Please use this identifier to cite or link to this item: https://doi.org/10.21256/zhaw-23885
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.
Sprengel, Jannik
Mathis, Flurin
Haag, Regula
Kern, Susanne
Bleiner, Davide
Vetter, Walter
Heeb, Norbert V.
et. al: No
DOI: 10.1016/j.chemosphere.2021.132938
10.21256/zhaw-23885
Published in: Chemosphere
Volume(Issue): 291, Part 2
Issue: 132938
Issue Date: 16-Nov-2021
Publisher / Ed. Institution: Elsevier
ISSN: 0045-6535
1879-1298
Language: English
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.
URI: https://digitalcollection.zhaw.ch/handle/11475/23885
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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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., Jannik SPRENGEL, Flurin MATHIS, Regula HAAG, Susanne KERN, Davide BLEINER, Walter VETTER und Norbert V. HEEB, 2021. Chemical synthesis and characterization of single-chain C18-chloroparaffin materials with defined degrees of chlorination. Chemosphere. 16 November 2021. Bd. 291, Part 2, Nr. 132938. DOI 10.1016/j.chemosphere.2021.132938
Knobloch, Marco C., Jannik Sprengel, Flurin Mathis, Regula Haag, Susanne Kern, Davide Bleiner, Walter Vetter, and Norbert V. Heeb. 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, 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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