + C 10 F 21 SO PFDS NH 4 PFDS KPFDS Perfluoroundecane sulfonic acid C 11 F 23 SO 3 H PFUnDS Perfluorododecane sulfonic acid C 12 F 25 SO 3 H PFDoDS Perfluoroalkane sulfinic acids Perfluorooctane sulfinic acid C 8 F 17 SO 2 H PFOSI 11

12 Perfluoroalkyl phosphonic acids Perfluorohexyl phosphonic acid O=P(OH) 2 C 6 F C6PFPA Perfluorooctyl phosphonic acid O=P(OH) 2 C 8 F C8PFPA Perfluorodecyl phosphonic acid O=P(OH) 2 C 10 F C10PFPA Perfluoroalkyl phosphinic acids Bis(perfluorohexyl) phosphinic acid O=P(OH)(C 6 F 13 ) C6/C6PFPIA Bis(perfluorooctyl) phosphinic acid O=P(OH)(C 8 F 17 ) C8/C8PFPIA Perfluoro(hexyloctyl) phosphinic acid O=P(OH)(C 6 F 13 )(C 8 F 17 ) C6/C8PFPIA Perfluoroalkyl iodides Perfluoro (or pentafluoro)ethyl iodide C 2 F 5 I PFEI Perfluorobutyl iodide C 4 F 9 I PFBI Perfluorohexyl iodide C 6 F 13 I PFHxI Perfluorooctyl iodide C 8 F 17 I PFOI Perfluorodecyl iodide C 10 F 21 I PFDI 12

13 Perfluorododecyl iodide C 12 F 25 I PFDoDI Perfluorotetradecyl iodide C 14 F 29 I PFTeDI Perfluorohexadecyl iodide C 16 F 33 I PFHxDI Perfluorooctadecyl iodide C 18 F 37 I PFODI (n:2) Fluorotelomer iodides 4:2 Fluorotelomer iodide C 4 F 9 CH 2 CH 2 I :2 FTI 6:2 Fluorotelomer iodide C 6 F 13 CH 2 CH 2 I :2 FTI 8:2 Fluorotelomer iodide C 8 F 17 CH 2 CH 2 I :2 FTI 10:2 Fluorotelomer iodide C 10 F 21 CH 2 CH 2 I :2 FTI 12:2 Fluorotelomer iodide C 12 F 25 CH 2 CH 2 I :2 FTI 14:2 Fluorotelomer iodide C 14 F 29 CH 2 CH 2 I :2 FTI 16:2 Fluorotelomer iodide C 16 F 33 CH 2 CH 2 I :2 FTI 18:2 Fluorotelomer iodide C 18 F 37 CH 2 CH 2 I :2 FTI (n:2) Fluorotelomer olefins 4:2 Fluorotelomer olefin C 4 F 9 CH=CH :2 FTO 6:2 Fluorotelomer olefin C 6 F 13 CH=CH :2 FTO 13

14 8:2 Fluorotelomer olefin C 8 F 17 CH=CH :2 FTO 10:2 Fluorotelomer olefin C 10 F 21 CH=CH :2 FTO 12:2 Fluorotelomer olefin C 12 F 25 CH=CH :2 FTO (n:2) Fluorotelomer alcohols 4:2Fluorotelomer alcohol C 4 F 9 CH 2 CH 2 OH :2 FTOH 6:2Fluorotelomer alcohol C 6 F 13 CH 2 CH 2 OH :2 FTOH 8:2Fluorotelomer alcohol C 8 F 17 CH 2 CH 2 OH :2 FTOH 10:2Fluorotelomer alcohol C 10 F 21 CH 2 CH 2 OH :2 FTOH 12:2 Fluorotelomer alcohol C 12 F 25 CH 2 CH 2 OH :2 FTOH 14:2 Fluorotelomer alcohol C 14 F 29 CH 2 CH 2 OH :2 FTOH 16:2 Fluorotelomer alcohol C 16 F 33 CH 2 CH 2 OH :2 FTOH 18:2 Fluorotelomer alcohol C 18 F 37 CH 2 CH 2 OH :2 FTOH (n:2) Fluorotelomer acrylates 4:2 Fluorotelomer acrylate C 4 F 9 CH 2 CH 2 OC(O)CH=CH :2 FTAC 6:2 Fluorotelomer acrylate C 6 F 13 CH 2 CH 2 OC(O)CH=CH :2 FTAC 8:2 Fluorotelomer acrylate C 8 F 17 CH 2 CH 2 OC(O)CH=CH :2 FTAC 14

