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0Environment International 49 (2012) 57-82
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Environment International
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Review
A novel abbreviation standard for organobromine, organochlorine and organophosphorus flame retardants and some characteristics of the chemicals
Ake Bergman a,*< Andreas Ryden a, Robin J. Law b, Jacob de Boerc, Adrian Covaci d, Mehran Alaee e, Linda Birnbaum f, Myrto Petreas g, Martin Rose h, Shinichi Sakai', Nele Van den Eede d, Ike van der Veen c
a Environmental Chemistry Unit, Department of Materials and Environmental Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden b The Centre for Environment, Fisheries and Aquaculture Science, Cefas Lowestoft Laboratory, Pakefield Road, Lowestoft, Suffolk NR33 0HT, UK c VU University, Institute for Environmental Studies, De Boelelaan 1087, 1081HV, Amsterdam, The Netherlands d Toxicological Centre, University of Antwerp, Universiteitsplein 1,2610 Wilrijk, Belgium e National Water Research Institute, 867 Lakeshore Road, Burlington, Ontario, Canada L7R 4A6
f National Institute of Environmental Health Sciences and National Toxicology Program, 111 T.W. Alexander Drive, MD B2-01, Research Triangle Park, NC 27709, USA g Environmental Chemistry Laboratory, California Department of Toxic Substances Control, 700 Heinz Street, Berkeley, CA 94710, USA h The Food and Environment Research Agency, Sand Hutton, York YO41 1LZ, UK i Environment Preservation Research Center, Kyoto University, Kyoto, Japan
ARTICLE INFO
ABSTRACT
Article history: Received 21 March 2012 Accepted 10 August 2012 Available online 13 September 2012
Keywords:
Brominated flame retardants Chlorinated flame retardants Phosphorus flame retardants Nomenclature Abbreviations
Physico-chemical properties
Ever since the interest in organic environmental contaminants first emerged 50 years ago, there has been a need to present discussion of such chemicals and their transformation products using simple abbreviations so as to avoid the repetitive use of long chemical names. As the number of chemicals of concern has increased, the number of abbreviations has also increased dramatically, sometimes resulting in the use of different abbreviations for the same chemical. In this article, we propose abbreviations for flame retardants (FRs) substituted with bromine or chlorine atoms or including a functional group containing phosphorus, i.e. BFRs, CFRs and PFRs, respectively. Due to the large number of halogenated and organophosphorus FRs, it has become increasingly important to develop a strategy for abbreviating the chemical names of FRs. In this paper, a two step procedure is proposed for deriving practical abbreviations (PRABs) for the chemicals discussed. In the first step, structural abbreviations (STABs) are developed using specific STAB criteria based on the FR structure. However, since several of the derived STABs are complicated and long, we propose instead the use of PRABs. These are, commonly, an extract of the most essential part of the STAB, while also considering abbreviations previously used in the literature. We indicate how these can be used to develop an abbreviation that can be generally accepted by scientists and other professionals involved in FR related work. Tables with PRABs and STABs for BFRs, CFRs and PFRs are presented, including CAS (Chemical Abstract Service) numbers, notes of abbreviations that have been used previously, CA (Chemical Abstract) name, common names and trade names, as well as some fundamental physico-chemical constants.
© 2012 Elsevier Ltd. All rights reserved.
Contents
1. Introduction ..............................................................58
1.1. History of organic flame retardants ................................................58
1.2. Aims...............................................................58
2. Methodology..............................................................59
2.1. Construction of STABs for BFRs, CFRs, and PFRs...........................................59
2.2. Construction of PRABs for BFRs, CFRs, and PFRs...........................................59
3. Discussion ...............................................................59
Acknowledgments..............................................................81
References..................................................................81
* Corresponding author. Tel.: +46 816 3997, +46 70 644 3861(Mobile). E-mail address: ake.bergman@mmk.su.se (A. Bergman).
0160-4120/$ - see front matter © 2012 Elsevier Ltd. All rights reserved. http://dx.doi.org/! 0.1016/j.envint.2012.08.003
A. Bergman et al. / Environment International 49 (2012) 57-82
1. Introduction
Even though the history of flame retardants (FRs) dates back thousands of years (Hindersinn, 1990), it is the recent developments, and in particular the use of organic FRs, that is of current concern. Two of the major groups of these FRs are (i) halogenated FRs that may be divided into brominated and chlorinated flame retardants (BFRs and CFRs, respectively), and (ii) phosphorus-containing flame retardants (PFRs). The BFRs, CFRs and PFRs cover the major proportion of organic FRs, although some FRs contain neither halogen nor phosphorus atoms (e.g. melamine, 1,3,5-triazine-2,4,6-triamine). FRs are incorporated as either additive or reactive ingredients, with the aim of increasing the fire resistance of materials. Hence, reactive FRs are incorporated into the oligomers or polymers being manufactured, while additive FRs are molded within the material to be flame retarded.
Some countries or states have rather unique regulations requiring furniture and electrical equipment to meet specific flammability tests, e.g. in the UK and Ireland (Arcadis EBRC, 2011); and in California in the USA (State ofCalifornia, 2000). However, there is growing evidence that these regulations may not offer the protection that was first intended (Babrauskas et al., 2012; DiGangi et al., 2010). Also, there is a growing body of knowledge which is raising concerns about these chemicals in relation to their persistence, bioaccumulation, toxicity and long range transport. The 'San Antonio Statement' (DiGangi et al., 2010) sets the scene as to why this topic is of major concern to the global society. The FR area is complex, with numerous individual chemicals comprising the BFRs, CFRs and PFRs. This highlights the need for a common vocabulary amongst scientists and others to be used when addressing these chemicals in order to avoid confusion.
1.1. History of organic flame retardants
Polychlorinated biphenyls (PCBs) were manufactured and applied as FRs from the late 1920s until the mid-1980s, although PCBs were also used in a multitude of other applications, particularly in electrical equipment. Other chlorinated compounds came into use as FR, probably from the 1960s onwards, sometimes also including a phosphate group, such as the tris-(2,3-dichloropropyl)phosphate (TDCPP) and tris-(1,3-dichloro-iso-propyl)phosphate (TDCIPP) (Gold et al., 1978). The brominated analog of the former compound, tris-(2,3-dibromopropyl)phos-phate (TDBPP) made the headlines in the 1970s due to its use in children's pajamas (Blum et al., 1978). In the beginning of the 1970s, an increasing number of BFRs, e.g. polybrominated biphenyls (PBBs) and polybrominated diphenyl ethers (PBDEs), came to the market. In 1997, the World Health Organization tried to list all major FRs, also including any inorganic chemicals used in that role (WHO/IPCS, 1997). Pijnenburg et al. (1995) made the first review of BFRs, including what was known of their analysis, toxicity and environmental occurrence, and numerous other reviews and/or assessment documents have been published since then (e.g. Bergman, 2005; Birnbaum and Staskal, 2004; D'Silva et al., 2004; de Boer et al., 2000; de Wit, 2002; Law et al., 2003). Among the most recent documents concerning BFRs are five published opinions from the European Food Safety Authority (EFSA) on PBBs (EFSA, 2010), PBDEs (EFSA, 2011a), hexabromocyclododecanes (HBCDDs) (EFSA, 2011b), TBBPA and its derivatives (EFSA, 2011c) and also an opinion concerning other phenolic BFRs and their derivatives (EFSA, 2012). EFSA is presently also preparing an opinion on emerging and novel BFRs, for publication in 2012. In 2011, a book on BFRs was published which covered a multitude of issues relating to BFRs (Eljarrat and Barceleo, 2011). Other major reviews of BFRs from 2005 onwards include Covaci et al. (2006, 2009, 2011), Law et al. (2006, 2008). A review on PFRs was recently published (van der Veen and de Boer, 2012) while, among the CFRs, only the Dechloranes have been comprehensively reviewed to date (Sverko et al., 2011).
The BFRs most commonly used today are tetrabromobisphenol A (TBBPA), decabromodiphenyl ether (DecaBDE) and HBCDD (also sometimes referred to as HBCD). Due to EU legislative measures and the inclusion of PentaBDE and OctaBDE among the Stockholm Convention POPs, there are now changes in the production and use of PBDEs, HBCDDs and many other BFRs, including some which are being used as replacements for now restricted formulations. DecaBDE is subjected to use restrictions according to the RoHS directive (Directive 2002/95/EC (OJ, 2003)) after the European Court of Justice decision from 2008 (OJ, 2008). However, these changes cannot be documented adequately as the producers do not make production figures available, regardless of where the chemicals are manufactured. Similarly, there is little information available on the current applications in which these compounds are being used. The situation is similar also for production and use of CFRs and PFRs.
It is safe to say that the use of BFRs has increased dramatically since the 1970s and their cumulative current production volume exceeds 200,000 t per year, based on available information (personal communication, V. Steukers, Albemarle, 2008; references in Eljarrat and Barceleo, 2011). Volumes of CFRs seem to be higher since, in 2007, the production of polychlorinated alkanes (PCAs) (also known as chlorinated paraffins (CPs)) amounted to up to 600,000 t per year, in China alone (Fiedler, 2010). These compounds are not solely used as flame retardants, however, and have a number of other applications (Nicholls et al., 2001). The worldwide production volume of PFRs in 2004 was slightly above 200,000 t per year (EFRA, 2007).
Due to the increased regulatory interest in and restrictions on PBDEs and HBCDD, alternative FRs are now being used in their place. It is, as shown below, difficult even to list those BFRs currently being offered for sale in the market. In the present document, we are therefore presenting all BFRs, CFRs and PFRs that have been proposed to date for use as FRs. Several FRs have only recently been detected in the environment, even though they may have been in use for some time, e.g. Dechlorane Plus (Sverko et al., 2011). The analysis, environmental fate and behavior of novel BFRs have been reviewed (Covaci et al., 2011; Papachlimitzou et al., 2012) and they are presently under review by EFSA. A suite of FRs has also been reported as present in materials and products taken recently from the Swiss retail market (Zennegg, 2011). In addition, other types of compounds are also used as FRs in a variety of applications, notably PFRs. Regarding the present use of CFRs, less has been published to date, even though some new chemicals have now been identified as CFRs. These are mainly related to the family of "Dechloranes" (Sverko et al., 2011) as further discussed below.
1.2. Aims
As the number of compounds in use as FRs, and for which environmental data are being reported increases, there is a pressing need to harmonize abbreviations by which these compounds can be described in the literature (for example, using TBBPA and PBDEs as described above, and BDE47 for 2,2',4,4'-tetrabromodiphenyl ether), with the aim of preventing future confusion. Unfortunately, a rather large number of abbreviations, for the less known FRs, are currently being used without any coordination. Following a request made at the BFR Symposium 2010 in Kyoto, we have now prepared a document which aims to promote improved harmonization, based on a set of criteria, of unique and practical abbreviations to be used for all BFRs, CFRs and PFRs identified to date. In this paper, we provide information relating to halogenated FRs and PFRs, including common, trade and systematic names, CAS numbers, physicochemical properties where known, together with recommended structured abbreviations (STABs) and practical abbreviations (PRABs). Also some general comments and suggestions are given with the aim of simplifying the abbreviation of the full chemical names of BFRs, CFRs and PFRs.
