Determination and correlation solubility of m-phenylenediamine in (methanol, ethanol, acetonitrile and water) and their binary solvents from 278.15 K to 313.15 K

doi:10.1016/j.cjche.2018.11.005

Abstract

Abstract: In this study, the solubility of m-phenylenediamine in four pure solvents (methanol, ethanol, acetonitrile and water) and three binary solvent (methanol + water), (ethanol + water) and (acetonitrile + water) systems were determined in the temperature ranging from 278.15 K to 313.15 K by using the gravimetric method under atmospheric pressure. In the temperature range of 278.15 K to 313.15 K, the mole fraction solubility values of m-phenylenediamine in water, methanol, ethanol, and acetonitrile are 0.0093-0.1533, 0.1668-0.5589, 0.1072-0.5356, and 0.1717-0.6438, respectively. At constant temperature and solvent composition, the mole fraction solubility of o-phenylenediamine in four pure solvents was increased as the following order:water < ethanol < methanol < acetonitrile; and in the three binary solvent mixtures could be ranked as follows:(ethanol + water) < (methanol + water) < (acetonitrile + water). The relationship between the experimental temperature and the solubility of m-phenylenediamine was revealed as follows:the solubility of mphenylenediamine in pure and binary solvents could be increased with the increase of temperature. The experimental values were correlated with the Jouyban-Acree model, van't Hoff-Jouyban-Acree model, modified Apelblat-Jouyban-Acree model, Sun model and Ma model. The standard dissolution enthalpy, standard dissolution entropy and the Gibbs energy were calculated based on the experimental solubility data. In the binary solvent mixtures, the dissolution of m-phenylenediamine could be an endothermic process. The solubility data, correlation equations and thermodynamic property obtained from this study would be invoked as basic data and models regarding the purification and crystallization process of m-phenylenediamine.

Key words: m-Phenylenediamine, Solubility, Solid-liquid equilibrium, Jouyban-Acree model, Thermodynamic property

摘要： In this study, the solubility of m-phenylenediamine in four pure solvents (methanol, ethanol, acetonitrile and water) and three binary solvent (methanol + water), (ethanol + water) and (acetonitrile + water) systems were determined in the temperature ranging from 278.15 K to 313.15 K by using the gravimetric method under atmospheric pressure. In the temperature range of 278.15 K to 313.15 K, the mole fraction solubility values of m-phenylenediamine in water, methanol, ethanol, and acetonitrile are 0.0093-0.1533, 0.1668-0.5589, 0.1072-0.5356, and 0.1717-0.6438, respectively. At constant temperature and solvent composition, the mole fraction solubility of o-phenylenediamine in four pure solvents was increased as the following order:water < ethanol < methanol < acetonitrile; and in the three binary solvent mixtures could be ranked as follows:(ethanol + water) < (methanol + water) < (acetonitrile + water). The relationship between the experimental temperature and the solubility of m-phenylenediamine was revealed as follows:the solubility of mphenylenediamine in pure and binary solvents could be increased with the increase of temperature. The experimental values were correlated with the Jouyban-Acree model, van't Hoff-Jouyban-Acree model, modified Apelblat-Jouyban-Acree model, Sun model and Ma model. The standard dissolution enthalpy, standard dissolution entropy and the Gibbs energy were calculated based on the experimental solubility data. In the binary solvent mixtures, the dissolution of m-phenylenediamine could be an endothermic process. The solubility data, correlation equations and thermodynamic property obtained from this study would be invoked as basic data and models regarding the purification and crystallization process of m-phenylenediamine.

关键词: m-Phenylenediamine, Solubility, Solid-liquid equilibrium, Jouyban-Acree model, Thermodynamic property

Pengbao Lian, Huipeng Zhao, Jianlong Wang, Lizhen Chen, Yong Xiang, Qinghua Ren. Determination and correlation solubility of m-phenylenediamine in (methanol, ethanol, acetonitrile and water) and their binary solvents from 278.15 K to 313.15 K[J]. Chinese Journal of Chemical Engineering, 2019, 27(5): 1149-1158.

