Distinct photoproducts of hydroxylated polybromodiphenyl ethers from different photodegradation pathways: A case of 2'-HO-BDE-68
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1 Electronic Supplementary aterial (ESI) for Environmental Science: Processes & Impacts. This journal is The Royal Society of Chemistry 214 Supplementary Information Distinct photoproducts of hydroxylated polybromodiphenyl ethers from different photodegradation pathways: A case of 2'-H-BDE-68 Qing Xie, Jingwen Chen*, Hongxia Zhao, Xingbao Wang, and Hong-Bin Xie Key Laboratory of Industrial Ecology and Environmental Engineering (inistry of Education), School of Environmental Science and Technology, Dalian University of Technology, Dalian 11624, China *Corresponding Author: Phone: ; jwchen@dlut.edu.cn Contents: 7 pages that include 1 text, 5 figures and tables. Abbreviations in the figures and tables of this supporting information Page S1 Text 1 Page S2 Figure S1-S5 Page S-S6 Table S1-S Page S6- S7 Abbreviations in the figures and tables of this supporting information Abbreviation 2,4-DBP di-h-dbb di-h-tbde BSTFA+TCS tri-h-dbb di-h-tebde 2,4,6-TBP Full name 2,4-dibromophenol dihydroxylated dibromobenzene 1,,8-tribromodibenzo-p-dioxin dihydroxylated tribromodiphenyl ether 1% trimethylchlorosilane (TCS) in N,-bis(trimethylsilyl)trifluoroacetamide (TCS) trihydroxylated dibromobenzene dihydroxylated tetrabromodiphenyl ether 2,4,6-tribromophenol Page S1
2 Text 1 GC/S conditions An Agilent 689GC/5975S equipped with a DB-XLB column ( m.25 mm,.25 μm film thickness, J&W Scientific) were used for the product analysis. The injector temperature was 28 ºC. 1 μl sample was auto injected into inlet at the splitless mode. Helium was used as the carry gas at a flow rate of 1 ml/min. The GC oven temperature was programmed as follows: start from 9 ºC for 2min, increase to 2 ºC at a rate of 15 ºC/min, then to 27 ºC at the rate of 2.5 ºC/min, thereafter to 1 ºC at 2 ºC/min and kept for 1.5 min. The temperatures of interface, EI source and NCI source were set at 28 ºC, 2 ºC and 15 ºC, respectively. The scan mode was operated at the m/z range of 6-8. Selected ion monitoring of m/z = 79 and 81 with the NCI source was adopted for quantification of the brominated compounds. Page S2
3 Abundance min ph = 2'-H-BDE min 2,4-DBP 29.6 min di-h-tbde 1. min di-h-dbb 27.6 min t (min) Abundance ,4-DBP di-h-dbb ph = 1 2'-H-BDE-68 di-h-tbde t (min) Fig. S1 Total ion chromatograms of the products from direct photolysis of 2'-H-BDE-68 when 68.4% (ph =) and 89.% (ph =1) of it photolyzed (The samples were derivatized by diazomethane and the chromatograms were obtained by GC-S with a negative chemical ionization source at the selective ion monitoring mode with m/z = 79 and 81). 5 CH CH CCH CH m/z--> (A) diazomethane derivatized 2,4-DBP CH 9 Si(CH ) 7 CH 4 SiCH CH CH Si(CH ) m/z--> (B) BSTFA+TCS derivatized 2,4-DBP 2 Page S
4 CH (CH ) CCH 25 1 m/z--> m/z--> CH CH Si CH 2 2 -Si(CH ) 2 -Si(CH ) CH (C) diazomethane derivatized di-h-dbb C m/z--> (E) Underivatized (D) BSTFA+TCS derivatized di-h-dbb m/z--> (F) Underivatized m/z--> CH CH ( H C ) x CH ) 2 x + y = 2 ( y 25 (G) diazomethane derivatized di-h-tbde Si(CH ) 2 CH CH 15 ( H C Si ) x ( Si CH ) y H C CH CH x + y = m/z--> (H) BSTFA+TCS derivatized di-h-tbde Fig. S2 ass spectra for the derivatized and underivatized products generated from direct photolysis of 2'-H-BDE-68, obtained with electron-impact ionization source (A, B, C, D, E, G and H) and negative chemical ionization source (F). Page S4
5 Fig. S Total ion chromatogram obtained by GC-S with a negative chemical ionization source at the selective ion monitoring mode (m/z = 79 and 81) for the diazomethane derivatized products generated from reaction of 2'-H-BDE-68 with 1 2 (ph = 1) when 64.8% of 2'-H-BDE-68 degraded. Fig. S4 Total ion chromatogram obtained by GC-S with a negative chemical ionization source at the selective ion monitoring mode (m/z = 79, 81) for the diazomethane derivatized products generated from reaction of 2'-H-BDE-68 with H (ph = ) when 1.6% of 2'-H-BDE-68 degraded. Page S5
6 Abundance C(CH ) 2 1 -CCH (A) (CH ) CH 1 26 m/z--> Abundance ( H C ) x ( CH ) y (B) x + y = (CH ) 2 1 -CH m/z--> Fig. S5 ass spectra (electron-impact ionization source) for the diazomethane derivatized tri-h-dbb (A) and di-h-tebde (B) generated from reaction of 2'-H-BDE-68 with H. Table S1. Formation and degradation rate constants (k p and k -p ), yields (Y) of the products generated from direct photolysis of 2'-H-BDE-68. Product 2,4-DBP ph = ph = 1 k p (min -1 ) k -p (min -1 ) Y (%) k p (min -1 ) k -p (min -1 ) Y (%) (8.9.2) 1-4 (5.2.8) di-h-dbb / * / * / * (..9) di-h-tbde (2.2.5) 1-5 ( ) (1..2) 1-4 (1.2 1.) ( ) 1-2 (. 1.8) / * ( ) 1 - (6.7 4.) (1.8.) 1-2 ( ) * The data were not obtained, as the detected concentrations were very low and with high uncertainties. Page S6
7 Table S2. Formation and degradation rate constants (k p and k -p ), and yields (Y) of the products generated from 1 2 and H reaction of 2'-H-BDE-68. Product k p (min -1 ) k -p (min -1 ) Y 1 2 reaction 2,4-DBP ( ) 1-2 (6.8 4.) 1-2 (7 25)% di-h-dbb (1.2.1) 1 - (1.4 1.) 1-2 (1.5.2)% di-h-tbdes (2.5.) 1-4 ( ) 1-2 (.2.)% H reaction 2,4-DBP (9. 1.8) (75 15)% di-h-tbdes (..9) (2.4.8)% Table S. Apparent product yields (Y app ) of the products from the reaction of 2'-H-BDE-68 with H. Degradation percentage of 2'-H-BDE % 19.% 1.6% 62.8% 84.1% di-h-dbb 8.% 11.% 15.2% 6.8%.4% 2,4,6-TBP 1.8% 2.6% 2.5% 1.1%.% tri-h-dbb.% 4.7% 4.5% 2.4%.% Page S7
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