33:
241:
148:
24:
397:
1475:
Peden-Adams, M. M.; Keil, D. E.; Romano, T.; Mollenhauer, M. A. M.; Fort, D. J.; Guiney, P. D.; Houde, M.; Kannan, K.; Muir, D. C.; Rice, C. D.; Stuckey, J.; Segars, A. L.; Scott, T.; Talent, L.; Bossart, G. D.; Fair, P. A.; Keller, J. M. (2009). "Health effects of perfluorinated compounds—What are
552:(ECF). From 1966 to the 1990s, 3M production increased to meet demand for POSF-based compounds. In 1999, 3M reported POSF was its most highly produced fluorochemical. Before 2000, 3M was the largest global producer of POSF (mainly at their
97:
1551:
586:. In 2005 global production was estimated to be between 73 and 162 tonnes, and by 2006 Chinese production was estimated at >200 tonnes. Total historical global production was estimated at ~120,000 tonnes in 2009.
582:
Immediately after the 2000–2002 3M phaseout, production plummeted, but dominant and growing production shifted to China. In 2004 Chinese production of PFOS-based compounds was estimated to be <50
1529:
1327:
1249:
889:
463:
410:
892:(Annex B) in May 2009. As such, POSF is not "banned" but has approved uses and exemptions—along with a program (SC-4/19) in Annex B that encourages reduced production.
1030:
1136:
936:
564:
529:
results in a 25% yield for POSF, less than that for shorter perfluorosulfonyl fluorides. The POSF obtained is impure as it is a mixture of linear and branched
451:(PFOS) and PFOS-based compounds. These compounds have a variety of industrial and consumer uses, but POSF-derived substances ultimately degrade to form PFOS.
1243:"Results of the 2006 OECD Survey on Production and Use Of PFOS, PFAS, PFOA, PFCA, Their Related Substances and Products/Mixtures Containing These Substances"
290:
458:
ceased POSF use in 2002 and global production plummeted. However, Chinese production grew after 3M's phaseout. As of May 2009, POSF and PFOS are listed as
1079:(1999) 3M. 1999. The science of organic fluorochemistry. 3M Company, February 5, 1999. (PDF readily accessible via a Google search for the article title.)
1510:
1153:
1109:
575:. For these reasons, and USEPA pressure, the primary American producer of PFOS, 3M, announced, in May 2000, the phaseout of the production of PFOS,
1369:"Report of the Conference of the Parties of the Stockholm Convention on Persistent Organic Pollutants on the work of its fourth meeting"
1354:
1386:
Report of the
Conference of the Parties of the Stockholm Convention on Persistent Organic Pollutants on the work of its fourth meeting
1342:
Report of the
Conference of the Parties of the Stockholm Convention on Persistent Organic Pollutants on the work of its fourth meeting
1556:
255:
787:
The
Stockholm Convention lists a variety of acceptable purposes and specific exemptions for POSF and PFOS (and it salts) including
1428:
Houde M, Martin JW, Letcher RJ, Solomon KR, Muir DC (June 2006). "Biological monitoring of polyfluoroalkyl substances: A review".
1462:
1194:"Perspectives on the Inclusion of Perfluorooctane Sulfonate into the Stockholm Convention on Persistent Organic Pollutants"
589:
Most, if not all industrially synthesized perfluorooctanesulfonyl derivatives, such as PFOS, have POSF as their precursor.
417:
815:
549:
459:
448:
378:
366:
198:
1170:
Weber, Joseph (5 June 2000). "3M's Big
Cleanup – Why it decided to pull the plug on its best-selling stain repellant".
818:
copolymer (ETFE) layers and radio-opaque ETFE production, in-vitro diagnostic medical devices, and CCD colour filters);
1536:
Perfluorooctane
Sulfonyl Fluoride as an Initiator in Hot-Filament Chemical Vapor Deposition of Fluorocarbon Thin Films
219:
32:
1355:"Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty"
597:
POSF and POSF-based polymers degrade to form PFOS which is not known to degrade by any environmental processes. POSF
1242:
672:
370:
901:
780:
579:, and PFOS-related products. 3M stated that they would have made the same decision regardless of USEPA pressure.
