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Influence of process parameters on the epoxidation of 2-buten-1-ol over titanium silicalite TS-1 catalyst

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Abstract

The influence of process parameters on the epoxidation of 2-buten-1-ol with 30 % hydrogen peroxide using the titanium silicalite TS-1 is presented. The studies were carried out under autogenic pressure (in autoclave). Methanol was used as a solvent in this process. The influence of temperature, 2-buten-1-ol to hydrogen peroxide mole ratio, amount of solvent used, TS-1 catalyst content, and reaction time on the reaction was studied. The major product of this reaction, 2,3-epoxybutan-1-ol (EB), has numerous applications in chemical industry.

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References

  • Aberhart, D. J., & Lin, L. J. (1974). Studies on the biosynthesis of β-lactam antibiotics. Part 1. Stereospecific syntheses of (2RS,3S)-[4,4,4,-2H3]-, (2RS,3S)-[4-3H]-(2RS,3R)-[4-3H]-and (2RS, 3S)-[4-13C]-Valine. Incorporation of (2RS,3S)-[4-13C]-Valine into Penicillin V. Journal of the Chemical Society, Perkin Transactions 1,20, 2320–2326. DOI: 10.1039/P19740002320.

    Article  Google Scholar 

  • Brill, W. F. (1963). The origin of epoxides in the liquid phase oxidation of olefins with molecular oxygen. Journal of the American Chemical Society, 85, 141–143. DOI: 10.1021/ja00885a006.

    Article  CAS  Google Scholar 

  • Corma, W. A., Reddy, T. J., & Renz, M. (1997). Diastereose-lective catalytic epoxidation of chiral allylic alcohols by TS-1 and Ti-BETA: Evidence for a hydrogen bonded, peroxy-type loaded complex as oxidizing species. Journal of Organic Chemistry, 62, 3631–3637. DOI: 10.1021/jo970364i.

    Article  Google Scholar 

  • Davies, L., McMorn, P., Bethell, D., Bulman Page, P. C., King, F., Hancock, F. E., & Hutchings, G. J. (2000). By-product formation causes leaching of Ti from the redox molecular sieve TS-1. Chemical Communication, 1807–1808. DOI: 10.1039/b002055i.

  • Davies, L. J., McMorn, P., Bethell, D., Bulman Page, P. C., King, F., Hancock, F. E., & Hutchings, G. J. (2001a). Oxidation of crotyl alcohol using Ti-β and Ti-MCM-41 catalysts. Journal of Molecular Catalysis A: Chemical, 165, 243–247. DOI: 10.1016/S1381-1169(00)00430-1.

    Article  CAS  Google Scholar 

  • Davies, L. J., McMorn P., Bethell, D., Bulman Page, P. C., King, F., Hancock, F. E., & Hutchings, G. J. (2001b). Epoxidation of crotyl alcohol using Ti-containing heterogeneous catalysts: comments on the loss of Ti by leaching. Journal of Catalysis, 198, 319–327. DOI: 10.1006/jcat.2000.3139.

    Article  CAS  Google Scholar 

  • Flanigen, E. M., Bennett, J. M., Grose, R. W., Cohen, J. P., Patton, R. L., Kirchner, R. M., & Smith, J. V. (1978). Silicalite, a new hydrophobic crystalline silica molecular sieve. Nature, 271, 512–516. DOI: 10.1038/271512a0.

    Article  CAS  Google Scholar 

  • Gontier, S., & Tuel, A. (1996). Synthesis of titanium silicalite-1 using amorphous SiO2 as silicon source. Zeolites, 16, 184–195. DOI: 10.1016/0144-2449(95)00127-1.

    Article  CAS  Google Scholar 

  • Hermann, W. A. (1993). Organic peroxygen chemistry. Berlin: Springer-Verlag.

    Google Scholar 

  • Hoft, E., Kosslick, H., Fricke, R., & Hamann, H.-J. (1996). Titanium containing molecular sieves as catalysts for selective oxidation reactions with hydrogen peroxide. Journal für Praktische Chemie-Chemiker-Zeitung, 338, 1–15.

    Article  Google Scholar 

  • Huybrechts, D. R. C., Buckens, P. L., & Jacobs, P. A. (1992). Physicochemical and catalytic properties of titanium silicalites. Journal of Molecular Catalysis, 71, 129–147. DOI: 10.1016/0304-5102(92)80012-6.

    Article  CAS  Google Scholar 

  • Jang, B. C., Munoz-Najar, U., Paik, J. H., Claffey, K., Yoshida, M., & Hla, T. (2003). Leptomycin B, an inhibitor of the nuclear export receptor CRM1, inhibits COX-2 expression. Journal of Biological Chemistry, 278, 2773–2776. DOI: 10.1074/jbc.C200620200.

    Article  CAS  Google Scholar 

  • Kerton, O. J., McMorn, P., Bethell, D., King, F., Hancock, F., Burrows, A., Kiely, C. J., Ellwood, S., & Hutchings G. (2005). Effect of structure of the redox molecular sieve TS-1 on the oxidation of phenol, crotyl alcohol and norbornylene. Physical Chemistry Chemical Physics, 7, 2671–2678. DOI: 10.1039/b503241e.

