A simple laboratory method for the generation of mixed brominated-chlorinated paraffin single chain mixtures
Brominated-chlorinated paraffins (Br-CPs) are a comparably new compound class that features both Cl and Br atoms on one or several alkane backbones. Due to legal restrictions in the use of conventional chlorinated paraffins (CPs), Br-CPs have the potential to become emerging contaminants. Currently,...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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KeAi Communications Co., Ltd.
2024-06-01
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| Series: | Emerging Contaminants |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405665023000926 |
| _version_ | 1797389405298622464 |
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| author | Walter Vetter Clara Hägele Karin Herrmann Tobias Schulz Sina Schweizer |
| author_facet | Walter Vetter Clara Hägele Karin Herrmann Tobias Schulz Sina Schweizer |
| author_sort | Walter Vetter |
| collection | DOAJ |
| description | Brominated-chlorinated paraffins (Br-CPs) are a comparably new compound class that features both Cl and Br atoms on one or several alkane backbones. Due to legal restrictions in the use of conventional chlorinated paraffins (CPs), Br-CPs have the potential to become emerging contaminants. Currently, their determination is hampered by the lack of suitable reference standards. Here, we present a simple synthesis procedure with single chain alkanes that leads to Br-CPs with ∼4–8 chlorine and 1 to 4 bromine substituents according to gas chromatography with electron capture negative ion mass spectrometry (GC/ECNI-MS). The single-chain Br-CP mixtures were obtained by the shared chlorination and bromination of eight single-chain alkanes (C10 to C17) at two reaction times, respectively. The carbon content of the 16 single-chain Br-CP products, determined by elemental analysis (EA), ranged from 30.8 to 43.8 %. The typical hump peak known from CPs was detected with GC with flame ionization detection (GC/FID), electron capture detection (GC/ECD) and GC/ECNI-MS. The complexity indicated that low-resolution mass spectrometry is not sufficient for an adequate analysis of Br-CPs. A mathematical formula was developed which allows to calculate all possible combinations of Br and Cl that are in line with the carbon content. The proton magnetic resonance spectroscopy (1H NMR) spectra showed similarities to the ones of CPs with one chemical shift range for protons on nonhalogenated carbons and one for protons with one halogen on the same carbon. |
| first_indexed | 2024-03-08T22:56:24Z |
| format | Article |
| id | doaj.art-51e485b1b46e4a7ebc46085bd5a9eef7 |
| institution | Directory Open Access Journal |
| issn | 2405-6650 |
| language | English |
| last_indexed | 2024-03-08T22:56:24Z |
| publishDate | 2024-06-01 |
| publisher | KeAi Communications Co., Ltd. |
| record_format | Article |
| series | Emerging Contaminants |
| spelling | doaj.art-51e485b1b46e4a7ebc46085bd5a9eef72023-12-16T06:08:21ZengKeAi Communications Co., Ltd.Emerging Contaminants2405-66502024-06-01102100294A simple laboratory method for the generation of mixed brominated-chlorinated paraffin single chain mixturesWalter Vetter0Clara Hägele1Karin Herrmann2Tobias Schulz3Sina Schweizer4Corresponding author. University of Hohenheim, Institute of Food Chemistry (170b), Garbenstr. 28, D-70599, Stuttgart, Germany.; University of Hohenheim, Institute of Food Chemistry (170b), Garbenstr. 28, 70599, Stuttgart, GermanyUniversity of Hohenheim, Institute of Food Chemistry (170b), Garbenstr. 28, 70599, Stuttgart, GermanyUniversity of Hohenheim, Institute of Food Chemistry (170b), Garbenstr. 28, 70599, Stuttgart, GermanyUniversity of Hohenheim, Institute of Food Chemistry (170b), Garbenstr. 28, 70599, Stuttgart, GermanyUniversity of Hohenheim, Institute of Food Chemistry (170b), Garbenstr. 28, 70599, Stuttgart, GermanyBrominated-chlorinated paraffins (Br-CPs) are a comparably new compound class that features both Cl and Br atoms on one or several alkane backbones. Due to legal restrictions in the use of conventional chlorinated paraffins (CPs), Br-CPs have the potential to become emerging contaminants. Currently, their determination is hampered by the lack of suitable reference standards. Here, we present a simple synthesis procedure with single chain alkanes that leads to Br-CPs with ∼4–8 chlorine and 1 to 4 bromine substituents according to gas chromatography with electron capture negative ion mass spectrometry (GC/ECNI-MS). The single-chain Br-CP mixtures were obtained by the shared chlorination and bromination of eight single-chain alkanes (C10 to C17) at two reaction times, respectively. The carbon content of the 16 single-chain Br-CP products, determined by elemental analysis (EA), ranged from 30.8 to 43.8 %. The typical hump peak known from CPs was detected with GC with flame ionization detection (GC/FID), electron capture detection (GC/ECD) and GC/ECNI-MS. The complexity indicated that low-resolution mass spectrometry is not sufficient for an adequate analysis of Br-CPs. A mathematical formula was developed which allows to calculate all possible combinations of Br and Cl that are in line with the carbon content. The proton magnetic resonance spectroscopy (1H NMR) spectra showed similarities to the ones of CPs with one chemical shift range for protons on nonhalogenated carbons and one for protons with one halogen on the same carbon.http://www.sciencedirect.com/science/article/pii/S2405665023000926 |
| spellingShingle | Walter Vetter Clara Hägele Karin Herrmann Tobias Schulz Sina Schweizer A simple laboratory method for the generation of mixed brominated-chlorinated paraffin single chain mixtures Emerging Contaminants |
| title | A simple laboratory method for the generation of mixed brominated-chlorinated paraffin single chain mixtures |
| title_full | A simple laboratory method for the generation of mixed brominated-chlorinated paraffin single chain mixtures |
| title_fullStr | A simple laboratory method for the generation of mixed brominated-chlorinated paraffin single chain mixtures |
| title_full_unstemmed | A simple laboratory method for the generation of mixed brominated-chlorinated paraffin single chain mixtures |
| title_short | A simple laboratory method for the generation of mixed brominated-chlorinated paraffin single chain mixtures |
| title_sort | simple laboratory method for the generation of mixed brominated chlorinated paraffin single chain mixtures |
| url | http://www.sciencedirect.com/science/article/pii/S2405665023000926 |
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