The development of efficient, inexpensive, and nontoxic catalysts for cycloaddition of CO2 with epoxides to produce five-membered cyclic carbonates is a very interesting topic. In this work, cycloaddition of CO2 with propylene oxide (PO) to produce propylene carbonate (PC) catalyzed by potassium halides (KCl, KBr, and KI) in the presence of cucurbit[6]uril (CB[6]) was studied at various conditions. It was discovered that the potassium halides and CB[6] had excellent synergetic effect in promoting the reaction, and the KI/CB[6] catalytic system was the most efficient among them. The decrease of the activity and selectivity of KI/CB[6] was negligible after the catalytic system was reused five times. Further study indicated that the KI/CB[6] catalytic system was also very active and selective for the cycloaddition of CO2 with other epoxides, such as glycidyl phenyl ether, epichlorohydrin, and styrene oxide. The mechanism for the synergetic effect of KI and CB[6] was also discussed.
Conference
International Conference on Green Chemistry (ICGC-4), IUPAC International Conference on Green Chemistry, ICGC, Green Chemistry , 4th, Foz do Iguaçu, Brazil, 2012-08-25–2012-08-29
References
1a W. Leitner. Angew. Chem., Int. Ed.34, 2207 (1995).10.1002/anie.199522071Search in Google Scholar
1b 10.1021/cr068357u, T. Sakakura, J. C. Choi, H. Yasuda. Chem. Rev.107, 2365 (2007).Search in Google Scholar PubMed
1c 10.1039/b821320h, T. Yu, R. Cristiano, R. G. Weiss. Chem. Soc. Rev.39, 1435 (2010).Search in Google Scholar PubMed
1d 10.1002/anie.201102010, M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kuhn. Angew. Chem., Int. Ed.50, 8510 (2011).Search in Google Scholar PubMed
1e 10.1016/j.ccr.2012.03.017, I. Omae. Coord. Chem. Rev.256, 1384 (2012).Search in Google Scholar
1f 10.1039/c0gc00059k, C. Y. Wu, H. Y. Cheng, R. X. Liu, Q. Wang, Y. F. Hao, Y. C. Yu, F. Y. Zhao. Green Chem.12, 1811 (2010).Search in Google Scholar
2a 10.1039/a608102i, T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara, T. Maeshima. Chem. Commun. 1129 (1997).Search in Google Scholar
2b 10.1039/c0gc00065e, M. North, R. Pasquale, C. Young. Green Chem.12, 1514 (2010).Search in Google Scholar
2c 10.1021/ja0164677, R. L. Paddock, S. T. Nguyen. J. Am. Chem. Soc.123, 11498 (2001).Search in Google Scholar PubMed
3a 10.1021/cr900393d, B. Schaffner, F. Schaffner, S. P. Verevkin, A. Borner. Chem. Rev.110, 4554 (2010).Search in Google Scholar PubMed
3b 10.1002/chem.200305583, M. Yoshida, M. Ihara. Chem.—Eur. J.10, 2886 (2004).Search in Google Scholar PubMed
3c W. L. Dai, S. L. Luo, S. F. Yin, C. T. Au. Appl. Catal., A366, 2 (2009).Search in Google Scholar
3d 10.1002/anie.200700990, J. Bayardon, J. Holz, B. Schäffner, V. Andrushko, S. Verevkin, A. Preetz, A. Börner. Angew. Chem., Int. Ed.46, 5971 (2007).Search in Google Scholar PubMed
3e 10.1039/b304963a, S. Fukuoka, M. Kawamura, K. Komiya, M. Tojo, H. Hachiya, K. Hasegawa, M. Aminaka, H. Okamoto, I. Fukawa, S. Konno. Green Chem.5, 497 (2003).Search in Google Scholar
3f 10.1021/jm990436t, K. Biggadike, R. M. Angell, C. M. Burgess, R. M. Farrell, A. P. Hancock, A. J. Harker, W. R. Irving, C. Ioannou, P. A. Procopiou, R. E. Shaw, Y. E. Solanke, O. M. P. Singh, M. A. Snowden, R. J. Stubbs, S. Walton, H. E. Weston. J. Med. Chem.43, 19 (1999).Search in Google Scholar PubMed