A. Bergman et al. / Environment International 49 (2012) 57-82
2. Methodology
All compounds listed were retrieved by reviewing the scientific literature for BFRs, CFRs and PFRs. Documents of particular use for identifying BFRs and CFRs were: WHO/IPCS (1994, 1995), WHO/IPCS (1997), Orn and Bergman (2004), Andersson et al. (2006); Harju et al. (2009), Letcher et al. (2009), Covaci et al. (2011), de Wit et al. (2011), Sverko et al. (2011); and for PFRs: van der Veen and de Boer (2012).
The compounds are presented in three separate groups (BFRs, CFRs and PFRs) and then listed in molecular mass order within each subgroup. The sub-grouping is given below. We have chosen to list FRs holding, for example, both a phosphorus group and a halogen substituent, in each of the groups to which they belong, i.e. a BFR with a chlorine substituent is also listed in the table containing CFRs (Table 3); a PFR containing bromine substituents is also listed as a BFR. This means that some of the chemicals are listed twice.
One further goal of the systematic work presented herein is to enable us to treat functional groups in chemicals in a similar way, which could also be applied for hitherto unknown BFRs, CFRs, and PFRs that may be identified as commercial products in the future. This may be exemplified by the way in which we handle ether and ester functional groups when structured abbreviations are made. Allyl ethers ofe.g. 2,4,6-tribromophenol and TBBPA are handled by naming the phenol entity first and then introducing one or two ether functionalities, the latter denoted "bis" (b), to give the STABs: TrBPh-AE and TBBPA-bAE, respectively. Other ethers are treated similarly, with the aryl group first and with the alkyl ether group linked to the word "ether". In order to minimize confusion, we propose the use of a set of standardized short forms for major parts of a molecule (or their name). The criteria for constructing the abbreviations are given below and in Table 1. The STABs of all BFRs, CFRs and PFRs are listed in plain letters under the PRABs of the same compound, presented in bold letters (Tables 2-4).
No inorganic FRs have been included in the present article since we feel that the chemical formula can be used for most of those chemicals.
2.1. Construction of STABs for BFRs, CFRs, and PFRs
1. Abbreviations should, as far as possible, be based on a "readable" common name of the chemical. This may lead to the use of an abbreviation, such as TBBPA originating from the common name tetrabromobisphenol A. The goal is to minimize use of non-interpretable names as a base of the abbreviation if it is possible to do so. However, some names and structures of the FRs are very complex and it is unavoidable that the STABs also become complex.
2. Functional groups, such as ether and ester groups, and glycidyl and allyl groups, should be handled the same way each time such a group appears in a compound. Alcohol functional groups are added as OH to the aliphatic chain name (e.g. MeOH for methanol, EtOH for ethanol, PrOH for propanol and PrDiOH for propanediol).
3. In cases where it is necessary to indicate the aliphatic chain or ring structure, this can be done by adding the lower case letters c for cyclo, bc for bicyclo; i for iso (c.f. Table 2). The default for an alkyl chain is "normal-" (n) and is omitted.
4. The "bis-" and "tris-" prefixes are written as "b" and "t", respectively.
5. The numbers of a particular substituent are given by the letters: Di; Tr; Te; Pe; Hx; Hp; O; N; D; UD; DD; TrD; TeD; for the series of 2-14 substituents.
6. The aliphatic chains or rings and aromatic entities are presented in Table 1.
2.2. Construction of PRABs for BFRs, CFRs, and PFRs
Since the STABs tend to be quite complicated, in numerous cases, we are proposing combinations of, in general, three to eight capital letters for PRABs. The PRABs take into account previously used abbreviations
and shortening of the STABs. In a few cases the suggested PRABs exceed eight letters, but this is in cases where no other possibility was obvious to us. The goal has been to present PRABs that are derived in a logical manner (based on the STABs) and are expected to be adopted by the scientific community.
3. Discussion
Among the FRs discussed in this article, we propose a hierarchy for clarification of the status of these chemicals in an environment and health perspective. First, it may be worth to stress that there is a difference in the definition of e.g. an "emerging chemical pollutant" and an "emerging issue". Further, an "established pollutant" could of course be an "emerging issue". Hence the following definitions are put forward for any FRs:
Established FRs (BFRs/CFRs/PFRs) are chemicals which are extensively documented regarding production and use as FRs, chemistry, fate, exposures, environment and health issues (i.e. (eco-)toxicity and/or human health effects).
Emerging FRs (BFRs/CFRs/PFRs) are chemicals which are documented regarding production and use as FRs that have been shown to occur/ distribute to the environment and/or wildlife, humans or other biological matrices.
Novel FRs (BFRs/CFRs/PFRs) are chemicals which are documented as potential FRs that have been shown to be present in materials or products.
Potential FRs (BFRs/CFRs/PFRs) are chemicals reported to have applications as FRs (e.g. in patents).
The numbers of established, emerging, novel and/or potential BFRs, CFRs and PFRs identified and reported in this paper are 55,18 and 23, respectively (Tables 2-4). These numbers do not include either congeners or enantiomers of a given FR. The DBP-TAZTO and its two congeners, BDBP-TAZTO and TDBP-TAZTO, are listed with their separate CAS numbers in Table 2, even though these homologues most likely occur together in the same technical BFR product. On the other hand, we list PBDEs as one group of BFRs (Table 2), chlorinated paraffins as three groups (SCCP; MCCP and LCCP), depending on alkane chain lengths even though they have separate CAS numbers (Table 3).
The use of a numbering system as proposed by Ballschmiter and Zell (1980) for the PCB congeners made a major impact on all subsequent discussions of this group of chemicals (Ballschmiter et al., 1992). Since PBBs and PBDEs are also dicyclic aromatic compounds, it has been possible to replicate the PCB numbering system for the PBBs and PBDEs. The same method for abbreviations is proposed herein for polybrominated diphenyl ethanes (PBDPE) and polybrominated dibenzyl ethanes (PBDBE), since these compounds are likewise, dicyclic aromatic chemicals.
The numbering system proposed by Ballschmiter et al., has also become valuable for referring to metabolites of PCBs, PBBs and PBDEs. The rules to apply are given in Textbox 1, referring to the work by Letcher et al. (2000). The same numbering system can be applied to the polybrominated phenoxy-PBDEs (PBPO-PBDE) (see Table 2).
Determine the PBDE or PBB number of the OH-BDE, OH-BB or PhO-BDE overlooking any hetero substituent (- OH, -OR, -SH, -OR, -SR or PhO-group)
Based on the numbering of the PBDE or PBB congener, give the hetero substituent the number (with or without the prime sign due to the structure) in which the substituent is placed.
Examples of the numbering of PBDE and BB metabolites are given in Fig. 1, and likewise of a polybromophenoxy-PBDE (PBPO-PBDE) congener.
A. Bergman et al. / Environment International 49 (2012) 57-82
5'-OH-BDE99
Br^^^ \¡^^SO2CH3 Br Br
4'-MeSO2-BDE101
Br 1 Br
3-OH-BB153
Br Br Br
4'-(2,3,4,5-TBPO)-BDE198
Fig. 1. Examples of abbreviations for PBB and PBDE metabolites, as of PBPhO-BDEs. The appropriate abbreviations are given under each structure.
The PCB-based numbering system cannot unfortunately be applied to any other of the BFRs, CFRs or PFRs. The proposed PRABs for the BFRs, CFRs and PFRs are given in bold in Tables 2, 3 and 4, respectively. The background for selection of the PRABs is given above. The structures of each of the BFR, CFR and PFR compounds are also shown within Tables 2-4, respectively, together with the chemical abstract name and their CAS number.
STABs of BFRs, CFRs and PFRs are also given in Tables 2-4 (under the practical abbreviations (plain text)). These abbreviations follow the criteria set up above, as far as possible. For most of the BFRs, CFRs and PFRs, this yields abbreviations that are easily interpretable in relation to the compound's structure and at least one of its chemical names. The name used as a basis for the STABs is shown first in the column presenting "Common names/ Trade names" in Tables 2-4. In cases where the abbreviation criteria have not been followed, this is commented on in footnotes (Table 2).
Several of the abbreviations are based on abbreviations which have already been in common use for a long time, described as established abbreviations. In such cases we are not proposing changes
to the abbreviations already in use. This leads, for example, to the use of TBBPA as part of the abbreviated name of each of its derivatives, but the attached functional group is abbreviated following the guidelines presented herein. We suggest, however, that the common abbreviation HBCD be changed to HBCDD, to avoid future intermix with hexabromocyclodecane (c.f. Table 2). However, since HBCD is so commonly used for hexabromocyclododecane, we do foresee that this abbreviation may be used also in the future. Therefore, we introduce HBCYD as the PRAB for hexabromocyclodecane. In addition to the specific recommendations given above, we also propose "PentaBDE", "OctaBDE" and "DecaBDE" when referring to the corresponding commercial products.
Chemicals belonging to the BFRs and CFRs are listed in Tables 2 and 3 respectively, presenting the proposed PRABs and STABs, other abbreviations that have been used previously, chemical abstract name, CAS number, and common names/commercial names. The type of FR is indicated as "R" for "Reactive BFR/CFR" and "A" for "Additive BFR/CFR". In an additional few columns are some properties of the individual compounds given, as extracted from CA (Scifinder, 2012) under the CAS number given in the table. The
Table 1
Abbreviations of functional groups or corresponding entities in a molecule to be applied when constructing structured abbreviations (STABs).
Letter Group Letter Group Letter Group
A Allyl Ac Acetate Acr Acrylate
AE Allyl ether Anh Anhydride Ant Anthracene
B Bromine Bn Benzyl BnB Benzylbromide
BnC Benzylchloride Bu Butane or butyl BuO Butoxy
Bz Benzo or benzene Bzo Benzoate
C Chlorine CaA Carboxylic acid
DD Dodecane or dodecyl De Decane or decyl Den Decen
E Ether Et Ethane or ethyl EtO Ethoxy
F Furan
GE Glycidyl ether
H Hexane or hexyl Ht Heptane or heptyl Hte Hepten
Im Imide In Indane
Me Methane or methyl
N Nonane or nonyl
O Octane or octyl OH Hydroxyl OPO Oxaphosphorinoxide
P Poly — if first in abbreviation Phosphate — if last in abbreviation Ph Phenol or phenyl PhO Phenoxy
Pht Phthalate Pr Propane or propyl Prt Propionate
Pt Pentane or pentyl
Re Resorcinol
Sty Styrene
T Toluene Taz Triazine Tazto Triazine-trione
Practical abbreviation (PRAB, in bold) for bromine containing flame retardants, together with structured abbreviations (STAB; plain text) are presented.