15 10:2 Fluorotelomer acrylate C 10 F 21 CH 2 CH 2 OC(O)CH=CH :2 FTAC 12:2 Fluorotelomer acrylate C 12 F 25 CH 2 CH 2 OC(O)CH=CH :2 FTAC 14:2 Fluorotelomer acrylate C 14 F 29 CH 2 CH 2 OC(O)CH=CH :2 FTAC 16:2 Fluorotelomer acrylate C 16 F 33 CH 2 CH 2 OC(O)CH=CH :2 FTAC 18:2 Fluorotelomer acrylate C 18 F 37 CH 2 CH 2 OC(O)CH=CH :2 FTAC (n:2) Fluorotelomer methacrylates 4:2 Fluorotelomer methacrylate C 4 F 9 CH 2 CH 2 OC(O)C(CH 3 )=CH :2 FTMAC 6:2 Fluorotelomer methacrylate C 6 F 13 CH 2 CH 2 OC(O)C(CH 3 )=CH :2 FTMAC 8:2 Fluorotelomer methacrylate C 8 F 17 CH 2 CH 2 OC(O)C(CH 3 )=CH :2 FTMAC 10:2 Fluorotelomer methacrylate C 10 F 21 CH 2 CH 2 OC(O)C(CH 3 )=CH :2 FTMAC 12:2 Fluorotelomer methacrylate C 12 F 25 CH 2 CH 2 OC(O)C(CH 3 )=CH :2 FTMAC 14:2 Fluorotelomer methacrylate C 14 F 29 CH 2 CH 2 OC(O)C(CH 3 )=CH :2 FTMAC 16:2 Fluorotelomer methacrylate C 16 F 33 CH 2 CH 2 OC(O)C(CH 3 )=CH :2 FTMAC 18:2 Fluorotelomer methacrylate C 18 F 37 CH 2 CH 2 OC(O)C(CH 3 )=CH :2 FTMAC 15

16 Polyfluoroalkyl phosphoric acid monoesters (= fluorotelomer phosphate monoesters) 4:2 Fluorotelomer phosphate monoester (O)P(OH) 2 (OCH 2 CH 2 C 4 F 9 ) :2 monopap 6:2 Fluorotelomer phosphate monoester (O)P(OH) 2 (OCH 2 CH 2 C 6 F 13 ) :2 monopap 8:2 Fluorotelomer phosphate monoester (O)P(OH) 2 (OCH 2 CH 2 C 8 F 17 ) :2 monopap 10:2 Fluorotelomer phosphate monoester (O)P(OH) 2 (OCH 2 CH 2 C 10 F 21 ) :2 monopap 12:2 Fluorotelomer phosphate monoester (O)P(OH) 2 (OCH 2 CH 2 C 12 F 25 ) :2 monopap Polyfluoroalkyl phosphoric acid diesters (= fluorotelomer phosphate diesters) 4:2 Fluorotelomer phosphate diester (O)P(OH)(OCH 2 CH 2 C 4 F 9 ) :2 dipap 4:2/6:2 Fluorotelomer phosphate diester (O)P(OH)(OCH 2 CH 2 C 4 F 9 )(OCH 2 CH 2 C 6 F 13 ) :2/6:2 dipap 6:2 Fluorotelomer phosphate diester (O)P(OH)(OCH 2 CH 2 C 6 F 13 ) :2 dipap 6:2/8:2 Fluorotelomer phosphate diester (O)P(OH)(OCH 2 CH 2 C 6 F 13 )(OCH 2 CH 2 C 8 F 17 ) :2/8:2 dipap 8:2 Fluorotelomer phosphate diester (O)P(OH)(OCH 2 CH 2 C 8 F 17 ) :2 dipap 8:2/10:2 Fluorotelomer phosphate diester (O)P(OH)(OCH 2 CH 2 C 8 F 17 )(OCH 2 CH 2 C 10 F 21 ) :2/10:2 dipap 10:2 Fluorotelomer phosphate diester (O)P(OH)(OCH 2 CH 2 C 10 F 21 ) :2 dipap 10:2/12:2 Fluorotel. phosphate diester (O)P(OH)(OCH 2 CH 2 C 10 F 21 )(OCH 2 CH 2 C 12 F 25 ) :2/12:2 dipap 12:2 Fluorotelomer phosphate diester (O)P(OH)(OCH 2 CH 2 C 12 F 25 ) :2 dipap 16

