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.
REFERENCES
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
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
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
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
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
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
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
Gad, S.C., Encyclopedia of Toxicology, 2014, pp. 904–906. https://doi.org/10.1016/b978-0-12-386454-3.00903-9
Podsiadło, S., Thermochimica Acta, 1995, vol. 256(2), pp. 367–373. https://doi.org/10.1016/0040-6031(94)02026-k
Seifer, G.B., Russ. J. Coord. Chem., 2002, vol. 28(5), pp. 301–324. https://doi.org/10.1023/a:1015531315785
Carofiglio, Tommaso, Varotto, Alessandro, and Tonellato, Umberto, J. Org. Chem., 2004, vol. 69(23), pp. 8121–8124. https://doi.org/10.1021/jo048713d
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
Yan, Y.G., Zhang, W.W., and Cai, K.Y., Guangzhou Chem. Ind., 2012, vol. 40, p. 57
Chen, H.Z., Yang, L., and Feng, X., Appl. Chem. Ind., 2016, vol. 45, pp. 953–957.
Zhang, L.P., Fu, F., Zhang, X.C., Wang, J.W., and Zhao, X.M., Food & Machinery, 2006, vol. 22, pp. 77–79.
US Patent 4109089P, 1978.
Lebedev, A.V., Sheludyakov, V.D., and Lebedeva, A.B., Russian J. Appl. Chem., 2014, vol. 87, pp. 793–795.
Chen, T.D., Wei, J.B., Yan, X.H., and Li, S.Q., Fine Chem. Intermediates, 2010, vol. 40, p. 67–69
Wojtowiez, J.A. and Eevmer, D.A.J., US Patent 4174444, Nov. 13, 1979.
Dadge, W.B., US Patent 4567258, 1986.
Otter, Den and Marinus, J.A.M., US Patent 4174444, 1979.
Sidner, B., US Patent 35639871971.
Jie, Y. and Gongying, W., Fine Chem. Ind., 1987, vol. 2, pp. 42–47.
AIST: Integrated Spectral Database System of Organic Compounds (Data were obtained from the National Institute of Advanced Industrial Science and Technology (Japan)).
Predicted NMR data calculated using Advanced Chemistry Development, Inc. (ACD/Labs) Software V11.01 (© 1994-2021 ACD/Labs.
Chiavaro, E., Differential Scanning Calorimetry, Oxfordshire: Taylor and Francis, 2014.
Coats, A.W. and Redfern, J.P., Analyst, 1963, vol. 88, p. 906. https://doi.org/10.1039/an9638800906
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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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DOI: https://doi.org/10.1134/S1070427222100135