The DOI matches its Crossref record.
Congener-specific partition properties of chlorinated paraffins evaluated with COSMOtherm and gas chromatographic retention indices
Published version of a preprint
Abstract
Chlorinated Paraffins (CPs) are high volume production chemicals and have been found in various organisms including humans and in environmental samples from remote regions. It is thus of great importance to understand the physical–chemical properties of CPs. In this study, gas chromatographic (GC) retention indexes (RIs) of 25 CP congeners were measured on various polar and nonpolar columns to investigate the relationships between the molecular structure and the partition properties. Retention measurements show that analytical standards of individual CPs often contain several stereoisomers. RI values show that chlorination pattern have a large influence on the polarity of CPs. Single Cl substitutions (–CHCl–, –CH 2 Cl) generally increase polarity of CPs. However, many consecutive –CHCl– units (e.g., 1,2,3,4,5,6-C 11 Cl 6 ) increase polarity less than expected from the total number of –CHCl– units. Polyparameter linear free energy relationship descriptors show that polarity difference between CP congeners can be explained by the H-bond donating properties of CPs. RI values of CP congeners were predicted using the quantum chemically based prediction tool COSMO thermX . Predicted RI values correlate well with the experimental data (R 2 , 0.975–0.995), indicating that COSMO thermX can be used to accurately predict the retention of CP congeners on GC columns.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
It has been reported in the literature that H atoms of halogenated aliphatic compounds can serve as H-bond donor sites (e.g., chloroform, hexachlorocyclohexanes, chlorinated paraffins) and affect the partition properties of the compounds.
“It has been reported in the literature that H atoms of halogenated aliphatic compounds can serve as H-bond donor sites (e.g., chloroform,38 hexachlorocyclohexanes,39 and chlorinated paraffins)40 and affect the partition properties of the compounds.”
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
No references could be resolved yet.
Research works printed but not linked: 24
- van Mourik, L. M., Gaus, C., Leonards, P. E. G. & de Boer, J. Chlorinated paraffins in the environment: a review on their production, fate, levels and trends between 2010 and 2015. Chemosphere 155, 415–428 (2016). · DOI
- Tomy, G. T., Fisk, A. T., Westmore, J. B. & Muir, D. C. G. Environmental chemistry and toxicology of polychlorinated n-alkanes. Rev. Environ. Contam. Toxicol. 158, 53–128 (1998).
- Sverko, E., Tomy, G. T., Märvin, C. H. & Muir, D. C. G. Improving the quality of environmental measurements on short chain chlorinated paraffins to support global regulatory efforts. Environ. Sci. Technol. 46, 4697–4698 (2012). · DOI
- Brandsma, S. H. et al. Chlorinated paraffins in car tires recycled to rubber granulates and playground tiles. Environ. Sci. Technol. 53, 7595–7603 (2019). · DOI
- Vorkamp, K., Balmer, J., Hung, H., Letcher, R. J. & Rigét, F. F. A review of chlorinated paraffin contamination in Arctic ecosystems. Emerg. Contam. 5, 219–231 (2019). · DOI
- Brandsma, S. H. et al. Medium-chain chlorinated paraffins (CPs) dominate in Australian sewage sludge. Environ. Sci. Technol. 51, 3364–3372 (2017). · DOI
- Nikiforov, V. A. Synthesis of polychloroalkanes. In Chlorinated Paraffins (ed. de Boer, J.) 41–82 (2010). https://doi.org/10.1007/698_2009_40. · DOI
- Yuan, B. et al. Accumulation of short-, medium-, and long-chain chlorinated paraffins in marine and terrestrial animals from Scandinavia. Environ. Sci. Technol. 53, 3526–3537 (2019). · DOI
