Abstract
A procedure was developed for preparing glyoxylic acid by glyoxal oxidation with nitric acid in the presence of hydrohalic acids with selective isolation of glyoxylic acid from the reaction mixture in the form of magnesium and calcium salts. Specific features of the synthesis of glyoxylic acid were demonstrated, and optimum conditions for each step of the process were determined. The highest yield of glyoxylic acid was obtained in oxidation of glyoxal with an HNO3 : HCl mixture. Oxidation in the presence of HF and HBr is characterized by lower yields because of low dissociation constant of HF and side redox reactions with HBr. Dilute solutions of glyoxylic acid were obtained by an exchange reaction of its calcium salt with a hydrofluoric acid solution at room temperature. An increase in the reaction temperature leads to an increase in the content of glycolic and oxalic acids formed by disproportionation of glyoxylic acid in the initial step of the exchange reaction.
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Lide, D.R., CRC Handbook of Chemistry and Physics, CRC, 2009, p. 770.
Lur’e. Yu.Yu., Spravochnik po analiticheskoi khimii (Handbook of Analytical Chemistry), Moscow: Khimiya, 1971, p. 96.
Simanova, S.A., Novyi spravochnik khimika i tekhnologa. Khimicheskoe ravnovesie. Svoistva rastvorov (New Chemist’s and Technologist’s Handbook. Chemical Equilibrium. Properties of Solutions), St. Petersburg: Professional, 2004, p. 190.
REFERENCES
Pozdniakov, M.A., Zhuk, I.V., Lyapunova, M.V., Salikov, A.S., Botvin, V.V., and Filimoshkin, A.G., Russ. Chem. Bull., 2019, vol. 68, no. 3, pp. 472–479. https://doi.org/10.1007/s11172-019-2442-2
Patent US 8754255 B2, Publ. 2008.
Mattioda, G. and Christidis, Y., Ullmann’s Encyclopedia of Industrial Chemistry, 2002, vol. 17, pp. 89–92. https://doi.org/10.1002/14356007.a12_495
Pozdniakov, M., Rubtsov, K., Botvin, V., Sorvanov, A., Knyazev, A., and Filimoshkin, A., Sep. Sci. Technol., 2017, vol. 52, no. 5, pp. 876–882. https://doi.org/10.1080/01496395.2016.1269129
Patent US 8426632 B2, Publ. 2013.
Ogata, Y., Org. Chem., Part C, 1978, vol. 381, pp. 295–342. https://doi.org/10.1016/B978-0-12-697252-8.50009-1
Pozdniakov, M.A., Salikov A.S., Botvin, V.V., Poleshchuk, O.K., and Filimoshkin, A.G., Russ. Chem. Bull., 2019, vol. 68, no. 4, pp. 802–808. https://doi.org/10.1007/s11172-019-24881
Lengyel, I., Nagy, I., and Bazsa, G., J. Phys. Chem., 1989, vol. 93, no. 7, pp. 2801–2807. https://doi.org/10.1021/j100344a021
Srinivasakannan, C., Vasanthakumar, R., Iyappan, K., and Rao, P.G., Chem. Biochem. Eng. Q., 2002, vol. 16, no. 3, pp. 125–129.
Patent RU 2541790, Publ. 2015.
Funding
The study was financially supported by the Ministry of Science and Higher Education of the Russian Federation within the framework of the Federal Target Program “Research and Development in Priority Directions of the Progress of the Scientific and Technological Complex of Russia in 2014–2020” (agreement no. 14.575.21.0170, unique project identifier RFMEFI57517X0170).
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Pozdniakov, M.A., Zhuk, I.V., Salikov, A.S. et al. Synthesis of Glyoxylic Acid by Glyoxal Oxidation in the Presence of Hydrohalic Acids. Russ J Appl Chem 93, 1571–1577 (2020). https://doi.org/10.1134/S107042722010122
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DOI: https://doi.org/10.1134/S107042722010122