Abstract
An easy-to-prepare recyclable catalyst of quaternary ammonium nature and based on commercially available and inexpensive macroporous polymeric sorbent Purolite A103 resin has been devised for the carbon dioxide addition to epoxides. The catalyst can be easily separated due to its 0.6–0.85 mm bead size and recycled at least seven times. The catalyst makes it possible to carry out the reaction under solvent-free conditions. It is insensitive to the steric and electronic effects of various epoxy substrates.
Similar content being viewed by others
References
S. Dabral, T. Schaub, Adv. Synth. Catal., 2019, 361, 223.
W. J. Peppel, Ind. Eng. Chem., 1958, 50, 767.
C. Calabrese, F. Giacalone, C. Aprile, Catalysts, 2019, 9, 325.
K. Xu, Chem. Rev., 2004, 104, 4303.
B. Schaffner, F. Schaffner, S. P. Verevkin, A. Borner, Chem. Rev., 2010, 110, 4554.
A. A. G. Shaikh, S. Sivaram, Chem. Rev., 1996, 96, 951.
L. Zhang, X. Fu, G. Gao, Chem. Cat. Chem., 2011, 3, 1359.
M. Liu, K. Gao, L. Liang, J. Sun, L. Sheng, M. Arai, Catal. Sci. Technol., 2016, 16, 6406.
B. M. Bhanage, S. Fujita, Y. Ikushima, M. Arai, Appl. Catal. A-Gen., 2001, 219, 259.
W. N. Sit, S. M. Ng, K. Y. Kwong, C. P. Lau, J. Org. Chem., 2005, 70, 8583.
J. Peng, Y. Deng, New. J. Chem., 2001, 25, 639.
J. Qin, V. A. Larionov, K. Harms, E. Meggers, Chem. Sus. Chem., 2019, 12, 320.
H. Bettner, J. Steinbauer, T. Werner, Chem. Sus. Chem., 2015, 8, 2655.
C. J. Whiteoak, A. Nova, F. Maseras, A. W. Kley, Chem. Sus. Chem., 2012, 5, 2032.
P. A. Carvalho, J. W. Comerford, K. J. Lamb, M. North, P. S. Reiss, Adv. Synth. Catal., 2019, 361, 345.
M. Nourian, F. Zadehahmadi, R. Kardanpour, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, M. Bahadori, Catal. Commun., 2017, 94, 42.
L. Han, H. Li, S. J. Choi, M. S. Park, S. M. Lee, Y. J. Kim, D. W. Park, Appl. Catal. A Gen., 2012, 429–430, 67.
F. D. Bobbink, A. P. Van Muyden, A. Gopakumar, Z. Fei, P. J. Dyson, Chem. Sus. Chem., 2017, 82, 144.
L. Tan, B. Tan, Chem. Soc. Rev., 2017, 46, 3322.
S. N. Sidorov, I. V. Volkov, V. A. Davankov, M. P. Tsyurupa, P. M. Valetsky, L. M. Bronstein, R. Karlinsey, J. W. Zwanziger, V. G. Matveeva, E.M. Sulman, N. V. Lakina, E. A. Wilder, R. J. Spontak, J. Am. Chem. Soc., 2001, 123, 10502.
E. Sulman, V. Matveeva, L. Bronstein, A. Sidorov, N. Lakina, S. Sidorov, P. Valetsky, Green. Chem., 2003, 5, 205.
E. Sulman, V. Doluda, S. Dzwigaj, E. Marceau, L. Kustov, O. Tkachenko, A. Bykov, V. Matveeva, M. Sulman, N. Lakina, J. Mol. Catal. A: Chem., 2007, 278, 112.
E. M. Sulman, V. G. Matveeva, L. M. Bronstein, M. G. Sulman, V. D. Doluda, A. V. Tokarev, E. V. Murzina, D. Yu. Murzin, Stud. Surf. Sci. Catal., 2006, 162, 119.
E. M. Sulman, A. A. Ivanov, V. S. Chernyavsky, M. G. Sulman, A. I. Bykova, A. I. Sidorov, V. Yu. Doluda, V. G. Matveeva, L. M. Bronstein, B. D. Stein, A. S. Kharitonov, Chem. Eng. J., 2011, 176–177, 33.
S. E. Lyubimov, M. V. Sokolovskaya, A. A. Korlyukov, O. P. Parenago, V. A. Davankov, J. Iran. Chem. Soc., 2020, 17, 1283.
S. E. Lyubimov, A. A. Vasil’ev, A. A. Korlyukov, M. M. Ilyin, S. A. Pisarev, V. V. Matveev, A. E. Chalykh, S. G. Zlotin, V. A. Davankov, React. Funct. Polym., 2009, 69, 755.
S. E. Lyubimov, E. A. Rastorguev, K. I. Lubentsova, A. A. Korlyukov, V. A. Davankov, Tetrahedron Lett., 2013, 54, 1116.
M. North, R. Pasquale, C. Young, Green. Chem., 2010, 12, 1514.
A. S. Nair, S. Cherian, N. Balachandran, U. G. Panicker, S. K. K. Sankaranarayanan, ACS Omega, 2019, 4, 13042.
J.-Z. Hwang, S.-C. Wang, P.-C. Chen, C.-Y. Huang, J.-T. Yeh, K.-N. Chen, J. Polym. Res., 2012, 19, 9900.
J. Nanclares, Z. S. Petrovic, I. Javni, M. Ionescu, F. Jaramillo, J. Appl. Polym. Sci., 2015, 132, 42492.
J. Jindrich, H. Dvorakova, A. Holy, Collect. Czech. Chem. Commun., 1992, 57, 1466.
N. Roques, US Pat. 0147789, 2004; https://patents.google.com/patent/US20040147789A1/en.
F. Chen, T. Dong, T. Xu, X. Li, C. Hu, Green Chem., 2011, 13, 2518.
J. Blankenburg, M. Wagner, H. Frey, Macromolecules, 2017, 50, 8885.
S. T. K. Kumar, L. Kumar, V. L. Sharma, A. Jain, R. K. Jain, J. P. Maikhuri, M. Kumar, P. K. Shukla, G. Gupta, Eur. J. Med. Chem., 2008, 43, 2247.
S. E. Lyubimov, M. V. Sokolovskaya, B. Chowdhury, A. V. Arzumanyan, R. Sh. Tukhvatshin, L. F. Ibragimova, A. A. Tyutyunov, V. A. Davankov, A. M. Muzafarov, Russ. Chem. Bull. (Int. Ed.), 2019, 68, 1866.
Z. Zhao, J. Qin, C. Zhang, Y. Wang, D. Yuan, Y. Yao, Inorg. Chem., 2017, 56, 4568.
Y. Tsutsumi, K. Yamakawa, M. Yoshida, T. Ema, T. Sakai, Org. Lett., 2010, 12, 5728.
V. Legros, G. Taing, P. Buisson, M. Schuler, S. Bostyn, J. Rousseau, C. Sinturel, A. Tatibouet, Eur. J. Org. Chem., 2017, 5032.
Author information
Authors and Affiliations
Corresponding author
Additional information
This study was financially supported by the Russian Science Foundation (Project No. 19-43-02031).
Rights and permissions
About this article
Cite this article
Lyubimov, S.E., Zvinchuk, A.A., Tyutyunov, A.A. et al. Synthesis of organic cyclic carbonates assisted by macroporous polystyrene-based catalyst. Russ Chem Bull 69, 2345–2348 (2020). https://doi.org/10.1007/s11172-020-3032-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-020-3032-z