Abstract
Alumina-supported potassium (K/Al2O3) catalysts using pseudo-boehmite as the precursor were prepared by the impregnation/calcination method, characterised by XRD, SEM, ICP, N2 adsorption/desorption, CO2-TPD methods and TG analysis, and applied to the vapour-phase condensation of methyl propionate with trioxane to produce methyl methacrylate. The results showed the catalysts’ properties to be mainly affected by the calcined temperature (TC) and the crystal structure. The sample calcined at 1100°C exhibited the highest catalytic activity when mixed phases were formed and provided the appropriate specific surface area (SBET) and surface basic properties. The effects of TC, K-loading and reaction conditions on the catalytic performance were also investigated in a fixed-bed reactor. The yield of methyl methacrylate attained 29.2 % under the optimised conditions, and the deactivated catalyst could be completely regenerated by calcination.
Acknowledgements
This work received financial support from the National Science Foundation of China (21403018) and Prospective Joint Research Project on the Industry, Education and Research of Jiangsu Province (BY2014037-03).
Supplementary data
Supplementary data associated with this article can be found in the online version of this paper (DOI: 10.1515/chempap-2016-0076).
References
Ai, M. (1990a). Reaction of methyl propionate with methylal over V–Si–P ternary oxide catalysts. Bulletin of the Chemical Society of Japan, 63, 3722–3724. DOI: 10.1246/bcsj.63.3722.Search in Google Scholar
Ai, M. (1990b). Reaction of propionic acid with methylal over vanadium–silicon–phosphorus oxide. Applied Catalysis, 63, 365–373. DOI: 10.1016/s0166-9834(00)81725-x.Search in Google Scholar
Ai, M., Fujihashi, H., Hosoi, S., & Yoshida, A. (2003). Production of methacrylic acid by vapor-phase aldol condensation of propionic acid with formaldehyde over silica-supported metal phosphate catalysts. Applied Catalysis A: General, 252, 185– 191. DOI: 10.1016/s0926-860x(03)00449-6.Search in Google Scholar
Ai, M. (2005). Formation of methyl methacrylate by condensation of methyl propionate with formaldehyde over silica-supported cesium hydroxide catalysts. Applied Catalysis A: General, 288, 211–215. DOI: 10.1016/j.apcata.2005.04.027.Search in Google Scholar
Albanesi, G., & Moggi, P. (1983). Methyl methacrylate by gas phase catalytic condensation of formaldehyde with methyl propionate. Applied Catalysis, 6, 293–306. DOI: 10.1016/0166-9834(83)80102-x.Search in Google Scholar
Amini, G., Najafpour, G. D., Rabiee, S. M., & Ghoreyshi, A. A. (2013). Synthesis and characterization of amorphous nano-alumina powders with high surface area for biodiesel production. Chemical Engineering & Technology, 36, 1708–1712. DOI: 10.1002/ceat.201300102.Search in Google Scholar
Chang, C. D., & Silvestri, A. J. (1977). The conversion of methanol and other O-compounds to hydrocarbons over zeolite catalysts. Journal of Catalysis, 47, 249–259. DOI: 10.1016/0021-9517(77)90172-5.Search in Google Scholar
Gaenzler, W., Kabs, K., & Schroeder, G. (1979). U.S. Patent No. 4147718 (A). Washington, D.C., USA: U.S. Patent and Trademark Office.Search in Google Scholar
Gogate, M. R., Spivey, J. J., & Zoeller, J. R. (1997). Synthesis of methyl methacrylate by vapor phase condensation of formaldehyde with propionate derivatives. Catalysis Today, 36, 243–254. DOI: 10.1016/s0920-5861(96)00241-6.Search in Google Scholar
Hidai, M., Koyasu, Y., Chikanari, K., & Uchida, Y. (1987). Synthesis of ketones and esters from olefins, carbon monoxide and alcohols by using ruthenium–iodide catalysts. Journal of Molecular Catalysis, 40, 243–254. DOI: 10.1016/0304-5102(87)80041-x.Search in Google Scholar
Hong, T. L., Liu, H. T., Yeh, C. T., Chen, S. H., Sheu, F. C., Leu, L. J., & Wang, C. I. (1997). Electron microscopic studies on pore structure of alumina. Applied Catalysis A: General, 158, 257–271. DOI: 10.1016/s0926-860x(97)00002-1.Search in Google Scholar
Isahak, W. N. R. W., Ismail, M., Jahim, J. M., Salimon, J., & Yarmo, M. A. (2012). Characterisation and performance of three promising heterogeneous catalysts in transesteri-fication of palm oil. Chemical Papers, 66, 178–187. DOI: 10.2478/s11696-011-0125-z.Search in Google Scholar
Islam, A., Taufiq-Yap, Y. H., Chu, C. M., Ravindra, P., & Chan, E. S. (2013). Transesterification of palm oil using KF and NaNO3 catalysts supported on spherical millimetric γ-Al2O3. Renewable Energy, 59, 23–29. DOI: 10.1016/j.renene.2013.01.051.Search in Google Scholar
Kirszensztejn, P., Przekop, R., Tolińska, A., & Maćkowska, E. (2009). Pyrolytic and catalytic conversion of rape oil into aromatic and aliphatic fractions in a fixed bed reactor on Al2O3 and Al2O3/B2O3 catalysts. Chemical Papers, 63, 226–232. DOI: 10.2478/s11696-008-0104-1.Search in Google Scholar
