Abstract
Phenol, polyphenols, as well as fluorinated alcohols actively catalyze the carboxylation of propylene oxide to form propylene carbonate in mild conditions (60°С, 7 at). The highest catalytic activity is characteristic of polyhydric phenols having neighbouring OH groups and alcohols with an enhanced acidity of OH protons. These catalysts in combination with tetrabutyammonium iodide exhibit activity at low concentrations (0.25 mol %) and ensure almost quantitative yields of propylene carbonate. The activity of the catalysts much increases with increasing ammonium salt amount (TOF up to 260), as well as temperature and initial СО2 pressure (TON up to 370).
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Noskov, Yu.G., Rush, S.N., Kron, T.E., Korneeva, G.A., Temkin, O.N., and Kuz’min, S.G., RF Patent 2440826, 2012; Byull. Izobret., 2012, no. 3.
Elman, A.R., Ovsyannikova, L.V., Davydov, I.E., Kushnarev, D.I., Gubanov, O.V., Zyryanov, S.M., and Sid’ko, Yu.A., RF Patent 2638837, 2017; Byull. Izobret., 2017, no. 35.
Plavnik, R.G., Nevmerzhitskii, V.I., Butorova, L.I., and Plavnik, T.E., Klin. Med., 2015, vol. 93, no. 9, p. 42.
Cheepsattayakorn, A. and Cheepsattayakorn, R., BioMed Res. Int., 2013, vol. 2013, article ID 702896. doi 10.1155/2013/702896
North, M., Pasquale, R., and Young, C., Green Chem., 2010, vol. 12, no. 9, p. 1514. doi 10.1039/c0gc00065e
Maeda, C., Taniguchi, T., Ogawa, K., and Ema, T., Angew. Chem. Int. Ed., 2015, vol. 54, no. 1, p. 134. doi 10.1002/anie. 201409729
Rulev, Y.A., Gugkaeva, Z., Maleev, V.I., North, M., and Belokon, Y.N., Beilstein J. Org. Chem., 2015, vol. 11, p. 1614. doi 10.3762/bjoc.11.176
Whiteoak, C.J., Nova, A., Maseras, F., and Kleij, A.W., ChemSusChem., 2012, vol. 5, no. 10, p. 2032. doi 10.1002/cssc.201200255
Alves, M., Grignard, B., Gennen, S., Mereau, R., Detrembleur, C., Jerome, C., and Tassaing, T., Catal. Sci. Technol., 2015, vol. 5, no. 9, p. 4636. doi 10.1039/c5cy00891c
Gennen, S., Alves, M., Méreau, R., Tassaing, T., Gilbert, B., Detrembleur, C., Jerome, C., and Grignard, B., ChemSusChem., 2015, vol. 8, no. 11, p. 1845. doi 10.1002/cssc.201500103
Shen, Y.-M., Duan, W.-L., and Shi, M., Adv. Synth. Catal., 2003, vol. 345, no. 3, p. 337. doi 10.1002/adsc.200390035
Hardman-Baldwin, A.M. and Mattson, A.E., ChemSusChem., 2014, vol. 7, no. 12, p. 3275. doi 10.1002/cssc.201402783
Wang, L., Zhang, G., Kodama, K., and Hirose, T., Green Chem., 2016, vol. 18, no. 5, p. 1229. doi 10.1039/C5GC02697K
Wang, X., Wang, L., Zhao, Y., Kodama, K., and Hirose, T., Tetrahedron, 2017, vol. 73, no. 8, p. 1190. doi 10.1016/j.tet.2017.01.018
Xiao, B., Sun, J., Wang, J., Liu, C., and Cheng, W., Synth. Commun., 2013, vol. 43, no. 22, p. 2985. doi 10.1080/00397911.2012.754471
Werner, T. and Tenhumberg, N., J. CO2 Util., 2014, vol. 7, p. 39. doi 10.1016/j.jcou.2014.04.002
Khimicheskaya entsiklopediya (Chemical Encyclopedia), Zefirov, N.S., Ed., Moscow: Bol’shaya Rossiiskaya Entsiklopedia, 1999, vol. 5, p. 74.
Kida, T., Sato, S.-I., Yoshida, H., Teragaki, A., and Akashi, M., Chem. Commun., 2014, vol. 50, p. 14245. doi 10.1039/c4cc06690a.
Khimicheskaya entsiklopediya (Chemical Encyclopedia), Zefirov, N.S., Ed., Moscow: Bol’shaya Rossiyskaya Entsiklopedia, 1995, vol. 4, p. 104.
TableCurve 2D v5.01.05, Automated Curve Fitting & Equation Discovery. SYSTAT Software (USA), 2002. https://www.syssoft.ru/Systat.
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Original Russian Text © А.R. Elman, S.A. Zharkov, and L.V. Ovsyannikova, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 8, pp. 1238–1244.
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Elman, А.R., Zharkov, S.A. & Ovsyannikova, L.V. Organic Catalysis: Synthesis of Propylene Carbonate by the Carboxylation of Propylene Oxide in the Presence of Phenols and Fluorinated Alcohols. Russ J Gen Chem 88, 1562–1567 (2018). https://doi.org/10.1134/S1070363218080029
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DOI: https://doi.org/10.1134/S1070363218080029