17 Semifluorinated nalkanes (Perfluorooctyl)ethane F(CF 2 ) 8 (CH 2 ) 2 H F 8 H 2 (Perfluorohexyl)octane F(CF 2 ) 6 (CH 2 ) 8 H F 6 H 8 (Perfluorohexyl)hexadecane F(CF 2 ) 6 (CH 2 ) 16 H F 6 H 16 (Perfluorooctyl)hexadecane F(CF 2 ) 8 (CH 2 ) 16 H F 8 H 16 (Perfluorohexadecyl)hexadecane F(CF 2 ) 16 (CH 2 ) 16 H F 16 H 16 Semifluorinated nalkenes (Perfluorohexyl)hexadecene F(CF 2 ) 6 CH=CH(CH 2 ) 14 H F 6 H 16 ene (Perfluorooctyl)hexadecene F(CF 2 ) 8 CH=CH(CH 2 ) 14 H F 8 H 16 ene (Perfluorohexadecyl)hexadecene F(CF 2 ) 16 CH=CH(CH 2 ) 14 H F 16 H 16 ene 17

18 (n:2) Fluorotelomer (saturated) aldehydes 4:2 Fluorotelomer aldehyde C 4 F 9 CH 2 CHO :2 FTAL 6:2 Fluorotelomer aldehyde C 6 F 13 CH 2 CHO :2 FTAL 8:2 Fluorotelomer aldehyde C 8 F 17 CH 2 CHO :2 FTAL 10:2 Fluorotelomer aldehyde C 10 F 21 CH 2 CHO :2 FTAL 12:2 Fluorotelomer aldehyde C 12 F 25 CH 2 CHO None available 12:2 FTAL (n:2) Fluorotelomer unsaturated aldehydes 4:2 Fluorotelomer unsaturated aldehyde C 3 F 7 CF=CHCHO :2 FTUAL 6:2 Fluorotelomer unsaturated aldehyde C 5 F 11 CF=CHCHO :2 FTUAL 8:2 Fluorotelomer unsaturated aldehyde C 7 F 15 CF=CHCHO :2 FTUAL 10:2 Fluorotelomer unsaturated aldehyde C 9 F 19 CF=CHCHO :2 FTUAL 12:2 Fluorotelomer unsaturated aldehyde C 11 F 23 CF=CHCHO None available 12:2 FTUAL 18

19 Perfluoroalkyl aldehydes Perfluoropentanal C 4 F 9 CHO PFPeAL Perfluoroheptanal C 6 F 13 CHO PFHpAL Perfluorooctanal C 7 F 15 CHO PFOAL Perfluorononanal C 8 F 17 CHO PFNAL Perfluoroundecanal C 10 F 21 CHO PFUnDAL Perfluoroalkyl aldehyde hydrates Perfluoropentanal hydrate C 4 F 9 CH(OH) PFPeAL.H 2 O Perfluoroheptanal hydrate C 6 F 13 CH(OH) PFHpAL.H 2 O Perfluorononanal hydrate C 8 F 17 CH(OH) PFNAL.H 2 O Perfluoroundecanal hydrate C 10 F 21 CH(OH) 2 None Available PFUnDAL.H 2 O 19

20 (n:2) Fluorotelomer (saturated) carboxylic acids 6:2 Fluorotelomer carboxylic acid C 6 F 13 CH 2 COOH :2 FTCA 8:2 Fluorotelomer carboxylic acid C 8 F 17 CH 2 COOH :2 FTCA 10:2 Fluorotelomer carboxylic acid C 10 F 21 CH 2 COOH :2 FTCA 12:2 Fluorotelomer carboxylic acid C 12 F 25 CH 2 COOH :2 FTCA (n:2) Fluorotelomer unsaturated carboxylic acids 6:2 Fluorotelomer unsaturated carboxylic acid 8:2 Fluorotelomer unsaturated carboxylic acid 10:2 Fluorotelomer unsaturated carboxylic acid 12:2 Fluorotelomer unsaturated carboxylic acid C 5 F 11 CF=CHCOOH :2 FTUCA C 7 F 15 CF=CHCOOH :2 FTUCA C 9 F 19 CF=CHCOOH :2 FTUCA C 11 F 23 CF=CHCOOH :2 FTUCA 20

