scholarly journals Predicting Partition Coefficients of Short-Chain Chlorinated Paraffin Congeners by COSMO-RS-Trained Fragment Contribution Models

2020 ◽  
Vol 54 (23) ◽  
pp. 15162-15169
Author(s):  
Satoshi Endo ◽  
Jort Hammer
Keyword(s):  
Partition Coefficients ◽  
Short Chain ◽  
Chlorinated Paraffin

scholarly journals Predicting Partition Coefficients of Short-Chain Chlorinated Paraffin Congeners by COSMO-RS-Trained Fragment Contribution Models

2020 ◽  
Author(s):  
Satoshi Endo ◽  
Jort Hammer
Keyword(s):  
Partition Coefficients ◽  
Environmental Fate ◽  
Training Data ◽  
Short Chain ◽  
Explanatory Variables ◽  
Fast Running ◽  
Potential Risks ◽  
Experimental Values ◽  
Chain Lengths ◽  
Chlorinated Paraffin

Chlorinated paraffins (CPs) are highly complex mixtures of polychlorinated <i>n</i>-alkanes with differing chain lengths and chlorination patterns. Knowledge on physicochemical properties of individual congeners is limited but needed to understand their environmental fate and potential risks. This work uses a sophisticated but time-demanding quantum chemically based method COSMO-RS and a fast-running fragment contribution approach to enable prediction of partition coefficients for a large number of short-chain chlorinated paraffin (SCCP) congeners. Fragment contribution models (FCMs) were developed using molecular fragments with a length of up to C<sub>4</sub> in CP molecules as explanatory variables and COSMO-RS-calculated partition coefficients as training data. The resulting FCMs can quickly provide COSMO-RS predictions for octanol–water (<i>K</i><sub>ow</sub>), air–water (<i>K</i><sub>aw</sub>), and octanol–air (<i>K</i><sub>oa</sub>) partition coefficients of SCCP congeners with an accuracy of 0.1–0.3 log units root mean squared errors. The FCM predictions for <i>K</i><sub>ow</sub> agree with experimental values for individual constitutional isomers within 1 log unit. The distribution of partition coefficients for each SCCP congener group was computed, which successfully reproduced experimental log <i>K</i><sub>ow</sub> ranges of industrial CP mixtures. As an application of the developed FCMs, the predicted <i>K</i><sub>aw</sub> and <i>K</i><sub>oa</sub> were plotted to evaluate the bioaccumulation potential of each SCCP congener group.<br>

scholarly journals Predicting Partition Coefficients of Short-Chain Chlorinated Paraffin Congeners by Combining COSMO-RS and Fragment Contribution Model Approaches

2020 ◽  
Author(s):  
Satoshi Endo ◽  
Jort Hammer
Keyword(s):  
Partition Coefficients ◽  
Environmental Fate ◽  
Short Chain ◽  
Linear Regression Models ◽  
Explanatory Variables ◽  
Fast Running ◽  
Potential Risks ◽  
Experimental Values ◽  
Chain Lengths ◽  
Chlorinated Paraffin

Chlorinated paraffins (CPs) are highly complex mixtures of polychlorinated <i>n</i>-alkanes with differing chain lengths and chlorination patterns. Knowledge on physicochemical properties of individual congeners is limited but needed to understand their environmental fate and potential risks. This work combines a sophisticated but time-demanding quantum chemically based method COSMO-RS and a fast-running fragment contribution approach to establish models to predict partition coefficients of a large number of short-chain chlorinated paraffin (SCCP) congeners. Molecular fragments of a length of up to C<sub>4</sub> in CP molecules were counted and used as explanatory variables to develop linear regression models for predicting COSMO-RS-calculated values. The resulting models can quickly provide COSMO-RS predictions for octanol–water (<i>K</i><sub>ow</sub>), air–water (<i>K</i><sub>aw</sub>), and octanol–air (<i>K</i><sub>oa</sub>) partition coefficients of SCCP congeners with an accuracy of 0.1–0.3 log units root mean squared errors (RMSE). The model predictions for <i>K</i><sub>ow</sub> agree with experimental values for individual constitutional isomers within 1 log unit. The ranges of partition coefficients for each SCCP congener group were computed, which successfully reproduced experimental log <i>K</i><sub>ow</sub> ranges of industrial CP mixtures. As an application of the developed approach, the predicted <i>K</i><sub>aw</sub> and <i>K</i><sub>oa</sub> were plotted to evaluate the bioaccumulation potential of each SCCP congener group.

