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Solid–Liquid Phase Equilibria of N,N′-[1,3-Phenylenebis(methylene)]bis(phosphoramidic acid) P,P,P′,P′-Tetraphenyl Ester in 10 Pure Solvents

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School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People’s Republic of China
School of Biochemical and Chemical Engineering, Nanyang Institute of Technology, Nanyang 473000, People’s Republic of China
*Fax: +86-10-68911040. E-mail: [email protected]
Cite this: J. Chem. Eng. Data 2014, 59, 5, 1533–1539
Publication Date (Web):April 7, 2014
https://doi.org/10.1021/je4010917
Copyright © 2014 American Chemical Society

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    Abstract

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    N,N′-[1,3-Phenylenebis(methylene)]bis(phosphoramidic acid) P,P,P′,P′-tetraphenyl ester (PNBE) was synthesized and characterized by elemental analysis, mass spectrometry, and IR and NMR spectroscopy. The melting point and the enthalpy of fusion of PNBE were obtained by differential scanning calorimetry, and the thermal stability of PNBE was measured by thermogravimetric analysis. The solubilities of PNBE in selected solvents were determined by a gravimetric method. The experimental data were correlated with the Wilson, nonrandom two-liquid (NRTL), and universal quasichemical (UNIQUAC) equations. The calculated results showed good agreement with the experimental data. Among them, the Wilson model gave the best description of the solubility data. The solubility parameter of PNBE was evaluated using the Scatchard–Hildebrand model. The data presented in this work will be helpful for the choice of solvents for the solution-casting process and optimization of the dissolution or purification of PNBE.

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    MS, IR, and 1H and 13C NMR spectra of PNBE and tables of molecular parameter values. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

    This article is cited by 6 publications.

    1. Baokuan Chen, Chaojun Du, Hui Zhou, Jingjing Wang, and Lijuan Wang . Solid–Liquid Phase Equilibrium of Phosphoramidic acid, N,N′-1,2-Ethanediylbis-P,P,P′,P′-tetraphenyl Ester in Selected Solvents. Journal of Chemical & Engineering Data 2015, 60 (6) , 1693-1698. https://doi.org/10.1021/je5010565
    2. Guo-Min Yu, Li-Sheng Wang, Jian Sun, and Lin-Kun Jiang . Solubilities of Three Phosphorus Flame Retardants in Selected Organic Solvents. Journal of Chemical & Engineering Data 2015, 60 (6) , 1803-1813. https://doi.org/10.1021/je501173n
    3. Peilei Jiao, Wenrui Zheng, Ziwen Guan, Lin He, Cuicui Zhang, Jiaying Tang. Theoretical study on the P–N bond dissociation enthalpy in phosphamide and phosphoramidate flame retardants. Journal of the Indian Chemical Society 2024, 101 (1) , 101114. https://doi.org/10.1016/j.jics.2023.101114
    4. José Luis Castrejón-Flores, Julieta Reyna-Luna, Yazmin M. Flores-Martinez, María Isabel García-Ventura, Angel Zamudio-Medina, Marco Franco-Pérez. Characterizing the thermal degradation mechanism of two bisphosphoramidates by TGA, DSC, mass spectrometry and first-principle theoretical protocols. Journal of Molecular Structure 2020, 1221 , 128781. https://doi.org/10.1016/j.molstruc.2020.128781
    5. William Acree, James S. Chickos. Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds and Ionic Liquids. Sublimation, Vaporization, and Fusion Enthalpies from 1880 to 2015. Part 2. C11–C192. Journal of Physical and Chemical Reference Data 2017, 46 (1) https://doi.org/10.1063/1.4970519
    6. Guo-Min Yu, Li-Sheng Wang, Chao-Jun Du, Jian Sun. Solubilities of phosphoric acid, P , P ′-1,4-phenylene P , P , P ′, P ′-tetraphenyl ester in the organic solvents. Fluid Phase Equilibria 2015, 388 , 6-15. https://doi.org/10.1016/j.fluid.2014.12.034

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