Zinc catalyst recycling in the preparation of (all-rac)-α-tocopherol from trimethylhydroquinone and isophytol
-
Juraj Gömöry
,
Milan Králik
Abstract
Recycling of ZnCl2 as a catalyst in the cyclocondensation of trimethylhydroquinone and isophytol to all-rac-α-tocopherol was studied. ZnCl2 was recycled at over 98 % efficiency in required purity by repeated extraction of the reaction streams with water, followed by switching of solvent to butyl acetate and then back to water. Recycled ZnCl2 had no negative effect on the yield of all-rac-α-tocopherol (maintaining over 90 %) at nearly total conversion of isophytol and only a 3 % molar excess of trimethylhydroquinone.
[1] Baldenius, K.-U., Bussche-Hünnefeld, L.v.d., Hilgemann, E., Hoppe, P., & Stürmer, R. (1996). Ullmann’s encyclopedia of industrial chemistry (pp. 478–488). Weinheim, Germany: Wiley-VCH. Search in Google Scholar
[2] Bonrath, W., Aquino, F., Haas, A., Hoppmann, S., Netscher, T., Pace, F., & Pauling, H. (2009). Methanetrisulfonic acid: A highly efficient strongly acidic catalyst for Wagner-Meerwein rearrangement, Friedel-Crafts alkylation and acylation reactions. Examples from vitamin E synthesis. Sustainability, 1, 161–168. DOI: 10.3390/su1020161. http://dx.doi.org/10.3390/su102016110.3390/su1020161Search in Google Scholar
[3] Bonrath, W., Dittel, C., Giraudi, L., Netscher, T., & Pabst, T. (2007a). Rare earth triflate catalysts in the synthesis of Vitamin E and its derivatives. Catalysis Today, 121, 65–70. DOI: 10.1016/j.cattod.2006.11.022. http://dx.doi.org/10.1016/j.cattod.2006.11.02210.1016/j.cattod.2006.11.022Search in Google Scholar
[4] Bonrath, W., Eggersdorfer, M., & Netscher, T. (2007b). Catalysis in the industrial preparation of vitamins and nutraceuticals. Catalysis Today, 121, 45–57. DOI: 10.1016/j.cattod.2006.11.021. http://dx.doi.org/10.1016/j.cattod.2006.11.02110.1016/j.cattod.2006.11.021Search in Google Scholar
[5] Bonrath, W., & Netscher, T. (2005). Catalytic processes in vitamins synthesis and production. Applied Catalysis A: General, 280, 55–73. DOI: 10.1016/j.apcata.2004.08.028. http://dx.doi.org/10.1016/j.apcata.2004.08.02810.1016/j.apcata.2004.08.028Search in Google Scholar
[6] Coman, S. M., Wuttke, S., Vimont, A., Daturi, M., & Kemnitz, E. (2008). Catalytic performance of nanoscopic, aluminium trifluoride-based catalysts in the synthesis of (all-rac)-α-tocopherol. Advanced Synthesis & Catalysis, 350, 2517–2524. DOI: 10.1002/adsc.200800411. http://dx.doi.org/10.1002/adsc.20080041110.1002/adsc.200800411Search in Google Scholar
[7] Cotton, F. A., Wilkinson, G., & Gaus, P. L. (1995). Basic inorganic chemistry. New York, NY, USA: Wiley. Search in Google Scholar
[8] Gömöry, J., Králik, M., & Kaszonyi, A. (2011). Towards the synthesis of (all-rac)-α-tocopherol from trimethylhydroquinone and isophytol at reduced pressure. Acta Chimica Slovaca, 4(1), 3–14. Search in Google Scholar
[9] Gömöry, J., Králik, M., Kaszonyi, A., & Mravec, D. (2010). Study of (all-rac)-α-tocopherol synthesis from trimethylhydroquinone and isophytol at the presence of solid catalysts. Acta Chimica Slovaca, 3(2), 110–121. Search in Google Scholar
[10] Hinze, R., Laufer, M. C., Hölderich, W. F., Bonrath, W., & Netscher, T. (2009). The use of Nafion/silica composite catalysts for synthesis of fine chemicals. Catalysis Today, 140, 105–111. DOI: 10.1016/j.cattod.2008.07.008. http://dx.doi.org/10.1016/j.cattod.2008.07.00810.1016/j.cattod.2008.07.008Search in Google Scholar
[11] Kemnitz, E., Coman, S. M., Rüdiger, S., & Wuttke, S. (2009). European patent application No. EP 2050743 A1. European patent office. Search in Google Scholar
[12] Schager, F., & Bonrath, W. (2000). Synthesis of D,L-α-tocopherol using ‘microencapsulated’ catalysts. Applied Catalysis A: General, 202, 117–120. DOI: 10.1016/S0926-860X(00)00456-7. http://dx.doi.org/10.1016/S0926-860X(00)00456-710.1016/S0926-860X(00)00456-7Search in Google Scholar
[13] The British Pharmacopoeia Commission (2010). The British pharmacopoeia (pp. 1–4). London, UK: The Stationary Office. Search in Google Scholar
[14] Wang, H., & Xu, B.-Q. (2004). Catalytic performance of Nafion/SiO2 nanocomposites for the synthesis of α-tocopherol. Applied Catalysis A: General, 275, 247–255. DOI: 10.1016/j.apcata.2004.07.038. http://dx.doi.org/10.1016/j.apcata.2004.07.03810.1016/j.apcata.2004.07.038Search in Google Scholar
[15] Wang, S., Bonrath, W., Pauling, H., & Kienzle, F. (2000). The synthesis of d,l-α-tocopherol in supercritical media. The Journal of Supercritical Fluids, 17, 135–143. DOI: 10.1016/S0896-8446(99)00050-9. http://dx.doi.org/10.1016/S0896-8446(99)00050-910.1016/S0896-8446(99)00050-9Search in Google Scholar
[16] Xing, H., Wang, T., & Dai, Y. (2009). Continuous synthesis of d,l-α-tocopherol catalyzed by sulfonic acid-functionalized ionic liquid in supercritical carbon dioxide. The Journal of Supercritical Fluids, 49, 52–58. DOI: 10.1016/j.supflu.2008.12.003. http://dx.doi.org/10.1016/j.supflu.2008.12.00310.1016/j.supflu.2008.12.003Search in Google Scholar
© 2011 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Lipid retention of novel pressurized extraction vessels as a function of the number of static and flushing cycles, flush volume, and flow rate