21 Other biotransformation products of n:2 FTOHs 4:3 Acid C 4 F 9 (CH 2 ) 2 COOH :3 Acid 5:3 Acid C 5 F 11 (CH 2 ) 2 COOH :3 Acid 6:3 Acid C 6 F 13 (CH 2 ) 2 COOH :3 Acid 7:3 Acid C 7 F 15 (CH 2 ) 2 COOH :3 Acid 5:3 Unsaturated carboxylic acid C 5 F 11 CH=CHCOOH 7:3 Unsaturated carboxylic acid C 7 F 15 CH=CHCOOH (E) (E) (Z) 5:3 UAcid 7:3 UAcid (n:2) Fluorotelomer sulfonic acids 4:2 Fluorotelomer sulfonic acid C 4 F 9 CH 2 CH 2 SO 3 H :2 FTSA 6:2 Fluorotelomer sulfonic acid C 6 F 13 CH 2 CH 2 SO 3 H :2 FTSA 8:2 Fluorotelomer sulfonic acid C 8 F 17 CH 2 CH 2 SO 3 H :2 FTSA 10:2 Fluorotelomer sulfonic acid C 10 F 21 CH 2 CH 2 SO 3 H :2 FTSA 21

22 (n:2) Fluorotelomer sulfonate anions 4:2 Fluorotelomer sulfonate anion C 4 F 9 CH 2 CH 2 SO 3 6:2 Fluorotelomer sulfonate anion C 6 F 13 CH 2 CH 2 SO 3 8:2 Fluorotelomer sulfonate anion C 8 F 17 CH 2 CH 2 SO :2 FTSA :2 FTSA :2 FTSA 10:2 Fluorotelomer sulfonate anion C 10 F 21 CH 2 CH 2 SO 3 None available 10:2 FTSA Perfluoroalkane sulfonyl fluorides Perfluorobutane sulfonyl fluoride C 4 F 9 SO 2 F PBSF Perfluoropentane sulfonyl fluoride C 5 F 11 SO 2 F PPeSF Perfluorohexane sulfonyl fluoride C 6 F 13 SO 2 F PHxSF Perfluoroheptane sulfonyl fluoride C 7 F 15 SO 2 F PHpSF Perfluorooctane sulfonyl fluoride C 8 F 17 SO 2 F POSF Perfluorononane sulfonyl fluoride C 9 F 19 SO 2 F PNSF Perfluorodecane sulfonyl fluoride C 10 F 21 SO 2 F PDSF 22

23 Perfluoroalkane sulfonamides Perfluorobutane sulfonamide C 4 F 9 SO 2 NH FBSA Perfluoropentane sulfonamide C 5 F 11 SO 2 NH FPeSA Perfluorohexane sulfonamide C 6 F 13 SO 2 NH FHxSA Perfluoroheptane sulfonamide C 7 F 15 SO 2 NH FHpSA Perfluorooctane sulfonamide C 8 F 17 SO 2 NH FOSA NMethyl perfluoroalkane sulfonamides NMethyl perfluorobutane sulfonamide C 4 F 9 SO 2 NH(CH 3 ) MeFBSA NMethyl perfluoropentane sulfonamide C 5 F 11 SO 2 NH(CH 3 ) MeFPeSA NMethyl perfluorohexane sulfonamide C 6 F 13 SO 2 NH(CH 3 ) MeFHxSA NMethyl perfluoroheptane sulfonamide C 7 F 15 SO 2 NH(CH 3 ) MeFHpSA NMethyl perfluorooctane sulfonamide C 8 F 17 SO 2 NH(CH 3 ) MeFOSA NEthyl perfluoroalkane sulfonamides NEthyl perfluorobutane sulfonamide C 4 F 9 SO 2 NH(C 2 H 5 ) EtFBSA NEthyl perfluoropentane sulfonamide C 5 F 11 SO 2 NH(C 2 H 5 ) EtFPeSA NEthyl perfluorohexane sulfonamide C 6 F 13 SO 2 NH(C 2 H 5 ) EtFHxSA 23

