Abstract
The equilibrium constants of seven sequential-parallel reactions of conversion of glycerin into glycerin trinitrate in aqueous HNO3 were measured. The effect of the acidity of the medium on the equilibrium nitration constants is correlated with processes of protonation of glycerin and its nitrates. The equilibrium nitration constants are higher for primary hydroxides than for secondary hydroxides, and they decrease in both series in going from glycerin to its dinitrates.
Similar content being viewed by others
Literature cited
J. D. Cox and G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York-London (1970), p. 643.
E. A. Miroshnichenko, L. I. Korchatova, V. P. Shelaputina, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1988 (1988).
F. Naum, Nitroglycerin and Nitroglycerin Substances (Dynamites) [Russian translation], Goskhimtekhizdat ONTI, Moscow-Leningrad (1934).
Yu. V. Karyakin and I. I. Angelov, Pure Chemicals [in Russian], Khimiya, Moscow (1974), p. 407.
L. T. Eremenko and A. M. Korolev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1436 (1966).
V. I. Atroshchenko and S. I. Kargin, Nitric Acid Technology [in Russian], Goskhimizdat, Moscow (1962), p. 523.
G. Perdoncin and G. Scarrano, J. Am. Chem. Soc.,99, No. 21, 6983 (1977).
C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd ed., Cornell University Press, Ithaca (1969).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1723–1729, August, 1990.
Rights and permissions
About this article
Cite this article
Kazakov, A.I., Lagodzinskaya, G.V., Andrienko, L.P. et al. Study of nitration equilibrium in the glycerin-aqueous nitric acid system. 1. Dependence of the equilibrium constants of nitration reactions on the temperature, acidity of the medium, and structure of the nitrated compound. Russ Chem Bull 39, 1560–1565 (1990). https://doi.org/10.1007/BF00961477
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00961477