Chemistry:Polybrominated diphenyl ethers

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Polybrominated diphenyl ethers or PBDEs, are a class of organobromine compounds that are used as flame retardants. Like other brominated flame retardants, PBDEs have been used in a wide array of products, including building materials, electronics, furnishings, motor vehicles, airplanes, plastics, polyurethane foams,[1] and textiles. They are structurally akin to polychlorinated diphenyl ethers (PCDEs), polychlorinated biphenyls (PCBs) and other polyhalogenated compounds, consisting of two halogenated aromatic rings. PBDEs are classified according to the average number of bromine atoms in the molecule. The life-saving benefits of fire retardants led to their popularization. Standards for mass transit vehicles continues to increase as of 2021.[2]

The health hazards of these chemicals have attracted scrutiny, especially in domestic settings.

Classes of PBDEs

Chemical structure of PBDEs

The family of PBDEs consists of 209 possible substances, which are called congeners (PBDE = C12H(10−x)BrxO (x = 1, 2, ..., 10 = m + n)). The number of isomers for mono-, di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, and decabromodiphenyl ethers are 3, 12, 24, 42, 46, 42, 24, 12, 3 and 1, respectively.[3] In the United States, PBDEs are marketed with the trade names DE-60F, DE-61, DE-62, and DE-71 applied to pentaBDE mixtures, DE-79 applied to octaBDE mixtures, and DE 83R and Saytex 102E applied to decaBDE mixtures. The available commercial PBDE products are not single compounds or even single congeners but rather mixtures of congeners.

Lower brominated PBDEs

These species average 1–4 bromine atoms per molecule and are regarded as more dangerous because they more efficiently bioaccumulate. Lower-brominated PBDEs have been known to affect hormone levels in the thyroid gland. Studies have linked them to reproductive and neurological risks at certain concentrations or higher.[4]

Higher brominated PBDEs

These species have average 5 or more bromine atoms per molecule.

The commercial mixture, named pentabromodiphenyl ether contains the pentabromo derivative predominantly (50–62%); however, the mixture also contains tetrabromides (24–38%) and hexabromides (4–8%), as well as traces of the tribromides (0–1%). In similar manner, commercial octabromodiphenyl ether is a mixture of homologs: hexa-, hepta-, octa-, nona-, and decabromides.