24 NEthyl perfluoroheptane sulfonamide C 7 F 15 SO 2 NH(C 2 H 5 ) EtFHpSA NEthyl perfluorooctane sulfonamide C 8 F 17 SO 2 NH(C 2 H 5 ) (sulfluramid) EtFOSA N,NDialkyl perfluoroalkane sulfonamides N,NDimethyl perfluorooctane sulfonamide C 8 F 17 SO 2 N(CH 3 ) Me 2 FOSA N,NDiethyl perfluorooctane sulfonamide C 8 F 17 SO 2 N(C 2 H 5 ) Et 2 FOSA Perfluoroalkane sulfonamido ethanols Perfluorobutane sulfonamidoethanol C 4 F 9 SO 2 NHCH 2 CH 2 OH FBSE Perfluoropentane sulfonamidoethanol C 5 F 11 SO 2 NHCH 2 CH 2 OH None available FPeSE Perfluorohexane sulfonamidoethanol C 6 F 13 SO 2 NHCH 2 CH 2 OH FHxSE Perfluoroheptane sulfonamidoethanol C 7 F 15 SO 2 NHCH 2 CH 2 OH FHpSE Perfluorooctane sulfonamidoethanol C 8 F 17 SO 2 NHCH 2 CH 2 OH FOSE 24

25 Perfluoroalkane sulfonamidoacetic acids Perfluorobutane sulfonamidoacetic acid C 4 F 9 SO 2 NHCH 2 COOH FBSAA Perfluoropentane sulfonamidoacetic acid C 5 F 11 SO 2 NHCH 2 COOH FPeSAA Perfluorohexane sulfonamidoacetic acid C 6 F 2n+1 SO 2 NHCH 2 COOH FHxSAA Perfluoroheptane sulfonamidoacetic acid C 7 F 15 SO 2 NHCH 2 COOH FHpSAA Perfluorooctane sulfonamidoacetic acid C 8 F 17 SO 2 NHCH 2 COOH FOSAA NMethyl perfluoroalkane sulfonamidoethanols NMethyl perfluorobutane sulfonamidoethanol NMethyl perfluoropentane sulfonamidoethanol NMethyl perfluorohexane sulfonamidoethanol NMethyl perfluoroheptane sulfonamidoethanol NMethyl perfluorooctane sulfonamidoethanol C 4 F 9 SO 2 N(CH 3 )CH 2 CH 2 OH MeFBSE C 5 F 11 SO 2 N(CH 3 )CH 2 CH 2 OH MeFPeSE C 6 F 13 SO 2 N(CH 3 )CH 2 CH 2 OH MeFHxSE C 7 F 15 SO 2 N(CH 3 )CH 2 CH 2 OH MeFHpSE C 8 F 17 SO 2 N(CH 3 )CH 2 CH 2 OH MeFOSE 25

26 NEthyl perfluoroalkane sulfonamidoethanols NEthyl perfluorobutane sulfonamidoethanol NEthyl perfluoropentane sulfonamidoethanol NEthyl perfluorohexane sulfonamidoethanol NEthyl perfluoroheptane sulfonamidoethanol NEthyl perfluorooctane sulfonamidoethanol C 4 F 9 SO 2 N(C 2 H 5 )CH 2 CH 2 OH EtFBSE C 5 F 11 SO 2 N(C 2 H 5 )CH 2 CH 2 OH EtFPeSE C 6 F 13 SO 2 N(C 2 H 5 )CH 2 CH 2 OH EtFHxSE C 7 F 15 SO 2 N(C 2 H 5 )CH 2 CH 2 OH EtFHpSE C 8 F 17 SO 2 N(C 2 H 5 )CH 2 CH 2 OH EtFOSE NMethyl perfluoroalkane sulfonamidoacetic acids and salts NMethyl perfluorobutane sulfonamidoacetic acid NMethyl perfluorohexane sulfonamidoacetic acid NMethyl perfluorooctane sulfonamidoacetic acid Potassium Nmethyl perfluorooctane sulfonamidoacetate C 4 F 9 SO 2 N(CH 3 )CH 2 COOH MeFBSAA C 6 F 13 SO 2 N(CH 3 )CH 2 COOH MeFHxSAA C 8 F 17 SO 2 N(CH 3 )CH 2 COOH MeFOSAA K + C 8 F 17 SO 2 N(CH 3 )CH 2 COO KMeFOSAA 26

