Brominated Flame

Retardants:

Assessing DecaBDE Debromination

in the Environment

HEATHER M. STAPLETON (PhD, MS, BS)

MAY 2006

28 Boulevard Charlemagne

1000 Brussels (Belgium)

Tel.: +32 2 234 3640

Fax.: +32 2 234 3649

info@env-health.org

www.env-health.org
About the Author

Heather Stapleton’s expertise is in the fate and

biotransformation of organic contaminants in

aquatic systems, focusing on persistent organic

pollutants (POPs), such as polychlorinated

biphenyls (PCBs) and polybrominated diphenyl

ethers (PBDEs). She is presently carrying out

research on DecaBDE debromination at Duke

University, Nicholas School Faculty, Environmental

Sciences and Policy Division in her capacity as an

Environmental Chemist.

I. Context from European Public Health

Alliance – Environment Network.

The draft addendum environmental risk assessment

report for decabromodiphenyl ether (DecaBDE)

was distributed to the Technical Committee for

New and Existing Substances (TC NES) on August

11, 2005 (The addendum can be found at the

European INventory of Existing Commercial

chemical Substances (EINECS),

[http://ecb.jrc.it/existing-chemicals/]) . The

previous risk assessment, agreed in May 2004, had

concluded that further information was required

before definitive conclusions could be drawn on the

concerns from DecaBDE to the environment.

One of the key areas identified for further

clarification was the extent and importance of the

debromination of DecaBDE in the environment.

The conclusion in the draft addendum prepared by

the UK government highlights that it is still not

possible to give a reliable assessment of the overall

significance of debromination based on expert

judgment. Although the conclusions state that the

published data on debromination heightened the

concern, it did not necessary mean that

debromination was a significant pathway in the

environment. This view was also elaborated in a

TNO report commissioned by the Brominated

Science Environment Forum1, an industry based

association.

1 A.O. Hanstveit MSc, Dr. C.T. Bowmer, Dr. A.P. Freidig. TNO

Netherlands Organisation for Applied Scientific Research. A review of

the anaerobic and abiotic degradation of the flame retardant

decabromodiphenyl ether (CAS # 1163-19-5) in the context of an EU

environmental risk assessment report, customer BSEF – Bromine

Science and Environmental Forum & The International Organization of

the Bromine Chemical Industry. 17 August 2005 (ECB TRACKING

NO. COM013_ENV_IND 09)

The intent of this overview is to provide a summary

on the significance and extent of DecaBDE

debromination in the environment. If DecaBDE is

a ‘significant’ pathway for the formation of lower

brominated congeners, there are both potential

adverse environmental and health consequences.

The potential persistency and bioaccumulation

properties of the lower congeners must be taken

into consideration in the risk assessment.

Moreover, there may be legal implications for

putting on the market indirectly through DecaBDE

and into the environment these lower congeners,

such as PentaBDE and OctBDE, which are already

restricted under existing EU regulation.

II. Introduction

Decabromodiphenyl ether (BDE 209) is a multihalogenated organic chemical used primarily as a

flame retardant in a commercial mixture known as

DecaBDE. It has been used as an additive flame

retardant since the late 1970s, and because it is well

suited to flame retard in particular plastics, its

market demand has increased significantly over the

past few decades with the increasing use of plastics

in electrical goods

1

. Commercially produced

DecaBDE consists primarily of BDE 209 (<97%)

with minor contributions (0.3 to 3.0%) of octa- and

nonaBDE congeners (or iso-forms), which are

impurities in the technical mixture. A particular

concern regarding BDE 209 is the potential for

degradation via debromination. Debromination is a

process by which bromine atoms are sequentially

removed or cleaved from an organic compound,

resulting in a smaller lower brominated molecule

which is slightly more water soluble. These lower

brominated congeners have the potential to be more

persistent and more bioaccumulative than their

larger parent chemical. 

III. Environmental Levels of DecaBDE

Numerous studies have investigated the prevalence

of polybrominated diphenyl ether (PBDE)

congeners in the environment 2, 3. 

