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Antisolvent Crystallization Method and Mixed Solvent Solubility Model Study of 2-Chloro-4,6-Dinitroresorcinol

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Abstract

Antisolvent crystallization method of 2-chloro-4,6-dinitroresorcinol was proposed and discussed for the first time. The yield of the product crystals was over 92.5%. Crystallization was carried out under the ambient temperature; ethanol was used as a solvent and water was used as an antisolvent. The technological conditions of antisolvent feed rate were studied, and 0.75 mL/min was the best operation. The solubility of 2-chloro-4,6-dinitroresorcinol in ethanol/water mixtures at 293.15–343.15 K was determined, and the Jouyban–Acree solubility equation was established. The mean deviation between experimental values and calculated ones was 1.81%.

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REFERENCES

  1. Kim, S. and Lee, Y.M., Rigid and microporous polymers for gas separation membranes, Prog. Polym. Sci., 2015, vol. 43, p. 1.

    Article  CAS  Google Scholar 

  2. Zhang, M.Q. and Rong, M.Z., Intrinsic self-healing of covalent polymers through bond reconnection towards strength restoration, Polym. Chem., 2013, vol. 41, no. 18, pp. 4878–4884. https://doi.org/10.1039/C3PY00005B

    Article  Google Scholar 

  3. Jiang, B., Zhang, T., and Huang, Y.D., Interfacially reinforced carbon fiber composites by grafting modified methylsilicone resin, Compos. Sci. Technol., 2017, vol. 140, p. 39.

    Article  CAS  Google Scholar 

  4. Chen, Y.M., Tang, M., and Chen, Y.P., Recrystallization and micronization of sulfathiazole by applying the supercritical antisolvent technology, Chem. Eng. J., 2010, vol. 165, no. 1, p. 358.

    Article  CAS  Google Scholar 

  5. Marco, D., Rossmann, M., Prosapio, V., Reverchon, E., and Braeuer, A., Control of particle size, at micrometric and nanometric range, using supercritical antisolvent precipitation from solvent mixtures: Application to PVP, Chem. Eng. J., 2015, vol. 273, p. 344.

    Article  Google Scholar 

  6. Shi, R.X. and Huang, Y.D., Study on thermodynamic properties of solvent extraction for 2-halo-4,6-dinitroresorcinol, Indian J. Chem. Technol., 2007, vol. 14, p. 100.

    CAS  Google Scholar 

  7. Shi, R.X., Huang, Y.D., and Jiao, L.Y., Crystallization kinetics of 2-halo-4,6-dinitroresorcinol by batch cooling crystallization method, Chem. Eng. Commun., 2007, vol. 194, p. 1176.

    Article  CAS  Google Scholar 

  8. Thorat, A.A. and Dalvi, S.V., Liquid antisolvent precipitation and stabilization of nanoparticles of poorly water soluble drugs in aqueous suspensions: Recent developments and future perspective, Chem. Eng. J., 2012, vol. 181, p. 1.

    Article  Google Scholar 

  9. Li, C.C. and Zeng, H.C., Coordination chemistry and antisolvent strategy to rare-earth solid solution colloidal spheres, J. Am. Chem. Soc., 2012, vol. 134, no. 46, p. 19084.

    Article  CAS  Google Scholar 

  10. Li, C.C., Dou, J., Chen, L.W., Lin, J.Y., and Zeng, H.C., Antisolvent precipitation for the synthesis of monodisperse mesoporous niobium oxide spheres as highly effective solid acid catalysts, ChemCatChem, 2012, vol. 4, no. 10, p. 1675. https://doi.org/10.1002/cctc.201100457

    Article  CAS  Google Scholar 

  11. Kiran, A.R., Aniruddha, B.P., and Parag, R.G., Ultrasound assisted antisolvent crystallization of benzoic acid: Effect of process variables supported by theoretical simulations, Ind. Eng. Chem. Res., 2013, vol. 52, no. 49, p. 17573.

    Article  Google Scholar 

  12. Oosterhof, H., Witkamp, G.-J., and van Rosmalen, G.M., Antisolvent crystallization of anhydrous sodium carbonate at atmospherical conditions, AIChE J., 2001, vol. 47, no. 3, p. 602. https://doi.org/10.1002/aic.690470310

    Article  CAS  Google Scholar 

  13. Min, J.L., Nan, H.C., Liu, J.J., Myung, Y.J., and Guang, J.C., Understanding the formation of indomethacin saccharin cocrystals by antisolvent crystallization, Cryst. Growth Des., 2013, vol. 13, no. 5, p. 2067.

    Article  Google Scholar 

  14. Zhao, D.S., Liu, M.S., Zhang, J., Li, J.P., and Ren, P.B., Synthesis, characterization, and properties of imidazole dicationic ionic liquids and their application in esterification, Chem. Eng. J., 2013, vol. 221, p. 99.

    Article  CAS  Google Scholar 

  15. Widenski, D.J., Abbas, A., and Romagnoli, J.A., Use of predictive solubility models for isothermal antisolvent crystallization modeling and optimization, Ind. Eng. Chem. Res., 2011, vol. 50, no. 13, p. 8304.

    Article  CAS  Google Scholar 

  16. Ó’Ciardhá, C.T., Hutton, K.W., Mitchell, N.A., and Frawley, P.J., Simultaneous parameter estimation and optimization of a seeded antisolvent crystallization, Cryst. Growth Des., 2012, vol. 12, no. 11, pp. 5247–5261. https://doi.org/10.1021/cg3006822

    Article  CAS  Google Scholar 

  17. Zhang, L., Hu, Z., Jiang, B., and Huang, Y.D., Solubility of 2-chloro-4,6-dinitroresorcinol in ethanol, methanol, acetic acid, ethyl acetate, and water, J. Chem. Eng. Data, 2011, vol. 56, no. 5, p. 2696.

    Article  CAS  Google Scholar 

  18. Smallwood, I.M., Handbook of Organic Solvent Properties, London: Arnold, 1996.

    Google Scholar 

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Funding

This work was supported by the National High Technology Research and Development Program of China (Program 863, no. 2012AA03A212) and Liaoning Province Department of Education Foundation (no. 901073).

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Correspondence to L. Zhang.

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Zhang, L., Yuan, H.Q. Antisolvent Crystallization Method and Mixed Solvent Solubility Model Study of 2-Chloro-4,6-Dinitroresorcinol. Theor Found Chem Eng 55, 123–128 (2021). https://doi.org/10.1134/S0040579521010176

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  • DOI: https://doi.org/10.1134/S0040579521010176

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