27 NEthyl perfluoroalkane sulfonamidoacetic acids and salts NEthyl perfluorobutane sulfonamidoacetic acid NEthyl perfluoropentane sulfonamidoacetic acid NEthyl perfluorohexane sulfonamidoacetic acid NEthyl perfluoroheptane sulfonamidoacetic acid NEthyl perfluorooctane sulfonamidoacetic acid Potassium Nethyl perfluorooctane sulfonamidoacetate C 4 F 9 SO 2 N(C 2 H 5 )CH 2 COOH EtFBSAA C 5 F 11 SO 2 N(C 2 H 5 )CH 2 COOH EtFPeSAA C 6 F 13 SO 2 N(C 2 H 5 )CH 2 COOH EtFHxSAA C 7 F 15 SO 2 N(C 2 H 5 )CH 2 COOH EtFHpSAA C 8 F 17 SO 2 N(C 2 H 5 )CH 2 COOH EtFOSAA K + C 8 F 17 SO 2 N(C 2 H 5 )CH 2 COO KEtFOSAA NMethyl perfluoroalkane sulfonamidoethyl acrylates NMethyl perfluorobutane sulfonamidoethyl acrylate NMethyl perfluoropentane sulfonamidoethyl acrylate NMethyl perfluorohexane sulfonamidoethyl acrylate C 4 F 9 SO 2 N(CH 3 )CH 2 CH 2 OC(O)CH=CH MeFBSAC C 5 F 11 SO 2 N(CH 3 )CH 2 CH 2 OC(O)CH=CH MeFPeSAC C 6 F 13 SO 2 N(CH 3 )CH 2 CH 2 OC(O)CH=CH MeFHxSAC 27

28 NMethyl perfluoroheptane sulfonamidoethyl acrylate NMethyl perfluorooctane sulfonamidoethyl acrylate C 7 F 15 SO 2 N(CH 3 )CH 2 CH 2 OC(O)CH=CH MeFHpSAC C 8 F 17 SO 2 N(CH 3 )CH 2 CH 2 OC(O)CH=CH MeFOSAC NEthyl perfluoroalkane sulfonamidoethyl acrylates NEthyl perfluorobutane sulfonamidoethyl acrylate NEthyl perfluoropentane sulfonamidoethyl acrylate NEthyl perfluorohexane sulfonamidoethyl acrylate NEthyl perfluoroheptane sulfonamidoethyl acrylate NEthyl perfluorooctane sulfonamidoethyl acrylate C 4 F 9 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)CH=CH EtFBSAC C 5 F 11 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)CH=CH EtFPeSAC C 6 F 13 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)CH=CH EtFHxSAC C 7 F 15 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)CH=CH EtFHpSAC C 8 F 17 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)CH=CH EtFOSAC NMethyl perfluoroalkane sulfonamidoethyl methacrylates NMethyl perfluorobutane sulfonamidoethyl methacrylate NMethyl perfluoropentane sulfonamidoethyl methacrylate NMethyl perfluorohexane sulfonamidoethyl methacrylate C 4 F 9 SO 2 N(CH 3 )CH 2 CH 2 OC(O)C(CH 3 )=CH MeFBSMAC C 5 F 11 SO 2 N(CH 3 )CH 2 CH 2 OC(O)C(CH 3 )=CH MeFPeSMAC C 6 F 13 SO 2 N(CH 3 )CH 2 CH 2 OC(O)C(CH 3 )=CH MeFHxSMAC 28

29 NMethyl perfluoroheptane sulfonamidoethyl methacrylate NMethyl perfluorooctane sulfonamidoethyl methacrylate C 7 F 15 SO 2 N(CH 3 )CH 2 CH 2 OC(O)C(CH 3 )=CH MeFHpSMAC C 8 F 17 SO 2 N(CH 3 )CH 2 CH 2 OC(O)C(CH 3 )=CH MeFOSMAC NEthyl perfluoroalkane sulfonamidoethyl methacrylates NEthyl perfluorobutane sulfonamidoethyl methacrylate NEthyl perfluoropentane sulfonamidoethyl methacrylate NEthyl perfluorohexane sulfonamidoethyl methacrylate NEthyl perfluoroheptane sulfonamidoethyl methacrylate NEthyl perfluorooctane sulfonamidoethyl methacrylate C 4 F 9 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)C(CH 3 )=CH EtFBSMAC C 5 F 11 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)C(CH 3 )=CH EtFPeSMAC C 6 F 13 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)C(CH 3 )=CH EtFHxSMAC C 7 F 15 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)C(CH 3 )=CH EtFHpSMAC C 8 F 17 SO 2 N(C 2 H 5 )CH 2 CH 2 OC(O)C(CH 3 )=CH EtFOSMAC 29