155:
728:
1385:
1368:
1341:
568:
437:
904:
studies, where concentrations that have been detected are considered sufficient to "alter health parameters".
1507:
537:
479:
1150:
715:
Sulfonamides and sulfonamidoethanols synthesized from POSF can in turn react to form a variety of different
932:
143:
1089:
1035:
840:
576:
374:
977:
1399:"U.N. treaty expanded by 9 more chemicals: Participating nations get one year to decide on next steps"
23:
1437:
1284:
1205:
1043:
986:
45:
613:
236:
63:
1130:
1114:
748:
1031:"A first global production, emission, and environmental inventory for perfluorooctane sulfonate"
975:
Lehmler, HJ (2005). "Synthesis of
Environmentally Relevant Fluorinated Surfactants – A Review".
264:
InChI=1S/C8F18O2S/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
274:
InChI=1/C8F18O2S/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
1453:
1302:
1223:
1059:
1002:
744:
526:
490:
486:
475:
1485:
1445:
1406:
1292:
1213:
1051:
994:
716:
609:
571:
after receiving data on the global distribution and toxicity of PFOS, the key ingredient in
553:
444:
313:
207:
1514:
1157:
1105:
773:
740:
534:
441:
125:
240:
147:
73:
1441:
1288:
1209:
1047:
990:
900:
The POSF degradation product, PFOS, is the dominant perfluorinated compound detected in
888:
At the Fourth
Conference of Parties, decision SC-4/17 put POSF, along with PFOS, in the
913:
795:
762:
388:
998:
1545:
1172:
1092:
Cleaning & Restoration. www.ascr.org, (October, 2006). Accessed
October 25, 2008.
769:
657:
653:
346:
136:
1489:
826:
1320:
187:
1535:
855:
852:
electric and electronic parts for some colour printers and colour copy machines;
732:
832:
736:
598:
572:
336:
116:
483:
1457:
1306:
1227:
1063:
1006:
50:
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Heptadecafluorooctane-1-sulfonyl fluoride
1398:
802:
668:
661:
557:
530:
174:
156:
1449:
1297:
1272:
1218:
1193:
1055:
1321:"Hazard Assessment of Perfluorooctane sulfonate (PFOS) and its Salts"
298:
C(C(C(C(C(F)(F)S(=O)(=O)F)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)(F)F
387:
Except where otherwise noted, data are given for materials in their
560:
facilities) and global production peaked at ~4500 tonnes per year.
1090:"The Fluorochemical Dilemma: What the PFOS/PFOA fuss is all about"
602:
583:
96:
86:
811:
metal plating (hard metal plating) only in closed-loop systems;
1552:
Persistent organic pollutants under the
Stockholm Convention
533:, with ~70% linear. POSF can also be obtained by ECF of the
224:
455:
1110:"E.P.A. Orders Companies to Examine Effects of Chemicals"
1357:. Geneva: Stockholm Convention Secretariat. 8 May 2008.
405:
1328:
Organisation for
Economic Co-operation and Development
1250:
Organisation for Economic Co-operation and Development
890:
Stockholm Convention on Persistent Organic Pollutants
731:, POSF-derivatives have chemical properties that are
858:
for control of red imported fire ants and termites;
824:insect baits for control of leaf-cutting ants from
1273:"Perfluorochemical Surfactants in the Environment"
186:
1192:Wang T, Wang Y, Liao C, Cai Y, Jiang G (2009).
72:
937:National Institute of Standards and Technology
801:etching agent for compound semiconductors and
794:photo-resist and anti-reflective coatings for
454:Because of environmental concerns over PFOS,
8:
1135:: CS1 maint: numeric names: authors list (
1151:"PFOS-PFOA Information: What is 3M Doing?"
783:(fire fighting foam) as fluorosurfactants.
239:
146:
124:
15:
1296:
1217:
719:for different applications and products.
206:
755:as stain and soil repellents for carpet;
1029:Paul AG, Jones KC, Sweetman AJ (2009).