- Determination of curcuminoids in substances and dosage forms by cyclodextrin-mediated capillary electrophoresis with diode array detection
- Interaction of Moringa oleifera seed lectin with humic acid
- Hybrid process scheme for the synthesis of ethyl lactate: conceptual design and analysis
- Zinc catalyst recycling in the preparation of (all-rac)-α-tocopherol from trimethylhydroquinone and isophytol
- Denitrification of simulated nitrate-rich wastewater using sulfamic acid and zinc scrap
- Anaerobic treatment of biodiesel by-products in a pilot scale reactor
- Preparation of magnesium hydroxide from nitrate aqueous solution
- Impact of the type of anodic film formed and deposition time on the characteristics of porous anodic aluminium oxide films containing Ni metal
- Synthesis and crystal and molecular structures of N,N′-methylenedipyridinium tetrachlorozincate(II) and N,N′-methylenedipyridinium tetrachlorocadmate(II)
- Effects of denaturing acid on the self-association behaviour of poly(ethylene glycol)-block-poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in ethanol
- Properties of poly(γ-benzyl l-glutamate) membrane modified by polyurethane containing carboxyl group
- Theoretical thermo-optical patterns relevant to glass crystallisation
- Morphology dependence of 1,2-diphenylethylenediamine-derived organogelator templates in solvents and their influence in the production of nanostructured silica
- Ferric hydrogensulphate as a recyclable catalyst for the synthesis of fluorescein derivatives
- An alternative synthetic process of p-acetaminobenzenesulfonyl chloride through combined chlorosulfonation by HClSO3 and PCl5
- An efficient and novel one-pot synthesis of 2,4,5-triaryl-1H-imidazoles catalyzed by UO2(NO3)2·6H2O under heterogeneous conditions
- Stereoselective synthesis of the polar part of mycestericins E and G
- A regio- and stereoselective three-component synthesis of 5-(trifluoromethyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine derivatives under solvent-free conditions
- Precautions in using global kinetic and thermodynamic models for characterization of drug release from multivalent supports
- A sandwich anion receptor by a BODIPY dye bearing two calix[4]pyrrole units
- What causes iron-sulphur bonds in active sites of one-iron superoxide reductase and two-iron superoxide reductase to differ?
- MTD-PLS and docking study for a series of substituted 2-phenylindole derivatives with oestrogenic activity
Articles in the same Issue
- Lipid retention of novel pressurized extraction vessels as a function of the number of static and flushing cycles, flush volume, and flow rate
- Determination of curcuminoids in substances and dosage forms by cyclodextrin-mediated capillary electrophoresis with diode array detection
- Interaction of Moringa oleifera seed lectin with humic acid
- Hybrid process scheme for the synthesis of ethyl lactate: conceptual design and analysis
- Zinc catalyst recycling in the preparation of (all-rac)-α-tocopherol from trimethylhydroquinone and isophytol
- Denitrification of simulated nitrate-rich wastewater using sulfamic acid and zinc scrap
- Anaerobic treatment of biodiesel by-products in a pilot scale reactor
- Preparation of magnesium hydroxide from nitrate aqueous solution
- Impact of the type of anodic film formed and deposition time on the characteristics of porous anodic aluminium oxide films containing Ni metal
- Synthesis and crystal and molecular structures of N,N′-methylenedipyridinium tetrachlorozincate(II) and N,N′-methylenedipyridinium tetrachlorocadmate(II)
- Effects of denaturing acid on the self-association behaviour of poly(ethylene glycol)-block-poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in ethanol
- Properties of poly(γ-benzyl l-glutamate) membrane modified by polyurethane containing carboxyl group
- Theoretical thermo-optical patterns relevant to glass crystallisation
- Morphology dependence of 1,2-diphenylethylenediamine-derived organogelator templates in solvents and their influence in the production of nanostructured silica
- Ferric hydrogensulphate as a recyclable catalyst for the synthesis of fluorescein derivatives
- An alternative synthetic process of p-acetaminobenzenesulfonyl chloride through combined chlorosulfonation by HClSO3 and PCl5
- An efficient and novel one-pot synthesis of 2,4,5-triaryl-1H-imidazoles catalyzed by UO2(NO3)2·6H2O under heterogeneous conditions
- Stereoselective synthesis of the polar part of mycestericins E and G
- A regio- and stereoselective three-component synthesis of 5-(trifluoromethyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine derivatives under solvent-free conditions
- Precautions in using global kinetic and thermodynamic models for characterization of drug release from multivalent supports
- A sandwich anion receptor by a BODIPY dye bearing two calix[4]pyrrole units
- What causes iron-sulphur bonds in active sites of one-iron superoxide reductase and two-iron superoxide reductase to differ?
- MTD-PLS and docking study for a series of substituted 2-phenylindole derivatives with oestrogenic activity
