Investigation of sorption phenomena by solid phase extraction and liquid chromatography for the determination of some ether derivatives of tetrabromobisphenol A

Abstract

To cite this version:Susanne Jonsson, Maritha Hörsing. Investigation of sorption phenomena by solid phase extraction and liquid chromatography for the determination of some ether derivatives of tetrabromobisphenol A. Journal of Physical Organic Chemistry, Wiley, 2009, 22 (11) AbstractObserved sorption and chromatographic behaviour served as a starting point for examination of four ether derivatives of the flame retardant tetrabromobisphenol (TBBPA); dihydroxyethyl (DHEE), dimethyl (DMe), diallyl (DAE) and dibromopropyl (DBPE). To date, there is little or no information about these compounds in the scientific literature. The targets in the present study had calculated log K ow values of 6.0-10. A broad range of different types of solvents were used in order to elucidate the mechanisms of sorption onto silica (glass) and two solid phase extraction cartridges based on polystyrene divinylbenzene polymers, hydroxylated (Isolute ENV+) and vinylpyrrolidone (Oasis HLB) containing units. Also, three chromatographic columns (C18, C8, and dual C18-based, i.e. a polar ligand together with C18 on a silica surface) were evaluated. The following were observed: desorption of the targets from silica surface by 1-propanol showed the best results and the yields were further improved by silylation of the surface. Regardless of the experimental test conditions applied, the lowest recovery was seen for the DMe derivative, followed by TBBPA itself, which had calculated log K ow values in between the other targets. A washing solution containing up to 70% of methanol could be used without elution of the targets from the . The dihydroxethyl ether derivative of TBBPA is most probably not affected by environmental relevant pH due to a likely high pKa (ca 15). Also, this study shows that the polar character of the dual-phase column was not as pronounced as asserted by the manufacturer.

Emerging Brominated Flame Retardants in the Environment

“…TBBPA-DHEE is a dihydroxylated compound, most probably not affected by environmentally relevant pH because of a likely high pK a ($15), [89]. The TBBPA family is very hydrophobic and, considering environmental partitioning, its members would preferably adsorb to solids [89].…”

“…TBBPA-DHEE is a dihydroxylated compound, most probably not affected by environmentally relevant pH because of a likely high pK a ($15), [89]. The TBBPA family is very hydrophobic and, considering environmental partitioning, its members would preferably adsorb to solids [89]. If present in the atmosphere, TBBPA-DBPE and TBBPA-DAE will, because of their low volatility, be attached to particles and hence their atmospheric transport behavior will be determined by particle transport [90].…”

Silver ion post-column derivatization electrospray ionization mass spectrometry for determination of tetrabromobisphenol A derivatives in water samples

“…21,22,38 Hyphenated HPLC with mass spectrometry (MS) employed different ionization sources, such as electrospray ionization (ESI), 18,39 atmospheric pressure chemical ionization (APCI) 20 and atmospheric pressure photoionization (APPI), 13 could determine only certain types of TBBPA derivatives. For example, ESI was able to ionize only the byproducts of TBBPA derivatives, but failed to ionize the main products because of their low proton affinities.…”

Recent advances in the analysis of TBBPA/TBBPS, TBBPA/TBBPS derivatives and their transformation products

“…Meanwhile, the combination of LC-C18 cartridges with LC-Si SPE cartridges for the extraction of TBBPA and less-brominated BPA from sewage sludge led to recoveries ranging from 75% to 105% [29]. The pH value of water samples should be considered, and the best recoveries were obtained when the pH of the sample was two units below the lowest pKa of the analyzed TBBPA and their derivatives [30]. For the cleanup of nonwater samples, the most widely used methods were gel permeation chromatography (GPC), activated silica gel column, and Florisil [6,31].…”