924:
295:
260:
235:
1187:
1185:
1183:
1128:
1024:
1022:
1020:
1018:
1016:
351:154 °C (309 °F; 427 K)
137:
970:
968:
966:
964:
962:
960:
958:
956:
954:
933:"Perfluoro-1-octanesulfonyl fluoride"
839:photo masks in the semiconductor and
267:Key: BHFJBHMTEDLICO-UHFFFAOYSA-N
7:
1100:
1098:
1075:
1073:
565:U.S. Environmental Protection Agency
548:In 1949, 3M began producing POSF by
876:coatings and coating additives; and
849:metal plating (decorative plating);
846:metal plating (hard metal plating);
478:by electrochemical fluorination of
277:Key: BHFJBHMTEDLICO-UHFFFAOYAY
177:
768:as specialty applications such as
462:(POPs) included in Annex B of the
14:
1374:. Geneva. 8 May 2009. p. 66.
999:10.1016/j.chemosphere.2004.11.078
861:chemically driven oil production;
814:certain medical devices (such as
758:as water repellents for clothing;
17:Perfluorooctanesulfonyl fluoride
430:Perfluorooctanesulfonyl fluoride
395:
31:
22:
1330:. 21 November 2002. p. 14.
391:(at 25 °C , 100 kPa).
1490:10.1016/j.reprotox.2008.11.016
1:
761:as fat and oil repellents in
751:derived from POSF have been:
460:persistent organic pollutants
1532:to the Stockholm Convention.
816:ethylene tetrafluoroethylene
550:electrochemical fluorination
449:perfluorooctanesulfonic acid
379:Perfluorobutanesulfonic acid
367:Perfluorooctanesulfonic acid
1476:the wildlife telling us?".
1271:Giesy JP, Kannan K (2002).
1573:
1530:PFOS Information submitted
1160:Accessed October 25, 2008.
808:aviation hydraulic fluids;
673:perfluorooctanesulfonamide
605:, however, occurs slowly.
371:Perfluorooctanesulfonamide
341:502.12 g/mol
781:aqueous film forming foam
385:
355:
306:
286:
251:
56:
44:
39:
30:
21:
1557:Perfluorinated compounds
914:Organofluorine compounds
870:textiles and upholstery;
569:perfluorinated compounds
1478:Reproductive Toxicology
538:octanesulfonyl chloride
480:octanesulfonyl fluoride
438:perfluorinated compound
1463:Supporting Information
1036:Environ. Sci. Technol.
841:liquid crystal display
667:POSF also reacts with
375:Perfluorooctanoic acid
1430:Environ. Sci. Technol
1277:Environ. Sci. Technol
1198:Environ. Sci. Technol
896:Environmental concern
729:carbon–fluorine bonds
447:. It is used to make
884:International status
879:rubber and plastics.
873:paper and packaging;
867:leather and apparel;
747:). The main uses of
739:("fat-afraid"), and
727:Because of multiple
652:Upon treatment with
616:to form PFOS salts:
567:began investigating
464:Stockholm Convention
46:Preferred IUPAC name
1442:2006EnST...40.3463H
1388:" (PDF). pp. 67–69.
1289:2002EnST...36..146G
1210:2009EnST...43.5171W
1048:2009EnST...43..386P
991:2005Chmsp..58.1471L
821:fire fighting foam;
749:chemical substances
614:potassium hydroxide
18:
1513:2011-07-26 at the
1506:. (June 2008). In
1156:2008-09-22 at the
1115:The New York Times
776:for airplanes; and
772:manufacturing and
735:("water-afraid"),
418:Infobox references
356:Related compounds
16:
1450:10.1021/es052580b
1298:10.1021/es022253t
1240:(December 2006).
1219:10.1021/es900464a
1108:(15 April 2003).