BDE 209 is a fully brominated PBDE congener

containing ten bromine atoms (See Figure 1). A

majority of environmental samples, specifically

Brominated Flame Retardants: Assessing DecaBDE Debromination in the Environment 2
human and biological samples, contain PBDE

congeners that are dominated by congeners with

four to six bromine atoms 4, 5. PentaBDE and

OctaBDE are two additional commercial

brominated flame retardant mixtures containing

PBDE congeners with four to eight bromine atoms

(see Table 1), and are believed to be the source of

these congeners in biological samples. However,

debromination of BDE 209 cannot be ruled out as a

source of these lower brominated congeners.

BDE 209 has been measured in house dust 6-8at

concentrations up to 10,000 ppb, which could be a

potential pathway of human exposure, particularly

for young children. Toddlers have a predisposition

to put dirty hands and toys in their mouth and

inadvertently ingest larger amounts of house dust.

This predilection has been responsible for large

cases of lead poisoning in U.S. children,9-11 due to

the high lead levels in house dust. No studies have

investigated the levels of PBDEs in children under

the age of 5; however, modeling studies suggest

toddlers are receiving greater exposure to PBDEs

than adults because of the high levels in house dust

12

. In some homes studied, BDE 209 comprises

90% of the total PBDE burden,7therefore, BDE

209 exposure could be unique to young children.

Conclusion

Debromination of BDE 209 cannot be ruled out as

a source of lower brominated congeners.

DecaBDE is mainly found in dust in the indoor

environment including our homes and cars which

may result in elevated exposures in children.

IV. Photolytic Debromination of BDE 209

 

BDE 209 absorbs sunlight in the UV region of the

electromagnetic spectrum that reaches the surface of

the earth. Due to this light absorption, BDE 209 is

susceptible to photodegradation, which can occur

significantly through debromination. A majority of

the UV spectrum is blocked by glass windows and

does not reach indoor environments. However,

substrates containing BDE 209 in direct sunlight do

receive UV radiation. Several studies have

investigated the photodegradation of BDE 209 to

determine the time it takes for 50% of the BDE 209

mass to degrade (known as the half-life). Half-lives

vary from a few minutes up to several years,

depending upon the substrate and light source

(Table 2). Söderström et al.

13 examined the

photolytic decomposition of BDE 209 in several

different types of substrates using both natural

sunlight and a UV-lamp. Their study demonstrated

that BDE 209 degraded very quickly in organic

solvents but was slower when adsorbed to sediment

and soils. Ahn et al.

14 also observed longer halflives of BDE 209 when adsorbed onto sediment and

minerals compared to dissolution in water and

organic solvents. These studies suggest that

adsorption of BDE 209 onto suspended material in

the water column decreases the photodegradation of

BDE 209 in aquatic environments. Stapleton 15

exposed BDE 209 spiked house dust to sunlight and

found that the half-life was approximately 220 hours

of continuous sunlight exposure, or assuming 10

hours of sunlight a day, approximately 22 days.

However, it is difficult to assess the magnitude and

duration of sunlight that house dust would be

exposed to in an average home. Most windows will

block out UV wavelengths of light which would

hinder degradation. In contrast, car dust has

recently been found to contain elevated levels of

BDE 209

(http://www.ecocenter.org/releases/20060111_aut

otoxics.shtml), which is susceptible to greater

sunlight exposure and in which debromination can

be expected to occur significantly.

The degradation products of BDE 209 photolysis

are primarily lower brominated PBDE congeners

formed via debromination. In soils, sediment and

house dust, the primary congeners identified are

hepta-, octa- and nonaBDE congeners

13-15

, and very

little degrades to congeners with fewer than six

bromine atoms. When dissolved in water or

Brominated Flame Retardants: Assessing DecaBDE Debromination in the Environment 3

O

2

3

4

5

2'

3'

4'

5'

6 6'

Polybrominated Diphenyl Ether (PBDE)

Brn n=1-10

 Figure 1. Structure of PBDE molecule.
organic solvents, BDE 209 degrades quite rapidly

and leads to greater formation of the lower

brominated congeners, including tri-, tetra- and

pentaBDE congeners, and also polybrominated

dibenzofurans (PBDFs)

13, 16, 17

. In the environment,

it is expected that BDE 209 will be found primarily

bound to solids in the water column, and bound to

particles in the atmosphere. Therefore, degradation

of BDE 209 dissolved in water (or organic solvents)

is not expected to be of environmental relevance.

Conclusion

It is difficult to assess the degree of BDE 209

photolytic debromination in house dust, soils and

sediments when exposed to light. However, in cars

debromination can be expected to occur more

significantly. Debromination in water is not

expected to be of environmental relevance.

