Formation of PBDD/F from PBDE in electronic waste in recycling processes and under simulated extruding conditions

Chemosphere xxx (2014) xxx–xxx

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Chemosphere

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Formation of PBDD/F from PBDE in electronic waste in recyclingprocesses and under simulated extruding conditions

0045-6535/$ - see front matter � 2014 Elsevier Ltd. All rights reserved.http://dx.doi.org/10.1016/j.chemosphere.2013.12.101

⇑ Corresponding author. Tel.: +41 58 765 4953.E-mail address: [email protected] (A.C. Gerecke).

Please cite this article in press as: Zennegg, M., et al. Formation of PBDD/F from PBDE in electronic waste in recycling processes and under simextruding conditions. Chemosphere (2014), http://dx.doi.org/10.1016/j.chemosphere.2013.12.101

Markus Zennegg a, Mathias Schluep a, Martin Streicher-Porte a,b, Peter Lienemann a,c, Regula Haag a,Andreas C. Gerecke a,⇑a Empa, Swiss Federal Laboratories for Materials Science and Technology, Ueberlandstrasse 129, Dübendorf CH-8600, Switzerlandb FHNW, University of Applied Sciences and Arts Northwestern Switzerland, Institute for Biomass and Resource Efficiency, Steinackerstrasse 5, CH-5210 Windisch, Switzerlandc ZHAW Zurich University of Applied Sciences, Einsiedlerstrasse 31, CH-8820 Wädenswil, Switzerland

h i g h l i g h t s

�Waste electronic and electric equipment contained PBDE above RoHS guideline values.� Reductive PBDE debromination was not observed in the studied recycling processes.� During simulated and real-world recycling formation of PBDD/Fs was observed.� The measured PBDD/F formation rates were between 2 � 10�5 and 2 � 10�4 RPBDE�1 min�1.

a r t i c l e i n f o

Article history:Received 16 October 2013Received in revised form 13 December 2013Accepted 21 December 2013Available online xxxx

Keywords:PBDEPBDD/FWaste electrical and electronic equipmentRecycling

a b s t r a c t

The increasing volumes of waste electrical and electronic equipment (WEEE) in Europe and developingeconomies demand for efficient disposal solutions. However, WEEE also contains toxic compoundsand, therefore, there is a need for recycling technologies for WEEE that creates revenue without causingenvironmental harm. Among other fast developing economies, South Africa is tempting to make use ofrecycled plastic.

Brominated flame retardants (BFRs) are additives used to protect plastic materials in electrical andelectronic equipment (EEE) against ignition. Some BFRs are known persistent organic pollutants (POPs)and some BFRs can be transformed into highly toxic compounds such as polybrominated dibenzofuransand dioxins (PBDD/Fs).

In this study, the contents of critical BFRs, i.e. polybrominated diphenyl ethers, and highly toxic PBDD/Fs were measured in WEEE material from Switzerland and South Africa. The formation of PBDD/Fs hasbeen observed in two South African recycling processes and under controlled laboratory conditions.

Total PBDE-contents in the South African and Swiss plastic waste varied between 1 � 103 and 7 � 106

lg kg�1. A few WEEE plastic fractions exceeded the RoHS limit of 1 � 106 lg kg�1 for PBDEs and thus theycould not be used for recycling products without special treatment.

The total content ofP

PBDFs was around 1 � 103 lg kg�1. Such contents in materials do not pose a riskfor consumer under normal conditions. Workers at recycling plants might be at risk. The measured for-mation rates of PBDFs were between 2 � 10�5 and 2 � 10�4 PPBDE�1 min�1.

� 2014 Elsevier Ltd. All rights reserved.

1. Introduction

Today, the scarce availability of raw materials as well as risingoil prices cause a high demand for secondary plastics on the worldmarket and consequently also their prices are rising rapidly. At thesame time, increasing volumes of waste electrical and electronicequipment (WEEE) in Europe and developing economies demandfor an efficient disposal solution, which preferably should close

the cycle of secondary raw materials. In 2008, the plastics sharefrom European WEEE over all categories was estimated to amountto 20.6%. which corresponds to about 300000 tons of WEEE plas-tics recovered or disposed of in the same year (Wäger et al.,2012). These factors have offered new business opportunities andhave stimulated the development of plastic recycling technologieson one hand and a prosperous global trade of waste plastic on theother hand. However, WEEE also contains toxic compounds, suchas heavy metals and brominated flame retardants and therefore,there is an urgent need for recycling technologies for WEEE thatcreates revenue without causing environmental harm.

