

Synthesis of Cyclic Carbonates from Olefin Oxides and Carbon Dioxide. Part 1. Catalysis by Ionic Liquids
https://doi.org/10.18412/1816-0387-2016-3-6-16
Abstract
The review deals with ionic liquid based catalytic systems for intensification of the reaction of olefin oxides with carbon dioxide. Ionic liquids based on derivatives of imidazole, pyridine, tertiary ammonia salts etc. are shown to be highly active to the processes under consideration; they can be used, under certain conditions, as alternatives to the traditional catalysts for cyclocarboxylation of olefin oxides. Specifics of the interaction between oxiranes and carbon dioxide in the presence on ionic liquids including the ones with promoting agents based on metal salts are considered. The mechanisms of the catalytic action of ionic liquids during synthesis of cyclocarbonates are discussed. Publications in the new field of catalytic cyclocarboxylation of olefin oxides in the presence of ionic liquids are inspected.
About the Authors
A. V. SulimovRussian Federation
A. V. Ovcharova
Russian Federation
A. A. Ovcharov
Russian Federation
T. A. Ryabova
G. M. Kravchenko
Russian Federation
S. A. Lysanov
Russian Federation
References
1. Крылов О.В. // Успехи химии. 1995. Т. 64. № 9. С. 935–959.
2. Shaikh A.-A.G., Sivaram S. // Chemical Reviews. 1996. Vol. 96. № 3. Р. 951–976.
3. Забалов М.В. Химия элементоорганических соединений и полимеров 2014. Москва, 2014. 121 с.
4. Платэ Н.А., Сливинский Е.В. Основы химии и технологии мономеров. М.: Наука: МАИК Наука/Интерпериодика, 2002. 696 с.
5. Михеев В.В. Неизоционатные уретаны: монография. Казань: КНИТУ, 2011. 292 с.
6. Строганов В.Ф., Савченко В.Н., Омельченко С.И. Циклокарбонаты и их применение для синтеза полимеров. М.: НИИТЭХИМ, 1984. 22 с.
7. Коренькова О.П. // Химическая промышленность. 1961. № 9. С. 33–38.
8. North M., Pasquale R., Young C. // Green Chemistry. 2010. Vol. 12. № 9. P. 1514–1539.
9. Peng J., Deng Y. // New Journal of Chemistry. 2001. Vol. 25. № 4. P. 639–641.
10. Kawanami H., Sasaki A., Matsui K., Ikushima Y. // Chemical Communications. 2003. № 7. P. 896–897.
11. Yamaguchi K., Ebitani K., Yoshida T., Yoshida H., Kaneda K. // Journal of the American Chemical Society. 1999. Vol. 121. № 18. P. 4526–4527.
12. Yano T., Matsui H., Koike T., Ishiguro H., Fujihara H., Yoshihara M., Maeshima T. // Chemical Communications. 1997. № 12. P. 1129–1130.
13. Paddock R.L., Nguyen S.T. Chemical CO2 // Journal of the American Chemical Society. 2001. Vol. 123. № 46. P. 11498–11499.
14. Shen Y.-M., Duan W.-L., Shi M. // The Journal of Organic Chemistry. 2003. Vol. 68. № 4. P. 1559–1562.
15. Caló V., Nacci A. , Monopoli A. , Fanizzi A. // Organic Letters. 2002. Vol. 4. № 15. P. 2561–2563.
16. Kossev K., Koseva N., Troev K. // Journal of Molecular Catalysis A: Chemical. 2003. Vol. 194. № 1–2. P. 29–37.
17. Yu K.M.K., Curcic I. , Gabriel J. , Morganstewart H., Tsang S.C. // The Journal of Physical Chemistry A. 2010. Vol. 114. № 11. P. 3863–3872.
18. Shiels R.A., Jones C.W. // Journal of Molecular Catalysis A: Chemical. 2007. Vol. 261. № 2. P. 160–166.
19. Freemantle M. An introduction to ionic liquids 2009: Cambridge. UK: RSC Publishing, 2009. 281 p.
20. Hallett J.P., Welton T. // Chemical Reviews. 2011. Vol. 111. № 5. P. 3508–3576.
21. Seki T., Grunwaldt J.-D., Baiker A. // The Journal of Physical Chemistry B. 2009. Vol. 113. № 1. P. 114–122.
22. Sun J., Zhang S., Cheng W., Ren J. // Tetrahedron Letters. 2008. Vol. 49. № 22. P. 3588–3591.
23. Wang L. // Journal of Industrial and Engineering Chemistry Research. 2014. Vol. 53. № 20. P. 8426–8435.
24. Zhou Y., Hu S., Ma X., Liang S., Jiang T., Han B. // Journal of Molecular Catalysis A: Chemical. 2008. Vol. 284. № 1–2. P. 52–57.
25. Sun J., Ren J., Zhang S., Chenget W. // Tetrahedron Letters. 2009. Vol. 50. № 4. P. 423–426.
26. Ma J., Liu J., Zhang Z., Han B. // Green Chemistry. 2012. Vol. 14. № 9. P. 2410–2420.
27. Ion A., Parvulescu V., Jacobs P., de Vos D. // Applied Catalysis A: General. 2009. Vol. 363. № 1–2. P. 40–44.
28. Kim H.S., Kim J.J., Lee B.G., Jung O.S., Jang H.G., Kang S.O. // Angewandte Chemie International Edition. 2000. Vol. 39. № 22. P. 4096–4098.
29. Ramin M., Grunwaldt J.-D., Baiker A. // Journal of Catalysis. 2005. Vol. 234. № 2. P. 256–267.
30. Kim H.S., Kim J.J., Kim H., Jang H.G. // Journal of Catalysis. 2003. Vol. 220. № 1. P. 44–46.
31. Palgunadi J., Kwon O-S., Lee H., Bae J.Y., Ahn B.S., Min N.-Y., Kim H.S. // Catalysis Today. 2004. Vol. 98. № 4. P. 511–514.