number formula name CAS Number InChIKey
PBDE-1 [math]\ce{ C12H9BrO }[/math] 2-bromodiphenyl ether 36563-47-0 RRWFUWRLNIZICP-UHFFFAOYSA-N
PBDE-2 [math]\ce{ C12H9BrO }[/math] 3-bromodiphenyl ether 6876-00-2 AHDAKFFMKLQPTD-UHFFFAOYSA-N
PBDE-3 [math]\ce{ C12H9BrO }[/math] 4-bromodiphenyl ether 101-55-3 JDUYPUMQALQRCN-UHFFFAOYSA-N
PBDE-4 [math]\ce{ C12H8Br2O }[/math] 2,2'-dibromodiphenyl ether 51452-87-0 JMSKYMHFNWGUJG-UHFFFAOYSA-N
PBDE-5 [math]\ce{ C12H8Br2O }[/math] 2,3-dibromodiphenyl ether 446254-14-4 JTYRXXKXOULVAP-UHFFFAOYSA-N
PBDE-6 [math]\ce{ C12H8Br2O }[/math] 2,3'-dibromodiphenyl ether 147217-72-9 GODQTPRKFHOLPH-UHFFFAOYSA-N
PBDE-7 [math]\ce{ C12H8Br2O }[/math] 2,4-dibromodiphenyl ether 171977-44-9 JMCIHKKTRDLVCO-UHFFFAOYSA-N
PBDE-8 [math]\ce{ C12H8Br2O }[/math] 2,4'-dibromodiphenyl ether 147217-71-8 RJQLQJZMLISKRJ-UHFFFAOYSA-N
PBDE-9 [math]\ce{ C12H8Br2O }[/math] 2,5-dibromodiphenyl ether 337513-66-3 URDWJMUOJJSXAE-UHFFFAOYSA-N
PBDE-10 [math]\ce{ C12H8Br2O }[/math] 2,6-dibromodiphenyl ether 51930-04-2 MUVDKHMQIZJFTC-UHFFFAOYSA-N
PBDE-11 [math]\ce{ C12H8Br2O }[/math] 3,3'-dibromodiphenyl ether 6903-63-5 ALSVFJIXSNRBLE-UHFFFAOYSA-N
PBDE-12 [math]\ce{ C12H8Br2O }[/math] 3,4-dibromodiphenyl ether 189084-59-1 SUUJFDKVPDCZQZ-UHFFFAOYSA-N
PBDE-13 [math]\ce{ C12H8Br2O }[/math] 3,4'-dibromodiphenyl ether 83694-71-7 BGPOVBPKODCMMN-UHFFFAOYSA-N
PBDE-14 [math]\ce{ C12H8Br2O }[/math] 3,5-dibromodiphenyl ether 46438-88-4 FOXBZJLXVUHYQZ-UHFFFAOYSA-N
PBDE-15 [math]\ce{ C12H8Br2O }[/math] 4,4'-dibromodiphenyl ether 2050-47-7 YAWIAFUBXXPJMQ-UHFFFAOYSA-N
PBDE-16 [math]\ce{ C12H7Br3O }[/math] 2,2',3-tribromodiphenyl ether 147217-74-1 VRNGWCVCSHJUEJ-UHFFFAOYSA-N
PBDE-17 [math]\ce{ C12H7Br3O }[/math] 2,2',4-tribromodiphenyl ether 147217-75-2 VYBFILXLBMWOLI-UHFFFAOYSA-N
PBDE-18 [math]\ce{ C12H7Br3O }[/math] 2,2',5-tribromodiphenyl ether 407606-55-7 FAZLXBWRNJAGSV-UHFFFAOYSA-N
PBDE-19 [math]\ce{ C12H7Br3O }[/math] 2,2',6-tribromodiphenyl ether 147217-73-0 YDFQHBRKURQGAH-UHFFFAOYSA-N
PBDE-20 [math]\ce{ C12H7Br3O }[/math] 2,3,3'-tribromodiphenyl ether 147217-76-3 RQJUBSPXDSGLRB-UHFFFAOYSA-N
PBDE-21 [math]\ce{ C12H7Br3O }[/math] 2,3,4-tribromodiphenyl ether 337513-67-4 RXWRVYYPLRPDOS-UHFFFAOYSA-N
PBDE-22 [math]\ce{ C12H7Br3O }[/math] 2,3,4'-tribromodiphenyl ether 446254-15-5 WZHNIFQVNBINLF-UHFFFAOYSA-N
PBDE-23 [math]\ce{ C12H7Br3O }[/math] 2,3,5-tribromodiphenyl ether 446254-16-6 XQHLKDAUZRXBGC-UHFFFAOYSA-N
PBDE-24 [math]\ce{ C12H7Br3O }[/math] 2,3,6-tribromodiphenyl ether 218304-36-0 GFLRHBRMAZDOIG-UHFFFAOYSA-N
PBDE-25 [math]\ce{ C12H7Br3O }[/math] 2,3',4-tribromodiphenyl ether 147217-77-4 AURKEOPYVUYTLO-UHFFFAOYSA-N
PBDE-26 [math]\ce{ C12H7Br3O }[/math] 2,3',5-tribromodiphenyl ether 337513-75-4 VUOBKVBAFJQQDB-UHFFFAOYSA-N
PBDE-27 [math]\ce{ C12H7Br3O }[/math] 2,3',6-tribromodiphenyl ether 337513-53-8 JUPZALSVNWJHII-UHFFFAOYSA-N
PBDE-28 [math]\ce{ C12H7Br3O }[/math] 2,4,4'-tribromodiphenyl ether 41318-75-6 UPNBETHEXPIWQX-UHFFFAOYSA-N
PBDE-29 [math]\ce{ C12H7Br3O }[/math] 2,4,5-tribromodiphenyl ether 337513-56-1 LTMKAFUXYKEDLR-UHFFFAOYSA-N
PBDE-30 [math]\ce{ C12H7Br3O }[/math] 2,4,6-tribromodiphenyl ether 155999-95-4 TVZAPPGLBLTACB-UHFFFAOYSA-N
PBDE-31 [math]\ce{ C12H7Br3O }[/math] 2,4',5-tribromodiphenyl ether 65075-08-3 PURZBWMLFRWRMG-UHFFFAOYSA-N
PBDE-32 [math]\ce{ C12H7Br3O }[/math] 2,4',6-tribromodiphenyl ether 189084-60-4 TYDVYKIQSZGUMV-UHFFFAOYSA-N
PBDE-33 [math]\ce{ C12H7Br3O }[/math] 2,3',4'-tribromodiphenyl ether 49690-94-0 BUQBQEYUVAKJQK-UHFFFAOYSA-N
PBDE-34 [math]\ce{ C12H7Br3O }[/math] 2,3',5'-tribromodiphenyl ether 446254-17-7 XMNXHCHZIPYCNA-UHFFFAOYSA-N
PBDE-35 [math]\ce{ C12H7Br3O }[/math] 3,3',4-tribromodiphenyl ether 147217-80-9 CDVYKQPKJYPWRO-UHFFFAOYSA-N
PBDE-36 [math]\ce{ C12H7Br3O }[/math] 3,3',5-tribromodiphenyl ether 147217-79-6 XUKPJLVONRTECE-UHFFFAOYSA-N
PBDE-37 [math]\ce{ C12H7Br3O }[/math] 3,4,4'-tribromodiphenyl ether 147217-81-0 YALAYFVVZFORPV-UHFFFAOYSA-N
PBDE-38 [math]\ce{ C12H7Br3O }[/math] 3,4,5-tribromodiphenyl ether 337513-54-9 DPGVQKLGQZZLMI-UHFFFAOYSA-N
PBDE-39 [math]\ce{ C12H7Br3O }[/math] 3,4',5-tribromodiphenyl ether 407606-57-9 UFFNOPDHJNQYKD-UHFFFAOYSA-N
PBDE-40 [math]\ce{ C12H6Br4O }[/math] 2,2',3,3'-tetrabromodiphenyl ether 337513-77-6 SXSUUFZWSVMTRL-UHFFFAOYSA-N
PBDE-41 [math]\ce{ C12H6Br4O }[/math] 2,2',3,4-tetrabromodiphenyl ether 337513-68-5 UAEBSKBXZAIRMX-UHFFFAOYSA-N
PBDE-42 [math]\ce{ C12H6Br4O }[/math] 2,2',3,4'-tetrabromodiphenyl ether 446254-18-8 HQDQKPAHIDGGMH-UHFFFAOYSA-N
PBDE-43 [math]\ce{ C12H6Br4O }[/math] 2,2',3,5-tetrabromodiphenyl ether 446254-19-9 LKMQHSYDVDIECC-UHFFFAOYSA-N
PBDE-44 [math]\ce{ C12H6Br4O }[/math] 2,2',3,5'-tetrabromodiphenyl ether 446254-20-2 VBGBGTYMDIVKNK-UHFFFAOYSA-N
PBDE-45 [math]\ce{ C12H6Br4O }[/math] 2,2',3,6-tetrabromodiphenyl ether 446254-21-3 VTFWUBIOZQCMQS-UHFFFAOYSA-N
PBDE-46 [math]\ce{ C12H6Br4O }[/math] 2,2',3,6'-tetrabromodiphenyl ether 446254-22-4 GBUUKJRFSKCMTB-UHFFFAOYSA-N
PBDE-47 [math]\ce{ C12H6Br4O }[/math] 2,2',4,4'-tetrabromodiphenyl ether 5436-43-1 XYBSIYMGXVUVGY-UHFFFAOYSA-N
PBDE-48 [math]\ce{ C12H6Br4O }[/math] 2,2',4,5-tetrabromodiphenyl ether 337513-55-0 FJGDNHOVDFREMP-UHFFFAOYSA-N
PBDE-49 [math]\ce{ C12H6Br4O }[/math] 2,2',4,5'-tetrabromodiphenyl ether 243982-82-3 QWVDUBDYUPHNHY-UHFFFAOYSA-N
PBDE-50 [math]\ce{ C12H6Br4O }[/math] 2,2',4,6-tetrabromodiphenyl ether 446254-23-5 FXUAKFRJBKFDSY-UHFFFAOYSA-N
PBDE-51 [math]\ce{ C12H6Br4O }[/math] 2,2',4,6'-tetrabromodiphenyl ether 189084-57-9 WKBBBTLDLKYGBI-UHFFFAOYSA-N
PBDE-52 [math]\ce{ C12H6Br4O }[/math] 2,2',5,5'-tetrabromodiphenyl ether 446254-24-6 CDTHXJORUCZHMD-UHFFFAOYSA-N
PBDE-53 [math]\ce{ C12H6Br4O }[/math] 2,2',5,6'-tetrabromodiphenyl ether 446254-25-7 SDVQGIMOFXMKHR-UHFFFAOYSA-N
PBDE-54 [math]\ce{ C12H6Br4O }[/math] 2,2',6,6'-tetrabromodiphenyl ether 446254-26-8 WCDCHQGVTZHVSO-UHFFFAOYSA-N
PBDE-55 [math]\ce{ C12H6Br4O }[/math] 2,3,3',4-tetrabromodiphenyl ether 446254-27-9 VIHUMJGEWQPWOT-UHFFFAOYSA-N
PBDE-56 [math]\ce{ C12H6Br4O }[/math] 2,3,3',4'-tetrabromodiphenyl ether 446254-28-0 NFOIVCGFYJIYIB-UHFFFAOYSA-N
PBDE-57 [math]\ce{ C12H6Br4O }[/math] 2,3,3',5-tetrabromodiphenyl ether 337513-82-3 CSIFWDKYUJLQEB-UHFFFAOYSA-N
