Abstract
The dioxane method for the isoprene production is a chemically two-stage process based on the splitting of 4,4-dimethyl-1,3-dioxane. The latter is synthesized by condensation of iso-C4H8 or tert-C4H9OH with CH2O (Prins reaction). One of the disadvantages of the considered method of isoprene synthesis is the formation of up to 30–40 wt % by-products (dihydropyrans, diols, unsaturated alcohols, etc.) at the stage of 4,4-dimethyl-1,3-dioxane synthesis. The insufficiently high selectivity of the 4,4-dimethyl-1,3-dioxane formation is due to the multichannel Prins reaction; therefore, a noticeable increase in the selectivity of the process cannot be achieved only by optimizing the currently implemented technological schemes of the dioxane method for the isoprene production. The parameters of the reaction of tert-С4H9OH with CH2O in the presence of carbon-containing porous materials were selected using the linear optimization method. It was found that the condensation of tert-C4H9OH with CH2O under catalysis conditions with both carbon nanotubes and porous glassy carbon can yield 4,4-dimethyl-1,3-dioxane with a selectivity of up to ~99 wt %.
Similar content being viewed by others
REFERENCES
Plate, N.A. and Slivinskii, E.V., Osnovy khimii i tekhnologii monomerov (Fundamentals of Chemistry and Technology of Monomers), Moscow: Nauka, 2002.
Miranda, P.O., Carballo, R.M., Ramirez, M.A., Martín, V.S., Padron, J.I., Arkvoc., 2007, no. 8, pp. 331–343. https://doi.org/10.3998/ark.5550190.0008.430
RF Patent 2255936 (Publ. 2005).
RF Patent 2330848 (Publ. 2008).
Wang, J., Jaenicke, S., Chuah, G.K., Hua, W., Yue, Y., and Gao, Z., Catal. Commun., 2011, vol. 12, no. 12, pp. 1131–1135. https://doi.org/10.1016/j.catcom.2011.03.034
Do, M.D., Jaenicke, S., and Chuah, G.K., Catal. Sci. Technol., 2012, vol. 2, pp. 1417–1424. https://doi.org/10.1039/C2CY20084H
Vasiliadou, E.S., Li, S., Caratzoulas, S., and Lobo, R.F., Catal. Sci. Technol., 2018, vol. 8, pp. 5794–5806. https://doi.org/10.1039/C8CY01667D
Vasiliadou, E.S., Gould, N.S., and Lobo, R.F., Chem. Cat. Chem., 2017, vol. 9, no. 3, pp. 4417–4425. https://doi.org/10.1002/cctc.201701315
Ogorodnikov, S.K., Formal’degid (Formaldehyde), Leningrad: Khimiya, 1984.
Kraikin, V.A., Musina, Z.N., Galkin, E.G., Kuznetsov, S.I., Egorov, A.E., and Salazkin S.N., Polym. Sci. Ser. A, 2006, vol. 48, no. 12, pp. 1287–1303. https://doi.org/10.1134/S0965545X06120108
Fadeeva, V.I., Shekhovtsova, T.N., and Ivanov, V.M., Osnovy analiticheskoi khimii. Prakticheskoe rukovodstvo (Fundamentals of Analytical Chemistry. Practical Guide), Moscow: Vysshaya shkola, 2001.
Aivazov, B.V., Osnovy gazovoi khromatografii (Fundamentals of Gas Chromatography), Moscow: Vysshaya shkola, 1977.
Wu, G., Wu, Y., Rao, G., and Liu, Y., Vysokomolekulyar. Soedin., Ser., B, 1997, vol. 39, no. 7, pp. 1237–1240.
Ovchinnikov, G.A., Gorskikh, V.A., Fassalova, I.I., Tukhvatshin, V.S., and Talipov, R.F., Izv. vuzov. Khimiya i khim. Tekhnologiya, 2018, vol. 61, no. 12, pp. 81–86. https://doi.org/10.6060/ivkkt.20186112.5542
Dykman, A.S., Leont’ev, P.Yu., and de Vekke, A.V., Izv. SPbGTI (TU), 2018, vol. 50, no. 24, pp. 39–42.
Author information
Authors and Affiliations
Contributions
R.F. Talipov: setting the objectives of the study and the plan of experimental work; V.S. Tukhvatshin: synthesis of 4,4-dimethyl-1,3-dioxane in the presence of carbon nanotubes; G.R. Talipova: synthesis of 4,4-dimethyl-1,3-dioxane in the presence of porous glassy carbon.
Corresponding author
Ethics declarations
The authors declare no conflict of interest requiring disclosure in this article.
Additional information
Translated from Zhurnal Prikladnoi Khimii, No. 7, pp. 860–864, July, 2022 https://doi.org/10.31857/S0044461822070040
Rights and permissions
About this article
Cite this article
Tukhvatshin, V.S., Talipov, R.F. & Talipova, G.R. Optimization of Conditions for the Synthesis of 4,4-Dimethyl-1,3-dioxane from tert-Butanol in the Presence of Carbon-Сontaining Porous Materials. Russ J Appl Chem 95, 943–947 (2022). https://doi.org/10.1134/S1070427222070047
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070427222070047