Physico-chemical studies of polymer-stabilized platinum catalysts for enantioselective hydrogenation of ketones
Abstract
The work is devoted to the synthesis of platinum catalytic systems
hypercrosslinked polystyrene based, studying of the obtained systems structure and their testing in a model reaction of enantioselective hydrogenation ethyl pyruvate whose product, R-ethyl lactate, can be used as a chiral monomer for biodegradable polymers productions. The obtained catalytic systems were characterized by XPS, TEM, XRD, diffuse reflectance infrared spectroscopy, low-temperature adsorption of nitrogen. The study found that the formation of Pt(0) nanoparticles begins at the stage of the precursor introducing into the polymer matrix, and the active phase forming particles have a narrow size distribution with a maximum near 2 nm. The maximum enantiomeric excess achieved in the test reaction is 75 %. There is possibility of premodification of the catalyst without loss of enantioselectivity in the hydrogenation process.
About the Authors
A. V. BykovaRussian Federation
M. B. Konyaeva
Russian Federation
G. N. Demidenko
Russian Federation
V. G. Matveeva
Russian Federation
I. Yu. Tyamina
Russian Federation
E. M. Sulman
Russian Federation
References
1. Davankov V., Tsyurupa M. // J. Chromatogr. A. 2005. V. 1087(1—2). P. 3—12.
2. Davankov A., Tsyurupa M.P., Alexienko N.N. // J. Chromatogr. A. 2005. V. 1100(1). P. 32—39.
3. Sychov C.S., Ilyin M.M., Davankov V.A. et al. // J. Chromatogr. A. 2004. V. 1030. P. 17—24.
4. Fontanals N., Galiа M., Cormack P.A.G. et al. // J. Chromatogr. A. 2005. V. 1075 (1—2). P. 51—56.
5. Fontanals N., Marcé R. M., Cormack P.A.G. et al. // J. Chromatogr. A. 2008. V. 1191(1—2). P. 118—124.
6. Fontanals N., Cormack P.A.G., Sherrington D.C. // J. Chromatogr. A. 2008. V. 1215(1—2). P. 21—29.
7. Bratkowska D., Marcé R.M., Cormack P.A.G. et al. // J. Chromatogr. A. V. 1217(10). P. 1575—1582.
8. Liu P., Long C., Qian H.M. et al. // Chinese Chemical Letters. 2009. V. 20(4). P. 492—495.
9. Chang C.-F., Chang C.-Y., Hsu K.-E. et al. // J. Environ. Eng. Manage. 2007. V. 17(5). P. 311—318.
10. Germain J., Hradil J., Früchet J.M.J. et al. // Chem. Mater. 2006, V. 18 (18). P. 4430—4435.
11. Tsyurupa M.P., Davankov V.A. // Reactive and Functional Polymers. 2006. V. 66(7). P. 768—779.
12. Sulman E.M., Matveeva V.G., Doluda Yu V. et al. //Applied Catalysis B: Environmental. 2010. V. 94. P. 200—210.
13. Никошвиил Л.Ж., Долуда В.Ю., Сульман Э.М. // Вестник МИТХТ. 2009. Т. 4. № 2. С. 95—99.
14. Sidorov S.N., Volkov I.V., Davankov V.A. et al. // J. Am. Chem. Soc. 2001. V. 123 (43). P. 10502—10510.
15. Matveeva V., Bykov A., Doluda V. et al.// Topics in Catalysis, 2009. V. 52, P. 387—393.
16. Валецкий П.М., Сульман М.Г., Бронштейн Л.М. и др. // Российские нанотехнологии. 2009. № 9—10. С. 94—108.
17. Nikoshvili L.Z., Sulman E.M., Demidenko G.N. et al. // Catalysis of Organic Reactions / [edited by] Stephen R.
18. Schmidt, CRC Press. 2007. P. 177—186.
19. Coloma F., Sepulveda-Escribano A., Fierro J.L.G. et al. // Langmuir. 1994. V. 10(3). P. 750.
20. Labinger J.A., Herring A.M., Bercaw J.E. // J. Am. Chem. Soc. 1990. V. 112(14). P. 5628.
21. Sen A., Lin M., Kao L.C. et al. // J. Am. Chem. Soc. 1992. V. 114(16), P. 6385.
22. Shi M. // J. Chem. Res. Synop. 1998. V. 9. P. 592.
23. Margitfalvi J.L., Hegedüs M., Tfirst E. // Tetrahedron Asymmetry. 1996. V. 7(2). Р. 571.
Review
For citations:
Bykova A.V., Konyaeva M.B., Demidenko G.N., Matveeva V.G., Tyamina I.Yu., Sulman E.M. Physico-chemical studies of polymer-stabilized platinum catalysts for enantioselective hydrogenation of ketones. Kataliz v promyshlennosti. 2012;(4):67-72. (In Russ.)