PBDE-58 [math]\ce{ C12H6Br4O }[/math] 2,3,3',5'-tetrabromodiphenyl ether 446254-29-1 SWOYBZHGPZIRHS-UHFFFAOYSA-N
PBDE-59 [math]\ce{ C12H6Br4O }[/math] 2,3,3',6-tetrabromodiphenyl ether 446254-30-4 DMAMJZQQOWYEHT-UHFFFAOYSA-N
PBDE-60 [math]\ce{ C12H6Br4O }[/math] 2,3,4,4'-tetrabromodiphenyl ether 446254-31-5 ARERIMFZYPFJAV-UHFFFAOYSA-N
PBDE-61 [math]\ce{ C12H6Br4O }[/math] 2,3,4,5-tetrabromodiphenyl ether 446254-32-6 NDRSXNBQWAOQPP-UHFFFAOYSA-N
PBDE-62 [math]\ce{ C12H6Br4O }[/math] 2,3,4,6-tetrabromodiphenyl ether 446254-33-7 YIQYWYZZLOZVRM-UHFFFAOYSA-N
PBDE-63 [math]\ce{ C12H6Br4O }[/math] 2,3,4',5-tetrabromodiphenyl ether 446254-34-8 HNICYXFGCWPYGC-UHFFFAOYSA-N
PBDE-64 [math]\ce{ C12H6Br4O }[/math] 2,3,4',6-tetrabromodiphenyl ether 446254-35-9 LDCXVFJUWKKBNY-UHFFFAOYSA-N
PBDE-65 [math]\ce{ C12H6Br4O }[/math] 2,3,5,6-tetrabromodiphenyl ether 446254-36-0 HPEUYVBOPJQVPN-UHFFFAOYSA-N
PBDE-66 [math]\ce{ C12H6Br4O }[/math] 2,3',4,4'-tetrabromodiphenyl ether 189084-61-5 DHUMTYRHKMCVAG-UHFFFAOYSA-N
PBDE-67 [math]\ce{ C12H6Br4O }[/math] 2,3',4,5-tetrabromodiphenyl ether 446254-37-1 OARGWSONVLGXQA-UHFFFAOYSA-N
PBDE-68 [math]\ce{ C12H6Br4O }[/math] 2,3',4,5'-tetrabromodiphenyl ether 446254-38-2 UFWGRLCUOLLWAO-UHFFFAOYSA-N
PBDE-69 [math]\ce{ C12H6Br4O }[/math] 2,3',4,6-tetrabromodiphenyl ether 327185-09-1 NHZNRCYNZJADTG-UHFFFAOYSA-N
PBDE-70 [math]\ce{ C12H6Br4O }[/math] 2,3',4',5-tetrabromodiphenyl ether 446254-39-3 GHQMTYWQVJZWAR-UHFFFAOYSA-N
PBDE-71 [math]\ce{ C12H6Br4O }[/math] 2,3',4',6-tetrabromodiphenyl ether 189084-62-6 COPAGYRSCJVION-UHFFFAOYSA-N
PBDE-72 [math]\ce{ C12H6Br4O }[/math] 2,3',5,5'-tetrabromodiphenyl ether 446254-40-6 GBBNZKQTOOZGIS-UHFFFAOYSA-N
PBDE-73 [math]\ce{ C12H6Br4O }[/math] 2,3',5',6-tetrabromodiphenyl ether 446254-41-7 WQFLVWXBCRJAQN-UHFFFAOYSA-N
PBDE-74 [math]\ce{ C12H6Br4O }[/math] 2,4,4',5-tetrabromodiphenyl ether 446254-42-8 LXCFDVVDUVPAGR-UHFFFAOYSA-N
PBDE-75 [math]\ce{ C12H6Br4O }[/math] 2,4,4',6-tetrabromodiphenyl ether 189084-63-7 BWCNKMFFUGBFGB-UHFFFAOYSA-N
PBDE-76 [math]\ce{ C12H6Br4O }[/math] 2,3',4',5'-tetrabromodiphenyl ether 446254-43-9 NCSWBJSFVPJPPK-UHFFFAOYSA-N
PBDE-77 [math]\ce{ C12H6Br4O }[/math] 3,3',4,4'-tetrabromodiphenyl ether 93703-48-1 RYGLOWMCGZHYRQ-UHFFFAOYSA-N
PBDE-78 [math]\ce{ C12H6Br4O }[/math] 3,3',4,5-tetrabromodiphenyl ether 446254-45-1 HWOBLTZZSVXBOJ-UHFFFAOYSA-N
PBDE-79 [math]\ce{ C12H6Br4O }[/math] 3,3',4,5'-tetrabromodiphenyl ether 446254-48-4 LELQGHJEUVRPEV-UHFFFAOYSA-N
PBDE-80 [math]\ce{ C12H6Br4O }[/math] 3,3',5,5'-tetrabromodiphenyl ether 103173-66-6 HFIOZJQRZKNPKJ-UHFFFAOYSA-N
PBDE-81 [math]\ce{ C12H6Br4O }[/math] 3,4,4',5-tetrabromodiphenyl ether 446254-50-8 ULFOIXCXIWHJDS-UHFFFAOYSA-N
PBDE-82 [math]\ce{ C12H5Br5O }[/math] 2,2',3,3',4-pentabromodiphenyl ether 327185-11-5 RQMSPGJESCCPQX-UHFFFAOYSA-N
PBDE-83 [math]\ce{ C12H5Br5O }[/math] 2,2',3,3',5-pentabromodiphenyl ether 446254-51-9 XAHYSNUYJLNDBX-UHFFFAOYSA-N
PBDE-84 [math]\ce{ C12H5Br5O }[/math] 2,2',3,3',6-pentabromodiphenyl ether 446254-52-0 PPIZNRAVQHNLJM-UHFFFAOYSA-N
PBDE-85 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4,4'-pentabromodiphenyl ether 182346-21-0 DMLQSUZPTTUUDP-UHFFFAOYSA-N
PBDE-86 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4,5-pentabromodiphenyl ether 446254-53-1 YMVWYUWOUOQCQP-UHFFFAOYSA-N
PBDE-87 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4,5'-pentabromodiphenyl ether 446254-54-2 WKYQUGCIKNOXFW-UHFFFAOYSA-N
PBDE-88 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4,6-pentabromodiphenyl ether 446254-55-3 OPZUHBCVIZNZFB-UHFFFAOYSA-N
PBDE-89 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4,6'-pentabromodiphenyl ether 446254-56-4 XGFLJLJXVIMCNR-UHFFFAOYSA-N
PBDE-90 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4',5-pentabromodiphenyl ether 446254-57-5 BATFXMGTVIESIQ-UHFFFAOYSA-N
PBDE-91 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4',6-pentabromodiphenyl ether 446254-58-6 HWNJTZKDPNZUSO-UHFFFAOYSA-N
PBDE-92 [math]\ce{ C12H5Br5O }[/math] 2,2',3,5,5'-pentabromodiphenyl ether 446254-59-7 QWSQOVAGRDRZLM-UHFFFAOYSA-N
PBDE-93 [math]\ce{ C12H5Br5O }[/math] 2,2',3,5,6-pentabromodiphenyl ether 446254-60-0 BRTPVPJQMWLDNO-UHFFFAOYSA-N
PBDE-94 [math]\ce{ C12H5Br5O }[/math] 2,2',3,5,6'-pentabromodiphenyl ether 446254-61-1 JOPASNJHCFYVHD-UHFFFAOYSA-N
PBDE-95 [math]\ce{ C12H5Br5O }[/math] 2,2',3,5',6-pentabromodiphenyl ether 446254-62-2 BZDYRALIEYVMEP-UHFFFAOYSA-N
PBDE-96 [math]\ce{ C12H5Br5O }[/math] 2,2',3,6,6'-pentabromodiphenyl ether 446254-63-3 ZFCJNRDWGBZUED-UHFFFAOYSA-N
PBDE-97 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4',5'-pentabromodiphenyl ether 446254-64-4 MAGYDGJRSCULJL-UHFFFAOYSA-N
PBDE-98 [math]\ce{ C12H5Br5O }[/math] 2,2',3,4',6'-pentabromodiphenyl ether 38463-82-0 OCLWEJVGAUFXQU-UHFFFAOYSA-N
PBDE-99 [math]\ce{ C12H5Br5O }[/math] 2,2',4,4',5-pentabromodiphenyl ether 60348-60-9 WHPVYXDFIXRKLN-UHFFFAOYSA-N
PBDE-100 [math]\ce{ C12H5Br5O }[/math] 2,2',4,4',6-pentabromodiphenyl ether 189084-64-8 NSKIRYMHNFTRLR-UHFFFAOYSA-N
PBDE-101 [math]\ce{ C12H5Br5O }[/math] 2,2',4,5,5'-pentabromodiphenyl ether 446254-65-5 QUZWDWNIWWAQDI-UHFFFAOYSA-N
PBDE-102 [math]\ce{ C12H5Br5O }[/math] 2,2',4,5,6'-pentabromodiphenyl ether 446254-66-6 JHFMCUVMAIQWRI-UHFFFAOYSA-N
PBDE-103 [math]\ce{ C12H5Br5O }[/math] 2,2',4,5',6-pentabromodiphenyl ether 446254-67-7 RJEMKRNASVHYKR-UHFFFAOYSA-N
PBDE-104 [math]\ce{ C12H5Br5O }[/math] 2,2',4,6,6'-pentabromodiphenyl ether 446254-68-8 CRSCWEYUPUKHPI-UHFFFAOYSA-N
PBDE-105 [math]\ce{ C12H5Br5O }[/math] 2,3,3',4,4'-pentabromodiphenyl ether 373594-78-6 LBPWAGZGYNOKAM-UHFFFAOYSA-N
PBDE-106 [math]\ce{ C12H5Br5O }[/math] 2,3,3',4,5-pentabromodiphenyl ether 446254-69-9 KLQKWMYXEWUAFP-UHFFFAOYSA-N
PBDE-107 [math]\ce{ C12H5Br5O }[/math] 2,3,3',4',5-pentabromodiphenyl ether 446254-70-2 OMGVAMFMRSETEG-UHFFFAOYSA-N
PBDE-108 [math]\ce{ C12H5Br5O }[/math] 2,3,3',4,5'-pentabromodiphenyl ether 446254-71-3 VBKPKHVLHGOKOJ-UHFFFAOYSA-N
PBDE-109 [math]\ce{ C12H5Br5O }[/math] 2,3,3',4,6-pentabromodiphenyl ether 446254-72-4 FXXXWTMLIQLDRP-UHFFFAOYSA-N
PBDE-110 [math]\ce{ C12H5Br5O }[/math] 2,3,3',4',6-pentabromodiphenyl ether 446254-73-5 LESZGJVTZILBTK-UHFFFAOYSA-N
PBDE-111 [math]\ce{ C12H5Br5O }[/math] 2,3,3',5,5'-pentabromodiphenyl ether 446254-74-6 PCHDCOXHJBWEPW-UHFFFAOYSA-N