- Glüge, J., Bogdal, C., Scheringer, M., Buser, A. M. & Hungerbühler, K. Calculation of physicochemical properties for short- and medium-chain chlorinated paraffins. J. Phys. Chem. Ref. Data 42, 023103 (2013). · DOI
- Endo, S. & Hammer, J. Predicting partition coefficients of short-chain chlorinated paraffin congeners by COSMO-RS-trained fragment contribution models. Environ. Sci. Technol. https://doi.org/10.1021/acs.est.0c06506 (2020). · DOI
- Yuan, B. et al. Chlorines are not evenly substituted in chlorinated paraffins: a predicted NMR pattern matching framework for isomeric discrimination in complex contaminant mixtures. Environ. Sci. Technol. Lett. https://doi.org/10.1021/acs.estlett.0c00244 (2020). · DOI
- Martos, P. A., Saraullo, A. & Pawliszyn, J. Estimation of air/coating distribution coefficients for solid phase microextraction using retention indexes from linear temperature-programmed capillary gas chromatography. Application to the sampling and analysis of total petroleum hydrocarbons in air. Anal. Chem. 69, 402–408 (1997). · DOI
- van Den Dool, H. & DecKratz, P. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr. A 11, 463–471 (1963). · DOI
- Endo, S. & Goss, K. U. Applications of polyparameter linear free energy relationships in environmental chemistry. Environ. Sci. Technol. 48, 12477–12491 (2014). · DOI · Paper page
- Abraham, M. H., Ibrahim, A. & Zissimos, A. M. Determination of sets of solute descriptors from chromatographic measurements. J. Chromatogr. A 1037, 29–47 (2004). · DOI · Paper page
- Arey, J. S., Green, W. H. & Gschwend, P. M. The electrostatic origin of Abraham’s solute polarity parameter. J. Phys. Chem. B 109, 7564–7573 (2005). · DOI
- Poole, C. F. & Poole, S. K. Separation characteristics of wall-coated open-tubular columns for gas chromatography. J. Chromatogr. A 1184, 254–280 (2008). · DOI
- Curvers, J., Rijks, J., Cramers, C., Knauss, K. & Larson, P. Temperature programmed retention indices: calculation from isothermal data. Part 1: Theory. J. High Resolut. Chromatogr. 8, 607–610 (1985). · DOI
- Goss, K.-U. Predicting equilibrium sorption of neutral organic chemicals into various polymeric sorbents with COSMO-RS. Anal. Chem. 83, 5304–5308 (2011). · DOI
- Schinkel, L. et al. Dealing with strong mass interferences of chlorinated paraffins and their transformation products: an analytical guide. TrAC Trends Anal. Chem. 106, 116–124 (2018). · DOI
- Schinkel, L. et al. Deconvolution of mass spectral interferences of chlorinated alkanes and their thermal degradation products: chlorinated alkenes. Anal. Chem. 89, 5923–5931 (2017). · DOI
- van Noort, P. C. M., Haftka, J. J. H. & Parsons, J. R. A simple McGowan specific volume correction for branching in hydrocarbons and its consequences for some other solvation parameter values. Chemosphere 84, 1102–1107 (2011). · DOI
- Goss, K.-U., Arp, H. P. H., Bronner, G. & Niederer, C. Partition Behavior of hexachlorocyclohexane isomers. J. Chem. Eng. Data 53, 750–754 (2008). · DOI · Paper page
- González, F. R., Castells, R. C. & Nardillo, A. M. Behavior of n-alkanes on poly(oxyethylene) capillary columns: evaluation of interfacial effects. J. Chromatogr. A 927, 111–120 (2001). · DOI
Cited by
Sorted by citations
Endo, S., Hammer, J., & Matsuzawa, S. (2023) · Environmental Science & Technology · doi:10.1021/acs.est.3c02545 · Cited by 54
Self-citation
Metadata
- Authors
- Hammer, J., Matsukami, H., & Endo, S.
- Venue
- Scientific Reports
- Published
- 2021-02-24
- Volume
- 11
- Issue
- 1
- ISSN
- 2045-2322
- PMC
- PMC7904792
- Cited by
- 12
- References
- 0
- Language
- en
- Funders
- Environmental Research and Technology Development Fund (SII-3)
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