The table also includes some basic physicochemical constants calculated using ACD/Labs Software V11.02. The STABs are constructed as described under "Methodology", incl. Table 1.
number
PRABs STABs
Previously used CA name and structure abbreviations
Common and trade names
Additive or reactive BFR
Log Kow
pressure
61S-SB-7 DBP
DiBPha
317B0-26-4 DBS
DiBStya
11B-79-6 TBP
TrBPha
327B-B9-S TBP-AE
TrBPh-AEa
2,4-BrPh
DBS DBrsty
2,4,6BrPh 246TBP 2,4,6-TBP TBP
TBrPhAE
Phenol, 2,4-dibromo-
Benzene, dibromoethenyl-Br2-
Phenol, 2,4,6-tribromo-
Benzene, 1,3,S-tribromo-2-(2-propen-1-yloxy)-
2,4-Dibromophenol
NSC S723 NSC 6213
Dibromostyrene
Styrene, ar,ar-dibromo- (BCI)
Flame Cut310K
2,4,6-Tribromophenol
1.3.5-Tribromo-2-hydroxybenzene Bromkal Pur 3
Bromol Flammex 3BP NSC 2136 PH 73
2.4.6-Tribromophenyl allyl ether
Benzene, 1,3,5-tribromo-2-(2-propenyloxy)- (9CI)
Allyl 2,4,6-tribromophenyl ether
Ether, allyl 2,4,6-tribromophenyl (7CI,8CI)
Pyroguard FR 100
NSC 35767
2-(allyloxy)-1,3,5-tribromobenzene Bromkal 64-3AE; PHE-65
2S1.9 3.47 pH-dep
3.6SE + 00
A/R 261.94 na na na na
A/R 330.B 4.4 pH-dep. 6.34± 0.23 2.00E-01
A/R 370.B S.04 13,100 na 2.40E-02
234BB-3B-2 TBX
TeBDiMeBza
39S69-21-6 TBCT
TeBCT Tea
TEBP-Anh
TeBPht-Anh
TBX p-TBX
TBCT TBoCT
Benzene, 1,2,4,S-tetrabromo-3,6-dimethyl-
Benzene, 1,2,3,4-tetrabromo-S-chloro-6-methyl-
randione, mo-
1.2.4.5-Tetrabromo-3,6-dimethylbenzene
2.3.5.6-Tetrabromo-p-xylene 1,4-Dimethyltetrabromobenzene 2,3,S,6-Tetrabromo-1,4-dimethylbenzene
2,3,4,S-Tetrabromo-6-chlorotoluene
Tetrabromo-o-chlorotoluene
2,3,4,S-tetrabromo-6-chloromethylbenzene
3.4.5.6-Tetrabromophthalic anhydride Phthalic anhydride, tetrabromo- (6CI,7CI,8CI)
4.5.6.7-Tetrabromobenzofuran-1,3-dione 4,5,6,7-Tetrabromoisobenzofuran-1,3-dione Bromphthal
FG 4000
FireMaster PHT 4 NSC 4874 PHT 4
Saytex RB 49
Tetrabromophthalic acid anhydride Tetrabromophthalic anhydride
A 421.7S 6.2 56,100 na 5.80E-03
442.17 6.29 62,800
1.72E-03
463.7 3.7
CAS PRABs Previously used CA name and structure
number STABs abbreviations
87-83-2
Benzene, 1,2,3,4, 5-pentabromo-6-methyl-
PBP PBPh
Phenol, 2,3,4,5,6-pentabromo-OH
PeBEtBz
PeBrEtBz PBEB
Benzene, 1,2,3,4,5-pentabromo-6-ethyl-
58495-09-3 PBBC PeBBnC
Benzene, 1,2,3,4,5-pentabromo-6-(chloromethyl)-XI
3555-11-1 PBP-AE PeBPh-AE
Benzene, 1,2,3,4,5-pentabromo-6-(2-propen-l-yloxy)-Br
BlV X ,Br
35109-60-5 TBP-DBPE
TrBPh-DiBPrE
Benzene, 1,3,5-tribromo-2-(2,3-dibromopropoxy)-Br Br
183658-27-7 EH-TBB
EtH-TeBBzo
EHTeBB
Benzoic acid, 2,3,4,5-tetrabromo-, 2-ethylhexyl ester Br
Brv ^L ,Br
Common and trade names Additive or MW Log Koc pKa Vapor
reactive BFR Kow pressure
Pentabromotoluene A 486.62 6.25 60,200 na 6.00E-04
1.2.3.4.5-Pentabromo-6-methylbenzene
2.3.4.5.6-Pentabromomethylbenzene 2,3.4,5,6-Pentabromotoluene Flammex 5BT
Pentabromomethylbenzene
Pentabromophenol A/R 488.59 5.22 pH-dep. 4.43 ±0.33 2.55E-03
Phenol, pentabromo- (6CI,7CI,8CI,9CI)
2,3,4,5,6-Pentabromophenol
Bromophenasic acid
Flammex 5BP
NSC 5717
Perbromophenol
Pentabromoethylbenzene A 500.65 6.76 1.14E + 05 na 1.56E-04
2,3,4,5,6-Pentabromoethylbenzene
Pentabromobenzyl chloride R 521.06 5.95 41,300 na 8.64E-06
2,3,4,5,6-Pentabromobenzyl chloride
Pentabromophenol allyl ether A/R 528.66 6.22 57,900 na 9.21 E-05
(Allyloxy)pentabromobenzene
Allyl pentabromophenyl ether
Flammex 5AE
Pentabromophenyl allyl ether
2,4,6-Tribromophenyl 2,3-dibromopropyl ether A 530.67 5.82 35,000 na 1.26E-05
2,3-Dibromopropyl 2,4,6-tribromophenyl ether Bromkal 73-5PE
1,3,5-tribromo-2- (2,3-dibromopropoxy )benzene
2-Ethylhexyl 2,3,4,5-tetrabromobenzoate
549.92 7.73 3.82E + 05 na
3.71E-07
87-82-1 НВВ НВВ Benzene, 1,2,3,4,5,6-hexabromo-
59447-55-1 РВВ-Асг PeBBn-Acr
38521-51-6 РВВВ PeBBnB
20566-35-2 НЕЕНР-ТЕВР
OHEtOEt-OHPr-TeBPht
TeBrPht
26040-51-7 ВЕН-ТЕВР bEtH-TeBPht
TeBrDEHP
BEHTBP
168434-45-5 TBPD-TBP
TeBPeDe-TrBPh
2-Propenoic acid, (2,3,4,5,6-pentabromophenyl)methyl ester
Benzene, 1,2,3,4,5-pentabromo-6-(bromomethyl)-Br
1,2-Benzenedicarboxylic acid, 3,4,5, 6-tetrabromo-,l-[2-( 2-hydroxyethoxy )e thyl ] 2-(2-hydroxypropyl) ester HO_
„ОН
1,2-Benzenedicarboxylic acid, 3,4,5, 06-tetrabromo-, l,2-bis(2-ethylhexyl) ester
Phenol, 2,4,6-tribromo-3-(tetrabromopentadecyl)-OH
Br-^^iL^Br
CigH27Brd
Hexabromobenzene
1,2,3.4,5,6-Hexabromobenzene
AFR1001
HBB (flame retardant)
NSC 113975
Perbromobenzene
Plasafety HBB
Pentabromobenzyl acrylate
2,3.4,5,6-Pentabromobenzyl acrylate
Actimer FR 1025M
FR 1025M
551.49 6.11 50,300
556.67 5.6
Pentabromobenzyl bromide 2,3,4,5,6-Pentabromobenzyl bromide
565.51 6.22 57,400
4.25E-06
2-(2-Hydroxyethoxy)ethyl 2-hydroxypropyl 3,4,5,6-tetrabromophthalate
Phthalic acid, tetrabromo-, 2-(2-hydroxyethoxy)ethyl 2-hydroxypropyl ester PHT 4-Diol Saytex RB 79
627.9 1.04 87.5
4.79E-13
Bis(2-ethylhexyl) tetrabromophthalate 1,2-Benzenedicarboxylic acid, 3,4,5,6-tetrabromo-, bis(2-ethylhexyl) ester (9CI)
Phthalic acid, tetrabromo-, bis(2-ethylhexyl) ester (8CI) DP 45
Di(2-ethylhexyl) tetrabromophthalate Pyronil 45 Uniplex FRP 45
706.14 9.34 2.88E + 06 na
3-(Tetrabromopentadecyl)-2,4,6-tribromophenol
(continued on next page)
number
PRABs STABs
Previously used CA name and structure abbreviations
TBBPA Phenol, 4,4'- ( 1 -methylethylidene )
TBBP-A bis[2,6-dibromo-
HCX J-, ^OH
39635-79-5 TBBPSb
TBBPS TBBP-S
Phenol, 4,4'-sulfonylbis[2,6-dibromo-
37853-61-5 TBBPA-BME TBBPA-bMeEc
70156-79-5 TBBPS-BME TBBPS-bMeEc
TBBPA ME
Benzene, 1,1'-(1 -methylethylidene ) bis[3,5-dibromo-4-methoxy-
o ^r y o
Benzene, l,l'-sulfonylbis[3, 5-dibromo-4-methoxy-
Common and trade names
Additive or MW reactive BFR
Log Koc Kow
Vapor pressure
Tetrabromobisphenol A
2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane
543.87 9.69 4.47E + 06 7.5/8.50 ± 1.88E-05 0.10
2,2-Bis(4-hydroxy-3,5-dibromophenyl)propane
2,2',6,6'-Tetrabromobisphenol A
3,3',5,5'-Tetrabromobisphenol A
3,5,3',5'-Tetrabromobisphenol A
4,4'-(l-Methylethylidene)bis[2,6-dibromophenol]
4,4'-Isopropylidenebis[2,6-dibromophenol]
BA 59BP
Bromdian
CP 2000
FG 2000
FR 1524
Fire Guard 2000
Firemaster BP 4A
Flame Cut 120G
Flame Cut 120R
GLCBA 59P
NSC 59775
PB 100
RB 100
Saytex CP 2000 Saytex RB 100 Saytex RB 100PC T 0032
Tetrabromodian Tetrabromodiphenylolpropane
Tetrabromobisphenol S A/R 565.85 5.81 pH-dep, 3.53 4.03E-10
3,3',5,5'-Tetrabromobisphenol S
3,5,3',5'-Tetrabromobisphenol S
4,4'-Dihydroxy-3,5,3',5'-tetrabromodiphenyl sulfone
4,4'-Sulfonylbis(2,6-dibromophenol)
Bis(3,5-dibromo-4-hydroxyphenyl) sulfone
Bis(4-hydroxy-3,5-dibromophenyl) sulfone
EB 400S
FG 400S
Flame Cut 160R
Tetrabromobisphenol A bismethyl ether A 571.92 10.35 1.00E + 07 na 2.25E-06
Tetrabromobisphenol A dimethyl ether Tetrabromobisphenol A methyl ether
Tetrabromobisphenol S bismethyl ether A 593.91 6.05 46,500 na 3.43E-11
(3,5-Dibromo-4-methoxyphenyl) sulfone Tetrabromobisphenol S dimethyl ether Tetrabromobisphenol S methyl ether
Phenol, 4,4'- ( 1 -methylethylidene ) bis[2,6-dibromo-, 1,1'- diacetate
