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Equilibrium Solubility of Biapenem in Different Neat and Binary Solvents: Experimental Determination and Model Correlation

  • Renjie Xu*
    Renjie Xu
    Guangling College, Yangzhou University, YangZhou, Jiangsu 225009, People’s Republic of China
    *E-mail: [email protected]
    More by Renjie Xu
  • Chunjuan Huang
    Chunjuan Huang
    Guangling College, Yangzhou University, YangZhou, Jiangsu 225009, People’s Republic of China
  • , and 
  • Jie Xu
    Jie Xu
    Guangling College, Yangzhou University, YangZhou, Jiangsu 225009, People’s Republic of China
    More by Jie Xu
Cite this: J. Chem. Eng. Data 2019, 64, 4, 1454–1460
Publication Date (Web):March 15, 2019
https://doi.org/10.1021/acs.jced.8b01051
Copyright © 2019 American Chemical Society

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    Abstract

    Abstract Image

    The equilibrium solubility is the basis of purification and further theoretical studies of biapenem. In this work, the solubility of biapenem in 10 pure solvents (methanol, ethanol n-propanol, isopropanol, acetone, N,N-dimethylformamide (DMF), acetonitrile, dimethyl sulfoxide (DMSO), N-methyl pyrrolidone (NMP), and ethyl acetate) and solvent mixtures (ethyl acetate + methanol) was measured by using a static equilibrium method at temperatures from 283.15 to 323.15 K, at p = 101.2 kPa. To sum up, the solubility was highest in NMP and lowest in acetone. The solubility from high to low is NMP (0.9663 × 10–4, 298.15 K) > DMSO (0.8655 × 10–4, 298.15 K) > DMF (0.7796 × 10–4, 298.15 K) > ethyl acetate (0.7161 × 10–4, 298.15 K) > acetonitrile (0.5169 × 10–4, 298.15 K) > methanol (0.3068 × 10–4, 298.15 K) > ethanol (0.2455 × 10–4, 298.15 K) > n-propanol (0.1966 × 10–4, 298.15 K) > isopropanol (0.1205 × 10–4, 298.15 K) > acetone (0.04576 × 10–4, 298.15 K). The experiment values in monosolvents were associated with the modified Apelblat equation. The experiment values in mixed solvents were associated with the Jouyban–Acree model, Apelblat–Jouyban–Acree model, and CNIBS/R-K model. From the correlation results, the largest RAD values of the above three models are 0.83%, 0.98%, and 0.60%, respectively. These models can all fit the experiment values very well. Accordingly, in values of solubility in the pure solvent correlation process, the maximum values of root-mean-square deviation (RMSD) and relative average deviation (RAD) are 0.42 × 10–6 and 0.80%, respectively. Furthermore, solute–solvent interactions have been studied in monosolvents. The hydrogen bonds play an important role in the dissolution process of biapenem. Especially, the experimental values have influences on purification, recrystallization, and formulation development of biapenem in production.

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    Cited By

    This article is cited by 6 publications.

    1. Xin Huang, Qiufen Wang, Shouxiang Jiang, Bin Wang, Wenjun Xie, Chengfei Wang, Haoran Li, Guan Wang, Gengxiu Zheng. Solubility Measurement and Model Correlation of N,N′-Oxalyldiglycine in Eleven Pure Solvents and a Binary Solvent from 293.15 to 333.15 K. Journal of Chemical & Engineering Data 2023, 68 (12) , 3423-3434. https://doi.org/10.1021/acs.jced.3c00424
    2. Zengai Guo, Wei Sun, Weiyang Lu, Gengxiu Zheng. Solubility Measurement, Model Correlation, and Solute–Solvent Interactions of Pidotimod in Nine Pure Solvents and Two Binary Solvents at Temperatures Ranging from 278.15 to 323.15 K. Journal of Chemical & Engineering Data 2020, 65 (11) , 5483-5497. https://doi.org/10.1021/acs.jced.0c00616
    3. Haifang Mao, Liqin Song, Chaoyang Wang, Pingyi Zhang, Kejia Liu, Ting Tang, Miaomiao Jin. Measurement and correlation of 4,4′-dihydroxydiphenylsulfone solubility in ten neat organic solvents at temperatures from 278.15 to 313.15 K. The Journal of Chemical Thermodynamics 2022, 174 , 106875. https://doi.org/10.1016/j.jct.2022.106875
    4. Haifang Mao, Hong Chen, Miaomiao Jin, Chaoyang Wang, Zuobing Xiao, Yunwei Niu. Measurement and correlation of solubility of o-vanillin in different pure and binary solvents at temperatures from 273.15 K to 303.15 K. The Journal of Chemical Thermodynamics 2020, 150 , 106199. https://doi.org/10.1016/j.jct.2020.106199
    5. Changfei Zhu, Renjie Xu, Yanyan Zhou, Hongkun Zhao. Biapenem in binary aqueous mixtures of N,N-dimethylformamide, N-methyl-2-pyrrolidone, isopropanol and ethanol: Solute-solvent and solvent-solvent interactions, solubility determination and preferential solvation. The Journal of Chemical Thermodynamics 2020, 149 , 106190. https://doi.org/10.1016/j.jct.2020.106190
    6. N. V. Bondarev. Empirical Models of Stability of Crown Ether Complexes with Alkaline and Alkaline-Earth Metals in Selected Pure Solvents. Russian Journal of General Chemistry 2020, 90 (6) , 1040-1050. https://doi.org/10.1134/S1070363220060171

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