1056:10.1021/es802216n
939:. 1990. p. 1
843:(LCD) industries;
745:fluorosurfactants
717:functional groups
608:POSF reacts with
487:hydrogen fluoride
442:sulfonyl fluoride
436:) is a synthetic
426:Chemical compound
424:
423:
362:Related compounds
220:CompTox Dashboard
98:Interactive image
1564:
1518:
1500:
1494:
1493:
1472:
1466:
1461:
1425:
1419:
1418:
1416:
1414:
1407:Associated Press
1395:
1389:
1382:
1376:
1375:
1373:
1365:
1359:
1358:
1351:
1345:
1338:
1332:
1331:
1325:
1317:
1311:
1310:
1300:
1283:(7): 146A–152A.
1268:
1262:
1261:
1259:
1257:
1247:
1238:
1232:
1231:
1221:
1189:
1178:
1177:
1167:
1161:
1147:
1141:
1140:
1134:
1126:
1124:
1122:
1106:Lee, Jennifer 8.
1102:
1093:
1086:
1080:
1077:
1068:
1067:
1026:
1011:
1010:
972:
949:
948:
946:
944:
929:
774:hydraulic fluids
521:F + 17 H + 34 e.
445:functional group
408:
402:
399:
398:
314:Chemical formula
244:
243:
228:
226:
210:
190:
179:
158:
150:
139:
128:
100:
76:
35:
26:
19:
1572:
1571:
1567:
1566:
1565:
1563:
1562:
1561:
1542:
1541:
1526:
1521:
1515:Wayback Machine
1501:
1497:
1474:
1473:
1469:
1436:(11): 3463–73.
1427:
1426:
1422:
1412:
1410:
1397:
1396:
1392:
1383:
1379:
1371:
1367:
1366:
1362:
1353:
1352:
1348:
1344:" (PDF). p. 67.
1339:
1335:
1323:
1319:
1318:
1314:
1270:
1269:
1265:
1255:
1253:
1245:
1241:
1239:
1235:
1191:
1190:
1181:
1169:
1168:
1164:
1158:Wayback Machine
1148:
1144:
1127:
1120:
1118:
1104:
1103:
1096:
1087:
1083:
1078:
1071:
1028:
1027:
1014:
985:(11): 1471–96.
974:
973:
952:
942:
940:
931:
930:
926:
922:
910:
898:
886:
741:surface tension
725:
710:
706:
702:
698:
694:
690:
686:
682:
647:
643:
639:
635:
631:
627:
623:
595:
546:
535:sulfonyl halide
520:
516:
512:
508:
504:
500:
472:
427:
420:
415:
414:
413: ?)
404:
400:
396:
392:
363:
330:
326:
322:
316:
302:
299:
294:
293:
282:
279:
278:
275:
269:
268:
265:
259:
258:
247:
229:
222:
213:
193:
180:
168:
131:
103:
90:
79:
66:
52:
51:
12:
11:
5:
1570:
1568:
1560:
1559:
1554:
1544:
1543:
1540:
1539:
1533:
1525:
1524:External links
1522:
1520:
1519:
1495:
1467:
1420:
1390:
1377:
1360:
1346:
1333:
1312:
1263:
1233:
1204:(14): 5171–5.
1179:
1162:
1142:
1094:
1081:
1069:
1012:
950:
923:
921:
918:
917:
916:
909:
906:
897:
894:
885:
882:
881:
880:
877:
874:
871:
868:
865:
862:
859:
853:
850:
847:
844:
837:
822:
819:
812:
809:
806:
799:
796:semiconductors
792:
791:photo-imaging;
785:
784:
777:
766:
763:food packaging
759:
756:
724:
721:
713:
712:
708:
704:
700:
696:
692:
688:
684:
680:
650:
649:
645:
641:
637:
633:
629:
625:
621:
594:
591:
545:
542:
523:
522:
518:
514:
510:
506:
502:
498:
471:
468:
425:
422:
421:
416:
394:
393:
389:standard state
386:
383:
382:
364:
361:
358:
357:
353:
352:
349:
343:
342:
339:
333:
332:
328:
324:
320:
317:
312:
309:
308:
304:
303:
301:
300:
297:
289:
288:
287:
284:
283:
281:
280:
276:
273:
272:
270:
266:
263:
262:
254:
253:
252:
249:
248:
246:
245:
232:
230:
218:
215:
214:
212:
211:
203:
201:
195:
194:
192:
191:
183:
181:
173:
170:
169:
167:
166:
162:
160:
152:
151:
141:
133:
132:
130:
129:
121:
119:
113:
112:
109:
108:Abbreviations
105:
104:
102:
101:
93:
91:
84:
81:
80:
78:
77:
69:
67:
62:
59:
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
13:
10:
9:
6:
4:
3:
2:
1569:
1558:
1555:
1553:
1550:
1549:
1547:
1537:
1534:
1531:
1528:
1527:
1523:
1517:(PDF). p. 28.
