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A Safe and Effective Strategy for the Synthesis of Cyanuric Acid Using the Solvent Method

  • Organic Synthesis and Industrial Organic Chemistry
  • Published:
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Abstract

Cyanuric acid is an organic intermediate widely used in organic synthesis, and the traditional production method of cyanuric acid is the pyrolysis urea method. Due to the shortcomings of uneven mass transfer, many by-products and poor environmental friendliness, the production of cyanuric acid is extremely limited. In this paper, an effective method has been developed to synthesize cyanuric acid with high yield in a short period of time through the addition-elimination reaction of dihydric alcohol and urea under alkaline conditions. The reaction time, molar ratio of reactants, reaction temperature and other influencing factors were studied. Under optimized conditions, the yield of cyanuric acid is over 90%. And further the proposed reaction mechanism is verified. The synthetic method provided in this article has the advantages of easy availability of raw materials and reusability, simple operation and short reaction time, which makes the method novel and environmentally friendly.

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REFERENCES

  1. Dong-Mei, She, Hai-Lin, Yu, Qi-Liang, Huang, Fen-Ming, Li, and Chun-Jiu, Li, Molecules, 2010, vol. 15(3), pp. 1898–1902. https://doi.org/10.3390/molecules15031898

    Article  CAS  Google Scholar 

  2. Anguang, Hu and Fan, Zhang, J. Physics: Condensed Matter, 2010, vol. 22(50), ID 505402. https://doi.org/10.1088/0953-8984/22/50/505402

    Article  CAS  Google Scholar 

  3. Pop, F., Socaci, C., Terec, A., Condamine, E., Varga, R.A., Raţ, C.I., Roncali, J., and Grosu, I., Tetrahedron, 2012, vol. 68, no. 41. https://doi.org/10.1016/j.tet.2012.07.100

    Article  Google Scholar 

  4. Patil, S.P. and Padmanabhan, D., J. Labelled Compounds and Radiopharmaceuticals, 2002, vol. 45(7), pp. 539–542. https://doi.org/10.1002/jlcr.579

    Article  CAS  Google Scholar 

  5. Avakyan, N., Greschner, A.A., Aldaye, F., Serpell, C.J., Toader, V., Petitjean, A., and Sleiman, H.F., Nature Chemistry, 2016, vol. 8, p. 368. https://doi.org/10.1038/nchem.2451

    Article  CAS  PubMed  Google Scholar 

  6. Hiroaki, Onoda, Atsushi, Takenaka, Kazuo, Kojima, and Hiroyuki, Nariai, Materials Chemistry and Physics, 2003, vol. 82(1), pp. 194–198. https://doi.org/10.1016/s0254-0584(03)00205-0

    Article  Google Scholar 

  7. Yu, Qiu and Lian, Gao, Materials Research Bulletin, 2005, vol. 40(5), pp. 794–799. https://doi.org/10.1016/j.materresbull.2005.02.003

    Article  CAS  Google Scholar 

  8. Gad, S.C., Encyclopedia of Toxicology, 2014, pp. 904–906. https://doi.org/10.1016/b978-0-12-386454-3.00903-9

    Article  Google Scholar 

  9. Podsiadło, S., Thermochimica Acta, 1995, vol. 256(2), pp. 367–373. https://doi.org/10.1016/0040-6031(94)02026-k

    Article  Google Scholar 

  10. Seifer, G.B., Russ. J. Coord. Chem., 2002, vol. 28(5), pp. 301–324. https://doi.org/10.1023/a:1015531315785

    Article  CAS  Google Scholar 

  11. Carofiglio, Tommaso, Varotto, Alessandro, and Tonellato, Umberto, J. Org. Chem., 2004, vol. 69(23), pp. 8121–8124. https://doi.org/10.1021/jo048713d

    Article  CAS  PubMed  Google Scholar 

  12. Lebedev, A.V., Sheludyakov, V.D., and Lebedeva, A.B., Russ. J. Appl. Chem., 2014, vol. 87(6), pp. 793–795. https://doi.org/10.1134/s1070427214060214

    Article  CAS  Google Scholar 

  13. Yan, Y.G., Zhang, W.W., and Cai, K.Y., Guangzhou Chem. Ind., 2012, vol. 40, p. 57

    Google Scholar 

  14. Chen, H.Z., Yang, L., and Feng, X., Appl. Chem. Ind., 2016, vol. 45, pp. 953–957.

    CAS  Google Scholar 

  15. Zhang, L.P., Fu, F., Zhang, X.C., Wang, J.W., and Zhao, X.M., Food & Machinery, 2006, vol. 22, pp. 77–79.

    Google Scholar 

  16. US Patent 4109089P, 1978.

  17. Lebedev, A.V., Sheludyakov, V.D., and Lebedeva, A.B., Russian J. Appl. Chem., 2014, vol. 87, pp. 793–795.

    Article  CAS  Google Scholar 

  18. Chen, T.D., Wei, J.B., Yan, X.H., and Li, S.Q., Fine Chem. Intermediates, 2010, vol. 40, p. 67–69

    CAS  Google Scholar 

  19. Wojtowiez, J.A. and Eevmer, D.A.J., US Patent 4174444, Nov. 13, 1979.

  20. Dadge, W.B., US Patent 4567258, 1986.

  21. Otter, Den and Marinus, J.A.M., US Patent 4174444, 1979.

  22. Sidner, B., US Patent 35639871971.

  23. Jie, Y. and Gongying, W., Fine Chem. Ind., 1987, vol. 2, pp. 42–47.

    Google Scholar 

  24. AIST: Integrated Spectral Database System of Organic Compounds (Data were obtained from the National Institute of Advanced Industrial Science and Technology (Japan)).

  25. Predicted NMR data calculated using Advanced Chemistry Development, Inc. (ACD/Labs) Software V11.01 (© 1994-2021 ACD/Labs.

  26. Chiavaro, E., Differential Scanning Calorimetry, Oxfordshire: Taylor and Francis, 2014.

    Book  Google Scholar 

  27. Coats, A.W. and Redfern, J.P., Analyst, 1963, vol. 88, p. 906. https://doi.org/10.1039/an9638800906

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

Financial Support from Zhengzhou University of China is gratefully acknowledged.

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Correspondence to Xiaohua Shi.

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Ren, Q., Qian, L., Yao, Y. et al. A Safe and Effective Strategy for the Synthesis of Cyanuric Acid Using the Solvent Method. Russ J Appl Chem 95, 1618–1626 (2022). https://doi.org/10.1134/S1070427222100135

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