4162-45-2 TBBPA-BHEE TBBPA-BHEE Ethanol, 2,2'-[(l-methylethylidene)
TBBPA-bOHEtEc TBBPA OHEE bis[(2,6-dibromo-4,l-phenylene)oxy]]bis-
33798-02-6 TBBPA-BO Ac
TBBPA-bOAcc
25327-89-3 TBBPA-BAE TBBPA-DAE Benzene, l.l'-(l-methylethylidene)
TBBPA-bAEc TBBPA-AE bis[3,5-dibromo-4- (2-propen-l-yloxy)-
55205-38-4 TBBPA-BA TBBPA-bAcrc
2-Propenoic acid, l,l'-[(l-methylethylidene) bis(2,6-dibromo-4,l-phenylene)l ester
3072-84-2 TBBPA-ВСЕ TBBPA-DGE Oxirane, 2,2'-[(l-methylethylidene)
TBBPA-bGEc TBBPA GE bis[(2,6-dibromo-4,l-
phenylene)oxymethylene]]bis-
3,3',5,5'-Tetrabromobisphenol A bisacetate Phenol, 4,4'- (1 -methylethylidene )bis[ 2,6-dibromo-, diacetate (9CI) Phenol, 4,4'-isopropylidenebis[ 2,6-dibromo-, diacetate (8CI)
2,2-Bis(4-acetoxy-3,5-dibromophenyl)propane 3,3',5,5'-Tetrabromobisphenol A diacetate
Tetrabromobisphenol A bis(2-hydroxyethyl) ether Ethanol, 2,2'-[isopropylidenebis[(2,6-dibromo-pphenylene)oxy]]di-
2,2-Bis[3,5-dibromo-4-(2-hydroxyethoxy) phenyl ]propane
2,2-Bis[3,5-dibromo-4-(p?>-hydroxyethoxy) phenyl ]propane
2,2-Bis[4-(2-hydroxyethoxy)-3,5-
dibromophenyl ]propane
2,2'-Isopropylidenebis[(2,6-dibromo-
pphenyleneoxy)diethanol]
4,4'-Isopropylidenebis[ 2- (2,6-
dibromophenoxy)ethanol]
AFR 1011
FG 3600
Fire Guard 3600
BA-EO 20
Tetrabromobisphenol A bis(allyl) ether
Benzene, 1,1'- (1 -methylethylidene )bis
[3,5-dibromo-4-(2-propenyloxy)- (9CI)
Propane, 2,2-bis[4- (allyloxy )-3,5-dibromophenyl ]- (8CI)
1,1 '-Isopropylidenebis[4- (ally loxy)-3,5-dibromobenzene]
2,2-Bis(3,5-dibromo-4-allyloxyphenyl)propane
2,2-Bis(4-allyloxy-3,5-dibromophenyl)propane
FG 3200
Fire Guard 3200
Flame Cut 122K
Pyroguard SR 319
SR 319
TBBPA-DE
Tetrabromobisphenol A allyl ether Tetrabromobisphenol A diallyl ether Tetrabromobisphenol A bisacrylate 2-Propenoic acid, (1-methylethylidene) bis(2,6-dibromo-4,l-phenylene) ester (9CI) 2,2',6,6'-Tetrabromobisphenol A diacrylate 4,4'-Isopropylidenebis(2,6-dibromophenyl acrylate) SR 640
Tetrabromobisphenol A diacrylate
Tetrabromobisphenol A bis(glycidyl) ether Propane, 2,2-bis[3,5-dibromo-4-(2,3-epoxypropoxy)phenyl ]- (7CI.8CI) 2,2-Bis(4-glycidyloxy-3,5-dibromophenyl)propane 2,2',6,6'-Tetrabromobisphenol A diglycidyl ether Glycidyl tetrabromodian ether
A 627.94 9.45 3.28E + 06 na 3.28E-09
A/R 631.98 8.51 1.01 E +06 13.76 2.89E-12
A/R 642 11.42 1.00E + 07 na 1.83E-08
R 651.97 9.37 2.99E + 06 na 3.84E-11
R 656 8.87 1.60E + 06 na 1.64E-10
(continued on next page)
number
PRABs STABs
Previously used CA name and structure abbreviations
37419-42-4
37853-59-1
TBBPA-BP
TBBPA-bPrtc
bTBPhOEtc
Phenol, 4,4'- ( 1 -methylethylidene )bis[ 2,6-dibromo-, dipropanoate (9CI)
BTBPE Benzene, l,l'-[l,2-ethanediylbis(oxy)]
TBEHxBrPoxE bis[2,4,6-tribromo-
TBBPA-BHEEBA
TBBPA-bOHEtEbAcrc
2-Propenoic acid, 1,1'-[(l-methylethylidene)bis[(2,6-dibromo-4,l-phenylene)oxy-2,l -ethanediyl] ] ester
1084889-51-9 OBTMPI 1025956-65-3 OBTrMePhln3 893843-07-7
21850-44-2 TBBPA-BDBPE
TBBPA-bDiBPrEc
Octalnd
Br-Indane
1H-Indene, 4,5,6,7-tetrabromo-2,3-dihydro-l,l, 3-trimethyl-3-(2,3,4,5-tetrabromophenyl)-
TBBPA-DBPE TBBPA-bis
Benzene,l,l'-(1 -methylethylidene ) bis[3,5-dibromo-4- (2,3-dibromopropoxy)-
Common and trade names
Additive or MW reactive BFR
Log Koc Kow
Vapor pressure
Tetrabromobisphenol A diglycidyl ether
Tebrabromobisphenol A bispropanoate
propane-2,2-diylbis(2,6-dibromo-4,l-phenylene)
dipropionate
656 10.47 1.00E + 07 na
4.17E-10
1,2-Bis (2,4,6-tribromophenoxy)ethane
687.64 8.31 7.92E + 05 na
BTBPE FF 680 FI 680 FM 680
FireMaster 680 FireMaster FF 680
Tetrabromobisphenol A bis(2-hydroxyethyl)ether R 740.07 10.76 1.00E + 07 na 1.96E-14
bisacrylate
2-Propenoic acid, (l-methylethylidene)bis[(2,6-dibromo-4,l-phenylene)oxy-2,l-ethanediyl] ester (9CI) BABA 50
Octabromotrimethylphenyl indane A 867.52 15.11 1.00E + 07 na 1.75E-12
Octalnd
4,5,6,7-tetrabromo-l,l,3-trimethyl-3-(2,3,4,5-tetrabromophenyl)-2,3-dihydro-lH-indene
Tetrabromobisphenol A bis(2,3- A 943.61 12.99 1.00E + 07 na 2.85E-15
dibromopropyl) ether
Propane, 2,2-bis[3,5-dibromo-4-(2,3-
dibromopropoxy)phenyl]- (8CI)
l,l'-Isopropylidenebis[3,5-dibromo-4-
(2,3-dibromopropoxy)benzene]
2,2-Bis[ 3,5-dibromo-4- (2,3-
dibromopropoxy )phenyl ]propane
2,2-Bis[4-(2,3-dibromopropoxy)-3,
5-dibromophenyl]propane
2,2-Bis[4-(2,3-dibromopropyloxy)-3,
5-dibromophenyl]propane
2,2-Bis[ [ 3,5-dibromo-4- (2,3-
dibromopropyloxy) ]pheny 1 ]propane
32588-76-4 EBTEBPI
N,N'-EtbTeBPhtIm BrPhtimi
1H-Isoindole-1,3(2H)-dione, 2,2'-(1,2-ethanediyl)bis[4,5,6,7-tetrabromo-
42757-55-1 TBBPS-BDBPE
TBBPS-bDiBPrEc
Benzene, 1,1'-sulfonylbis[3,5-dibromo-4-(2,3-dibromopropoxy)-
84852-53-9 DBDPE
BDPE-209
DBDiPhEtb
DBDPE DBDE EBPE DeBrPylE
Benzene,1,1'-(1,2-ethanediyl)bis [2,3,4,5,6-pentabromo-
497107-13-8 DBDBE
BDBE-209
DBDiBnE
Benzene, 1,1'-[oxybis(methylene)]bis [2,3,4,5,6-pentabromo- (9CI)
3,3',5,5'-Tetrabromobisphenol A bis(2,3-dibromopropyl) ether 4,4'-Isopropylidenebis[2,6-dibromo-1-(2,3-dibromopropoxy)benzene] Bis(2,3-dibromopropoxy)tetrabromobisphenol A Bromkal 66-8 D 5532 FG 3100 FR 720
Fire Guard 3100 Flame Cut 121K Flame Cut 121R GX 5532 HP 800A PE 68
PE 68 (fireproofing agent) Pyroguard SR 720 SR 720
Saytex HP 800A Saytex HP 800AG TBBPA-DBPE
Tetrabromobisphenol A 2,3-dibromopropyl ether
N,N'-Ethylenebis(tetrabromophthalimide) A
Phthalimide, N,N'-ethylenebis[tetrabromo-
(8CI); 1,2- Bis(tetrabromophthalimido)ethane
BT 93WFG
Citex BT 93
Saytex BT 93
Saytex BT 93W
2,2'-(ethane-1,2-diyl)bis(4,5,6,7-tetrabromoisoindoline-1,3-dione)
Tetrabromobisphenol S bis(2,3-dibromopropyl ether) A
4,4'-Bis(2,3-dibromopropoxy)-3,3',5,5'-
tetrabromodiphenyl sulfone
Bis[3,5-dibromo-4-(2,3-
dibromopropoxy)phenyl] sulfone
Flame Cut 161R
Nonnen 52
Nonnen PR 2
Decabromodiphenyl ethane A
951.47 6.63 96,500
965.6 8.68 1.26E + 06 na
971.22 11.1 1.00E + 07 na
Decabromodibenzyl ether Bis(2,3,4,5,6-pentabromobenzyl) ether
987.22 10.34 9.99E + 06 na
2.31E-16
CAS PRABs Previously used CA name and structure
number STABs abbreviations
58965-66-5 4'-PeBPOBDE2<)8 DPeTeBrBz TeDB-DiPhOBzd
34571-16-9 HCTBPH Dec 604
HxCTeBPh-bcHen
Polybrominated biphenyls
Benzene, l,2,4,5-tetrabromo-3,6-bis(2,3,4,5,6-pentabromophenoxy)-
Bicyclo[2.2.1 ]hept-2-ene, 1,2,3,4,7,7-hexachloro-5-(2,3,4,5-tetrabromophenyl)-Br
3322-93-8 DBE-DBCH DiBEt-DiBcH
BrCyHx
3194-57-8 TBCO TBCO
a-/(5-TeBcO
51936-55-1 DBHCTD HCDBCO
DiBHxC-TrcTrDen
25495-98-1 HBCYD HBCD
HxBcDe3
Cyclohexane, l,2-dibromo-4-(l,2-dibromoethyl)-Br
Cyclooctane, 1,2,5,6-tetrabromo-Br-^/ V-Br
1,4-Methanobenzocyclooctene, 7,8-dibromo-l,2,3,4,11,11-hexachloro-l,4,4a,5,6,7,8,9,10,10adecahydro-Cl
Cyclodecane, hexabromo-
3194-55-6 HBCDD (HBCD)
HxBcDD1 b
HBCDD HBCD
Cyclododecane, 1,2,5,6,9,10-hexabromo-
Common and trade names Additive or MW Log Koc pKa Vapor
reactive BFR Kow pressure
Polybrominated biphenyls A
Polybrominated diphenyl ethers A
Polybrominated phenoxy benzenes Polybrominated diphenyl oxides