PBDE-112 [math]\ce{ C12H5Br5O }[/math] 2,3,3',5,6-pentabromodiphenyl ether 446254-75-7 MFBMNSFADPTAKZ-UHFFFAOYSA-N
PBDE-113 [math]\ce{ C12H5Br5O }[/math] 2,3,3',5',6-pentabromodiphenyl ether 446254-76-8 OGZHLJXRGZFVLI-UHFFFAOYSA-N
PBDE-114 [math]\ce{ C12H5Br5O }[/math] 2,3,4,4',5-pentabromodiphenyl ether 446254-77-9 SFNAUTSNWPPDSY-UHFFFAOYSA-N
PBDE-115 [math]\ce{ C12H5Br5O }[/math] 2,3,4,4',6-pentabromodiphenyl ether 446254-78-0 BKTLDVXDOVSTEV-UHFFFAOYSA-N
PBDE-116 [math]\ce{ C12H5Br5O }[/math] 2,3,4,5,6-pentabromodiphenyl ether 189084-65-9 ACRQLFSHISNWRY-UHFFFAOYSA-N
PBDE-117 [math]\ce{ C12H5Br5O }[/math] 2,3,4',5,6-pentabromodiphenyl ether 446254-79-1 SOJBOGWFDBDWEG-UHFFFAOYSA-N
PBDE-118 [math]\ce{ C12H5Br5O }[/math] 2,3',4,4',5-pentabromodiphenyl ether 446254-80-4 VTMFEPLDDHZBGI-UHFFFAOYSA-N
PBDE-119 [math]\ce{ C12H5Br5O }[/math] 2,3',4,4',6-pentabromodiphenyl ether 189084-66-0 KXEOYBYEJCRPGB-UHFFFAOYSA-N
PBDE-120 [math]\ce{ C12H5Br5O }[/math] 2,3',4,5,5'-pentabromodiphenyl ether 417727-71-0 AKSBEUHDCRZJAN-UHFFFAOYSA-N
PBDE-121 [math]\ce{ C12H5Br5O }[/math] 2,3',4,5',6-pentabromodiphenyl ether 446254-81-5 GVGNVZBJVFDAAO-UHFFFAOYSA-N
PBDE-122 [math]\ce{ C12H5Br5O }[/math] 2,3,3',4',5'-pentabromodiphenyl ether 446254-82-6 CDNHGSPFIUITTN-UHFFFAOYSA-N
PBDE-123 [math]\ce{ C12H5Br5O }[/math] 2,3',4,4',5'-pentabromodiphenyl ether 446254-83-7 SBKMUEQNZNDYFW-UHFFFAOYSA-N
PBDE-124 [math]\ce{ C12H5Br5O }[/math] 2,3',4',5,5'-pentabromodiphenyl ether 446254-84-8 FGHJTAAHIFEHLT-UHFFFAOYSA-N
PBDE-125 [math]\ce{ C12H5Br5O }[/math] 2,3',4',5',6-pentabromodiphenyl ether 446254-85-9 SESXKFPOVUVGLR-UHFFFAOYSA-N
PBDE-126 [math]\ce{ C12H5Br5O }[/math] 3,3',4,4',5-pentabromodiphenyl ether 366791-32-4 SJNIIWPIAVQNRK-UHFFFAOYSA-N
PBDE-127 [math]\ce{ C12H5Br5O }[/math] 3,3',4,5,5'-pentabromodiphenyl ether 446254-86-0 RATMRXKBPDCKCZ-UHFFFAOYSA-N
PBDE-128 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',4,4'-hexabromodiphenyl ether 182677-28-7 WFLVELCLEGVBIH-UHFFFAOYSA-N
PBDE-129 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',4,5-hexabromodiphenyl ether 446254-87-1 PRNCVYAUCSGSOE-UHFFFAOYSA-N
PBDE-130 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',4,5'-hexabromodiphenyl ether 446254-88-2 YURCHLXPAGSJHU-UHFFFAOYSA-N
PBDE-131 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',4,6-hexabromodiphenyl ether 446254-89-3 MGKVPJFIGGBCBA-UHFFFAOYSA-N
PBDE-132 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',4,6'-hexabromodiphenyl ether 446254-90-6 FFEKBOKDYRZGRV-UHFFFAOYSA-N
PBDE-133 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',5,5'-hexabromodiphenyl ether 446254-91-7 XTBFPFHQPGZZJX-UHFFFAOYSA-N
PBDE-134 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',5,6-hexabromodiphenyl ether 446254-92-8 MIBDGPWSGDWIQR-UHFFFAOYSA-N
PBDE-135 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',5,6'-hexabromodiphenyl ether 446254-93-9 AMGHASDTWACNCS-UHFFFAOYSA-N
PBDE-136 [math]\ce{ C12H4Br6O }[/math] 2,2',3,3',6,6'-hexabromodiphenyl ether 446254-94-0 NTWGDSLWLUPCDW-UHFFFAOYSA-N
PBDE-137 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,4',5-hexabromodiphenyl ether 446254-95-1 HSTYYNPYXZYIAG-UHFFFAOYSA-N
PBDE-138 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,4',5'-hexabromodiphenyl ether 182677-30-1 IZFQCEZFGCMHOM-UHFFFAOYSA-N
PBDE-139 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,4',6-hexabromodiphenyl ether 446254-96-2 YESDYWNWEVPOLZ-UHFFFAOYSA-N
PBDE-140 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,4',6'-hexabromodiphenyl ether 243982-83-4 FLRODCDHJZNIGA-UHFFFAOYSA-N
PBDE-141 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,5,5'-hexabromodiphenyl ether 446254-97-3 XTXIYMGRRUJOIT-UHFFFAOYSA-N
PBDE-142 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,5,6-hexabromodiphenyl ether 446254-98-4 LJDGJCNHVGGOFW-UHFFFAOYSA-N
PBDE-143 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,5,6'-hexabromodiphenyl ether 446254-99-5 RQLZDUSZXOOBTM-UHFFFAOYSA-N
PBDE-144 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,5',6-hexabromodiphenyl ether 446255-00-1 ZMSJCQOCTPYCQP-UHFFFAOYSA-N
PBDE-145 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4,6,6'-hexabromodiphenyl ether 446255-01-2 BTKLHMBWCRVCLC-UHFFFAOYSA-N
PBDE-146 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4',5,5'-hexabromodiphenyl ether 446255-02-3 HGXPYDNHBUCRTR-UHFFFAOYSA-N
PBDE-147 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4',5,6-hexabromodiphenyl ether 116995-33-6 OWBKWMDBTWHGHS-UHFFFAOYSA-N
PBDE-148 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4',5,6'-hexabromodiphenyl ether 446255-03-4 OJMHGSMSQZEBFH-UHFFFAOYSA-N
PBDE-149 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4',5',6-hexabromodiphenyl ether 446255-04-5 UJOUSZKYGGTPFQ-UHFFFAOYSA-N
PBDE-150 [math]\ce{ C12H4Br6O }[/math] 2,2',3,4',6,6'-hexabromodiphenyl ether 446255-05-6 SQNOZOVDXXSLSG-UHFFFAOYSA-N
PBDE-151 [math]\ce{ C12H4Br6O }[/math] 2,2',3,5,5',6-hexabromodiphenyl ether 446255-06-7 NGOQQUYCSISZMY-UHFFFAOYSA-N
PBDE-152 [math]\ce{ C12H4Br6O }[/math] 2,2',3,5,6,6'-hexabromodiphenyl ether 446255-07-8 BYBJJARTBKUIJD-UHFFFAOYSA-N
PBDE-153 [math]\ce{ C12H4Br6O }[/math] 2,2',4,4',5,5'-hexabromodiphenyl ether 68631-49-2 RZXIRSKYBISPGF-UHFFFAOYSA-N
PBDE-154 [math]\ce{ C12H4Br6O }[/math] 2,2',4,4',5,6'-hexabromodiphenyl ether 207122-15-4 VHNPZYZQKWIWOD-UHFFFAOYSA-N
PBDE-155 [math]\ce{ C12H4Br6O }[/math] 2,2',4,4',6,6'-hexabromodiphenyl ether 35854-94-5 HRSCBOSGEKXXSI-UHFFFAOYSA-N
PBDE-156 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4,4',5-hexabromodiphenyl ether 405237-85-6 JSDPCMJWYRDQEV-UHFFFAOYSA-N
PBDE-157 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4,4',5'-hexabromodiphenyl ether 446255-08-9 JUOAMVUIJQJZSZ-UHFFFAOYSA-N
PBDE-158 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4,4',6-hexabromodiphenyl ether 446255-09-0 KRYHHTVQOOJNHQ-UHFFFAOYSA-N
PBDE-159 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4,5,5'-hexabromodiphenyl ether 446255-10-3 IDYFFNCFLRCOPZ-UHFFFAOYSA-N
PBDE-160 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4,5,6-hexabromodiphenyl ether 446255-11-4 OCVOYHGOXIIONK-UHFFFAOYSA-N
PBDE-161 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4,5',6-hexabromodiphenyl ether 446255-12-5 WEYWRBBPPKSRGU-UHFFFAOYSA-N