3g 10.1021/ie020678i, J. H. Clements. Ind. Eng. Chem. Res.42, 663 (2003).Search in Google Scholar
4a 10.1016/j.cattod.2011.08.042, J. L. Song, B. B. Zhang, P. Zhang, J. Ma, J. L. Liu, H. L. Fan, T. Jiang, B. X. Han. Catal. Today183, 130 (2012).Search in Google Scholar
4b 10.1002/cssc.201100839, J. Qu, C. Y. Cao, Z. F. Dou, H. Liu, Y. Yu, P. Li, W. G. Song. ChemSusChem5, 652 (2012).Search in Google Scholar PubMed
4c 10.1039/c2gc35150a, J. Ma, J. L. Song, H. Z. Liu, J. L. Liu, Z. F. Zhang, T. Jiang, H. L. Fan, B. X. Han. Green Chem.14, 1743 (2012).Search in Google Scholar
4d 10.1039/c0cc04829a, S. G. Liang, H. Z. Liu, T. Jiang, J. L. Song, G. Y. Yang, B. X. Han. Chem. Commun.47, 2131 (2011).Search in Google Scholar PubMed
4e 10.1039/b815105a, J. L. Song, Z. F. Zhang, B. X. Han, S. Q. Hu, W. J. Li, Y. Xie. Green Chem.10, 1337 (2008).Search in Google Scholar
4f 10.1021/jo0348221, J. W. Huang, M. Shi. J. Org. Chem.68, 6705 (2003).Search in Google Scholar PubMed
4g 10.1039/a901943j, T. S. Zhao, Y. Z. Han, Y. H. Sun. Phys. Chem. Chem. Phys.1, 3047 (1999).Search in Google Scholar
4h 10.1021/jo00075a011, N. Kihara, N. Hara, T. Endo. J. Org. Chem.58, 6198 (1993).Search in Google Scholar
5a 10.1039/b916235f, B. Barkakaty, K. Morino, A. Sudo, T. Endo. Green Chem.12, 42 (2010).Search in Google Scholar
5b 10.1039/b006682f, H. Kawanami, Y. Ikushima. Chem. Commun. 2089 (2000).Search in Google Scholar
6 10.1021/ja9902165, K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida, K. Kaneda. J. Am. Chem. Soc.121, 4526 (1999).Search in Google Scholar
7 10.1006/jcat.2000.3145, M. Tu, R. J. Davis. J. Catal.199, 85 (2001).Search in Google Scholar
8 10.1023/B:CATL.0000006329.37210.fd, R. Srivastava, D. Srinivas, P. Ratnasamy. Catal. Lett.91, 133 (2003).Search in Google Scholar
9 10.1039/b207750g, B. M. Bhanage, S.-i. Fujita, Y. Ikushima, K. Torii, M. Arai. Green Chem.5, 71 (2003).Search in Google Scholar
10a 10.1021/jo00108a042, W. J. Kruper, D. D. Dellar. J. Org. Chem.60, 725 (1995).Search in Google Scholar
10b 10.1039/b305617a, F. W. Li, C. G. Xia, L. W. Xu, W. Sun, G. X. Chen. Chem. Commun. 2042 (2003).Search in Google Scholar PubMed
10c 10.1016/j.jcat.2004.07.018, X. B. Lu, Y. J. Zhang, K. Jin, L. M. Luo, H. Wang. J. Catal.227, 537 (2004).Search in Google Scholar
10d 10.1002/ejic.200700521, J. Meléndez, M. North, R. Pasquale. Eur. J. Inorg. Chem. 3323 (2007).Search in Google Scholar
10e 10.1002/cctc.201100031, A. Decortes, A. W. Kleij. ChemCatChem3, 831 (2011).Search in Google Scholar
11 10.1021/ja00343a038, T. Aida, S. Inoue. J. Am. Chem. Soc.105, 1304 (1983).Search in Google Scholar
12 10.1039/b500074b, Y. Du, F. Cai, D. L. Kong, L. N. He. Green Chem.7, 518 (2005).Search in Google Scholar
13a 10.1002/chem.200700210, J. L. He, T. B. Wu, Z. F. Zhang, K. L. Ding, B. X. Han, Y. Xie, T. Jiang, Z. M. Liu. Chem.—Eur. J.13, 6992 (2007).Search in Google Scholar PubMed
13b 10.1002/anie.200701467, Y. Xie, Z. F. Zhang, T. Jiang, J. L. He, B. X. Han, T. B. Wu, K. L. Ding. Angew. Chem., Int. Ed.46, 7255 (2007).Search in Google Scholar PubMed
13c 10.1002/app.34622, Y. B. Xiong, Y. J. Wang, H. Wang, R. M. Wang, Z. P. Cui. J. Appl. Polym. Sci.123, 1486 (2012).Search in Google Scholar