References

[1] K. Venkataraman, L.M. Fieser, M. Fieser, The Chemistry of Synthetic Dyes, Academic Press, New York, 1952.
[2] H.K. Aktien, D. Holthausen, Oxidation hair dyes comprising m-phenylenediamine derivatives as coupling components, US Pat., 4684371, Aug 4, 1987.
[3] I.L. Bensheim, A.W. Heidelberg, WR.B. Alsbach, Oxidation hair dye composition based on 4,5-diaminopyrazole and m-phenylenediamine derivatives, US Pat., 5718731, Feb 17, 1998.
[4] N.B. Gaddam, S. Shubha, Preparation and solubility of a partial ladder copolymer from p-phenylenediamine and o-phenetidine, Makromol. Chem. 183(1982) 1129-1136.
[5] T.T. Guo, X.Y. Kang, T.T. Zhang, F. Liao, Uniform copper oxide-poly(mphenylenediamine) microflowers:Synthesis and application for the adsorption of methyl orange, RSC Adv. 5(2015) 17817-17823.
[6] Y. Tanaka, M. Murata, Adducts of m-phenylenediamine with phenyl-, allyl-and butyl-glycidyl ethers as hardenenrs for epoxy resins, J. Jpn. Soc. Colour Mater. 40(1967) 10-18.
[7] T. Higashihara, C. Zhang, A. Tsukuda, T. Ochi, M. Ueda, Direct synthesis and meltdrawing property of aramids by bulk polycondensation of isophthalic acid with m-phenylenediamine and 3,4-oxydianiline, J. Appl. Polym. Sci. 124(2012) 4398-4402.
[8] F. Chen, M. Murata, Y. Hiraku, N. Yamashita, S. Oikawa, S. Kawanishi, DNA damage induced by m-phenylenediamine and its derivative in the presence of copper ion, Free Radic. Res. 29(1998) 197-205.
[9] P.D. Ren, S.F. Pan, T.W. Dong, S.H. Wu, The novel reduction systems:NaBH₄-SbCl₃ or NaBH₄-BiCl₃ for conversion of nitroarenes to primary amines, Synth. Commun. 25(1995) 3799-3803.
[10] Y.X. Liu, Z.J. Wei, J.X. Chen, J.Y. Zhang, X.X. Li, X.H. Wei, A novel catalyst for liquid phase hydrogenation of m-dinitrobenzene to m-phenylenediamine, Chin. Chem. Lett. 16(2005) 531-533.
[11] Y.X. Liu, Z.J. Wei, J.Y. Zhang, Synthesis of m-phenylenediamine from m-dinitrobenzene over silica-supported nickel catalyst, Korean J. Chem. Eng. 23(2006) 902-907.
[12] Y.X. Liu, J.X. Chen, J.Y. Zhang, Effects of the supports on activity of supported nickel catalysts for hydrogenation of m-dinitrobenzene to m-phenylenediamine, Chin. J. Chem. Eng. 15(2007) 63-67.
[13] J.X. Chen, J.X. Zhang, J.Y. Zhang, Effects of La₂O₃, Li₂O and K₂O promoters on properties of a Ni-SiO₂ catalyst for hydrogenation of m-dinitrobenzene to m-phenylenediamine, React. Kinet. Catal. Lett. 93(2008) 359-366.
[14] Y.X. Liu, Z.J. Wei, S.G. Deng, J.Y. Zhang, Hydrogenation of m-dinitrobenzene to mphenylenediamine over La₂O₃-promoted Ni-SiO₂ catalysts, J. Chem. Technol. Biotechnol. 84(2009) 1381-1389.
[15] N.V. Sidgwick, J.A. Neill, CCCXXVI.-The solubility of the phenylenediamines and of their monoacetyl derivatives, J. Chem. Soc. Trans. 123(1923) 2813-2819.
[16] D.Y. Zhang, Y.L. Wang, S.Y. Ma, G. Wu, H.X. Hao, Determination of solubility and induction time of ceftazidime, J. Chem. Eng. Data 53(2013) 176-182.
[17] G.B. Yao, Q.C. Yao, Z.X. Xia, Z.H. Li, Solubility determination and correlation for o-phenylenediamine in (methanol, ethanol, acetonitrile and water) and their binary solvents from T=(283.15-318.15) K, J. Chem. Thermodyn. 105(2017) 179-186.
[18] A. Jouyban, Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixtures, J. Pharm. Pharm. Sci. 11(2008) 32-58.
[19] L.Z. Chen, T.B. Zhang, M. Li, J. Li, D.L. Cao, Solubility of 2,2',4,4',6,6'-hexanitrostilbene in binary solvent of N,N-dimethylformamide and acetonitrile, J. Chem. Thermodyn. 95(2016) 99-104.
[20] Z.M. Zhou, Y.X. Qu, J.D. Wang, S. Wang, J.S. Liu, M. Wu, Measurement and correlation of solubilities of (z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid in different pure solvents and binary mixtures of water +(ethanol, methanol, or glycol), J. Chem. Eng. Data 57(2012) 1344-1346.
[21] S. Vahdati, A. Shayanfar, J. Hanaee, F. Martínez, W.E. Acree Jr., A. Jouyban, Solubility of carvedilol in ethanol + propylene glycol mixtures at various temperatures, Ind. Eng. Chem. Res. 52(2013) 16630-16636.
[22] G.C. Lan, J.L. Wang, L.Z. Chen, H. Hou, J. Li, Y.P. Gao, Experimental determination of solubility and metastable zone width of 3,4-bis(3-nitrofurazan-4-yl)furoxan (DNTF) in (acetic acid + water) systems from (298.15 K-338.15 K), J. Chem. Thermodyn. 89(2015) 264-269.
[23] C.B. Du, R.J. Xu, S. Han, J. Xu, L. Meng, J. Wang, H.K. Zhao, Solubility determination and correlation for 1,8-dinitronaphthalene in (acetone + methanol), (toluene + methanol) and (acetonitrile + methanol) mixed solvents, J. Chem. Thermodyn. 94(2016) 24-30.
[24] A. Noubigh, A. Mgaidi, M. Abderrabba, Solubility of gallic acid in liquid mixtures of (ethanol + water) from (293.15 K +318.15 K), J. Chem. Thermodyn. 55(2012) 75-78.
[25] D.J.W. Grant, M. Mehdizadeh, A.H.L. Chow, J.E. Fairbrother, Non-linear van't Hoff solubility-temperature plots and their pharmaceutical interpretation, Int. J. Pharm. 18(1984) 25-38.
[26] W.E. Acree, Comments concerning ‘Model for solubility estimation in mixed solvent systems’, Int. J. Pharm. 127(1996) 27-30.
[27] L. Zhou, P.P. Zhang, G.D. Yang, R. Lin, W.R. Wang, T.T. Liu, L.Q. Zhang, J.Y. Zhang, Solubility of chrysin in ethanol and water mixtures, J. Chem. Eng. Data 59(2014) 2215-2220.