Tetradecabromo-l,4-diphenoxybenzene A 1366.85 12.67 1.00E + 07 9.17E-17
Bis(pentabromophenoxy)benzene l,4-Bis(pentabromophenoxy)tetrabromobenzene BT 120 Saytex 120
Pentabromophenoxy-nonabromodiphenyl ether
l,2,3.4,7,7-hexachloro-5-(2,3.4,5- A 692.5 10.24 8.86E + 06 na 1.61E-08
tetrabromophenyl)-Bicyclo[ 2.2.1 ]hept-2-ene
2-Norbornene, 1,2,3,4,7,7-hexachloro-
5-(tetrabromophenyl)- (8CI)
5-(Tetrabromophenyl)-l,2,3,4,7,7-
hexachloro-2-norbornene
Dechlorane 604 Component A
Hexachlorocyclopentadiene-
tetrabromostyrene adduct
Dechlorane 604
4- (1,2-Dibromoethyl )-l ,2-dibromocyclohexane A 427.8 4.82 10,000 na 2.97E-03
1 - (1,2-Dibromoethyl )-3,4-dibromocy clohexane
1,2-Dibromo-4-(l ,2-dibromoethyl )cy clohexane Saytex BCL 462 Citex BCL 462
1,2,5,6-Tetrabromocyclooctane A 427.8 5.28 17,800 na 4.79E-03
NSC 167079
5,6-Dibromo-l,10,l 1,12,13,13-hexachloro- A 540.76 7.62 3.32E + 05 na 8.27E-07
ll-tricyclo[ 8.2.1.02,9 ]tridecene
7,8-dibromo-l,2,3,4,11,11-hexachloro-
1,4,4a,5,6,7,8,9,l 0,1 Oa-decahydro-
1,4-methanobenzo[8 ]annulene*
Saytex BC 26
Citex BC 26
* Name as suggested by ChemDraw
Hexabromocyclodecane A 613.64 na na na na
1,2,5,6,9,10-Hexabromocyclododecane A 641.7 7.92 4.86E + 05 na 1.04E-07
Bromkal 73-6D FR 1206 FR 1206HT Pyroguard SR 104
57829-89-7 DBP-TAZTO
DiBPr-DiA-Tazto
l,3,5-Triazine-2,4,6(lH,3H,5H)-trione, l-(2,3-dibromopropyl)-3,5-di-2-propen-l-yl-
Vr° Br
N N ,br Ï Br
75795-16-3 BDBP-TAZTO
bDiBPr-A-Tazto
l,3,5-Triazine-2,4,6(lH,3H,5H)-trione, l,3-bis(2,3-dibromopropyl)-5-(2-propen-l-yl)-
°ynY°
52434-90-9 TDBP-TAZTO TBC
tDiBPr-Tazto BrTriaz
l,3,5-Triazine-2,4,6(lH,3H,5H)-trione, 1,3.5-tris(2,3-dibromopropyl )-
°ynY°
Br, N N ,Br
25713-60-4 TTBP-TAZ
tTrBPhO-Taz
BrPhTriaz 1,3.5-Triazine, 2,4,6-tris(24.6-tribromophenoxy)-
.oyMyO Br' ^ ~BrNYN Br
Br' ^ "Br
SR 104 YM 88A
l-(2,3-Dibromopropyl)-3,5-diallyl-l,3,5- A/R 409.07 2.66 667 na 2.16E-06
Triazine-24.6(lH,3H,5H)-trione
l-(2,3-Dibromopropyl)-3,5-di-2-propenyl-l,3,5-
Triazine-24.6(lH,3H,5H)-trione
l,3-Bis(2,3-dibromopropyl)-5-allyl-l,3,5-Triazine-2,4,6(lH,3H,5H)-trione
l,3-Bis(2,3-dibromopropyl)-5-(2-propen-l-yl)-l,3,5-Triazine-2,4,6(lH,3H,5H)-trione l-Allyl-3,5-bis(2,3-dibromopropyl)-1,3,5-triazinane- 2,4,6-trione
568.88 3.55 2040
1.19E-09
1.3.5-Tris(2,3-dibromopropyl)-l,3,5-triazine-
2.4.6- trione
l,3,5-Tris(2,3-dibromopropyl) isocyanurate
1.3.5-Tris(2,3-dibromopropyl)-2,4,6-trioxohexahydrotriazine
AFR 1002 FC 140R FCP 660CN FR 930
Fire Cut P 660 Fire Cut P 660CN TAIC 6B TBC
TBC (fireproofing agent) Tris(2,3-dibromopropyl) isocyanurate Tris(2,3-dibromopropyl) isocyanurate Tris(2,4,6-tribromophenoxy)-s-triazine s-Triazine, 2,4,6-tris(2,4,6-tribromophenoxy)- (8CI)
2.4.6-Tris(2,4,6-tribromophenoxy)-l,3,5-triazine FR 245
FR 368 GX 6145
Pyroguard SR 245 SR 245
728.67 4.45 6260
1067.43 12.97 1.00E + 07 na
2.69E-23
Table 2 (continued)
number
PRABs STABs
Previously used CA name and structure abbreviations
Common and trade names
Additive or MW Log Koc pKa
reactive BFR Kow
pressure
19186-97-1 TTBNPP
tBbBMePrP
TrisPhos TTBNP
1-Propanol, 3-bromo-2,2-bis(bromomethyl)-, 1,1',1"-phosphate
tDBPrP
1-Propanol, 2,3-dibromo-, 1,1',1"-phosphate
bBMe-PrDiOH
1,3-Propanediol, 2,2-bis(bromomethyl) /-OH
522-92-5
tBMe-EtOH
1-Propanol, 3-bromo-2,2-bis(bromomethyl)-i—OH
Tris(tribromoneopentyl) phosphate
Tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate
1-Propanol, 3-bromo-2,2-bis(bromomethyl)-, phosphate (3:1) CR 900 FR 370 FR 372
Flame Cut 175 Flame Cut 175R Kronitex PB 370 PB 370
Reoflam FR 370 TPB 3070
Tris[2,2-bis(bromomethyl)-3-bromopropyl] phosphate Tris(2,3-dibromopropyl) phosphate Fyrol HB 32
1018.46 7.55 3.04E + 05 na
1.41E-17
697.61 3.71 2485
Dibromoneopentyl glycol
2.2-Bis(bromomethyl)-1,3-propanediol
1.3-Dibromo-2,2-bis(hydroxymethyl)propane 1,3-Dibromo-2,2-dihydroxymethylpropane 1,3-Dibromo-2,2-dimethylolpropane 2,2-Dibromomethyl-1,3-propanediol
FR 1138 FR 522 NSC 9001
Pentaerythritol dibromide
Pentaerythritol dibromohydrin
2,2,2-Tris(bromomethyl)ethanol
Tribromoneopentyl alcohol
2,2-Bis(bromomethyl)-3-bromo-1-propanol
3-Bromo-2,2-bis(bromomethyl)-1-propanol
3-Bromo-2,2-bis(bromomethyl)propanol
3-Bromo-2,2-bis(bromomethyl)propyl alcohol
FR 1360
FR 513
NSC 20521
Pentaerythritol tribromide Pentaerythritol tribromohydrin
261.94 0.41 39.9
324.84 2.06 315
1.60E-03
a It is possible to add the positions for the bromine substituents in front of the abbreviation. b Well established abbreviation. No change is proposed.
c TBBPA or TBBPS derivatives are constructed as a mix of the traditional abbreviations and the novel abbreviations are added for the functionalisation of the hydroxyl group. d PBPhO-PBDE stands for polybromophenoxy-PBDE, in analogy with e.g. MeO-PBDE.
Practical abbreviation (PRAB, in bold) for chlorine containing flame retardants, together with structured abbreviations (STAB; plain text) are presented.
The table also includes some basic physicochemical constants calculated using ACD/Labs Software V11.02. The STABs are constructed as described under "Methodology", incl. Table 1.
number
PRABs STABs
Previously used CA name abbreviations
Common and trade names
Additive or MW reactive BFR
Log Kow
pKa Vapor pressure
HCP-Anh
TeCPht-Anh
1,3-Isobenzofurandione, 4,5,6,7-tetrachloro-
39569-21-6 TBCT
TeBCMeBza
4-tetrabromo-5-chloro-6-methyl-
77-47-4
HxCcPe(dien)
1,3-Cyclopentadiene, 1,2,3,4,5,5-hexachloro-
115-27-5
HCBCH-DCAnh
HxCbcHte-DiCaAnh
4,7-Methanoisobenzofuran-1,3-dione, 4,5,6,7,8 hexachloro-3a,4,7,7a-tetrahydro-
Tetrachlorophthalic anhydride
Phthalic anhydride, tetrachloro- (6CI,8CI)
1,3-Dioxy-4,5,6,7-tetrachloroisobenzofuran
3,4,5,6-Tetrachlorophthalic anhydride
NSC 1484
Niagathal
Tetrachlorophthalic acid anhydride 2,3,4,5-tetrabromo-6-chloromethylbenzene 2,3,4,5-Tetrabromo-6-chlorotoluene Tetrabromo-o-chlorotoluene
285.9 3.5
na 1.41E-03
442.17 6.29 62,800
na 1.72E-03
Hexachlorocyclopentadiene Cyclopentadiene, hexachloro- (7CI) 1,2,3,4,5,5-Hexachloro-1,3-cyclopentadiene 1,2,3,4,5,5-Hexachlorocyclopentadiene C 56
Graphlox HRS 1655
Hexachloro-1,3-cyclopentadiene NSC 9235
Perchlorocyclopentadiene 8- 1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride
5-Norbornene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachloro- (6CI,8CI)
Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride,1, 4,5,6,7,7-hexachloro- (5CI) 1,4,5,6,7,7-Hexachloro-5-bicyclo[2.2.1]heptene-2,3-dicarboxylic anhydride
1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride
1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]-5-heptene-2,3-
dicarboxylic acid anhydride
2,3-Dicarboxy-1,4,5,6,7,7-
hexachlorobicyclo[2.2.1]hept-5-ene anhydride
3,4,5,6,7,7-Hexachloro-1,2,3,6-tetrahydro-3,6-
endomethylenephthalic anhydride
Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid,
1,4,5,6,7,7-hexachloro-, anhydride
Chloran 542
Chlorendic anhydride
HET Anhydride