13d 10.1002/adsc.201000261, C. R. Qi, J. W. Ye, W. Zeng, H. F. Jiang. Adv. Synth. Catal.352, 1925 (2010).Search in Google Scholar
14a 10.1002/cssc.201200255, C. J. Whiteoak, A. Nova, F. Maseras, A. W. Kleij. ChemSusChem5, 2032 (2012).Search in Google Scholar PubMed
14b 10.1039/b916764c, K. Motokura, S. Itagaki, Y. Iwasawa, A. Miyaji, T. Baba. Green Chem.11, 1876 (2009).Search in Google Scholar
14c 10.1016/j.tetlet.2005.12.077, Y. Du, J.-Q. Wang, J.-Y. Chen, F. Cai, J.-S. Tian, D.-L. Kong, L.-N. He. Tetrahedron Lett.47, 1271 (2006).Search in Google Scholar
14d 10.1021/jo051077e, W. N. Sit, S. M. Ng, K. Y. Kwong, C. P. Lau. J. Org. Chem.70, 8583 (2005).Search in Google Scholar PubMed
14e 10.1039/b210007j, L.-N. He, H. Yasuda, T. Sakakura. Green Chem.5, 92 (2003).Search in Google Scholar
15a 10.1039/c2gc16039k, Z. Z. Yang, Y. N. Zhao, L. N. He, J. Gao, Z. S. Yin. Green Chem.14, 519 (2012).Search in Google Scholar
15b 10.1039/c2gc16335g, J. Sun, J. Wang, W. Cheng, J. Zhang, X. Li, S. Zhang, Y. She. Green Chem.14, 654 (2012).Search in Google Scholar
15c J. K. Lee, Y. J. Kim, Y. S. Choi, H. Lee, J. S. Lee, J. Hong, E. K. Jeong, H. S. Kim, M. Cheong. Appl. Catal., B111, 621 (2012).10.1016/j.apcatb.2011.11.015Search in Google Scholar
15d 10.1002/cssc.201000305, J. Sun, L. Han, W. Cheng, J. Wang, X. Zhang, S. Zhang. ChemSusChem4, 502 (2011).Search in Google Scholar PubMed
15e 10.1002/cssc.200700097, W. L. Wong, P. H. Chan, Z. Y. Zhou, K. H. Lee, K. C. Cheung, K. Y. Wong. ChemSusChem1, 67 (2008).Search in Google Scholar PubMed
15f 10.1039/b612164k, A. L. Zhu, T. Jiang, B. X. Han, J. C. Zhang, Y. Xie, X. M. Ma. Green Chem.9, 169 (2007).Search in Google Scholar
15g 10.1039/b212823c, H. Kawanami, A. Sasaki, K. Matsui, Y. Ikushima. Chem. Commun. 896 (2003).Search in Google Scholar
16 10.1006/jcat.2002.3662, H. Yasuda, L. N. He, T. Sakakura. J. Catal.209, 547 (2002).Search in Google Scholar
17 10.1021/ja042207o, F. Shi, Q. Zhang, Y. Ma, Y. He, Y. Deng. J. Am. Chem. Soc.127, 4182 (2005).Search in Google Scholar
18 10.1002/anie.200460675, J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs. Angew. Chem. Int. Ed.44, 4844 (2005).Search in Google Scholar
19a 10.1002/(SICI)1521-3773(19980202)37:1/2<78::AID-ANIE78>3.0.CO;2-9, D. Whang, J. Heo, J. H. Park, K. Kim. Angew. Chem., Int. Ed.37, 78 (1998).Search in Google Scholar
19b 10.1021/ja0319846, C. Márquez, R. R. Hudgins, W. M. Nau. J. Am. Chem. Soc.126, 5806 (2004).Search in Google Scholar
20a 10.1021/jo00168a070, W. L. Mock, T. A. Irra, J. P. Wepsiec, T. L. Manimaran. J. Org. Chem.48, 3619 (1983).Search in Google Scholar
20b 10.1039/b108519k, T. C. Krasia, J. H. G. Steinke. Chem. Commun. 22 (2002).Search in Google Scholar
20c 10.1021/la700803k, M. V. S. N. Maddipatla, L. S. Kaanumalle, A. Natarajan, M. Pattabiraman, V. Ramamurthy. Langmuir.23, 7545 (2007).Search in Google Scholar
20d 10.1002/chem.201202083, B. C. Pemberton, R. Raghunathan, S. Volla, J. Sivaguru. Chem—Eur. J.18, 12178 (2012).Search in Google Scholar
21 10.1016/S0378-3812(00)00487-8, H. Zhang, B. Han, Z. Hou, Z. Liu. Fluid. Phase. Equilibr.179, 131 (2001).Search in Google Scholar
22 10.1021/ja993376p, J. Kim, I.-S. Jung, S.-Y. Kim, E. Lee, J.-K. Kang, S. Sakamoto, K. Yamaguchi, K. Kim. J. Am. Chem. Soc.122, 540 (2000).Search in Google Scholar
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