1516:
1512:
1509:
1505:
1499:
1496:
1491:
1487:
1483:
1479:
1471:
1468:
1464:
1459:
1455:
1451:
1447:
1443:
1439:
1435:
1431:
1424:
1421:
1409:. 11 May 2009
1408:
1404:
1400:
1394:
1391:
1387:
1381:
1378:
1370:
1364:
1361:
1356:
1350:
1347:
1343:
1337:
1334:
1329:
1322:
1316:
1313:
1308:
1304:
1299:
1294:
1290:
1286:
1282:
1278:
1274:
1267:
1264:
1251:
1244:
1237:
1234:
1229:
1225:
1220:
1215:
1211:
1207:
1203:
1199:
1195:
1188:
1186:
1184:
1180:
1175:
1174:
1173:Business Week
1166:
1163:
1159:
1155:
1152:
1146:
1143:
1138:
1132:
1117:
1116:
1111:
1107:
1101:
1099:
1095:
1091:
1085:
1082:
1076:
1074:
1070:
1065:
1061:
1057:
1053:
1049:
1045:
1042:(2): 386–92.
1041:
1038:
1037:
1032:
1025:
1023:
1021:
1019:
1017:
1013:
1008:
1004:
1000:
996:
992:
988:
984:
980:
979:
971:
969:
967:
965:
963:
961:
959:
957:
955:
951:
938:
934:
928:
925:
919:
915:
912:
911:
907:
905:
903:
902:biomonitoring
895:
893:
891:
883:
878:
875:
872:
869:
866:
863:
860:
857:
854:
851:
848:
845:
842:
838:
835:
834:
829:
828:
823:
820:
817:
813:
810:
807:
804:
800:
797:
793:
790:
789:
788:
782:
778:
775:
771:
770:semiconductor
767:
764:
760:
757:
754:
753:
752:
750:
746:
743:lowering (as
742:
738:
734:
730:
722:
720:
718:
678:
677:
676:
674:
670:
665:
664:is obtained.
663:
659:
658:sulfonic acid
655:
654:sulfuric acid
619:
618:
617:
615:
611:
606:
604:
600:
592:
590:
587:
585:
580:
578:
574:
570:
566:
563:In 1999, the
561:
559:
555:
551:
543:
541:
539:
536:
532:
528:
496:
495:
494:
492:
488:
485:
481:
477:
469:
467:
465:
461:
457:
452:
450:
446:
443:
439:
435:
431:
419:
412:
407:
390:
384:
380:
376:
372:
368:
365:
360:
359:
354:
350:
348:
347:Boiling point
345:
344:
340:
338:
335:
334:
318:
315:
311:
310:
305:
296:
292:
285:
271:
261:
257:
250:
242:
238:
237:DTXSID5027140
234:
233:
231:
221:
217:
216:
209:
205:
204:
202:
200:
197:
196:
189:
185:
184:
182:
176:
172:
171:
164:
163:
161:
159:
154:
153:
149:
145:
142:
140:
138:ECHA InfoCard
135:
134:
127:
123:
122:
120:
118:
115:
114:
110:
107:
106:
99:
95:
94:
92:
88:
83:
82:
75:
71:
70:
68:
65:
61:
60:
55:
47:
43:
38:
34:
29:
25:
20:
1508:PFAA Days II
1503:
1502:Peden-Adams
1498:
1484:(3–4): 414.