scholarly journals Predicting Partition Coefficients of Short-Chain Chlorinated Paraffin Congeners by Combining COSMO-RS and Fragment Contribution Model Approaches

2020 ◽  
Author(s):  
Satoshi Endo ◽  
Jort Hammer
Keyword(s):  
Partition Coefficients ◽  
Environmental Fate ◽  
Short Chain ◽  
Linear Regression Models ◽  
Explanatory Variables ◽  
Fast Running ◽  
Potential Risks ◽  
Experimental Values ◽  
Chain Lengths ◽  
Chlorinated Paraffin

Chlorinated paraffins (CPs) are highly complex mixtures of polychlorinated <i>n</i>-alkanes with differing chain lengths and chlorination patterns. Knowledge on physicochemical properties of individual congeners is limited but needed to understand their environmental fate and potential risks. This work combines a sophisticated but time-demanding quantum chemically based method COSMO-RS and a fast-running fragment contribution approach to establish models to predict partition coefficients of a large number of short-chain chlorinated paraffin (SCCP) congeners. Molecular fragments of a length of up to C<sub>4</sub> in CP molecules were counted and used as explanatory variables to develop linear regression models for predicting COSMO-RS-calculated values. The resulting models can quickly provide COSMO-RS predictions for octanol–water (<i>K</i><sub>ow</sub>), air–water (<i>K</i><sub>aw</sub>), and octanol–air (<i>K</i><sub>oa</sub>) partition coefficients of SCCP congeners with an accuracy of 0.1–0.3 log units root mean squared errors (RMSE). The model predictions for <i>K</i><sub>ow</sub> agree with experimental values for individual constitutional isomers within 1 log unit. The ranges of partition coefficients for each SCCP congener group were computed, which successfully reproduced experimental log <i>K</i><sub>ow</sub> ranges of industrial CP mixtures. As an application of the developed approach, the predicted <i>K</i><sub>aw</sub> and <i>K</i><sub>oa</sub> were plotted to evaluate the bioaccumulation potential of each SCCP congener group.

scholarly journals Predicting Partition Coefficients of Short-Chain Chlorinated Paraffin Congeners by COSMO-RS-Trained Fragment Contribution Models

2020 ◽  
Author(s):  
Satoshi Endo ◽  
Jort Hammer
Keyword(s):  
Partition Coefficients ◽  
Environmental Fate ◽  
Training Data ◽  
Short Chain ◽  
Explanatory Variables ◽  
Fast Running ◽  
Potential Risks ◽  
Experimental Values ◽  
Chain Lengths ◽  
Chlorinated Paraffin

Chlorinated paraffins (CPs) are highly complex mixtures of polychlorinated <i>n</i>-alkanes with differing chain lengths and chlorination patterns. Knowledge on physicochemical properties of individual congeners is limited but needed to understand their environmental fate and potential risks. This work uses a sophisticated but time-demanding quantum chemically based method COSMO-RS and a fast-running fragment contribution approach to enable prediction of partition coefficients for a large number of short-chain chlorinated paraffin (SCCP) congeners. Fragment contribution models (FCMs) were developed using molecular fragments with a length of up to C<sub>4</sub> in CP molecules as explanatory variables and COSMO-RS-calculated partition coefficients as training data. The resulting FCMs can quickly provide COSMO-RS predictions for octanol–water (<i>K</i><sub>ow</sub>), air–water (<i>K</i><sub>aw</sub>), and octanol–air (<i>K</i><sub>oa</sub>) partition coefficients of SCCP congeners with an accuracy of 0.1–0.3 log units root mean squared errors. The FCM predictions for <i>K</i><sub>ow</sub> agree with experimental values for individual constitutional isomers within 1 log unit. The distribution of partition coefficients for each SCCP congener group was computed, which successfully reproduced experimental log <i>K</i><sub>ow</sub> ranges of industrial CP mixtures. As an application of the developed FCMs, the predicted <i>K</i><sub>aw</sub> and <i>K</i><sub>oa</sub> were plotted to evaluate the bioaccumulation potential of each SCCP congener group.<br>

Refinement and Extension of COSMO-RS-Trained Fragment Contribution Models for Predicting Partition Properties of C10–20 Chlorinated Paraffin Congeners