V. Microbial and Reductive Debromination of

BDE 209

One published study has investigated the microbial

mediated debromination of BDE 209 under

anaerobic (no oxygen) conditions. Gerecke et al.

18

used microflora from sewage sludge to examine the

bacterial mediated degradation of BDE 209. Their

results indicated that debromination of BDE 209

did occur, leading to the formation of nona- and

octaBDE congeners. The observed first order

degradation rate, 1.0 x 10

-3 day-1

, is equivalent to a

half life of approximately 690 days. However, this

degradation rate was accelerated by the use of

primers to increase degradation potential. Without

the use of primers, the observed degradation rate

was 50% lower, resulting in a half-life of

approximately 3.8 years. Therefore, anaerobic

bacteria can initiate debromination of BDE 209,

albeit at a slower rate than photolytic

debromination. Given the hydrophobic nature of

BDE 209, and the large volumes that enter water

treatment facilities, anaerobic degradation may be

important in sewage sludge digesters. However, the

time that BDE 209 spends in the sewage sludge

(residence time) will greatly impact it’s ability to

anaerobically degrade.

Reductive debromination of BDE 209 has also been

reported to occur with mineral catalysts. Keum and

Li 19 documented a stepwise debromination process

using zero-valent iron and sulfide minerals. Zerovalent iron was a good oxidant for degradation,

resulting in a BDE 209 half-life of about one day.

The use of iron sulfide and sodium sulfide reduced

the debromination/degradation rate to 2 and 33%

of the rate observed for zero-valent iron. Both the

iron and sulfides resulted in debromination down to

congeners with two and three bromines. In all

experiments, the initial rate of degradation was rapid

and then decreased over time as lower brominated

congeners were formed that appeared to be more

stable. While this study demonstrates the possibility

and feasibility of reductive debromination by

minerals, this process is unlikely to occur naturally

in the environment. PBDEs will have a greater

tendency to be bound to natural organic matter and

soils in the environment before binding directly to

the mineral surface, which is necessary for the

mineral to act as an oxidant.

Conclusion

In sewage anaerobic bacteria can initiate

debromination of BDE 209, albeit at a slower rate

than photolytic debromination, but due to the large

volumes of DecaBDE in sewage sludge this may be

significant. 

VI. Metabolic Debromination

Debromination of BDE 209 has also been observed

in laboratory in vivo studies with fish and rats,

suggesting it is metabolized. In four separate

studies, fish fed food spiked with

decabromodiphenyl ether were found to accumulate

lower brominated congeners

20-23

. The assimilation

and debromination of BDE 209 varied among the

three fish species examined, which included rainbow

trout, common carp and lake trout. Common carp

accumulated no BDE 209 in their tissues, but they

did accumulate one penta-, three hexas-, two heptasand one octaBDE congener that appeared to result

from the debromination of BDE 209. In two

separate and independent research studies on

rainbow trout, accumulation of BDE 209 was

observed, although the uptake was less than 1% in

both studies. However, both studies observed an

increase in hexa-, hepta-, octa- and nonaBDE

congeners over time that comprised a higher

percentage of the PBDE body burden relative to the

BDE 209 body burden. One study found an

accumulation of 0.13% of the BDE 209 dose 20,

while the second study observed an uptake of 3.2%

of the BDE 209 dose

23

. Lake trout were found to

Brominated Flame Retardants: Assessing DecaBDE Debromination in the Environment 4
accumulate approximately 5% of the BDE 209 dose

and debromination was hypothesized to occur.

However, the diet in this latter study consisted of a

cocktail of 13 BDEs and it was impossible to

characterize debromination of BDE 209. 

Stapleton et al.,

23 recently conducted several in vitro

experiments using fish liver microsomes to

characterize metabolic biotransformation of BDE

209. Microsomes are cell fractions which contain

active enzymes from fish that typically metabolize

endogenous compounds (i.e. natural hormones).

Using carp and rainbow trout liver microsomes,

Stapleton found that as much as 65% of BDE 209

was debrominated in a twenty four hour period.

Carp microsomes rapidly debrominated as much as

30% of the BDE 209 mass to form BDE 155 and

BDE 154 (hexaBDEs). In contrast, rainbow trout

debrominated only 22% of the BDE 209 mass

primarily to octa- and nonaBDE congeners. This

study demonstrates that there are species specific

differences in the biotransformation/debromination

capacity of fish, and possibly, other organisms.