PBDE-162 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4',5,5'-hexabromodiphenyl ether 446255-13-6 UKPNCLHMNJCGCJ-UHFFFAOYSA-N
PBDE-163 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4',5,6-hexabromodiphenyl ether 446255-14-7 NUEAHMLXQFHEJN-UHFFFAOYSA-N
PBDE-164 [math]\ce{ C12H4Br6O }[/math] 2,3,3',4',5',6-hexabromodiphenyl ether 446255-15-8 UJVYVXIHTJOJBZ-UHFFFAOYSA-N
PBDE-165 [math]\ce{ C12H4Br6O }[/math] 2,3,3',5,5',6-hexabromodiphenyl ether 446255-16-9 KXERERDGMTWBGZ-UHFFFAOYSA-N
PBDE-166 [math]\ce{ C12H4Br6O }[/math] 2,3,4,4',5,6-hexabromodiphenyl ether 189084-58-0 KVYODBMKQYVNEK-UHFFFAOYSA-N
PBDE-167 [math]\ce{ C12H4Br6O }[/math] 2,3',4,4',5,5'-hexabromodiphenyl ether 446255-17-0 NMUPLZRHSXJCJQ-UHFFFAOYSA-N
PBDE-168 [math]\ce{ C12H4Br6O }[/math] 2,3',4,4',5',6-hexabromodiphenyl ether 53551-87-4 HWZAPXGFMVEGPW-UHFFFAOYSA-N
PBDE-169 [math]\ce{ C12H4Br6O }[/math] 3,3',4,4',5,5'-hexabromodiphenyl ether 446255-18-1 JKFBMDHBJYKFKL-UHFFFAOYSA-N
PBDE-170 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',4,4',5-heptabromodiphenyl ether 327185-13-7 DLPNCMQTNWLTHD-UHFFFAOYSA-N
PBDE-171 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',4,4',6-heptabromodiphenyl ether 446255-19-2 FRMMMROUUPQUMZ-UHFFFAOYSA-N
PBDE-172 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',4,5,5'-heptabromodiphenyl ether 407606-59-1 DSRRSKFMOJQETR-UHFFFAOYSA-N
PBDE-173 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',4,5,6-heptabromodiphenyl ether 446255-20-5 NLBLNZDNOSSGPW-UHFFFAOYSA-N
PBDE-174 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',4,5,6'-heptabromodiphenyl ether 446255-21-6 VUUWOHUOYUGBEO-UHFFFAOYSA-N
PBDE-175 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',4,5',6-heptabromodiphenyl ether 6255-22-7 YATZWTXATDYQCK-UHFFFAOYSA-N
PBDE-176 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',4,6,6'-heptabromodiphenyl ether 407606-61-5 SWUALKCOTZOSMY-UHFFFAOYSA-N
PBDE-177 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',4,5',6'-heptabromodiphenyl ether 446255-23-8 ZHUHLPXIJIBQBJ-UHFFFAOYSA-N
PBDE-178 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',5,5',6-heptabromodiphenyl ether 446255-24-9 UWUVZUPEEORCRG-UHFFFAOYSA-N
PBDE-179 [math]\ce{ C12H3Br7O }[/math] 2,2',3,3',5,6,6'-heptabromodiphenyl ether 446255-25-0 COVXWWKOLMNRQE-UHFFFAOYSA-N
PBDE-180 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4,4',5,5'-heptabromodiphenyl ether 446255-26-1 STMBXVOJNOJRPZ-UHFFFAOYSA-N
PBDE-181 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4,4',5,6-heptabromodiphenyl ether 189084-67-1 GVNRIAPLVGNZPL-UHFFFAOYSA-N
PBDE-182 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4,4',5,6'-heptabromodiphenyl ether 442690-45-1 ZYHDTADADSNMLV-UHFFFAOYSA-N
PBDE-183 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4,4',5',6-heptabromodiphenyl ether 207122-16-5 ILPSCQCLBHQUEM-UHFFFAOYSA-N
PBDE-184 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4,4',6,6'-heptabromodiphenyl ether 117948-63-7 JHDCZVAQPRXHEL-UHFFFAOYSA-N
PBDE-185 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4,5,5',6-heptabromodiphenyl ether 405237-86-7 YRNMIFAQDSUFTR-UHFFFAOYSA-N
PBDE-186 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4,5,6,6'-heptabromodiphenyl ether 446255-27-2 WUFQDCMRKKDNSF-UHFFFAOYSA-N
PBDE-187 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4',5,5',6-heptabromodiphenyl ether 446255-28-3 RFZPXOBFDARWHV-UHFFFAOYSA-N
PBDE-188 [math]\ce{ C12H3Br7O }[/math] 2,2',3,4',5,6,6'-heptabromodiphenyl ether 116995-32-5 YGYDHFDPVGAMTL-UHFFFAOYSA-N
PBDE-189 [math]\ce{ C12H3Br7O }[/math] 2,3,3',4,4',5,5'-heptabromodiphenyl ether 259087-35-9 CQVLRTUESBMMJW-UHFFFAOYSA-N
PBDE-190 [math]\ce{ C12H3Br7O }[/math] 2,3,3',4,4',5,6-heptabromodiphenyl ether 189084-68-2 OUEYHQIMJGHOQN-UHFFFAOYSA-N
PBDE-191 [math]\ce{ C12H3Br7O }[/math] 2,3,3',4,4',5',6-heptabromodiphenyl ether 446255-30-7 BNBFKFHSIPERIM-UHFFFAOYSA-N
PBDE-192 [math]\ce{ C12H3Br7O }[/math] 2,3,3',4,5,5',6-heptabromodiphenyl ether 407578-53-4 ABLZOLAUBUSUHT-UHFFFAOYSA-N
PBDE-193 [math]\ce{ C12H3Br7O }[/math] 2,3,3',4',5,5',6-heptabromodiphenyl ether 446255-34-1 AUFJSWANTKXCFZ-UHFFFAOYSA-N
PBDE-194 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',4,4',5,5'-octabromodiphenyl ether 32536-52-0 ORYGKUIDIMIRNN-UHFFFAOYSA-N
PBDE-195 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',4,4',5,6-octabromodiphenyl ether 446255-38-5 GPQLSLKPHQEEOP-UHFFFAOYSA-N
PBDE-196 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',4,4',5,6'-octabromodiphenyl ether 446255-39-6 IEWFKOVTVJNWFF-UHFFFAOYSA-N
PBDE-197 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',4,4',6,6'-octabromodiphenyl ether 117964-21-3 AAFUUKPTSPVXJH-UHFFFAOYSA-N
PBDE-198 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',4,5,5',6-octabromodiphenyl ether 446255-42-1 IBKRHVDFFHQOSC-UHFFFAOYSA-N
PBDE-199 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',4,5,5',6'-octabromodiphenyl ether 446255-43-2 JNSLJYRXDGBNBE-UHFFFAOYSA-N
PBDE-200 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',4,5,6,6'-octabromodiphenyl ether 446255-46-5 JWMXGEPFVCRXQR-UHFFFAOYSA-N
PBDE-201 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',4,5',6,6'-octabromodiphenyl ether 446255-50-1 HQWFMMKREWXIGN-UHFFFAOYSA-N
PBDE-202 [math]\ce{ C12H2Br8O }[/math] 2,2',3,3',5,5',6,6'-octabromodiphenyl ether 67797-09-5 AHNZLQAZTWRRDW-UHFFFAOYSA-N
PBDE-203 [math]\ce{ C12H2Br8O }[/math] 2,2',3,4,4',5,5',6-octabromodiphenyl ether 337513-72-1 RTUZOQFRIPIWPS-UHFFFAOYSA-N
PBDE-204 [math]\ce{ C12H2Br8O }[/math] 2,2',3,4,4',5,6,6'-octabromodiphenyl ether 446255-54-5 YZABCBOJTHQTSX-UHFFFAOYSA-N
PBDE-205 [math]\ce{ C12H2Br8O }[/math] 2,3,3',4,4',5,5',6-octabromodiphenyl ether 446255-56-7 CVMKCYDBEYHNBM-UHFFFAOYSA-N
PBDE-206 [math]\ce{ C12HBr9O }[/math] 2,2',3,3',4,4',5,5',6-nonabromodiphenyl ether 63387-28-0 CYRHBNRLQMLULE-UHFFFAOYSA-N
PBDE-207 [math]\ce{ C12HBr9O }[/math] 2,2',3,3',4,4',5,6,6'-nonabromodiphenyl ether 437701-79-6 IEEVDIAVLGLVOW-UHFFFAOYSA-N
PBDE-208 [math]\ce{ C12HBr9O }[/math] 2,2',3,3',4,5,5',6,6'-nonabromodiphenyl ether 437701-78-5 ASGZXYIDLFWXID-UHFFFAOYSA-N
PBDE-209 [math]\ce{ C12Br10O }[/math] decabromodiphenyl ether 1163-19-5 WHHGLZMJPXIBIX-UHFFFAOYSA-N