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2 M. Zennegg et al. / Chemosphere xxx (2014) xxx–xxx

Brominated flame retardants (BFRs) are additives used to pro-tect plastic materials in electrical and electronic equipment (EEE)against ignition. Some BFRs (e.g., pentabromodiphenyl ether (Pen-taBDE)) are known persistent organic pollutants (POPs) and thus,they were banned from being used in new EEE in the EU (Directive2002/95/EC of the European Parliament and of the Council of 27January 2003 on the restriction of the use of certain hazardous sub-stances in electrical and electronic equipment, ‘‘RoHS’’ directive)and Switzerland (Chemical Risk Reduction Ordinance, ORRChem).In the EU also the contents of decabromodiphenyl ether (DecaBDE)might not exceed 0.1% in EEE as set by the RoHS directive. However,DecaBDE, decabromodiphenyl ethane and other BFRs, which mightbe transformed into toxic compounds such as polybrominated dib-enzofurans and dioxins, are certainly present in currently used elec-tronic equipment. As a consequence, special attention needs to begiven to the large amount of WEEE containing BFRs. WEEE plasticcontaining banned BFRs clearly has to be eliminated from the sec-ondary raw material cycle at the recycling process in order to avoidtheir repeated appearance in new products. WEEE plastic contain-ing non restricted BFR needs either to be treated under controlledconditions without the formation of harmful transformation prod-ucts (Ebert and Bahadir, 2003) or should also be eliminated fromthe secondary raw material. The second option, however, wouldlead to a loss of potentially valuable secondary plastic.

While first recycling technologies with efficient removal andsafe handling of BFRs start to appear, plastic from WEEE basis getsmixed and recycled with plastic from other waste categories de-spite their BFR content (Sepulveda et al., 2010). Due to good mar-ket prices and rising waste volumes fast developing economiessuch as South Africa are tempted to make use of recycled plasticfor other purposes, such as for building material in social housingprograms.

Current global practice of plastic recycling poses a risk that crit-ical BFRs and secondary pollutants cross-contaminate new prod-ucts (Schlummer et al., 2007; Sepulveda et al., 2010; Wägeret al., 2012). A better understanding of the fate of BFRs duringthe recycling process of plastic would provide a better basis to de-velop new material recovery technologies and define sustainableapproaches to close the cycle of plastic from WEEE in a secondaryraw material loop.

The study has three objectives (i) to identify the level of criticalBFRs and their toxic transformation products (i.e., PentaBDE, Octa-BDE, DecaBDE and also polybrominated dibenzodioxins and -fur-ans) present in the mass flow of Swiss and South African WEEErecycler; (ii) to investigate treatment techniques for WEEE contain-ing BFR without formation of harmful transformation products; (iii)to describe whether detoxification of the plastic mass flow occurs.

2. Materials and methods

2.1. Samples

Samples originated from two plastic recycling facilities in SouthAfrica and from a central WEEE processing facility in Switzerland.One South African facility produced fence poles (samples P1–P6),the other roof tiles (samples T1–T8). From both facilities, sampleshave been taken on two separate days (April 2009), from all rawrecycling materials, from intermediate mixture and materials aswell as from the final products. The collection of samples followedthe processing of the same batch. Therefore, all samples from therecycling process originated from the same starting material. Inputconsisted from various plastic materials, the contribution of WEEEplastic, suspected to contain BFRs, was 9% and 21% for the tile andfence pole process, respectively. Details on the processes and thesamples are given in the Supporting Information.

Please cite this article in press as: Zennegg, M., et al. Formation of PBDD/F frextruding conditions. Chemosphere (2014), http://dx.doi.org/10.1016/j.chemos

In Switzerland, samples were collected from a large WEEE recy-cler. Samples were taken at the main facility. Casings of computermonitors and TVs were screened for bromine by a handheld XRFinstrument. Samples that were tested positive for bromine wereselected. This included 10 out of 20 tested computer monitorsand 6 out 24 tested TV-monitors. Three rounds slices (diameter25 mm) of each casing were cut out. One slice was used for XRF-analysis. The other slices were mixed and crushed into pieces ofless than 3 mm. These samples were used for thermal exposureexperiments or direct analysis.

2.2. Simulation of extrusion process/thermal exposure of WEEE

Ground plastic materials from South Africa and Switzerlandwere placed at 225 �C for up to 20 min in a torque rheometer(Thermo Scientific), which simulates and measures conditions dur-ing extrusion processes. The mixing chamber was thermally equil-ibrated and filled with 30 g of plastic material, which correspondedto 50% filling of the chamber. Samples (approx. 0.5 g) were takenevery 2–4 min with a spatula (see Table S10). Mixing rotationwas 1 Hz. There was only marginal torque exerted by the readilymolten WEEE plastic.

