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Publicly Available Published by De Gruyter January 1, 2009

Acylation of different amino derivatives with fatty acids on UL-MFI-type catalysts

Mariana Musteata , Vasile Musteata , Alina Dinu , Mihaela Florea , Vinh-Thang Hoang , Do Trong-On , Serge Kaliaguine and Vasile I. Pârvulescu

Abstract

Acylation of different amino derivatives (ethanol amine, diethanol amine, N-aminoethylpiperazine) was carried out under green conditions with oleic acid or tail oil fatty acids. The experiments were carried out using as heterogeneous catalysts mesoporous Al-Meso and UL-ZSM-5 with Si/Al ratios between 100 and 20, in the range of the temperatures 80-180 °C without any solvent or in octane or water. The efficiency of the catalysts for the acylation of the investigated substrates appeared to be directly dependent on the Si/Al ratio and the size of the pores. The selectivity toward esters or amides was firstly controlled by temperature, and then by the Si/Al ratios. Additionally, both the conversion and selectivity were controlled by the solvent in which the reaction was carried out. The use of water led mostly to a mixture of esters and amides.


Conference

International IUPAC Conference on Green-Sustainable Chemistry, IUPAC International Conference on Green Chemistry, ICGC, Green Chemistry , 1st, Dresden, Germany, 2006-09-10–2006-09-15


References

1. (a) J. D. Riedel. DE Patent 181175 (1903);Search in Google Scholar

1. (b) S. Yano et al. JP Patent 63216852 (1988) for Kao Corp., Japan.Search in Google Scholar

2. J. D. Kohtz, H. Y. Lee, N. Gaiano, J. Segal, E. Ng, T. Larson, D. P. Baker, E. A. Garber, K. P. Williams, G. Fishell. Development 128, 2351 (2001).10.1242/dev.128.12.2351Search in Google Scholar PubMed

3. doi:10.1002/ardp.200400964, O. Bekircan, M. Kuxuk, B. Kahveci, S. Kolaylı. Arch. Pharm. Chem. Life Sci. 338, 365 (2005).Search in Google Scholar

4. (a) doi:10.1021/cr030035s, L. Yet. Chem. Rev. 103, 4283 (2003);Search in Google Scholar

4. (b) doi:10.2174/0929867033457827, J. A. Beutler, T. C. McKee. Curr. Med. Chem. 10, 787 (2003).Search in Google Scholar

5. doi:10.1002/anie.200462577, O. Soltani, J. K. De Brabander. Angew. Chem., Int. Ed. 44, 1696 (2005).Search in Google Scholar

6. doi:10.1021/ja011364+, R. M. Garbaccio, S. J. Stachel, D. K. Baeschlin, S. J. Danishefsky. J. Am. Chem. Soc. 123, 10903 (2001).Search in Google Scholar

7. J. M. Freitas, L. M. Abrantes, T. Darbre. Helv. Chim. Acta 88, 2471 (2005) and refs. herein.10.1002/hlca.200590183Search in Google Scholar

8. (a) doi:10.1021/ja00278a053, M. Therisod, A. M. Klibanov. J. Am. Chem. Soc. 108, 5638 (1986);Search in Google Scholar

8. (b) doi:10.1055/s-1992-26255, K. Faber, S. Riva. Synthesis 895 (1992);Search in Google Scholar

8. (c) doi:10.1039/p19950002203, N. B. Bashir, S. J. Phythian, A. J. Reason, S. M. Roberts. J. Chem. Soc., Perkin Trans. 1 2203 (1995);Search in Google Scholar

8. (d) doi:10.1016/S0008-6215(99)00163-9, S. M. Andersen, I. Lundt, J. Marcussen, S. Yu. Carbohydr. Res. 320, 250 (1999).Search in Google Scholar

9. doi:10.1002/(SICI)1097-0290(19980305)57:5<505::AID-BIT1>3.0.CO;2-K, J. A. Arcos, M. Bernabe, C. Otero. Biotechnol. Bioeng. 57, 505 (1998).Search in Google Scholar

10. doi:10.1002/lipi.19960981003, L. Cao, U. T. Bornscheuer, R. D. Schmid. Fett. Lipid 98, 332 (1996).Search in Google Scholar

11. (a) doi:10.1039/c39890000934, F. Bjorkling, S. E. Godtfredsen, O. Kirk. J. Chem. Soc., Chem. Commun. 934 (1989);Search in Google Scholar

11. (b) doi:10.1055/s-1990-26802, K.Adelhorst, F. Bjorkling, S. E. Godtfredsen, O. Kirk. Synthesis 112 (1990).Search in Google Scholar

12. doi:10.1002/(SICI)1097-4660(199804)71:4<309::AID-JCTB859>3.0.CO;2-L, C. Tsitsimpikou, H. Stamatis, V. Sereti, H. Daflos, F. N. Kolisis. J. Chem. Technol. Biotechnol. 71, 309 (1998).Search in Google Scholar

13. doi:10.1016/0006-291X(91)91859-B, A. Jochen, J. Hays, E. Lianos, S. Hager. Biochem. Biophys. Res. Commun. 177, 797 (1991).Search in Google Scholar

14. M. Bouzouba, G. Leclerc, J. D. Ehrhardt, G. Andermann. Bull. Soc. Chim. Fr. 1230 (1985).Search in Google Scholar

15. doi:10.1246/cl.2001.592, N. Kihara, J.-I. Shin, Y. Ohga, T. Takata. Chem. Lett. 592 (2001).Search in Google Scholar

16. doi:10.1002/1521-3773(20010903)40:17<3248::AID-ANIE3248>3.0.CO;2-M, D. Trong-On, S. Kaliaguine. Angew. Chem., Int. Ed. 40, 3248 (2001).Search in Google Scholar

Published Online: 2009-01-01
Published in Print: 2007-01-01

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