Etherification of glycerol with tert-butyl alcohol catalysed by ion-exchange resins
-
K. Klepáčová
,
D. Mravec
Abstract
The reaction of glycerol with tert-butyl alcohol in the liquid phase on acid Amberlyst-type ion-exchange resins was studied. The influence of temperature, mole ratio n(TBA)/n(G), water and swelling of gel, and macroreticular type of polymer catalysts on etherification reaction was investigated. The most favourable reaction temperature is 75°C. The conversion of glycerol and yield of glycerol tert-butyl ethers has increased with the mole ratio n(TBA)/n(G). Dry form of macroreticular catalysts provided the best results. Etherification reaction of glycerol with isobutylene in non-aqueous conditions gives the highest yield of desired ethers. The influence of water was studied. The gel forms of ion-exchange resins have very low catalytic activity. It can be concluded that water has an inhibition effect on ion-exchange resins. By comparing the gel and macroreticular forms of Amberlyst ion-exchange resins it can be concluded that very acid forms of macroreticular ion-exchange resins with a high degree of crosslinking are more active catalysts for the studied reaction due to their pores which are sufficiently large so that the voluminous tert-butyl ethers of glycerol can be formed. It was estimated that tert-butyl alcohol as tert-butylation agent is not suitable for etherification of glycerol with the formation of di-and triethers.
[1] Bradin, D. S., U.S. 5,578,090 (1996). Search in Google Scholar
[2] Barrault, J., Pouilloux, Y., Clacens, J. M., Vanhove, C., and Bancquart, S., Catal. Today 75, 177 (2002). http://dx.doi.org/10.1016/S0920-5861(02)00062-710.1016/S0920-5861(02)00062-7Search in Google Scholar
[3] Macho, V., Polievka, M., Kavala, M., and Novák, L., Czechoslov. 190755 (1978). Search in Google Scholar
[4] Gupta, V. P., U.S. 5,476,971 (1995). Search in Google Scholar
[5] Kesling, H. S., Karas, L. J., and Liotta, F. J., U.S. 5,308,365 (1994). Search in Google Scholar
[6] Marchionna, M., Patrini, R., Sanfilippo, D., Paggini, A., Giavazzi, F., and Pellegrini, L., Stud. Surf. Sci. Catal. 136, 489 (2001). http://dx.doi.org/10.1016/S0167-2991(01)80351-710.1016/S0167-2991(01)80351-7Search in Google Scholar
[7] Noureddini, H., U.S. 6,015,440 (2000). Search in Google Scholar
[8] Hoek, I., Nijhuis, T. A., Stankiewicz, A. I., and Moulijn, J. A., Appl. Catal., A 266, 109 (2004). http://dx.doi.org/10.1016/j.apcata.2004.02.00510.1016/j.apcata.2004.02.005Search in Google Scholar
[9] Du Toit, E. and Nicol, W., Appl. Catal., A 277, 219 (2004). http://dx.doi.org/10.1016/j.apcata.2004.09.01510.1016/j.apcata.2004.09.015Search in Google Scholar
[10] Yang, B.-L., Yang, S.-B., and Yao, R.-Q., React. Funct. Polym. 44, 167 (2000). http://dx.doi.org/10.1016/S1381-5148(99)00092-910.1016/S1381-5148(99)00092-9Search in Google Scholar
[11] Linnekoski, J. A., Krause, A. O. I., and Struckmann, L. K., Appl. Catal., A 170, 117 (1998). http://dx.doi.org/10.1016/S0926-860X(98)00040-410.1016/S0926-860X(98)00040-4Search in Google Scholar
[12] Gauthier, M. A., Luo, J., Calvet, D., Ni, C., Zhu, X. X., Garon, M., and Buschmann, M. D., Polymer 45, 8201 (2004). http://dx.doi.org/10.1016/j.polymer.2004.09.05510.1016/j.polymer.2004.09.055Search in Google Scholar
© 2006 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Calibrationless determination of electroactive species using chronoamperograms at collector segment of interdigitated microelectrode array
- The β-carotene dilemma: ESR study with coordinated peroxyl radicals
- Determination of 5-hydroxymethylfurfural after Winkler and by the HPLC method for authentication of honey
- A simple linear sweep voltammetric method for the determination of double-stranded DNA with malachite green
- Spectral and electrochemical study of coordination molecules Cu4OX6L4: 3-Pyridylmethanol and 4-pyridylmethanol Cu4OBrnCl(6−n)(pm)4 complexes
- Magnetic, spectral, and thermal behaviour of 2-chloro-4-nitrobenzoates of Co(II), Ni(II), and Cu(II)
- Synthesis, characterization, and biological activities of some transition metal(II) complexes with the thiosemicarbazone derived from 4-[1-(4-methylphenylsulfonyl)-1H-indol-3-yl]but-3-en-2-one
- Crystal structure and thermal chemical properties of 2-(2,4-dimethylanilino)-3-methyl-6-diethylaminofluorane
- Etherification of glycerol with tert-butyl alcohol catalysed by ion-exchange resins
- Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines
- Synthetic approaches towards bisspiro[naphthalene-2(1H),3′-(3H)pyrazol]-1-one-containing compounds
- Mild Pfitzner—Moffat oxidation of the (1→3)-β-D-glucan from Saccharomyces cerevisiae
- Limited sample recovery in coupled methods of high-performance liquid chromatography of synthetic polymers
Articles in the same Issue
- Calibrationless determination of electroactive species using chronoamperograms at collector segment of interdigitated microelectrode array
- The β-carotene dilemma: ESR study with coordinated peroxyl radicals
- Determination of 5-hydroxymethylfurfural after Winkler and by the HPLC method for authentication of honey
- A simple linear sweep voltammetric method for the determination of double-stranded DNA with malachite green
- Spectral and electrochemical study of coordination molecules Cu4OX6L4: 3-Pyridylmethanol and 4-pyridylmethanol Cu4OBrnCl(6−n)(pm)4 complexes
- Magnetic, spectral, and thermal behaviour of 2-chloro-4-nitrobenzoates of Co(II), Ni(II), and Cu(II)
- Synthesis, characterization, and biological activities of some transition metal(II) complexes with the thiosemicarbazone derived from 4-[1-(4-methylphenylsulfonyl)-1H-indol-3-yl]but-3-en-2-one
- Crystal structure and thermal chemical properties of 2-(2,4-dimethylanilino)-3-methyl-6-diethylaminofluorane
- Etherification of glycerol with tert-butyl alcohol catalysed by ion-exchange resins
- Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines
- Synthetic approaches towards bisspiro[naphthalene-2(1H),3′-(3H)pyrazol]-1-one-containing compounds
- Mild Pfitzner—Moffat oxidation of the (1→3)-β-D-glucan from Saccharomyces cerevisiae
- Limited sample recovery in coupled methods of high-performance liquid chromatography of synthetic polymers