30 Figure S1. Terminology Decision Flowcharts How to determine nomenclature an Overview Fluorinated Polymer Is the substance a polymer or not? Non Polymer Fluorinated Polymer Decision Fluorinated Polymer Fluoropolymer What is the type of fluorinated polymer? Look at the polymer backbone. Perfluoropolyether (PFPE) Fluorinated Acrylate Fluorinated Urethane Fluorinated Oxetane Sidechain fluorinated 30

31 NonPolymer Decision Tree Non Polymer Poly fluorinated Substance Is the substance perfluorinated? Perfluorinated Substance 1. What is the atomic composition and chemical structure of the polyfluorinated substance? 2. What commercial manufacturing process does the substance originate from? What is the functional group X attached to the perfluoroalkyl chain in C n F 2n+1 X? What s X? X = F Perfluorocarbon Fluorotelomer Based X = C, P, or S oxidized Perfluoroalkyl Acid Electrochemical Fluorination (ECF) Based Fluorinated (Poly) Ether Based X = I, Cl, Br Perfluoroalkyl Halide X = CHO Perfluoroalkyl Aldehyde 31

32 Example #1 8:2 Fluorotelomer alcohol Substance Chemical Structure Question Conclusion F(CF 2 ) 8 CH 2 CH 2 OH Polymer or NonPolymer? Non Polymer F(CF 2 ) 8 CH 2 CH 2 OH F(CF 2 ) 8 CH 2 CH 2 OH F(CF 2 ) 8 CH 2 CH 2 OH F(CF 2 ) 8 CH 2 CH 2 OH Perfluorinated? No. The substance has a perfluoroalkyl chain, F(CF 2 ) 8, but all hydrogen on carbons are not replaced with fluorine Process Origin? Perfluoroalkyl chain with an ethylene spacer (CH 2 CH 2 ). Fluorotelomer origin Functionality Alcohol Eight fluorinated carbons, two nonfluorinated carbons, therefore 8:2 Polyfluorinated Fluorotelomer origin Fluorotelomer Alcohol (FTOH) 8:2 Fluorotelomer Alcohol (8:2 FTOH) 32

33 Example #2 Perfluorobutane sulfonamide Substance Chemical Structure Question Conclusion F(CF 2 ) 4 SO 2 NH 2 F F F F F F F F F Polymer or Non Polymer? NH 2 S O O NonPolymer Perfluorinated? F(CF 2 ) 4 SO 2 NH 2 F(CF 2 ) 4 SO 2 NH 2 F(CF 2 ) 4 SO 2 NH 2 Yes. All hydrogens on all four carbons are replaced with fluorine. Perfluorobutyl Perfluoroalkyl Acid? No. Has no acid functionality Process Origin? Perfluoroalkyl chain with a sulfone, SO 2, spacer. Electrochemical fluorination (ECF) origin Perfluorinated ECF origin F(CF 2 ) 4 SO 2 NH 2 Functionality Sulfonamide Perfluorobutanesulfonamide (FBSA) 33

34 Example #3 Perfluorohexyl phosphonic acid Substance Chemical Structure Question Conclusion F(CF 2 ) 6 P(=O)(OH) 2 F F F F F F F F F F F F F P O OH OH Polymer or Non Polymer? NonPolymer Perfluorinated? F(CF 2 ) 6 P(=O)(OH) 2 F(CF 2 ) 6 P(=O)(OH) 2 Yes. All hydrogens on all six carbons are replaced with fluorine. Perfluorohexyl Perfluoroalkyl Acid? Yes. Phosphonic, P(=O)(OH) 2, acid Perfluorinated Perfluoroalkyl acid F(CF 2 ) 6 P(=O)(OH) 2 Perfluorohexyl phosphonic acid (C6PFPA) 34

35 Example #4 Sidechain Fluorinated Acrylate Polymer (Fluorotelomer origin) Substance Chemical Structure Question Conclusion Polymer or NonPolymer? Polymer Fluoropolymer? No. The polymer backbone contains no fluorine bound to carbon. Sidechain fluorinated? Yes Sidechain fluorinated polymer Polymer Type? Acrylate Sidechain fluorinated acrylate polymer 35