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Solubility, Model Correlation, and Solvent Effect of 2-Amino-3-methylbenzoic Acid in 12 Pure Solvents

  • Anfeng Zhu*
    Anfeng Zhu
    Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, Jiangsu Engineering Laboratory for Environment Functional Materials, Jiangsu Collaborative Innovation Center of Regional Modern Agriculture & Environmental Protection, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, P.R. China
    *Tel.: +86 517 83525085. E-mail: [email protected]
    More by Anfeng Zhu
  • Kun Hong*
    Kun Hong
    National & Local Joint Engineering Research Center for Deep Utilization Technology of Rock-Salt Resource, Faculty of Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, P.R. China
    *Tel.: +86 517 83559061. E-mail: [email protected]
    More by Kun Hong
  • Fengxia Zhu
    Fengxia Zhu
    Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, Jiangsu Engineering Laboratory for Environment Functional Materials, Jiangsu Collaborative Innovation Center of Regional Modern Agriculture & Environmental Protection, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, P.R. China
    More by Fengxia Zhu
  • Benlin Dai
    Benlin Dai
    Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, Jiangsu Engineering Laboratory for Environment Functional Materials, Jiangsu Collaborative Innovation Center of Regional Modern Agriculture & Environmental Protection, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, P.R. China
    More by Benlin Dai
  • Xu Jiming
    Xu Jiming
    Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, Jiangsu Engineering Laboratory for Environment Functional Materials, Jiangsu Collaborative Innovation Center of Regional Modern Agriculture & Environmental Protection, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, P.R. China
    More by Xu Jiming
  • , and 
  • Wei Zhao
    Wei Zhao
    Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, Jiangsu Engineering Laboratory for Environment Functional Materials, Jiangsu Collaborative Innovation Center of Regional Modern Agriculture & Environmental Protection, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, P.R. China
    More by Wei Zhao
Cite this: J. Chem. Eng. Data 2019, 64, 4, 1713–1724
Publication Date (Web):March 21, 2019
https://doi.org/10.1021/acs.jced.8b01226
Copyright © 2019 American Chemical Society

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    Abstract

    Abstract Image

    In this experiment, the research of solution process for 2-amino-3-methylbenzoic acid in different solvents is essential for its purification. The solubility values in pure methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, acetone, acetonitrile, 2-butanone, ethyl acetate, 1,4-dioxane, toluene, and cyclohexane were established with the isothermal saturation method at temperatures T = 278.15 to 318.15 K under pressure of 101.2 kPa. The solubility of 2-amino-3-methylbenzoic acid in mole fraction increased with a rise of temperature. Moreover, at a certain temperature, the order of the solubility data from high to low is 1,4-dioxane > acetone > 2-butanone > ethyl acetate > acetonitrile > methanol > ethanol > 1-propanol > 1-butanol > 2-propanol > toluene > cyclohexane. The modified Apelblat equation, λh equation, Wilson model, and NRTL model were used to correlate the experimental data. The values of root-mean-square deviation (RMSD) and relative average deviation (RAD) were not exceeding 4.51 × 10–4 and 1.87%, respectively. In order to choose the best model for 2-amino-3-methylbenzoic acid, the relative applicability of these models was evaluated by Akaike Information Criterion (AIC). Furthermore, solute–solvent and solvent–solvent interactions have been studied. The mixing properties of 2-amino-3-methylbenzoic acid were computed. From the analysis results, the mixing process of 2-amino-3-methylbenzoic acid was an endothermic, spontaneous, and entropy-driven process. In particular, purification, recrystallization, and formulation development of 2-amino-3-methylbenzoic acid in the industry were effected by its solubility values.

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    Cited By

    This article is cited by 7 publications.

    1. Miao Ma, Jidong Wang, Xiaotong Yang, Zhong Zhao. Determination and Simulation of the Solubility of Bifonazole in 14 Pure Solvents at 283.15–323.15 K. Journal of Chemical & Engineering Data 2023, 68 (7) , 1748-1762. https://doi.org/10.1021/acs.jced.2c00765
    2. Huimin Liu, Shui Wang, Chao Qu, Manman Li, Yixin Qu. Solid–Liquid Equilibrium of Chlorpropamide in 14 Pure Solvents at Temperature of 283.15 to 323.15 K. Journal of Chemical & Engineering Data 2020, 65 (5) , 2859-2871. https://doi.org/10.1021/acs.jced.0c00169
    3. Anfeng Zhu, Kun Hong, Fengxia Zhu, Benlin Dai, Xu Jiming, Wei Zhao. Solubility Determination and Model Correlation of Pymetrozine and Evaluation of the Effect of Solvent Properties and Composition. Journal of Chemical & Engineering Data 2019, 64 (7) , 3148-3155. https://doi.org/10.1021/acs.jced.9b00229
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