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Solubility Determination, Modeling, and Thermodynamic Dissolution Properties of Benzenesulfonamide in 16 Neat Solvents from 273.15 to 324.45 K

  • Yajun Li
    Yajun Li
    Guangdong Provincial Engineering Laboratory of Biomass High Value Utilization, Guangdong Provincial Key Laboratory of Sugarcane Improvement and Biorefinery, Guangzhou Key Laboratory of Biomass Comprehensive Utilization, Guangdong Provincial Bioengineering Institute (Guangzhou Sugarcane Industry Research Institute), Guangzhou 510316, China
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  • Kui Wu*
    Kui Wu
    School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China
    *E-mail: [email protected] (K.W.).
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  • , and 
  • Lei Liang*
    Lei Liang
    Guangdong Provincial Engineering Laboratory of Biomass High Value Utilization, Guangdong Provincial Key Laboratory of Sugarcane Improvement and Biorefinery, Guangzhou Key Laboratory of Biomass Comprehensive Utilization, Guangdong Provincial Bioengineering Institute (Guangzhou Sugarcane Industry Research Institute), Guangzhou 510316, China
    *E-mail: [email protected] (L.L.).
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Cite this: J. Chem. Eng. Data 2019, 64, 8, 3606–3616
Publication Date (Web):July 16, 2019
https://doi.org/10.1021/acs.jced.9b00360
Copyright © 2019 American Chemical Society

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    Abstract

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    Benzenesulfonamide (BSA) is known as an important chemical material and intermediate in chemical industry. Information concerning solid–liquid equilibrium of BSA in different solvents is essential for the development of its separation and reaction process. In this work, the equilibrium solubility of BSA in 16 neat solvents, namely, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-pentanol, isopentanol, acetone, ethyl acetate, acetonitrile, cyclohexanone, cyclopentanone, methyl acetate, ethyl formate, and dichloromethane was determined by a static gravimetric method within the temperature range of 273.15–324.45 K under atmospheric pressure. The solubility of BSA increases with the rising temperature in all selected solvents. The obtained solubility was mathematically represented by using the Apelblat model, λh equation, nonrandom two-liquid (NRTL) equation, and the Wilson equation in order to correlate the experimental data with the adjustable parameters. The dissolution properties of BSA, including Gibbs energy (ΔdisG), molar enthalpy (ΔdisH), and molar entropy (ΔdisS) were determined according to the Wilson model and the solubility data. Positive values of the dissolution enthalpy and entropy illustrated that the dissolution processes of BSA in these solvents are endothermic and entropy-driven.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.9b00360.

    • RD between the computed solubility of BSA with four models and the experimental data (PDF)

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    Cited By

    This article is cited by 8 publications.

    1. Xinyi Lü, Xiaotong Yang, Xiaoli Wu, Jidong Wang, Zhong Zhao. Determination and Simulation of Menadiol Diacetate Solubility in 14 Solvents at Temperatures from 283.15 to 323.15 K. Journal of Chemical & Engineering Data 2023, 68 (4) , 977-993. https://doi.org/10.1021/acs.jced.2c00734
    2. Yajun Li, Chuanli Lu, Ruirong Chen, Kui Wu. Determination, Correlation, and Thermodynamic Analysis of the Solid–Liquid Phase Equilibrium of 1,4-Dicyanobenzene in Pure Solvents at Various Temperatures. Journal of Chemical & Engineering Data 2020, 65 (10) , 4991-5002. https://doi.org/10.1021/acs.jced.0c00604
    3. Yang Li, Yang Zhang, Xue Zhong Wang. Solubility of Dimethyl 2,2′-Azobis(2-methylpropionate) in 15 Pure Solvents and in a Methanol + Water Binary Solvent System. Journal of Chemical & Engineering Data 2020, 65 (4) , 1411-1424. https://doi.org/10.1021/acs.jced.9b00842
    4. Trisha Kandi, Ramya Motati, Saikiran Motati, Nikita Shanmugam, Amy Zhou, Emily Yao, Catherine Webber, William E. Acree. Updated Abraham model correlations for describing solute transfer into both 2-Pentanol and 3-Methyl-1-butanol based on much larger data sets. Physics and Chemistry of Liquids 2023, 2 , 1-16. https://doi.org/10.1080/00319104.2023.2235709
    5. Piotr Cysewski, Tomasz Jeliński, Maciej Przybyłek. Finding the Right Solvent: A Novel Screening Protocol for Identifying Environmentally Friendly and Cost-Effective Options for Benzenesulfonamide. Molecules 2023, 28 (13) , 5008. https://doi.org/10.3390/molecules28135008
    6. Laine Longacre, Emily Wu, Chelsea Yang, Miles Zhang, Sneha Sinha, Advika Varadharajan, William E. Acree. Development of Abraham Model Correlations for Solute Transfer into the tert-Butyl Acetate Mono-Solvent and Updated Equations for Both Ethyl Acetate and Butyl Acetate. Liquids 2022, 2 (4) , 258-288. https://doi.org/10.3390/liquids2040016
    7. Jinlu Qu, Yuan Zhang, Dingqiang Lu, Xinxian Wang. Solubility parameter and solution thermodynamic properties of Form I Trimebutine maleate in six mono-solvents and three binary mixed solvents at different temperatures. Journal of Molecular Liquids 2022, 367 , 120503. https://doi.org/10.1016/j.molliq.2022.120503
    8. Alyssa Daniel, Kelly Kim, Neel Shanmugam, Sneha Sinha, Advika Varadharajan, William E. Acree. Abraham model correlations for solute transfer into cyclopentanone. Physics and Chemistry of Liquids 2022, 60 (6) , 964-976. https://doi.org/10.1080/00319104.2022.2098296

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