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|Publication type:||Article in scientific journal|
|Type of review:||Peer review (publication)|
|Title:||Chemical synthesis and characterization of single-chain C18-chloroparaffin materials with defined degrees of chlorination|
|Authors:||Knobloch, Marco C.|
Heeb, Norbert V.
|Volume(Issue):||291, Part 2|
|Publisher / Ed. Institution:||Elsevier|
|Subjects:||Chlorinated olefins (COs); Chlorinated paraffins (CPs); Long-chain chlorinated paraffins (LCCPs); Single-chain CPs; Standard material|
|Subject (DDC):||540: Chemistry|
|Abstract:||Technical chlorinated paraffins (CPs) are produced via radical chlorination of n-alkane feedstocks with different carbon chain-lengths (∼C10-C30). Short-chain CPs (SCCPs, C10-C13) are classified as persistent organic pollutants (POPs) under the Stockholm Convention. This regulation has induced a shift to use longer-chain CPs as substitutes. Consequently, medium-chain (MCCPs, C14-C17) and long-chain (LCCPs, C>17) CPs have become dominant homologues in recent environmental samples. However, no suitable LCCP-standard materials are available. Herein, we report on the chemical synthesis of single-chain C18-CP-materials, starting with a pure n-alkane and sulfuryl chloride (SO2Cl2). Fractionation of the crude product by normal-phase liquid-chromatography and pooling of suitable fractions yielded in four C18-CP-materials with different chlorination degrees (mCl,EA = 39-52%). In addition, polar side-products, tentatively identified as sulfite-, sulfate- and bis-sulfate-diesters, were separated from CPs. The new single-chain materials were characterized by LC-MS, 1H-NMR and EA. LC-MS provided Relative retention times for different C18-CP homologues and side-products. Mathematical deconvolution of full-scan mass spectra revealed the presence of chloroparaffins (57-93%) and chloroolefins (COs, 7-26%) in the four single-chain C18-CP-materials. Homologue distributions and chlorination degrees were deduced for CPs and COs. 1H-NMR revealed chemical shift ranges of mono-chlorinated (δ = 3.2-5.3 ppm) and non-chlorinated (δ = 1.0-3.2 ppm) hydrocarbon moieties. The synthesized C18-single-chain standard materials and respective spectroscopic data are useful to identify and quantify LCCPs in various materials and environmental samples. CP- and CO-distributions resemble the ones of existing SCCP and MCCP reference materials and technical mixtures. Furthermore, these materials now allow specific studies on the environmental fate and the transformation of long-chain chloroparaffins and chloroolefins.|
|Fulltext version:||Published version|
|License (according to publishing contract):||CC BY 4.0: Attribution 4.0 International|
|Departement:||Life Sciences and Facility Management|
|Organisational Unit:||Institute of Chemistry and Biotechnology (ICBT)|
|Appears in collections:||Publikationen Life Sciences und Facility Management|
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|2021_Knobloch-etal_Single-chain-C18-chloroparaffin-materials_Chemosphere.pdf||8.27 MB||Adobe PDF|
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Knobloch, M. C., Sprengel, J., Mathis, F., Haag, R., Kern, S., Bleiner, D., Vetter, W., & Heeb, N. V. (2021). Chemical synthesis and characterization of single-chain C18-chloroparaffin materials with defined degrees of chlorination. Chemosphere, 291, Part 2(132938). https://doi.org/10.1016/j.chemosphere.2021.132938
Knobloch, M.C. et al. (2021) ‘Chemical synthesis and characterization of single-chain C18-chloroparaffin materials with defined degrees of chlorination’, Chemosphere, 291, Part 2(132938). Available at: https://doi.org/10.1016/j.chemosphere.2021.132938.
M. C. Knobloch et al., “Chemical synthesis and characterization of single-chain C18-chloroparaffin materials with defined degrees of chlorination,” Chemosphere, vol. 291, Part 2, no. 132938, Nov. 2021, doi: 10.1016/j.chemosphere.2021.132938.
Knobloch, Marco C., et al. “Chemical Synthesis and Characterization of Single-Chain C18-Chloroparaffin Materials with Defined Degrees of Chlorination.” Chemosphere, vol. 291, Part 2, no. 132938, Nov. 2021, https://doi.org/10.1016/j.chemosphere.2021.132938.
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