2021 ◽  
Author(s):  
Satoshi Endo
Keyword(s):  
Partition Coefficients ◽  
Aqueous Solubility ◽  
Stochastic Algorithm ◽  
Training Set ◽  
Subcooled Liquid ◽  
Conformer Generation ◽  
Model Predictions ◽  
Predicted Values ◽  
Chlorinated Paraffin ◽  
Long Chain

COSMO-RS-trained fragment contribution models (FCMs) to predict partition properties of chlorinated paraffin (CP) congeners were refined and extended. The improvement includes (i) the use of an improved conformer generation method for COSMO-RS, (ii) extension of training and validation sets for FCMs up to C<sub>20</sub> congeners covering short-chain (SCCPs), medium-chain (MCCPs) and long-chain CPs (LCCPs), and (iii) more realistic simulation of industrial CP mixture compositions by using a stochastic algorithm. Extension of the training set markedly improved the accuracy of model predictions for MCCPs and LCCPs, as compared to the previous study. The predicted values of the log octanol/water partition coefficients (<i>K</i><sub>ow</sub>) for CP mixtures agreed well with experimentally determined values from the literature. Using the established FCMs, this study provided a set of quantum chemically based predictions for 193 congener groups (C<sub>10–20</sub>, Cl<sub>0–21</sub>) regarding <i>K</i><sub>ow</sub>, air/water (<i>K</i><sub>aw</sub>), and octanol/air (<i>K</i><sub>oa</sub>) partition coefficients, subcooled liquid vapor pressure (VP) and aqueous solubility (<i>S</i><sub>w</sub>) in a temperature range of 5–45 °C as well as the respective enthalpy and internal energy changes.<br><br>This is a preprint version and has not yet been peer reviewed.

Mechanism of carcinogenicity of a short chain chlorinated paraffin, Chlorowax 500C, in male fischer 344 rats in comparison to 1,4-dichlorobenzene and d-limonene

Toxicology ◽  
2000 ◽  
Vol 148 (1) ◽  
pp. 63 ◽  
Author(s):  
G.D. Warnasuriya ◽  
J.R. Foster ◽  
B.M. Elcombe ◽  
C.R. Elcombe
Keyword(s):  
Short Chain ◽  
Fischer 344 Rats ◽  
Fischer 344 ◽  
Chlorinated Paraffin

Short-chain chlorinated paraffin (SCCP) pollution from a CP production plant in China: Dispersion, congener patterns and health risk assessment

Chemosphere ◽  
2018 ◽  
Vol 211 ◽  
pp. 456-464 ◽  
Author(s):  
Peiwen Wang ◽  
Nan Zhao ◽  
Yang Cui ◽  
Wei Jiang ◽  
Lina Wang ◽  
...  
Keyword(s):  
Risk Assessment ◽  
Health Risk ◽  
Health Risk Assessment ◽  
Short Chain ◽  
Production Plant ◽  
Chlorinated Paraffin

Comparison of quantitative analytical methods of short chain chlorinated paraffins in chlorinated paraffin mixtures

2016 ◽  
Vol 34 (3) ◽  
pp. 346
Author(s):  
Yuanna XING ◽  
Anhong FENG ◽  
Linquan YE ◽  
Zhihui LIN ◽  
Qian CHEN ◽  
...  
Keyword(s):  
Analytical Methods ◽  
Short Chain ◽  
Chlorinated Paraffins ◽  
Chlorinated Paraffin

Quantifying Short-Chain Chlorinated Paraffin Congener Groups

2017 ◽  
Vol 51 (18) ◽  
pp. 10633-10641 ◽  
Author(s):  
Bo Yuan ◽  
Christian Bogdal ◽  
Urs Berger ◽  
Matthew MacLeod ◽  
Wouter A. Gebbink ◽  
...  
Keyword(s):  
Short Chain ◽  
Chlorinated Paraffin

scholarly journals Integration of metabolomics and transcriptomics reveals short-chain chlorinated paraffin-induced hepatotoxicity in male Sprague-Dawley rat

2019 ◽  
Vol 133 ◽  
pp. 105231 ◽  
Author(s):  
Ningbo Geng ◽  
Xiaoqian Ren ◽  
Yufeng Gong ◽  
Haijun Zhang ◽  
Feidi Wang ◽  
...  
Keyword(s):  
Short Chain ◽  
Sprague Dawley ◽  
Sprague Dawley Rat ◽  
Chlorinated Paraffin
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