2.3. Analysis of PBDD/F

60 g sample (polymer material) were soxhlet extracted for 24 hwith toluene. The extraction efficiency was checked by re-extract-ing the sample with toluene for additional 24 h. The toluene ex-tract was adjusted to 250 mL and an aliquot of 1 mL was finallyused for the analysis of PBDD/F. The aliquot was spiked with a mix-ture of 13C12 labeled PBDD/F (CIL EDF-5382, PBDD/F Cleanup Spike,Cambridge Isotope Laboratories), used as internal standard for thequantitative determination of polybrominated dibenzo-p-dioxinsand furans. The spiked sample was treated with concentrated sul-furic acid and extracted three times with 2 mL n-hexane. The n-hexane extract was further cleaned by low pressure chromatogra-phy on a multilayer silica gel column (acid, alkaline, and neutralsilica, total 12 g) followed by a basic alumina column (6.5 g of basicalumina super I) and an activated carbon column (300 mg of 8%Carbon AX-21 on Celite 545). The n-hexane extract was loadedonto the multilayer silica column and eluted with 90 mL n-hexaneto the basic alumina column. The basic alumina column was in afirst step eluted with 60 mL 4% dichloromethane in n-hexane(elimination of diortho substituted PCB). Secondly the PBDD/Fswere eluted from the alumina onto the carbon column with80 mL dichloromethane in n-hexane (1:1). The carbon columnwas washed additionally with 80 mL dichloromethane in n-hexane(1:1) to get rid of interfering PBDE. The eluate was loaded to a sec-ond carbon column which was used to check possible break-through of PBDD/F from the first carbon column. The latter waseluted with 80 mL toluene in the reverse direction to collectPBDD/F. To toluene fraction was concentrated to 1 mL using arotary evaporater at 45 �C and 70 mbar. The fraction with thePBDD/F was transferred to a 0.5 mL GC-Vial and further concen-trated to 10 lL under a gentle stream of nitrogen. Finally the13C12 labeled 2,4,6,8-TeBDF (CIL EF-5384-4X, Cambridge isotopeLaboratories) was added as recovery standard.

Instrumental conditions and exact masses and signal ratios forthe identification of PBDD/Fs are given in the Supporting Informa-tion – Chapter 3.

2.4. Analysis of PBDE

An aliquot of 10 lL out of 250 mL of the crude extract from theanalytical procedure for PBDD/Fs (see above) was spiked with amixture of 13C12 labeled BDE congeners. The solution was diluted

om PBDE in electronic waste in recycling processes and under simulatedphere.2013.12.101


Fig. 2. Relative contributions of octa- and nonabrominated diphenyl ethers. The redarrows indicate that thermal treatment took place between these samples. (Forinterpretation of the references to color in this figure legend, the reader is referredto the web version of this article.)

M. Zennegg et al. / Chemosphere xxx (2014) xxx–xxx 3

with toluene to 100 lL and was directly forwarded to the GC/HRMS analysis. As no further cleanup of the sample was necessary,no recovery standard was added to the sample. Instrumental con-ditions are given in the Supporting Information – Chapter 3.

3. Results and discussion

3.1. Content of polybrominated diphenyl ethers (PBDEs)

PBDE-contents in plastic materials that are flameproof by PBDEstypically range between 5 � 106 and 3 � 108 lg kg�1 (0.5–30%)(Alaee et al., 2003). Thus, if the investigated plastic materialswould have been entirely flameproof by PBDEs, contents in thatrange have to be expected.

Total PBDE-contents in the South African (SA) and Swiss (CH)plastic waste vary between 1 � 103 and 7 � 106 lg kg�1 (Fig. 1).Especially low-density, non-WEEE plastic exhibited low PBDE con-tents (P1, P2, P3 and T1). This had to be expected as low-densityplastics such as PE are often used in applications (e.g., drinking bot-tle) that do not require flame protection measures. However, alsothe PBDE content in the plastic waste from WEEE (P4, T2 and Swisssamples) were lower (1 � 105 and 7 � 106 lg kg�1) than in materi-als that were flameproof by PBDEs (5 � 106 and 3 � 108 lg kg�1).This shows that a large fraction of the sampled waste materialwas not flameproof with PBDEs. XRF investigations of the Swisssamples resulted in higher Br contents, thus, these samples mustcontain also non-PBDE brominated flame retardants. In a relatedstudy (Zennegg, 2011), bis-tribromophenoxy ethane and decabro-modiphenyl ethane have been found regularly in plastic materialsfrom Switzerland. Non-PBDE brominated flame retardants arefound also in other recent studies (e.g. Ali et al., 2011; Covaciet al., 2011; Wäger et al., 2012). Both South African products (rooftiles and fence poles) did not exceed the RoHS limit for PBDEs, de-spite the fact that the WEEE input into the process exceeded theRoHS limit value of 1 � 106 lg kg�1.