Hexachloro-5-norbornene-2,3-dicarboxylic anhydride Hexachloroendomethylene tetrahydrophthalic anhydride Kayahard CLA NSC 22229
endo-1,4,5,6,7,7-Hexachloro-1,2,3,4-tetrahydro-5-norbornene-2,3-dicarboxylic acid anhydride
370.83 1.33
na 9.79E-07
CAS PRABs Previously used CA name
number STABs abbreviations
115-28-6 HCBCH-DCA HETacid Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic
HxCbcHte-DiCaA acid.l ,4,5,6,7,7-hexachloro-
51936-55-1 DBHCTD HCDBCO 1,4-Methanobenzocyclooctene, 7,8-dibromo-
DiBHxCTrcTrDenb 1,2,3,4,11,11 -hexachloro-1,4,4a,5,6,7,8,9,10,
1Oadecahydro-
2385-85-5 MIREX MIREX l,3,4-Metheno-lH-cyclobuta[cd]pentalene,l,
Per-CPecDe 1 a,2,2,3,3a,4,5,5,5a,5b,6-dodecachlorooctahydro-
31107^14-5 DDC-DBF Dec 602
DDC-DiMeDiBzFb
1,4:6,9-Dimethanodibenzofuran,l ,2,3,4,6, 7,8,9,10,10,11,11 -dodecachloro-1,4,4a, 5a,6,9,9a,9b-octahydro-
Common and trade names
Additive or MW Log Koc pKa Vapor pressure
reactive BFR Kow (Pa)
l,4,5,6,7,7-Hexachlorobicyclo-(2,2,l )hept-5-en- R
2,3-dicarboxylic acid
5-Norbornene-2,3-dicarboxylic acid, 1,4,5,6,7,7-hexachloro-(6CI,8CI); 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic acid
l,4,5,6,7,7-Hexachlorodicyclo-(2.2.1 )-5-heptene-2,3-dicarboxylic acid
2H,3H-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chlorendic acid HET acid
Hexachloroendomethylenetetrahydrophthalic acid NSC 22231 NSC 41876
5,6-Dibromo-l ,10,11,12,13,13-hexachloro-l 1 - A
tricyclo[8.2.1.02,9]tridecene
7,8-Dibromo-l ,2,3,4,11,11 -hexachloro-1,4,
4a,5,6,7,8,9,10,10a-decahydro-l,4-methanobenzo
[8]annulene
Saytex BC 26
Citex BC 26
Perchloropentacyclodecane Perchloropentacyclo[5.2.1.02,6.03,9.05,8]decane l,3,4-Metheno-lH-cyclobuta[cd]pentalene, dodecachlorooctahydro- (7CI) 1,3-Cyclopentadiene, 1,2,3,4,5,5-hexachloro-, dimer Dechlorane Dechlorane 4070 Dodecachlor
Dodecachlorooctahydro-l,3,4-metheno-
2Hcyclobuta[cd]pentalene
Dodecaclor
ENT 25719
GC 1283
Hexachlorocyclopentadiene dimer Mirex
NSC 124102 NSC 26107 NSC 37656 Paramex
Perchlorodihomocubane
Perchloropentacyclo[5.3.0.02,6.03,9.04,8]decane
1,2,3,4,6,7,8,9,10,10,11,11 -Dodecachloro-1, A
4,4a,5a,6,9,9a,9b-octahydro-l,4:6,9-
dimethanodibenzofuran
Dechlorane 602
388.84 4.6 pH-dep. 1.26 4.49E-08
540.76 7.62 3.32E + 05 na 8.27E-07
545.54 7.11 1.75E + 05 na 1.01 E-04
613.62 8.3 7.78E + 05 na 1.48E-09
13560-89-9 DDC-CO DP
DDCDiMeDiBzcO"
l,4:7,10-Dimethanodibenzo[a,e]cyclooctene, 1,2,3,4,7,8,9,10,13,13,14,14-dodecachloro-1,4,4a,5,6,6a,7,10,10a,l 1,12,12a-dodecahydro-
13560-92-4 DDC-Ant Dec 603
DDC-TrMeAntb
34571-16-9 HCTBPH Dec 604
HxCTeBPhbcHen
See * SCCPC SCCP
1,4:5,8:9,10-Trimethanoanthracene,l ,2,3,4, 5,6,7,8,12,12,13,13-dodecachloro-l ,4,4a,5,8, 8a,9,9a,10,1 Oa-decahydro-
Bicyclo[2.2.1 ]hept-2-ene, 1,2,3,4,7,7-hexachloro-5- (2,3,4,5-tetrabromophenyl) -
Allanes, C10-13, chloro CxH(2x-y + 2)Cly
See* MCCPC MCCP Allanes, C14-17, chloro
CxH(2x-y + 2)Cly
See* LCCPC LCCP Alkanes, Cl 8-30, chloro
CxH(2x —y + 2)Cly
115-96-8 TCEP TCEP Ethanol, 2-chloro-, phosphate (3:1)
tCEtP Ck
Dodecachlorodimethanodibenzocyclooctane A 653.72 10.12 7.67E + 06 na 1.37E-11
1,2,3,4,7,8,9,10,13,13,14,14-Dodecachloro-
1,4,4a,5,6,6a,7,10,10a,l 1,12,12a-dodecahydro-
l,4:7,10-dimethanodibenzo[a,e]cyclooctane
Bis (hexachlorocyclopentadieno) cyclooctane
Dechloran A
Dechlorane Plus
Dechlorane Plus 1000
Dechlorane Plus 25
Dechlorane Plus 2520
Dechlorane Plus 35
Dechlorane Plus 515
Dodecachlorododecahydrodimethanodibenzocyclooctane Dodecachlorododecahydrodimethanodibenzocyclooctene
1,2,3,4,5,6,7,8,12,12,13,13-Dodecachloro-l,4,4a,5,8,8a,9,9a, A 637.68 9.14 2.24E + 06 na 9.16E-10
10,10a-decahydro-l,4:5,8:9,10-Trimethanoanthracene
l,2,3,4,7,7-Hexachloro-5-(2,3,4,5-tetrabromophenyl)- A 692.5 10.24 8.86E + 06 na 1.61E-08
Bicyclo[2.2.1 ]hept-2-ene
2-Norbornene, 1,2,3,4,7,7-hexachloro-5-
(tetrabromophenyl) - (8CI)
5-(Tetrabromophenyl)-l,2,3,4,7,7-hexachloro-
2-norbornene
Dechlorane 604 Component A Hexachlorocyclopentadiene-tetrabromostyrene adduct Dechlorane 604
Short-chained chlorinated paraffins A na na na na na
CI 0-13 chloro alkanes
Chloro alkanes
C10-13
Hordalub 500
Witaclor 149
Witaclor 171P
sPCA 60
Medium-chained chlorinated paraffins A na na na na na
Long-chained chlorinated paraffins A na na na na na
Tris(chloroethyl) phosphate A 285.49 1.47 150 na 1.44E-02
Amgard TCEP
Celluflex CEF Disflamoll TCA Fyrol CEF
(continued on next page)
number
PRABs STABs
Previously used CA name abbreviations
Common and trade names
Additive or MW reactive BFR
Log Kow
pKa Vapor pressure (Pa)
78-43-3
tDiCPrP
1-Propanol, 2,3-dichloro-, 1,1',1 "-phosphate
13674-87-8 TDCIPP tDiCiPrP
TDCIPP
2-Propanol, 1,3-dichloro-, phosphate (3:1)
38051-10-4 BCMP-BCEP
bCMePrDiOHbbCEtP
Phosphoric acid, P,P'-[2,2-bis(chloromethyl)-1,3-propanediyl] P,P,P',P'-tetrakis (2-chloroethyl) ester
Fyrol CF Genomoll P NSC 3213 Niax 3CF
Niax Flame Retardant 3CF TCEP
Tri(2-chloroethyl) phosphate Tri(chloroethyl) phosphate Tri(K-chloroethyl) phosphate Tris(2-chloroethyl) orthophosphate Tris(2-chloroethyl) phosphate Tris(K-chloroethyl) phosphate Tris(2,3-dichloropropyl) phosphate 1-Propanol, 2,3-dichloro-, phosphate (3:1) (8CI,9CI) Celluflex FR 2 Fyrol 32B
Tri(2,3-dichloropropyl) phosphate Tris(2,3-dichloro-n-propyl) phosphate
Tris(1,3-dichloroisopropyl) phosphate 3PC-R
Antiblaze 195 CRP
CRP (fireproofing agent) FR10
FR10 (phosphate) Fyrol FR 2 PF 38 PF 38/3 TDCPP
Tris(1,3-dichloro-2-propyl) phosphate Tris(1-chloromethyl-2-chloroethyl)phosphate Tris[2-chloro-1-(chloromethyl)ethyl] phosphate 2,2-Bis(chloromethyl)-1,3-propanediol bis[bis(2-chloroethyl)phosphate]
Phosphoric acid, 2,2-bis(chloromethyl)-1,3-propanediyl tetrakis(2-chloroethyl) ester (9CI) Phosphoric acid, bis(2-chloroethyl) ester, diester with 2,2-bis(chloromethyl)-1,3-propanediol (7CI) 2,2-Bis(chloromethyl)-1,3-propanediol 2-chloroethanol phosphate (1:4:2)
2,2-Bis(chloromethyl)-1,3-propanediyl
bis[bis(2-chloroethyl)phosphate]
Amgard V 6
Antiblaze 100
Antiblaze AB 100
Antiblaze V 6
Phosgard 2XC20
na 8.67E-07
430.9 3.27
na 5.43E-06
582.99 2.52
na 1.61E-12
a It is possible to add the positions for the chlorine substituents in front of the abbreviation. b Some structural element is left out in the proposed STAB to minimize the complexity thereof. c Well established abbreviation. No change is proposed.
# CAS numbers for SCCP, MCCP and LCCP: 61788-76-9, 63449-39-8, 68920-70-7, 71011-12-6, 84082-38-2, 84776-07-8, 84776-06-7, 85049-26-9, 85422-92-0, 85535-85-9, 85535-84-8, 85535-86-0, 85536-22-7, 85681-73-8, 97553-43-0,
97659-46-6,106232-86-4,106232-85-3, 108171-27-3,108171-26-2.
Practical abbreviation (PRAB, in bold) for phosphorus containing flame retardants, together with structured abbreviations (STAB; plain text) are presented, The table also includes some basic physicochemical constants calculated using ACD/ Labs Software V11.02. The STABs are constructed as described under "Methodology", incl. Table 1.