Stapleton hypothesizes that thyroid hormone

enzymes are responsible for this observed

debromination, which is similar to endogenous

metabolism of thyroid hormones.

In rats, metabolism of BDE 209 appears to occur

through different mechanisms. Two studies have

examined the uptake of BDE 209 in rats and both

identified hydroxyl- and methoxyBDE congeners in

tissues and plasma and only trace levels of

nonaBDE congeners. This suggests that rats may

initially debrominate BDE 209, but then other

metabolic pathways become more dominant,

resulting in the formation of more polar metabolites

that are likely to be excreted.

Conclusion

Some fish appear capable of debrominating BDE

209 through metabolism. The extent of the

metabolism varies among fish and it is difficult to

determine the extent of debromination that would

occur in the wild. 

VII. Human Debromination Potential

In a recent study, Thuresson et al.24 measured

PBDE levels in workers occupationally exposed to

BDE 209. Analysis of their serum identified several

hepta- and octa-BDE congeners that were not

present in the decaBDE commercial mixture nor in

the reference groups. The congener pattern

observed in these workers was very similar to the

congener pattern observed in the rainbow trout by

Stapleton et al.

23

. A follow up study examined the

BDE concentrations in these workers when they

had taken a vacation and reduced their exposure to

BDE 209

24

. This study found that while BDE 209

concentrations decreased in these workers with a

half life of approximately 15 days, concentrations of

the hepta- and octaBDE congeners increased,

suggesting that debromination of BDE 209 was

occurring in humans. 

More studies are needed to determine if BDE 209

debromination does occur in human tissues.

Exposure to BDE 209 is suggested to be greater for

young children relative to adults, due to the higher

levels present in house dust and thus, may need to

be investigated further. 

Conclusion

Studies suggest that DecaBDE debrominates in

humans however, more studies are needed to

confirm this analysis.

VIII. Summary

Table 1 compares the PBDE congeners that are

present in the commercial mixtures to the congeners

that have been identified as products of BDE 209

debromination. As evident in the table, all the

congeners present in the commercial products also

can be formed via debromination of DecaBDE. Of

particular concern in human and environmental

samples is the accumulation of lower brominated

congeners (i.e. tetra-, penta- and hexaBDEs). Based

on the current data available, the potential for

significant formation of these congeners in the

environment due to debromination is low. The only

studies demonstrating formation/production of

these congeners from debromination occurred when

BDE 209 was dissolved in organic solvents and

exposed to sunlight and/or UV sources, which is

not environmentally relevant. Additionally,

reductive debromination catalyzed by iron and iron

sulfides also can lead to these congeners. However,

the likelihood of BDE 209 being directly bound to

Brominated Flame Retardants: Assessing DecaBDE Debromination in the Environment 5
these types of mineral surfaces in the environment is

also low. 

In contrast, the formation of hexaBDE congeners

(e.g. BDE 153, BDE 154 and BDE 155) from

debromination of DecaBDE has more realistic

probabilities. Metabolic debromination resulted in

the formation of several hexaBDE congeners,

including BDE 154, in several fish species 20, 21, 23. In

these studies, less than 1% of the BDE 209

exposure debrominated to the hexaBDE congeners,

but as much as 2% debrominated into hepta-, octaand nonaBDE congeners. In the past year, a few

studies have documented a shift in the PBDE

congener patterns in human tissues. In most

studies, BDE 47 (tetraBDE) was the largest

contributor to the PBDE body burden; however

recent studies suggests some populations have a

PBDE body burden dominated by BDE 153, a

hexaBDE

25, 26

. The reason for this is unknown but

could be related to debromination of BDE 209,

exposure to different PBDE commercial sources, or

to longer half-lives for BDE 153 relative to BDE

47. 

Photolyitic debromination of DecaBDE in dust,

soils and sediments also leads to the formation of

several hepta-, octa- and nonaBDE congeners,

which is environmentally relevant. Because house,

office and car dust are enriched in BDE 209, the

potential for debromination is high when exposed

to sunlight. Current studies suggest that photolytic

debromination of BDE 209 leads to significant

accumulation of hepta-, octa- and nonaBDE

congeners which are persistent and potentially

bioaccumulative. There are very few studies which

have investigated the bioaccumulation potential and

environmental levels of hepta- through nonaBDE

congeners, which makes an assessment of their fate

difficult. More studies are needed to determine the

levels of these congeners in the environment

(particularly in sediment and dust) in order to

determine if debromination of BDE 209 is

occurring. 