3.2. PBDE pattern

The PBDE pattern in the samples was either dominated by cong-eners that are main components of technical OctaBDE or DecaBDE(La Guardia et al., 2006). The characteristic congeners of technicalPentaBDE was always found at contents below 1 � 104 lg kg�1,which could indicate that the market has shifted away from thisflame retardant already some years ago. The total PBDE contentin the Swiss TV-monitors exceeded the RoHS-limit of1 � 106 lg kg�1.

Fig. 1. Contents of polybrom


Lower brominated diphenyl ethers are of higher toxicologicalconcern than higher brominated diphenyl ethers (Birnbaum andStaskal, 2004; Gerecke et al., 2005) and a transformation fromhigher to lower brominated diphenyl ethers could occur underthermal exposure. However, the pattern of Octa- and NonaBDEs,which are not key components of the technical products, did notchange during the investigated processes (Fig. 2). Therefore, wedid not obtain evidence for substantial debromination of the pres-ent PBDEs.

3.3. Content of polybrominated dibenzofurans (PBDFs)


PBDFs was around 1 � 103 lg kg�1,except for the pole process in South Africa, where contents were

inated diphenyl ethers.



Fig. 3. Contents of polybrominated dibenzofurans (PBDFs).

Fig. 4. PBDF pattern in finished products from SA and in composite WEEE samplesfrom Switzerland.


just below 1 � 102 lg kg�1 (Fig. 3). The corresponding WHO-TEQequivalent contents were between 0.1 and 10 lg kg�1. The tolera-ble daily intake for dioxin-TEQ is 1–4 pg d�1 kg�1. Thus an inges-tion of 28 and 4 mg d�1 of the investigated products would leadto an uptake (assuming complete resorption) equal to the TDI foran adult of 70 kg and a toddler of 10 kg, respectively. Such uptakerates appear unlikely for the investigated products under normalcircumstances. However, exposure to dust at the production site(Thuresson et al., 2005) or children playing in areas, with a highdust load from decaying products, could lead to an uptake in therange of the TDI, as the total uptake of dust by a toddler is esti-mated to be 100 mg d�1 (USEPA, 1997). Thus, workers need to beprotected and it should be avoided that children come into contactwith large amount of dust from such materials.

One of the very few specific limits for PBDFs is contained in theGerman ‘‘Chemikalienverbotsverordnung’’ (ChemVerbotsV). Thesum of four specific PBDD and PBDFs, among them 2,3,4,7,8-penta-bromodibenzofuran, in a product might not exceed 1 lg kg�1. Ascan been seen from Fig. 3, the tile product exceeds this limit by afactor of three. All other investigated materials were below thislimit value.

3.4. PBDF pattern

The PBDF pattern is dominated in all samples by penta, hexa andhepta congeners (see Fig. 4). Lower brominated congeners accountfor less than 15%. The fingerprint of the penta to hepta-PBDFs wascomparable throughout all the samples. During thermal exposureof the samples, there was no consistent trend in the alteration ofthe patterns. In the tile samples, lower brominated PBDFs wereformed, whereas this observation could not be made in the othersamples. Throughout all original samples, polybrominated dibenzo-dioxins were not observed above 120 lg kg�1. Concentrations ofindividual PBDD/Fs are listed in Tables 5–7 in the SupportingInformation. 1,2,3,4,6,7,8-HpBDF had the highest concentrations,


which was also found for ashes and flue gas from municipal solidwaste incinerators (Wang et al., 2010).