CAS number PRABs STABs
Previously used CA name abbreviations
Common and trade names
Log Kow Koc
Vapor pressure (Pa)
512-56-1
78-40-0
126-71-6
126-73-8
78-51-3
tBuOEtP
TnPP TPrP
TiBP TIP
TBEP TBXP
Phosphoric acid, trimethyl ester
Phosphoric acid, triethyl ester
Phosphoric acid, tripropyl ester
Phosphoric acid, tris(2-methylpropyl) ester
Phosphoric acid, tributyl ester
Ethanol, 2-butoxy-, 1,1',1 "-phosphate
Tris(methyl) phosphate Trimethyl phosphate CCRIS 610 NSC 58985
Phosphoric acid, trimethyl ester NCI-C03781
Trimethoxyphosphineoxide Methyl phosphate Tris(ethyl) phosphate Triethyl phosphate Ethyl phosphate Aurora KA-1638 Fyrol TEP
Phosphoric acid, triethyl ester
Tris(propyl) phosphate
Tri-n-propyl phosphate
TPP Propyl phosphate
Tripropyl phosphate
Phosphoric acid tri-n-propyl ester
Tris(n-propyl) phosphate
Tris(isobutyl) phosphate
Phosphoric acid, triisobutyl ester
Tris(2-methylpropyl) phosphate
Antifoam TIP
Daiguard 400
NSC 62222
Reomol TIBP
Tris(butyl) phosphate
Tri-n-butyl phosphate
MCS2495
Butyl phosphate
Celluphos 4
Disflamoll TB
Kronitex TBP
Phos-Ad 100
Antifoam T
Tributylphosphate
Phosphoric acid, tri-n-butyl ester
Tris(2-butoxyethyl) phosphate
Ethanol,2-butoxy-, phosphate (3:1)
Phosphoric acid, tris(2-butoxyethyl)ester
2-Butoxyethanol phosphate
Amgard TBEP
Hostaphat B310
Ethanol, 2-butoxy-,1,1',1 "-phosphate Phosflex T-BEP
Tris(2-butoxyethyl) phosphate Tris(2-n-butoxyethyl) phosphate
140.08 -0.65 3.2-12
1.13E + 02
182.16 0.80
224.24 1.87
266.32 3.60
5.24E + 01
5.77E-01
1.71E + 00
266.32 4.00
1.51E-01
398.48 3.75
3.33E-06
Table 4 (continued)
CAS number PRABs Previously used CA name
STABs abbreviations
78-42-2 TEHP TEHP Phosphoric acid, tris(2-ethylhexyl) ester
tEtHP TOF
115-96-8 TCEP TCEP Ethanol, 2-chloro-, phosphate (3:1)
tCEtP 0
O'^O—Cl
13674-84-5 TCIPP TCPP 2-Propanol, 1-chloro-, 2,2',2"-phosphate
78-43-3 TDCPP
tDiCPrP
1-Propanol, 2,3-dichloro-, 1,1',1 "-phosphate
Common and trade names
MW Log Kow Koc Vapor pressure
Tris(butoxyethyl) phosphate
Tris(2-ethylhexyl) phosphate
2-Ethylhexanol,phosphate (3:1)
DisflamollTOF
Trioctyl phosphate
Tris(2-ethylhexyl) phosphate
Durad TOP
Flexol TOF
NSC 407921
Reomol TOF
Tris(chloroethyl) phosphate 3CF
Amgard TCEP
Celluflex CEF Disflamoll TCA Fyrol CEF Fyrol CF Genomoll P NSC 3213 Niax 3CF
Niax Flame Retardant 3CF Tris(2-chloroethyl) phosphate Tris(chloroethyl) phosphate Tris(B-chloroethyl) phosphate Tris(2-chloroethyl) orthophosphate Tris(2-chloroethyl) phosphate Tris(B-chloroethyl) phosphate Tris ( 2 -chloroisopropyl ) phosphate 2-Propanol, 1-chloro-, phosphate (3:1) Fyrol PCF Antiblaze 80
l-Chloro-2-Propanol Phosphate (3:1) Amgard TMCP Hostaflam OP 820
Phosphoric acid, tris(2-chloro-l-methylethyl) ester Tri-(2-chloroisopropyl) phosphate Tris(l-chloro-2-propyl) phosphate Tris(2-chloro-1 -methylethyl) phosphate Tris(p.-chloropropyl) phosphate Tris(chloroisopropyl) phosphate Tris(2,3-dichloropropyl) phosphate 1-Propanol, 2,3-dichloro-, phosphate (3:1) (8CI.9CI) Celluflex FR 2
434.64 9.49 617,000 1.10E-05
285.49 1.47 150 1.44E-02
327.56 2.59 275 2.69E-03
430.9 2.98 998 8.67E-07
13674-87-8 TDCIPP tDiCiPP
TDCPP TDCiPP
38051-1CM BCMP-BCEP
bCMePrDiOHbbCEtP
2-Propanol, 1,3-dichloro-, phosphate (3:1)
ck „ ja
Phosphoric acid, P,P'-[2,2-bis(chloromethyl)-l, 3-propanediyl] P,P,P',P'-tetrakis(2-chloroethyl) ester
1047637-37-5 BCMP-BCMEP
bCMePrDiOHbb CMeEtP
U-OPFR
Phosphoric acid, P.P '-[2,2-bis(chloromethyl)-l, 3-propanediyl] P,P,P',P '-tetrakis(2-chloro-1-methylethyl) ester
Fyrol 32B
Tris(2,3-dichloropropyl) phosphate Tris(2,3-dichloro-n-propyl) phosphate
Tris(l,3-dichloroisopropyl) phosphate 3PC-R
Antiblaze 195 CRP
CRP (fireproofing agent) FR 10
FRIO (phosphate) Fyrol FR 2 PF 38 PF 38/3 TDCPP
Tris ( 1,3 -dichloro-2 -propyl ) phosphate Tris(l-chloromethyl-2-chloroethyl)phosphate Tris[2-chloro-l-(chloromethyl)ethyl] phosphate 2,2-Bis(chloromethyl)-l,3-propanediol bis[bis(2-chloroethyl) phosphate]
Phosphoric acid, 2,2-bis(chloromethyl)-l,
3-propanediyl tetrakis(2-chloroethyl) ester (9CI)
Phosphoric acid, bis(2-chloroethyl) ester, diester with
2,2-bis(chloromethyl)-l,3-propanediol (7CI)
2,2-Bis(chloromethyl)-l,3-propanediol
2-chloroethanol phosphate (1:4:2)
2,2-Bis(chloromethyl)-l,3-propanediyl
bis[bis(2-chloroethyl) phosphate]
Amgard V 6
Antiblaze 100
Antiblaze AB 100
Antiblaze V 6
Phosgard 2XC20
2,2-Bis(chloromethyl)-l,3-propanediol bis[bis(2-chlorol-methylethyl) phosphate]
2,2-Bis(chloromethyl)propane-l ,3-diyl tetrakis ( 1 -chloropropan-2-yl) bis (phosphate)
430.9 3.27 1440 5.43E-06
582.99 2.52 557 1.61E-12
639.1 3.93 3280 1.96E-13
(continued on next page)
CAS number PRABs Previously used CA name
STABs abbreviations
126-72-7 TDBPP TDBPP 1-Propanol, 2,3-dibromo-, 1,1',1 "-phosphate
tDiBPrP O
19186-97-1 TTBNPP CR 900 1-Propanol, 3-bromo-2,2-bis(bromomethyl)-,
tBbBMe-PrP FR 370 1,1',1 "-phosphate
-Br ,Br
Br^Co.p'° _ /-Br
Rr—'
46355-07-1 IPPP Phosphoric acid, mono(l-methylethyl)
iPrPhP monophenyl ester
Common and trade names
MW Log Kow Koc Vapor pressure
Tris(2,3-dibromopropyl) phosphate 1-Propanol, 2,3-dibromo-, phosphate (3:1) (6CI,8CI,9CI) Phosphoric acid, tris(2,3-dibromopropyl) ester (6CI) 3PBR
Anfram 3PB Apex 462-5 Bromkal P 67-6HP ES 685
FireMaster LV-T 23P FireMaster T 23 FireMaster T 23P Flammex AP Flammex LV-T 23P Flammex T 23P Fyrol HB 32 NSC 3240 Phoscon FR 150 Phoscon PE 60 Phoscon UF-S T23P TDBPP Tris
Tris (flame retardant) Zetofex ZN
Tris(tribromoneopentyl) phosphate
Tris [3-bromo-2,2 -bis ( bromomethyl ) propyl ] phosphate
1-Propanol, 3-bromo-2,2-bis(bromomethyl)-, phosphate (3:1) CR 900 FR 370 FR 372
Flame Cut 175 Flame Cut 175R Kronitex PB 370 PB 370
Reoflam FR 370 TPB 3070
Tris[2,2-bis(bromomethyl)-3-bromopropyl] phosphate Isopropyl phenyl phosphate
697.61 3.71 2485 3.17E-09
1018.46 7.55 3.04E + 05 1.41E-17
216.17 1.71 na 5.49E-02
35948-25-5 DOPO
DiBzOPO
6H-Dibenz[ c,e ] [ 1,2 ] oxaphosphorin, 6-oxide 0
115-86-6 TPHP TPP Phosphoric acid, triphenyl ester
tPhP TPhP
O-P-O .0
1330-78-5 TMPP TCP Phosphoric acid, tris(methylphenyl) ester
tMePhP TTP \
2502-15-0 TIPPP tiPrPhP
57583-54-7 PBDPP
RebDiPhP
Phenol, 4-(l-methylethyl)-, phosphate (3:1)
Phosphoric acid, P,P'-l,3-phenylene P,P,P', P'- tetraphenyl ester
3,4:5,6-Dibenzo-2H-l,2-oxaphosphorin-2-oxide
6-Hydroxy-6H-dibenz[ c,e ] [ 1,2 ] oxaphosphorin
9,10-Dihydro-9-oxa-l O-phosphaphenanthren-10-oxide
9,10-Dihydro-9-oxa-l O-phosphaphenanthrene 10-oxide
9,10-Dihydro-9-oxa-l O-phosphorylphenanthrene-10-oxide
HCA (heat stabilizer) Hiretar 101 Sanko HCA Ukanol DOPO Ukanol GKF
Tris (phenyl) phosphate
Triphenyl phosphate
Phosphoric acid, triphenyl ester
Phosflex TPP
Kronitex TPP
Celluflex TPP
Disflamoll TP
Tris(methylphenyl) phosphate
Tricresyl phosphate (mixture of ortho, meta, para)
TBT Cresyl phosphate
Tritolyl phosphate
Phosphoric acid, tricresyl ester
Phosphoric acid, tritolyl ester
Celluflexl 79c
Disflamolltkp
Flexolplasticizer TCP
Fyrquell50
Imolsl40
Kronitex
Lindol
Nci-c61041
Phosflexl 79a
Tris(4-isopropylphenyl) phosphate Phenol, p-isopropyl-, phosphate (3:1) (8CI) p-Cumenyl phosphate ((C9H110)3P0) (7CI) Tris (p-isopropylphenyl) phosphate
Resorcinol bis(diphenyl phosphate)
Phosphoric acid, 1,3-phenylene tetraphenyl ester (9CI)
1,3-Phenylene bis(diphenyl phosphate)
ADK Stab PFP
ADK Stab PFR
BPHPPO
CR 733S
Fyrolflex RDP
216.17 na na 4.15E-04
326.29 4.59 2630 8.37E-04
368.37 5.11 4680 8.00E-05
452.52 6.75 1.12E + 05 3.89E-07
574.46 7.08 1.69E + 05 5.01E-11
MW Log Kow Koc Vapor pressure
LDP 301 Mark PFK Nonnen R0111-10 PFR
Reofos RDP
Resorcinol tetraphenyl diphosphate Tetraphenyl m-phenylene bisphosphate Tetraphenyl m-phenylene diphosphate Tetraphenyl resorcinol bis(diphenyl phosphate) Tetraphenyl resorcinol diphosphate WSFR-RDP
m-Phenylene bis(diphenyl phosphate)
CAS number PRABs Previously used CA name Common and trade names
STABs abbreviations
139189-30-3 PBDMPP
RebDiDiMePhP
Phosphoric acid, P,P'-1,3-phenylene P,P,P', P'-tetrakis(2,6-dimethylphenyl) ester
5945-33-5
BPA-BDPP
BPAbDiPhP
Phosphoric acid, P,P'-[(1-methylethylidene)di-4, 1-phenylene] P,P,P',P'-tetraphenyl ester
Resorcinol bis[di(2,6-dimethylphenyl) phosphate] Phosphoric acid, 1,3-phenylene tetrakis (2,6-dimethylphenyl) ester (9CI) 1,3-Phenylenebis(2,6-dimethylphenyl phosphate) ADK Stab FP 500 FP 500 PX 200
PX 200 (phosphate) Resorcinol bis(di-2,6-xylyl phosphate) Resorcinol bis[bis(2,6-dimethylphenyl) phosphate] Tetrakis(2,6-dimethylphenyl) m-phenylene bisphosphate Tetrakis(2,6-dimethylphenyl) m-phenylene diphosphate Tetrakis(2,6-xylyl) m-phenylene diphosphate Bisphenol A bis(diphenyl phosphate) Phosphoric acid, (1-methylethylidene)di-4, 1-phenylene tetraphenyl ester (9CI) Phosphoric acid, diphenyl ester, diester with 4,4'-isopropylidenediphenol (7CI) Phosphoric acid, isopropylidenedi-p-phenylene tetraphenyl ester (8CI)
2,2-Bis[4-[bis(phenoxy)phosphoryloxy]phenyl]propane
4,4'-(Isopropylidenediphenyl) bis(diphenyl phosphate)
ADK Stab FP 600
ADK Stab FP 700
BPA-DP
Bisphenol A tetraphenyl diphosphate CG 963 CR 741S CR 742 E 890 FP 600 FP 700 FP 750
Fyrolflex BDP NcendX P 30 Ncendex P 30
Resorcinol bis(diphenyl phosphate)-Bisphenol A Bis(diphenyl phosphate) copolymer Tetraphenyl bisphenol A bisphosphate WSFR-BDP
686.67 10.28 9.34E + 06 4.44E-13
692.63 8.29
7.70E + 05 1.97E-15
A. Bergman et al. / Environment International 49 (2012) 57-82
BFRs presented in Table 2 are structured as follows, with increasing molar masses for each subgroup:
1. Aromatic BFRs
One aromatic ring compounds
Benzenes, including alkyl substituted benzenes Phenols (simple) and one ring phenols being derivatized Benzoic acid esters and phthalate esters Two ring aromatic systems
Neutrals aromatics (PBB and PBDEs, polybrominated trimethylophenyl indanes, others) TBBPA TBBPS and derivatives Three ring aromatics
2. BFRs containing both aromatic and cycloaliphatic structures
3. Cycloaliphatic BFRs
4. Heterocyclic BFRs (triazine rings)
5. Brominated phosphate esters as BFRs
6. Aliphatic BFRs
The BFRs are characterized by moderate to very high log Kow, with very few exceptions. Four of the BFRs listed are phenolic chemicals, two are one-phenyl ring compounds and two are bisphenols, which leads to a pH-dependent water solubility for each of these chemicals.