32. Fujita S.-i., Nishiura M., Arai M. // Catalysis Letters. 2010. Vol. 135. № 3-4. P. 263–268.
33. Sun J., Fujita S.-i., Zhao F., Arai M. // Green Chemistry. 2004. Vol. 6. № 12. P. 613–616.
34. Sun J., Fujita S.-I., Zhao F., Arai M. // Applied Catalysis A: General. 2005. Vol. 287. № 2. P. 221–226.
35. Ramin M., Grunwaldt J.-D., Baiker A. // Applied Catalysis A: General. 2006. Vol. 305. № 1. P. 46–53.
36. Yu J.-I., Ju H.Y., Kim K.-H., Park D.-W. // Korean Journal of Chemical Engineering. 2010. Vol. 27. № 2. P. 446–451.
37. Li F., Xiao L., Xia C., Huet B. // Tetrahedron Letters. 2004. Vol. 45. № 45. P. 8307–8310.
38. He Q., O'Brien J.W., Kitselman K.A., Tompkins L.E., Curtis G.C.T., Kerton F.M. // Catalysis Science & Technology. 2014. Vol. 4. № 6. P. 1513–1528.
39. Wang J.-Q., Kong D.-L., Chen J.-Y., Cai F., He L.-N. // Journal of Molecular Catalysis A: Chemical. 2006. Vol. 249. № 1–2. P. 143–148.
40. Wang J.-Q., Yue X.-D., Cai F., He L.-N. // Catalysis Communications. 2007. Vol. 8. № 2. P. 167–172.
41. Zhu A., Jiang T., Han B., Zhang J., Xie Y., Ma X. // Green Chemistry. 2007. Vol. 9. № 2. P. 169–172.
42. Takahashi T., Watahiki T., Kitazume S., Yasuda H., Sakakura T. // Chemical Communications. 2006. № 15. P. 1664–1666.
43. Sakai T., Tsutsumi Y., Ema T. // Green Chemistry. 2008. Vol. 10. № 3. P. 337–341.
44. Han L., Park S.-W., Park D.-W. // Energy & Environmental Science. 2009. Vol. 2. № 12. P. 1286–1292.
45. Han L., Choi H.-J., Choi S.-J., Liu B., Park D.-W. // Green Chemistry. 2011. Vol. 13. № 4. P. 1023–1028.
46. Xie Y., Ding K., Liu Z., J. Li, An G., Tao R., Sun Z., Yang Z. // Chemistry – A European Journal. 2010. Vol. 16. № 22. P. 6687–6692.
47. Xie Y., Zhang Z., Jiang T., He J., Han B., Wu T., Ding K. // Angewandte Chemie International Edition. 2007. Vol. 46. № 38. P. 7255–7258.
48. Qiao K., Ono F., Bao Q., Tomida D., Yokoyama C. // Journal of Molecular Catalysis A: Chemical. 2009. Vol. 303. № 1–2. P. 30–34.
49. Han L., Li H., Choi S.-J., Park M.-S., Lee S.-M., Kim Y.-J., Park D.-W. // Applied Catalysis A: General. 2012. Vol. 429–430. P. 67–72.
50. Zheng X., Luo S., Zhang L., Cheng J.-P. // Green Chemistry. 2009. Vol. 11. № 4. P. 455–458.
51. Shim H.-L., Udayakumar S., Yu J.-I., Kim I., Park D.-W. // Catalysis Today. 2009. Vol. 148. № 3–4. P. 350–354.
52. Udayakumar S., Raman V., Shim H.-L., Park D.-W. // Applied Catalysis A: General. 2009. Vol. 368. № 1–2. P. 97–104.
53. Xiao L.-F., Li F.-W., Peng J.-J., Xia C.-G. // Journal of Molecular Catalysis A: Chemical. 2006. Vol. 253. № 1–2. P. 265–269.
54. Zhang X., Guzmán I., Aguila G., Araya P. // Catalysis Communications. 2009. Vol. 11. № 1. P. 43–46.
55. Udayakumar S., Lee M.-K., Shim H.-L., Park D.-W. // Applied Catalysis A: General. 2009. Vol. 365. № 1. P. 88–95.
56. Udayakumar S., Park S.-W., Park D.-W., Choi B.-S. // Catalysis Communications. 2008. Vol. 9. № 7. P. 1563–1570.
57. Zhao Y., Tian J.-S., Qi X.-H., Han Z.-N., Zhuang Y.-Y., He L.-N. // Journal of Molecular Catalysis A: Chemical. 2007. Vol. 271. № 1–2. P. 284–289.
58. Dai W.-L., Chen L., Yin S.-F., Luo S.-L., Au C.-T. // Catalysis Letters. 2010. Vol. 135. № 3-4. P. 295–304.
59. Xu L.-W., Yang M.-S., Jiang J.-X., Qiu H.-Y., Lai G.-Q. // Central European Journal of Chemistry. 2007. Vol. 5. № 4. P. 1073–1083.
60. Jutz F., Andanson J.-M., Baiker A. // Chemical Reviews. 2011. Vol. 111. № 2. P. 322–353.
Review
For citations:
Sulimov A.V., Ovcharova A.V., Ovcharov A.A., Ryabova T.A., Kravchenko G.M., Lysanov S.A. Synthesis of Cyclic Carbonates from Olefin Oxides and Carbon Dioxide. Part 1. Catalysis by Ionic Liquids. Kataliz v promyshlennosti. 2016;16(3):6-16. (In Russ.) https://doi.org/10.18412/1816-0387-2016-3-6-16