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Influence of some Chromium Complexes on the Conversion Rate of Glycidol – Fatty Acid Reaction

Einfluss einiger Chrom-Komplexe auf die Umsetzungsrate der Glycidol-Fettsäure-Reaktion
R. Janiš , A. Klásek , J. Krejčí and J. Bobálová

Abstract

Monoacylglycerols – thanks to their amphipathic properties – belong among non-ionogenic surfactants. Their additional unique properties, such as antistatic, microbicidal, and lubricating, are also well known. One possibility for preparing pure individual monoacylglycerols is the reaction of fatty acid with glycidol. In this paper, the catalysis of this reaction with some chromium(III) complexes is described. Compounds prepared in high yields were 1-monoacylglycerols of caprylic, capric, lauric, oleic, and palmitic acids, the purity of which was verified by high performance liquid chromatography.

Kurzfassung

Monoacylglycerole gehören aufgrund ihrer amphipathischen Eigenschaften zu den nichtionogenen Tensiden. Ihre antistatischen, mikrobiziden und schmierenden Eigenschaften sind ebenfalls gut bekannt. Eine Möglichkeit zur Darstellung von reinen individuellen Monoacylglycerolen ist die Reaktion von Fettsäure mit Glycidol. In der vorliegenden Arbeit wird die Katalyse dieser Reaktion mit einigen Chrom(III)-Komplexen beschrieben. So wurden in hoher Ausbeute 1-Monoacylglycerole der Capryl-, Caprin-, Laurin-, Öl- und Palmitinsäuren dargestellt. Der Reinheitsgrad dieser Verbindungen wurde mittels Hochdruckflüssigkeitschromatographie überprüft.


1Rahula Janiš, Tomas Bata University, Faculty of Technology, Nám. TGM-275, CZ-762 72 Zlín, Czech Republic, Phone: +42 05 76 03 12 18, Fax: +42 05 76 03 15 63, E-mail:

Dr. Rahula Janiš, born 1952 in Zlín, studied at the Faculty of Technology at the Technical University in Brno. He obtained his PhD from the same university in 1988. At the present time, he is working at Tomas Bata University in Zlín. His main field of research is the synthesis and exploitation of monoglycerides.

Prof. Dr. Antonín Klásek was born in 1941 in Olomouc. He studied at the Prague Institute of Chemistry and Chemical Technology and graduated from there in 1965. He obtained his PhD from the same institute in 1969. He worked at the Department of Medicinal Chemistry in the Faculty of Medicine at Palacký University in Olomouc. At the present time, he holds a professor's chair at the Faculty of Technology, Tomas Bata University in Zlín. He is involved in research work on the synthesis of heterocycles.

Dr. Jirí Krejčí, born 1943, studied the chemical technology of polymers at the Technical University in Pardubice (Dipl. Ing.). He obtained his PhD (1982) at the Faculty of Technology in Zlín and he has been working there since then. He is engaged in research on biopolymers and their reactions.

Ing. Jana Bobálová, born in 1978 in Zlín, studied at the Faculty of Technology at Tomas Bata University in Zlín and graduated from there in 2001. At the present time, she is working on a PhD at the same university in the field of Chemistry and Materials Technology.


References

1. Baumann, H., Buehler, M., Foche, H., Herisinger, F., Zoebelein, H. and Falbe, J.: Angew. Chem. Int. Ed. Engl.27 (1988) 42.Search in Google Scholar

2. Chang, C. M. and Bodmeier, R.: Int. J. Pharm.147 (1997) 135.Search in Google Scholar

3. Geragty, P. B., Attwood, D., Collet, J. H., Sharma, H. and Dandike, Y.: Biomaterials18 (1997) 215.Search in Google Scholar

4. Chang, C. M. and Bodmeier, R.: J. Control Release46 (1997) 215.Search in Google Scholar

5. Kabara, J. J.: J. Am. Oil Chem. Soc.61 (1984), 397.10.1007/BF02678802Search in Google Scholar

6. Bornscheuer, U. T.: Enzyme Microb. Technol.17 (1995) 725.Search in Google Scholar

7. Suhara, Y., Takayama, H., Nakane, S., Miyashita, T., Waku, K. and Sugiura, T.: Chem. Pharm. Bull.48 (2000) 903.Search in Google Scholar

8. Lai, D. T., Hattori, N. and O'Connor, C. J.: J. Am. Oil Chem. Soc.76 (1999) 845.Search in Google Scholar

9. Caron, M. and Sharpless, K. B.: J. Org. Chem.50 (1985) 1557.10.1002/ejoc.201190033Search in Google Scholar

10. Chong, J. M. and Sharpless, K. B.: J. Org. Chem.50 (1985) 1560.10.1002/ejoc.201190094Search in Google Scholar

11. Lok, C. M., Mank, A. P. and Ward, J. P.: Chem. Phys. Lipids36 (1985) 329.Search in Google Scholar

12. Cauvel, A., Renard, G. and Brunel, D.: J. Org. Chem.62 (1997) 749.Search in Google Scholar

13. Agular, L. M. G. and Vergas, R. M.: J. Am. Oil Chem. Soc.75 (1998) 755.Search in Google Scholar

14. Martinez, L. E., Leighton, J. L., Carsten, D. H. and Jacobsen, E. N.: J. Am. Chem. Soc.117 (1995) 5897.Search in Google Scholar

15. Bukowska, A. and Bukowski, W.: J. Chem. Technol. Biot.67 (1996) 176.Search in Google Scholar

16. Bukowska, A., Bukowski, W. and Mossety-Leszczak, B.: J. Chem. Technol. Biot.74 (1999) 1145.Search in Google Scholar

17. Kozlovskii, R. A., Makarov, M. G., Shvets, V. F. and Maksimova, N. A.: Kinet. Catal.41 (2000) 737.Search in Google Scholar

18. Klásek, A., Šimoníková, J. and Svoboda, P.: Chem. Prum.29 (1979) 352 (Czech).Search in Google Scholar

19. Janiš, R., Krejcí, J. and Klásek, A.: Eur. J. Lipid Sci. Technol. (2000) 351.10.1002/(SICI)1438-9312(200005)102:5<351::AID-EJLT351>3.0.CO;2-JSearch in Google Scholar

20. SDBSIntegrated Spectral Data Base System for Organic Compounds. http://www.aist.go.jp/SDBS.Search in Google Scholar

21. Mouloungui, Z., Rakotondrazafy, V., Peyrou, G., Gachen, Ch. and Eychenne, V.: Agro-Food Ind. Hi-Tec.9 (4) (1998) 10.Search in Google Scholar

22. Koehler, P. and Grosch, W.: J. Agr. Food Chem.47 (5) (1999) 1863.10.1021/jf980891iSearch in Google Scholar

23. Greenwood, N. N. and Earnshaw, A.: Chemistry of the Elements. Pergamon Press, Oxford1984.Search in Google Scholar

24. Eshel, M. and Bino, A.: Inorg. Chim. Acta320 (2001) 127.Search in Google Scholar

25. CAS No. 39430-51-8, Aldrich Cat. No. 31,810-8.Search in Google Scholar

Received: 2004-11-23
Published Online: 2013-05-08
Published in Print: 2005-03-01

© 2005, Carl Hanser Publisher, Munich

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