Health and environmental concerns

Since the 1990s, environmental concerns were raised because of the high hydrophobicity of PBDEs and their high resistance to degradation processes. People are exposed to low levels of PBDEs through ingestion of food and by inhalation. PBDEs bioaccumulate in blood, breast milk, and fat tissues. Personnel associated with the manufacture of PBDE-containing products are exposed to highest levels of PBDEs. Bioaccumulation is of particular concern in such instances, especially for personnel in recycling and repair plants working on PBDE-containing products. People are also exposed to these chemicals in their domestic environment because of their prevalence in common household items. Studies in Canada have found significant concentrations of PBDEs in common foods such as salmon, ground beef, butter, and cheese.[5] PBDEs have also been found at high levels in indoor dust, sewage sludge, and effluents from wastewater treatment plants. Increasing PBDE levels have been detected in the blood of marine mammals such as harbor seals.

There is also growing concern that PBDEs share the environmental long life and bioaccumulation properties of polychlorinated dibenzodioxins.[6]

It is not known if PBDEs can cause cancer in people, although liver tumors developed in rats and mice that ate extremely large amounts of decaBDE throughout their lifetime. Lower-brominated PBDEs have not yet been tested for cancer in animals. The International Agency for Research on Cancer (IARC) has classified PBDE as a Group 3 carcinogen (not classifiable as to its carcinogenicity to humans) based on inadequate evidence of carcinogenicity in humans and inadequate or limited evidence in experimental animals. The EPA assigns the cancer category Group D (not classifiable as to human carcinogenicity) to mono-, di-, tri-, tetra-, penta-, hexa-, octa-, and nonaBDEs and reports “inadequate information” to classify the specific congeners 2,2’,4,4’-tetraBDE, 2,2’,4,4’,5-pentaBDE, and 2,2’,4,4’,5,5’-hexaBDE. However, EPA assigns a classification of “suggestive evidence of carcinogenic potential” for decaBDE. The Department of Health and Human Services has not classified PBDEs as carcinogens. The American Conference of Governmental Industrial Hygienists (ACGIH) has no data regarding cancer classifications for PBDEs.[7]

Case studies

PBDEs have been shown to have hormone-disrupting effects, in particular, on estrogen and thyroid hormones[8] and can interfere with both metabolic and oncogenic pathways.[9] A 2009 animal study conducted by the US Environmental Protection Agency (EPA) demonstrates that deiodination, active transport, sulfation, and glucuronidation may be involved in disruption of thyroid homeostasis after perinatal exposure to PBDEs during critical developmental time points in utero and shortly after birth.[10] The adverse effects on hepatic mechanism of thyroid hormone disruption during development have been shown to persist into adulthood.[citation needed] The EPA noted that PBDEs are particularly toxic to the developing brains of animals.[10] Peer-reviewed studies have shown that even a single dose administered to mice during development of the brain can cause permanent changes in behavior, including hyperactivity.[11]