3.5. Formation of PBDFs during thermal exposure

The main concern in the recycling plastic material containingbrominated flame retardants is the formation of polybrominateddibenzofurans as this was observed for pure polymers (Donnellyet al., 1989; Brenner and Knies, 1990; Dumler et al., 1990; Luijket al., 1990, 1992; McAllister et al., 1990) and recently also forrecycling materials (Schlummer et al., 2007). In this study, we as-sessed the extent of this reaction in real recycling processes andunder controlled laboratory conditions. To compare the results,the formation of PBDF was normalized to the PBDE content andtime. The observed normalized PBDF-formation rates were allwithin one order of magnitude (Fig. 5). Surprisingly the tempera-ture did not exert a major influence on the transformation rateand also the type of PBDEs (deca or octa congeners) did not showan important influence. The formation of

PPBDFs varied between

2 � 10�5 and 2 � 10�4 PPBDE�1 min�1. Thus after a thermal expo-sure of 5 min a maximum of 0.1% of PBDEs was transformed intoPBDFs. Donnelly (Donnelly et al., 1989) examined the formationof PBDFs in pure polymers containing PBDEs. They found normal-ized rates between 3 � 10�7 and 1 � 10�3 PPBDE�1 min�1 in HIPSand PBT, respectively, which is below and above the rates, whichwe found for recycled plastic. Thus, we did not get any evidencefor accelerated formation of PBDF in recycling material comparedto pure polymers. Interestingly, also Donnelly did not observe asimple correlation between temperature and formation of PBDFs,which suggests that various formation and degradation reactionsare competing with each other.

The formation of 2,3,4,7,8-pentrabromodibenzofuran was be-low 2 � 10�7 PPBDE�1 min�1. Thus, in five minute not more than1 � 10�6 PPBDE�1 would be formed. The RoHS limit for PBDEs(0.1% = 106 lg kg�1) and the limit value for single PBDFs(1 lg kg�1) in the German ChemVerbotsV are separated by six or-ders of magnitude. Thus, a material, which fulfills the RoHS for



Fig. 5. Formation rate normalized to PBDE-content and time (on mass basis). In the SA fence pole process and in the Swiss monitor samples, 2-, 3-, 4-, 7-, 8-PentaBDF was notdetected and no formation rate could be calculated.

M. Zennegg et al. / Chemosphere xxx (2014) xxx–xxx 5

PBDEs is expected to fulfill also the German ChemVerbotsV, if thetime of thermal exposure is shorter than 5 min.

4. Conclusions

Total PBDE-contents in the South African (SA) and Swiss (CH)plastic waste varied between 1 � 103 and 7 � 106 lg kg�1. Lowcontents were found in plastic fractions, which are not expectedto be flameproof (e.g., PE bottles), whereas mixed WEEE plasticcontained the highest PBDE contents. A few WEEE plastic fractionsexceeded the RoHS limit for PBDEs and thus they could not be usedfor direct recycling without special treatment.


PBDFs was around 1 � 103 lg kg�1,except for the pole process in South Africa, where contents werebelow 1 � 102 lg kg�1. Such contents in materials do not pose arisk for consumer under normal conditions. However, toddlersare taking up substantial amount of dusts, thus, it should beavoided that WEEE recycling products can decay in area, wherekids are playing. Also, workers at recycling plants need to beprotected.

The formation of toxic PBDFs was assessed during thermalexposure in the recycling processes and under laboratory condi-tions. The formation rate was between 2 � 10�5 and 2 � 10�4P

PBDE�1 min�1. However, the formation of PBDFs from PBDEswas such that under normal conditions, the limit value for PBDFsin the German ‘‘Chemikalienverbotsordnung’’ (ChemVerbotsV)should not be exceeded if the PBDE contents in the raw WEEEare below the RoHS value. Today, alternative brominated flameretardants such as decabromdiphenyl ethane are used. TheirPBDD/F-formation potential is yet unknown and should be studiedin the future.

The study showed that PBDEs and PBDD/Fs are present in WEEEand plastic recycling products. However, we did not receive anyindication for the formation of critical PBDD/Fs contents undernormal process conditions (i.e., PBDE contents do not largely ex-ceed RoHS limits and temperature is not abusive) and, under suchconditions, building materials from recycling products will notcause harmful exposure to PBDEs and PBDD/Fs. However, toddlersshould avoid contact with decaying recycling materials and work-ers need to be protected properly.

Acknowledgements

The authors are grateful to the many people, who contributedto this project: Clemens Frank for his support with the torque


rheometer, the e-Waste Association of South Africa (eWASA) forfacilitating the contacts in South Africa, the South African recyclersfor letting us sample their processes and Matthias Kolb for the sup-port in the sampling campaigns.

Appendix A. Supplementary material

Supplementary data associated with this article can be found, inthe online version, at http://dx.doi.org/10.1016/j.chemosphere.2013.12.101.

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Formation of PBDD/F from PBDE in electronic waste in recycling processes and under simulated extruding conditions