CFRs are listed in Table 3. The table is organized in a similar manner as Table 2, starting with aromatic CFRs and ending with aliphatic CFRs. The CFRs are also characterized by intermediate to high log Kow constants.
PFRs are listed in Table 4. The PFRs are presented in two groups, those containing an aromatic part (substituent) and those with only aliphatic ester groups, potentially bearing halogen substituents. Some of the PFRs also contain chlorine substituents, which enhance their log Kow, and possibly their bioaccumulation potential (van der Veen and de Boer, 2012).
Finally, it is our hope that the proposed PRABs for BFRs, CFRs and PFRs, in this document, will result in a general acceptance and use among scientists and stakeholders in the field. If used as proposed, it will result in less confusion when BFRs, CFRs or PFRs are being reported, even though the abbreviations may, in a few cases, be perceived as somewhat complicated.
Acknowledgments
NVDE and AC acknowledge PhD and post-doctoral fellowships from the Flanders Research Foundation (FWO). AR acknowledges faculty funding from Stockholm University and Stockholm University's Strategic Marine Environmental Research Funds through the Baltic Ecosystem Adaptive Management (BEAM). The opinions expressed here are those of the authors and do not necessarily reflect the views of the California Department of Toxic Substances Control, or of NIEHS, NIH, or the U.S. Government.
References
Andersson PL, Oberg K, Orn U. Chemical characterization of brominated flame retardants and identification of structurally representative compounds. Environ Toxicol Chem 2006;25:1275-82. Arcadis EBRC. Evaluation of data on flame retardants in consumer products. Final
report to the European Commission; 2011. p. 402. Babrauskas V, Blum A, Daley R, Birnbaum L Flame retardants in furniture foam: benefits and risks. Fire Safety Science — Proceedings of the 10th International Symposium of the International Association for Fire Safety Science, London; 2012. Ballschmiter K, Zell. Analysis of polychlorinated biphenyls (PCB) by glass capillary gas
chromatography. Fresenius Z Anal Chem 1980;302:20-31. Ballschmiter K, Bacher R, Mennell A, Fisher R, Riehle U, Swerev M. The determination of chlorinated biphenyls, chlorinated dibenzodioxins and dibenzofurans by GC-MS. J High Resolut Chromatogr 1992;15:260-70. Bergman A The abysmal failure of preventing human and environmental exposure to persistent brominated flame retardants: a brief historical review of BFRs. In: Alaee M, Reiner E, Clement R, editors. Commemorating 25 years of Dioxin Symposia; 2005. p. 32-40.
Birnbaum LS, Staskal DF. Brominated flame retardants: cause for concern? Environ Health Perspect 2004;112:9-17.
Blum A, Gold MD, Ames BN, Jones FR, Hett EA, Dougherty RC, et al. Children absorb tris-BP flame retardant from sleepwear: urine contains the mutagenic metabolite, 2,3-dibromopropanol. Science 1978;201:1020-3.
Covaci A, Gerecke AC, Law RJ, Voorspoels S, Kohler M, Heeb NV, et al. Hexabromo-cyclododecanes (HBCDs) in the environment and humans: a review. Environ Sci Technol 2006;40:3679-88.
Covaci A, Voorspoels S, Abdallah M, Geens T, Harrad S, Law R. Analytical and environmental aspects of the flame retardant tetrabromobisphenol-A and its derivatives. J Chromatogr A 2009;1219:346-63.
Covaci A, Harrad S, Abdallah MA-E, Ali N, Law RJ, Herzke D, et al. Novel brominated flame retardants: a review of their analysis, environmental fate and behaviour. Environ Int 2011;37:532-56.
de Boer J, de Boer K, Boon JP. Polybrominated biphenyls and diphenylethers. In: Paasivirta J, editor. The handbook of environmental chemistry. Part K: new types of persistent halogenated compoundsHeidelberg, Germany: Springer-Verlag; 2000. p. 61-95.
de Wit CA. An overview of brominated flame retardants in the environment. Chemosphere 2002;46:583-624.
de Wit CA, Kierkegaard A, Ricklund N, Sellström U. Emerging brominated flame retardants in the environment. In: Eljarrat E, Barcelo D, editors. The handbook of environmental chemistry. Brominated flame retardantsBerlin Heidelberg, Germany: Springer-Verlag; 2011. p. 241-86.
DiGangi J, Blum A, Bergman A de Wit CA, Lucas D, Mortimer D, et al. San Antonio statement on brominated and chlorinated flame retardants. Environ Health Perspect 2010;118: A516-8.
D'Silva K, Fernandes A, Rose M. Brominated organic micro-pollutants — igniting the flame retardant issue. Crit Rev Environ Sci Technol 2004;34:141-207.
EFRA European Flame Retardants Association. Market Statistics; 2007. http://www.cefic-efra.com/Content/Default.asp?PageID=200 (last accessed on 12 December 2011).
EFSA. Scientific opinion on polybrominated biphenyls (PBBs) in food. EFSA J 2010;8: 1789. [151 pp.].
EFSA Scientific opinion on polybrominated diphenyl ethers (PBDEs) in food. EFSAJ 2011a;9:2156. [274 pp.].
EFSA. Panel on Contaminants in the Food Chain (CONTAM); scientific opinion on hexabromocyclododecanes (HBCDDs) in food. EFSAJ 2011b;9:2296.
EFSA. Scientific opinion on tetrabromobisphenol A (TBBPA) and its derivatives in food. EFSAJ 2011c;9:2477.
EFSA. Scientific opinion on brominated flame retardants (BFRs) in food: brominated phenols and their derivatives. EFSAJ 2012;10:2634.
Eljarrat E, Barceleo D. Brominated flame retardants. New York: Springer; 2011.
Fiedler H. Short-chain chlorinated paraffins: production, use and international regulations. In: De Boer J, editor. The handbook of environmental chemistry. Chlorinated paraffinsBerlin Heidelberg, Germany: Springer-Verlag; 2010. p. 1-40.
Gold MD, Blum A, Ames BN. Another flame retardant, tris-(1,3-dichloro-2-propyl)-phosphate, and its expected metabolites are mutagens. Science 1978;200:785-7.
Harju M, Heimstad ES, Herzke D, Sandaanger T, Posner S, Wania F. Current state of knowledge and monitoring requirements: emerging "new" brominated flame retardants in flame retarded products and the environment. Norwegian Pollution Control Authority; 2009. p. 1-114.
Hindersinn RR. Historical aspects of polymer fire retardance. In: Nelson GL, editor. Fire and polymers hazard identification and prevention. American Chemical Society Symposium SeriesNew York: American Chemical Society; 1990.
Law RJ, Alaee M, Allchin CR, Boon JP, Lebeuf M, Lepom P, et al. Levels and trends of polybrominated diphenylethers (PBDEs) and other brominated flame retardants in wildlife. Environ Int 2003;29:757-70.
Law RJ, Allchin CR, de Boer J, Covaci A, Herzke D, lepom P, et al. Levels and trends of brominated flame retardants in the European environment. Chemosphere 2006;64: 187-208.
Law RJ, Herzke D, Harrad S, Morris S, Bersuder P, Allchin CR. Levels and trends of HBCD and BDEs in the European and Asian environments, with some information for other BFRs. Chemosphere 2008;73:223-41.
Letcher RJ, Klasson-Wehler E, Bergman A. Methyl sulfone and hydroxylated metabolites of polychlorinated biphenyls. The handbook of environmental chemistry volume 3K: anthropogenic compounds. Berlin Heidelberg, Germany: Springer-Verlag; 2000. p. 315-59.
Letcher RJ, Gebbink WA, Sonne C, Born EW, McKinney MA, Dietz R. Bioaccumulation and biotransformation of brominated and chlorinated contaminants and their metabolites in ringed seals (Pusa hispida) and polar bears (Ursus maritimus) from East Greenland. Environ Int 2009;35:1118-24.
Nicholls CR, Allchin CR, Law RJ. Levels of short and medium chain length polychlorinated n-alkanes in environmental samples from selected industrial areas in England and Wales. Environ Pollut 2001;114:415-30.
OJ. Off J Eur Union 2003;L 37:19-23. [13.02.2003].
OJ. Off J Eur Union 2008;C 116:2-3. [09.5.2008].
Örn U, Bergman A. An attempt to assess the present commercial production of brominated flame retardants. Third International Workshop on Brominated Flame Retardants, BFR 2004, Toronto, Canada; 2004. p. 467-72.
Papachlimitzou A, Barber JL, Losada S, Bersuder P, Law RJ. A review of the analysis of novel brominated flame retardants. J. Chromatogr. A 2012;1219:15-28.
Pijnenburg AMCM, Everts JW, de Boer J, Boon JP. Polybrominated biphenyl and diphenylether flame retardants: analysis, toxicity and environmental occurrence. Rev Environ Contam Toxicol 1995;141:1-26.
State of California. Department of Consumer Affairs. Bureau of Home Furnishings and Thermal Insulation, 117. Technical Bulletins, Sacramento, California; 2000. p. 133.
A. Bergman et al. / Environment International 49 (2012) 57-82
Sverko E, Tomy GT, Reiner EJ, Li Y-F, McCarry BE, Arnot JA, et al. Dechlorane plus and related compounds in the environment: a review. Environ Sci Technol 2011;45: 5088-98.
van der Veen I, de Boer J. Phosphorus flame retardants: properties, production, environmental occurrence, toxicity and analysis. Chemosphere 2012;88:1119-52. WHO/IPCS. Environmental Health Criteria 162. Brominated diphenyl ethers; 1994. p. 347. WHO/IPCS. Environmental Health Criteria 172. Tetrabromobisphenol A and derivatives; 1995. p. 139.
WHO/IPCS. Environmental Health Criteria 192. Flame retardants: a general introduction; 1997. p. 133.
Zennegg M. Identification of novel brominated flame retardants in new products of the Swiss market. Organohalogen Compd 2011;73:1238-41.