Swedish scientists first reported substances related to pentaBDE were accumulating in human breast milk.[12] Studies by the Swedish Society for Nature Conservation found for the first time very high levels of more highly brominated PBDEs (BDE-209) in eggs of peregrine falcons.[13] Two forms of PBDEs, penta- and octaBDE, are no longer manufactured in the United States because of health and safety concerns. Based on a comprehensive risk assessment under the Existing Substances Regulation 793/93/EEC, the European Union has completely banned the use of penta- and octaBDE since 2004.[14] However, both chemicals are still found in furniture and foam items made before the phase-out was completed. The most common PBDEs used in electronics are decaBDE. DecaBDE is banned in Europe for this use and in some U.S. states. For PBDE, EPA has set reference dose of 7 micrograms per kilogram of body weight, which is "believed to be without appreciable effects". However, Linda Birnbaum, PhD, a senior toxicologist formerly with the EPA (now at NIEHS) notes concern: "What I see is another piece of evidence that supports the fact that levels of these chemicals in children appear to be higher than the levels in their parents; I think this study raises a red flag."[15] A previous study by the Environmental Working Group in 2003 published test results showing that the average level of fire-retardants in breast milk from 20 American mothers was 75 times higher than the average levels measured in Europe.[16]

Increasing levels of PBDEs in the environment may be responsible for the increasing incidence of feline hyperthyroidism.[17] A study in 2007 found PBDE levels in cats 20- to 100-fold greater than median levels in U.S. adults, although it was not adequately powered to establish an association between hyperthyroid cats and serum PBDE levels.[18] Subsequent studies have indeed found such an association.[19][20][21]

An experiment conducted at Woods Hole Oceanographic Institution in 2005 showed that the isotopic signature of methoxy-PBDEs found in whale blubber contained carbon-14, the naturally occurring radioactive isotope of carbon. Methoxy-PBDEs are produced by some marine species.[22] If the methoxy-PBDEs in the whale had come from artificial (human-made) sources, they would have contained only stable isotopes of carbon because virtually all PBDEs that are produced artificially use petroleum as the source of carbon; all carbon-14 would have long since completely decayed from that source.[23] The isotopic signatures of the PBDEs themselves were not evaluated. The carbon-14 may instead be in methoxy groups enzymatically added to man-made PBDEs.

A 2010 study found that children with higher concentrations of PBDE congeners 47, 99 and 100 in their umbilical cord blood at birth scored lower on tests of mental and physical development between the ages of one and six. Developmental effects were particularly evident at four years of age, when verbal and full IQ scores were reduced 5.5 to 8.0 points for those with the highest prenatal exposures after correcting for sex, ethnicity, tobacco smoke exposure, and mother's IQ.[24]

Sediment contamination

Increasing environmental concentrations and changing distributions of PBDEs in sediments of the Clyde River Estuary in Scotland, UK have been assessed.[25] Analysis of six sediment cores each of 1 m depth from Glasgow city to Greenock revealed that total concentrations increased toward the river bed surface (0–10 cm). Amounts of PBDE ranged from 1 to 2,645 µg/kg (dry wt. sediment) with a mean of 287 µg/kg (dry wt. sediment).[25] Down-core PBDE congener profiles showed that higher concentrations were due to elevated levels of BDE-209. The majority of the sediment records clearly showed a change from mainly lower molecular weight BDEs 47,99, 183, 153 at lower depths to BDE-209 near the surface, a change in congener and homologue group patterns that corresponds to the restrictions of penta- and octaBDE commercial mixtures under EU law in 2004–2006.

While biodegradation is not considered the main pathway for PBDEs, photolysis and pyrolysis can be of interest in studies of transformation of PBDEs.[26][27]

Regulations of PBDEs

In August, 2003, the State of California outlawed the sale of penta- and octaBDE and products containing them, effective January 1, 2008.[28] PBDEs are ubiquitous in the environment, and, according to the EPA, exposure may pose health risks. According to U.S. EPA's Integrated Risk Information System, evidence indicates that PBDEs may possess liver toxicity, thyroid toxicity, and neurodevelopmental toxicity.[29][30] In June 2008, the U.S. EPA set a safe daily exposure level ranging from 0.1 to 7 ug per kg body weight per day for the four most common PBDE congeners.[31][30][32][29] In April 2007, the legislature of the state of Washington (state) passed a bill banning the use of PBDEs.[33] The State of Maine Department of Environmental Protection found that all PBDEs should be banned.[34] In May 2007, the legislature of the state of Maine passed a bill phasing out the use of decaPBDE.[35]

The European Union decided to ban the use of two classes of flame retardants, in particular, PBDEs and polybrominated biphenyls (PBBs) in electric and electronic devices. This ban was formalised in the RoHS Directive, and an upper limit of 1 g/kg for the sum of PBBs and PBDEs was set. In February 2009, the Institute for Reference Materials and Measurements released two certified reference materials to help analytical laboratories better detect these two classes of flame retardants. The reference materials were custom-made to contain all relevant PBDEs and PBBs at levels close to the legal limit.

At an international level, in May 2009 the Parties of the Stockholm Convention on Persistent Organic Pollutants (POPs) decided to list commercial pentaBDE and commercial octaBDE as POP substances. This listing is due to the properties of hexaBDE and heptaBDE, which are components of commercial octaBDE, and to the properties of tetraBDE and pentaBDE, which are the main components of commercial pentaBDE.[36] In 2017, it was decided to also list decaBDE.[37][38]