Conclusion

The potential for significant formation of BDE 47,

BDE 99 and BDE 100 in the environment due to

debromination is low as the only study showing this

is not environmentally relevant. The formation of

hexaBDE has more realistic probability and could

be related to debromination of DecaBDE in

humans. Photolyitic debromination of DecaBDE in

dust, soils and sediments, leading to the formation

of hepta-, octa- and nonaBDE congeners is

environmentally relevant; not withstanding more

research on the significance of these lower

congeners fate in the environment.

Brominated Flame Retardants: Assessing DecaBDE Debromination in the Environment 6
Table 1. PBDE congeners identified in commercial mixtures and in debromination studies.

Congener identifications in the PentaBDE and OctaBDE commercial mixtures are from reference

27

.

Substitution Congener PentaBDE OctaBDE DecaBDE Formed From

Debromination

Reference

2,4,4’-tribromo BDE 28 X X

17

,

19

2,2’,4,4’-tetrabromo BDE 47 X X

17

,

13

,

19

2,2’,4,5’-tetrabromo BDE 49 X X

17

2,3’,4,4’-tetrabromo BDE 66 X X

19

2,2’3,4,4’-pentabromo BDE 85 X X

14

,

17

2,2’,4,4’,5-pentabromo BDE 99 X X

17

,

13

,

19

2,2’,4,4’,6-pentabromo BDE 100 X X

17

,

19

2,2’,3,4,4’,5’-hexabro

mo

BDE 138 X X

17

,

19

2,2’,4,4’,5,5’-hexabro

mo

BDE 153 X X

17

,

13

,

19

2,2’,4,4’,5,6’-hexabro

mo

BDE 154 X X

17

,

13

,

19

,

21, 23

2,2’,4,4’,6,6’-hexabro

mo

BDE 155 X X

21, 23

2,2’,3,4,4’,5’,6-

heptabromo

BDE 183 X X X

14

,

17

,

13

,

19

2,2’,3,4,4’,6,6’-heptabr

omo

BDE 184 X

23

2,2’,3,3’,4,4’,5,6’-octab

romo

BDE 196 X X

14

,

17

,

18

2,2’,3,3’,4,4’,6,6’-octab

romo

BDE 197 X X

14

,

17

,

18

2,2’,3,3’,4,5’,6,6’-octab

romo

BDE 201 X

23

2,2’,3,3’,5,5’,6,6’-octab

romo

BDE 202 X

23

2,2’,3,3’,4,5,5’,6-

octabromo

BDE 203 X X X

18

2,2’,3,3’,4,4’,5,5’,6-

nonabromo

BDE 206 X X X

14

,

17

,

13

2,2’,3,3’,4,4’,5,6,6’-non

abromo

BDE 207 X X X

14

,

17

,

13

,

18

2,2’,3,3’,4,5,5’,6,6’-non

abromo

BDE 208 X X X

14

,

17

,

13

,

18

2,2’,3,3’,4,4’,5,5’,6,6’-d

ecabromo

BDE 209 X X

Brominated Flame Retardants: Assessing DecaBDE Debromination in the Environment 7
Table 2. Photolytic half-lives of BDE 209 under various conditions.

Light Source Substrate Half Life (Reference)

UV lamp Organic Solvent <0.25 H13;

UV lamp Silica Gel <0.25 H13;

UV lamp Sand 12 H13;

UV lamp Sediment 40-60 H13; 150 D14;

UV lamp Soil 150-200 H13

UV lamp Methanol/water 0.5 H16

UV lamp Minerals 36 D – 3.9 Y14

Sunlight Hydrated on Quartz 35 H28;

Sunlight Hydrated with Humics on Quartz 70 H28

Sunlight Humic Acid Coated Sand 435 H28

Sunlight Hexane <0.25 H17

Sunlight Minerals 261-990 D14

Sunlight Sand 13-37 H13

Sunlight Sediment 30-80 H13

Sunlight House Dust 220 H 15

H- Hours; D- Days; Y- Years

Brominated Flame Retardants: Assessing DecaBDE Debromination in the Environment 8
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