1481:
1477:
1470:
1433:
1429:
1423:
1411:. Retrieved
1402:
1393:
1380:
1363:
1349:
1336:
1315:
1280:
1276:
1266:
1254:. Retrieved
1252:. p. 10
1236:
1201:
1197:
1171:
1165:
1145:
1119:. Retrieved
1113:
1088:Aziz Ullah.
1084:
1039:
1034:
982:
976:
941:. Retrieved
927:
899:
887:
856:insecticides
831:
825:
786:
726:
714:
666:
651:
607:
596:
588:
581:
562:
547:
524:
509:F + 17 F → C
473:
453:
433:
429:
428:
111:POSF, PFOSF
57:Identifiers
1413:5 September
1176:(3684): 96.
978:Chemosphere
733:hydrophobic
632:F + KOH → C
554:Decatur, AL
476:synthesized
307:Properties
144:100.005.638
1546:Categories
920:References
833:Acromyrmex
737:lipophobic
660:PFOS tetra
599:hydrolysis
593:Reactivity
573:Scotchgard
544:Production
337:Molar mass
208:KPV81L86O0
117:ChemSpider
85:3D model (
64:CAS Number
1256:30 August
1131:cite news
830:spp. and
484:anhydrous
470:Synthesis
373:(PFOSA),
165:206-200-6
157:EC Number
1511:Archived
1458:16786681
1403:NBC News
1307:11999053
1228:19708337
1154:Archived
1064:19238969
1007:15694468
908:See also
864:carpets;
805:filters;
671:to form
612:such as
527:reaction
491:equation
474:POSF is
377:(PFOA),
369:(PFOS),
331:S
74:307-35-7
1438:Bibcode
1285:Bibcode
1206:Bibcode
1044:Bibcode
987:Bibcode
943:10 July
803:ceramic
669:ammonia
662:hydrate
648:K + HF.
558:Antwerp
531:isomers
489:by the
440:with a
411:what is
409: (
381:(PFBS)
175:PubChem
1538:(PDF).
1465:(PDF).
1456:
1305:
1226:
1121:15 May
1062:
1005:
691:F + NH
584:tonnes
406:verify
403:
291:SMILES
40:Names
1504:et al
1372:(PDF)
1324:(PDF)
1246:(PDF)
836:spp.;
610:bases
603:water
525:This
256:InChI
87:JSmol
1454:PMID
1415:2009
1303:PMID
1258:2009
1224:PMID
1149:3M:
1137:link
1123:2009
1060:PMID
1003:PMID
945:2009
827:Atta
723:Uses
656:the
577:PFOA
556:and
434:POSF
199:UNII
188:9388
126:9019
1486:doi
1446:doi
1293:doi
1214:doi
1052:doi
995:doi
779:in
707:SNH
695:→ C
601:in
482:in
225:EPA
178:CID
1548::
1482:27
1480:.
1452:.
1444:.
1434:40
1432:.
1405:.
1401:.
1326:.
1301:.
1291:.
1281:36
1279:.
1275:.
1248:.
1222:.
1212:.
1202:43
1200:.
1196:.
1182:^
1133:}}
1129:{{
1112:.
1097:^
1072:^
1058:.
1050:.
1040:43
1033:.
1015:^
1001:.
993:.
983:58
981:.
953:^
935:.
701:17
687:SO
685:17
675::
644:SO
638:17
628:SO
626:17
540:.
517:SO
515:17
505:SO
503:17
493::
466:.
456:3M
325:18
1492:.
1488::
1460:.
1448::
1440::
1417:.
1384:"
1340:"
1309:.
1295::
1287::
1260:.
1230:.
1216::
1208::
1139:)
1125:.
1066:.
1054::
1046::
1009:.
997::
989::
947:.
798:;
765:;
711:.
709:2
705:2
703:O
699:F
697:8
693:3
689:2
683:F
681:8
679:C
646:3
642:2
640:O
636:F
634:8
630:2
624:F
622:8
620:C
519:2
513:F
511:8
507:2
501:H
499:8
497:C
432:(
401:N
329:2
327:O
323:F
321:8
319:C
227:)
223:(
89:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