References

  1. ↑ "Identification of flame retardants in polyurethane foam collected from baby products". Environ. Sci. Technol. 45 (12): 5323–31. 2011. doi:10.1021/es2007462. PMID 21591615. Bibcode: 2011EnST...45.5323S. 
  2. ↑ Beard, Adrian; Battenberg, Christian; Sutker, Burton J. (2021). "Flame Retardants". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–26. doi:10.1002/14356007.a11_123.pub2. ISBN 978-3-527-30385-4. 
  3. ↑ Frank Rahman (2001). "Polybrominated diphenyl ether (PBDE) flame retardants". Science of the Total Environment 275 (1–3): 1–17. doi:10.1016/s0048-9697(01)00852-x. PMID 11482396. Bibcode: 2001ScTEn.275....1R. 
  4. ↑ Kellyn S. Betts (2001-12-07). "Rapidly rising PBDE levels in North America". Environmental Science & Technology. http://pubs.acs.org/subscribe/journals/esthag-w/2001/dec/science/kb_pbde.html. 
  5. ↑ Globe and Mail article "Common foods laced with chemical"
  6. ↑ "The PBDEs: An Emerging Environmental Challenge and Another Reason for Breast-Milk Monitoring Programs". http://ehp.niehs.nih.gov/docs/2000/108p387-392hooper/hooper-full.html. 
  7. ↑ Breysse, Patrick N. (March 2017). "TOXICOLOGICAL PROFILE FOR POLYBROMINATED DIPHENYL ETHERS (PBDEs)". https://www.atsdr.cdc.gov/toxprofiles/tp207.pdf. 
  8. ↑ Costa, L. G.; Giordano, G. (2011). "Is decabromodiphenyl ether (BDE-209) a developmental neurotoxicant?". NeuroToxicology 32 (1): 9–24. doi:10.1016/j.neuro.2010.12.010. PMID 21182867. 
  9. ↑ Renzelli, V.; Gallo, M. (2023). "Polybrominated Diphenyl Ethers (PBDEs) and Human Health: Effects on Metabolism, Diabetes and Cancer". Cancers 24 (15(17):4237): 4237. doi:10.3390/cancers15174237. PMID 37686512. 
  10. ↑ 10.0 10.1 "Effects of perinatal PBDE exposure on hepatic phase I, phase II, phase III, and deiodinase 1 gene expression involved in thyroid hormone metabolism in male rat pups". Toxicol. Sci. 107 (1): 27–39. 2009. doi:10.1093/toxsci/kfn230. PMID 18978342. 
  11. ↑ Kuriyama, Sergio N.; Talsness, Chris E.; Grote, Konstanze; Chahoud, Ibrahim (2005). "Developmental exposure to low-dose PBDE-99: effects on male fertility and neurobehavior in rat offspring". Environmental Health Perspectives 113 (2): 149–154. doi:10.1289/ehp.7421. PMID 15687051. 
  12. ↑ "Polybrominated diphenyl ethers in breast milk from Uppsala County, Sweden". Environ. Res. 93 (2): 186–94. October 2003. doi:10.1016/S0013-9351(03)00049-5. PMID 12963403. Bibcode: 2003ER.....93..186L. 
  13. ↑ "Higher brominated diphenyl ethers and hexabromocyclododecane found in eggs of peregrine falcons (Falco peregrinus) breeding in Sweden". Environ. Sci. Technol. 38 (1): 93–6. January 2004. doi:10.1021/es034614q. PMID 14740722. Bibcode: 2004EnST...38...93L. 
  14. ↑ "DIRECTIVE 2003/11/EC OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL". http://eur-lex.europa.eu/LexUriServ/site/en/oj/2003/l_042/l_04220030215en00450046.pdf. 
  15. ↑ WebMD article "Fire Retardants Found in Children's Blood"
  16. ↑ Food Consumer article "Toxic Compounds in Toddlers & Preschoolers 3x Higher Than in Moms"
  17. ↑ Anthes, Emily (2017-05-16). "The Mystery of the Wasting House-Cats". The New York Times. ISSN 0362-4331. https://www.nytimes.com/2017/05/16/magazine/the-mystery-of-the-wasting-house-cats.html. 
  18. ↑ Dye, J.A.; Venier, Marta; Zhu, Lingyan; Ward, Cynthia R.; Hites, Ronald A.; Birnbaum, Linda S. (2007). "Elevated PBDE Levels in Pet Cats: Sentinels for Humans?". Environmental Science & Technology 41 (18): 6350–6356. doi:10.1021/es0708159. PMID 17948778. Bibcode: 2007EnST...41.6350D. 
  19. ↑ Norrgran, Jessica; Jones, Bernt; Bignert, Anders; Athanassiadis, Ioannis; Bergman, Åke (2015-04-21). "Higher PBDE Serum Concentrations May Be Associated with Feline Hyperthyroidism in Swedish Cats". Environmental Science & Technology 49 (8): 5107–5114. doi:10.1021/acs.est.5b00234. ISSN 0013-936X. PMID 25807268. Bibcode: 2015EnST...49.5107N. 
  20. ↑ Guo, Weihong; Gardner, Stephen; Yen, Simon; Petreas, Myrto; Park, June-Soo (2016-02-02). "Temporal Changes of PBDE Levels in California House Cats and a Link to Cat Hyperthyroidism". Environmental Science & Technology 50 (3): 1510–1518. doi:10.1021/acs.est.5b04252. ISSN 0013-936X. PMID 26699103. Bibcode: 2016EnST...50.1510G. 
  21. ↑ Walter, Kyla M.; Lin, Yan-ping; Kass, Philip H.; Puschner, Birgit (2017). "Association of Polybrominated Diphenyl Ethers (PBDEs) and Polychlorinated Biphenyls (PCBs) with Hyperthyroidism in Domestic Felines, Sentinels for Thyroid Hormone Disruption". BMC Veterinary Research 13 (1): 120. doi:10.1186/s12917-017-1031-6. ISSN 1746-6148. PMID 28468659. 
  22. ↑ A. Malmvärn; Y. Zebühr; L. Kautsky; Å. Bergman; L. Asplund (2008). "Hydroxylated and methoxylated polybrominated diphenyl ethers and Polybrominated dibenzo-p-dioxins in red alga and cyanobacteria living in the Baltic Sea". Chemosphere 72 (6): 910–916. doi:10.1016/j.chemosphere.2008.03.036. PMID 18457860. Bibcode: 2008Chmsp..72..910M. 
  23. ↑ Emma L. Teuten; Li Xu; Christopher M. Reddy (2005). "Two Abundant Bioaccumulated Halogenated Compounds Are Natural Products". Science 307 (5711): 917–920. doi:10.1126/science.1106882. PMID 15705850. Bibcode: 2005Sci...307..917T. 
  24. ↑ Herbstman, J. B.; Sjödin, A.; Kurzon, M.; Lederman, S. A.; Jones, R. S.; Rauh, V.; Needham, L. L.; Tang, D. et al. (2010). "Prenatal Exposure to PBDEs and Neurodevelopment". Environmental Health Perspectives 118 (5): 712–719. doi:10.1289/ehp.0901340. PMID 20056561. 
  25. ↑ 25.0 25.1 Vane, Christopher H.; Ma, Yun-Juan; Chen, She-Jun; Mai, Bi-Xian (2009). "Increasing polybrominated diphenyl ether (PBDE) contamination in sediment cores from the inner Clyde Estuary, UK". Environmental Geochemistry and Health 32 (1): 13–21. doi:10.1007/s10653-009-9261-6. ISSN 0269-4042. PMID 19347590. http://nora.nerc.ac.uk/id/eprint/9129/1/Vane_etal_2010_EGH.pdf. 
  26. ↑ Hutzinger O et al. (1987). "Polybrominated dibenzodioxins and dibenzofurans". Chemosphere 16 (8–9): 1877–1880. doi:10.1016/0045-6535(87)90181-0. Bibcode: 1987Chmsp..16.1877H. 
  27. ↑ Watanabe I et al. (1987). "Polybrominated diphenyl ethers in marine fish, shellfish and river sediments in Japan". Chemosphere 16 (10–12): 2389–2396. doi:10.1016/0045-6535(87)90297-9. Bibcode: 1987Chmsp..16.2389W. 
  28. ↑ "BILL NUMBER: AB 302, An act to add Chapter 10 (commencing with Section 108920) to Part 3 of Division 104 of the Health and Safety Code, relating to toxic substances.". http://www.leginfo.ca.gov/pub/03-04/bill/asm/ab_0301-0350/ab_302_bill_20030811_chaptered.html. 
  29. ↑ 29.0 29.1 US Environmental Protection Agency. Toxicological Profile for Decabromodiphenyl ether (BDE-209), Integrated Risk Information System, June 2008.
  30. ↑ 30.0 30.1 US Environmental Protection Agency. Toxicological Profile for 2,2',4,4',5-Pentabromodiphenyl ether (BDE-99), Integrated Risk Information System, June 2008.
  31. ↑ US Environmental Protection Agency. Toxicological Profile for 2,2',4,4'-Tetrabromodiphenyl ether (BDE-47), Integrated Risk Information System, June 2008.
  32. ↑ US Environmental Protection Agency. Toxicological Profile for 2,2',4,4',5,5'-Hexabromodiphenyl ether (BDE-153), Integrated Risk Information System, June 2008.
  33. ↑ "Chemical ban puts industry on the defensive." State of Washington bans use of PBDEs.
  34. ↑ [1][yes|permanent dead link|dead link}}] "DEP urges legislative ban on fire retardant"
  35. ↑ "Maine Legislature votes to ban toxic Deca flame retardant." State of Maine bans use of DecaBDE.
  36. ↑ House, Stockholm Convention Clearing. "Information on the 16 chemicals added to the Stockholm Convention". http://chm.pops.int/Convention/ThePOPs/TheNewPOPs/tabid/2511/Default.aspx. 
  37. ↑ Reference: C.N.766.2017.TREATIES-XXVII.15 (Depositary Notification)
  38. ↑ Sharkey, Martin; Harrad, Stuart; Abou-Elwafa Abdallah, Mohamed; Drage, Daniel S.; Berresheim, Harald (2020). "Phasing-out of legacy brominated flame retardants: The UNEP Stockholm Convention and other legislative action worldwide". Environment International 144: 106041. doi:10.1016/j.envint.2020.106041. PMID 32822924. 

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