    Article  CAS  Google Scholar 

  • Khouw, C. B., & Davis, M. E. (1995). Catalytic activity of titanium silicalites synthesized in the presence of alkali-metal and alkaline-earth ions. Journal of Catalysis, 151, 77–86. DOI: 10.1006/jcat.1995.1010.

    Article  CAS  Google Scholar 

  • Kobayashi, M., Wang, W., Tsutsui, Y., Sugimoto, M., & Murakami, N. (1998). Absolute stereostructure and total synthesis of Leptomycin B. Tetrahedron Letters, 39, 8291–8294. DOI: 10.1016/S0040-4039(98)01809-7.

    Article  CAS  Google Scholar 

  • Matsushima, Y., Nakayama, T., Tohyama, S., Kakinuma, K., & Eguchi, T. (2001). Versatile route to 2,6-dideoxyamino sugars from non-sugar materials: Syntheses of vicenisamine and kedarosamine. Journal of the Chemical Society, Perkin Transactions 1, 6, 569–577. DOI: 10.1039/b008878l.

    Article  Google Scholar 

  • Nishi, K., Yoshida, M., Fujiwara, D., Nishikawa, M., Hori-nouchi, S., & Beppu, T. (1994). Leptomycin B targets a regulatory cascade of crm1, a fission yeast nuclear protein, involved in control of higher order chromosome structure and gene expresion. Journal of Biological Chemistry, 269, 6320–6324.

    CAS  Google Scholar 

  • Notari, B. (1991). Titanium silicalite: A new selective oxidation catalyst. In R. K. Grasselli & A. W. Sleight (Eds.), Structure-activity and selectivity relationships in heterogenous catalysis (pp. 243–255). Amsterdam: Elsevier Science Publishers B.V.

    Google Scholar 

  • Pasto, M., Moyano, A., Pericas, M. A., & Riera, A. (1995). Enantioselctive synthesis of fully protected anti 3-amino-2-hydroxy butyrates. Tetrahedron Asymmetry, 6, 2329–2342. DOI: 10.1016/0957-4166(95)00309-D.

    Article  CAS  Google Scholar 

  • Perego, G., Bellussi, G., Corno, C., Taramasso, M., Buonomo, F., & Esposito, A. (1986). Titanium-silicalite: a novel derivative in the pentasil family. In Y. Murakami (Ed.), Studies in Surface Science and Catalysis, Vol. 28, New developments in zeolite science and technology (pp. 129–136). Amsterdam: Elsevier Science Publishers B.V.

    Google Scholar 

  • Raczko, J. (2003). From furan to open-chain systems. Synthesis of C1-C9 fragment of tylonolide. Tetrahedron, 59, 10181–10186. DOI: 10.1016/j.tet.2003.10.071.

    Article  CAS  Google Scholar 

  • Reddy, J. S., Kumar, R., & Ratnasamy, P. (1990). Titanium silicalite-2: Synthesis, characterization and catalytic properties. Applied Catalysis, 58, L1–L4. DOI: 10.1016/S0166-9834(00)82273-3.

    Article  CAS  Google Scholar 

  • Tanner, D. (1993). Stereocontrolled synthesis via chiral aziridines. Pure & Applied Chemistry, 65, 1319–1328. DOI: 10.1351/pac199365061319.

    Article  CAS  Google Scholar 

  • Thangaraj, A., Kumar, R., & Ratnasamy, P. (1990). Direct catalytic hydroxylation of benzene with hydrogen peroxide over titanium-silicate zeolites. Applied Catalysis, 57, L1–L3. DOI: 10.1016/S0166-9834(00)80718-6.

    Article  CAS  Google Scholar 

  • Tuel, A., & Taarit, Y. B. (1995). A new template for the synthesis of titanium silicalites with the ZSM-48 structure. Zeolites, 15, 164–170. DOI: 10.1016/0144-2449(94)00023-L.

    Article  CAS  Google Scholar 

  • Ullmann’s Encyklopedie der technischen Chemie (1983). Weinhem: Verlag Chemie.

  • Waychunas, G. A. (1987). Synchrotron radiation XANES spectroscopy of Ti in minerals: Effect of Ti bonding distances, Ti valence, and site geometry on absorption edge structure. American Mineralogist, 72, 89–101.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemical Technology, Szczecin University of Technology, ul. Pulaskiego 10, PL-70-322, Szczecin, Poland

    Agnieszka Wróblewska, Ewelina Ławro & Eugeniusz Milchert

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  1. Agnieszka Wróblewska
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  2. Ewelina Ławro
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  3. Eugeniusz Milchert
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Correspondence to Agnieszka Wróblewska.

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Wróblewska, A., Ławro, E. & Milchert, E. Influence of process parameters on the epoxidation of 2-buten-1-ol over titanium silicalite TS-1 catalyst. Chem. Pap. 62, 147–153 (2008). https://doi.org/10.2478/s11696-008-0004-4

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  • DOI: https://doi.org/10.2478/s11696-008-0004-4

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