Li, B., Yan, R., Wang, L., Diao, Y., Li, Z., & Zhang, S. (2013). Synthesis of methyl methacrylate by aldol condensation of methyl propionate with formaldehyde over acid–base bifunctional catalysts. Catalysis Letters, 143, 829–838. DOI: 10.1007/s10562-013-1040-4.Search in Google Scholar
Li, B., Yan, R., Wang, L., Diao, Y., Li, Z., & Zhang, S. (2014). SBA-15 supported cesium catalyst for methyl methacrylate synthesis via condensation of methyl propi-onate with formaldehyde. Industrial & Engineering Chemistry Research, 53, 1386–1394. DOI: 10.1021/ie403422s.Search in Google Scholar
Maldonado, A., M., Essayem, N., Christ, L., & Figueras, F. (2013). Transesterification of acrylates by heterogeneous basic catalysis. Applied Catalysis A: General, 468, 1–8. DOI: 10.1016/j.apcata.2013.08.001.Search in Google Scholar
Moroz, É. M., Shefer, K. I., Zyuzin, D. A., & Shmakov, A. N. (2011). A study of the local structure of aluminas obtained by different methods. Journal of Structural Chemistry, 52, 326–329. DOI: 10.1134/s0022476611020120.Search in Google Scholar
Nagai, K. (2001). New developments in the production of methyl methacrylate. Applied Catalysis A: General, 221, 367–377. DOI: 10.1016/s0926-860x(01)00810-9.Search in Google Scholar
Palekar, V. M., Jung, H., Tierney, J. W., & Wender, I. (1993). Slurry phase synthesis of methanol with a potassium methoxide/copper chromite catalytic system. Applied Catalysis A: General, 102, 13–34. DOI: 10.1016/0926-860x(93)85152-f.Search in Google Scholar
Sandesh, S., Shanbhag, G. V., & Halgeri, A. B. (2013). Transesterification of glycerol to glycerol carbonate using KF/Al2O3 catalyst: The role of support and basicity. Catalysis Letters, 143, 1226–1234. DOI: 10.1007/s10562-013-1043-1.Search in Google Scholar
Stefanov, P., Todorova, S., Naydenov, A., Tzaneva, B., Kolev, H., Atanasova, G., Stoyanova, D., Karakirova, Y., & Alek-sieva, K. (2015). On the development of active and stable Pd–Co/γ-Al2O3 catalyst for complete oxidation of methane. Chemical Engineering Journal, 266, 329–338. DOI: 10.1016/j.cej.2014.12.099.Search in Google Scholar
Tai, J., & Davis, R. J. (2007). Synthesis of methacrylic acid by aldol condensation of propionic acid with formaldehyde over acid–base bifunctional catalysts. Catalysis Today, 123, 42–49. DOI: 10.1016/j.cattod.2007.02.004.Search in Google Scholar
Travalloni, L., Gomes, A. C. L., Gaspar, A. B., & da Silva, M. A. P. (2008). Methanol conversion over acid solid catalysts. Catalysis Today, 133–135, 406–412. DOI: 10.1016/j.cattod.2007.12.060.Search in Google Scholar
Wang, B., Ran, W., Sun, W., & Wang, K. (2012). Direct oxidative esterification of aldehyde with alcohol to ester over Pd/styrene-divinyl benzene copolymer catalyst. Industrial & Engineering Chemistry Research, 51, 3932–3938. DOI: 10.1021/ie202701k.Search in Google Scholar
Yang, Y., Jiao, X., Chen, B., & Chen, D. (2013). Preparation of fine-grained α-alumina powder from seeded boehmite. Journal of Nanoparticle Research, 15, 1855–1863. DOI: 10.1007/s11051-013-1855-3.Search in Google Scholar
© 2016 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Original Paper
- Fluorescence-enhanced optical sensor for detection of Al3+ in water based on functionalised nanoporous silica type SBA-15
- Original Paper
- 3′-O-(3-Chloropivaloyl)quercetin, α-glucosidase inhibitor with multi-targeted therapeutic potential in relation to diabetic complications
- Original Paper
- Production of high-content galacto-oligosaccharides mixture using β-galactosidase and Kluyveromyces marxianus entrapped in polyvinylalcohol gel
- Original Paper
- Efficient utilization of inulin and glycerol as fermentation substrates in erythritol and citric acid production using Yarrowia lipolytica expressing inulinase
- Original Paper
- Production and characterization of surfactant-stable fungal keratinase from Gibberella intermedia CA3-1 with application potential in detergent industry
- Original Paper
- Vapour-phase condensation of methyl propionate with trioxane over alumina-supported potassium catalyst
- Original Paper
- Slow pyrolysis of pre-dried sewage sludge
- Original Paper
- Synthesis, antioxidant, antibacterial, and DFT study on a coumarin based salen-type Schiff base and its copper complex
- Original Paper
- Identification of selective oxidation of TiC/SiC composite with X-ray diffraction and Raman spectroscopy
- Original Paper
- Toxicity of zinc oxide nanoparticles to the annelid Enchytraeus crypticus in agar-based exposure media
- Original Paper
- Synthesis and antibacterial evaluation of novel Schiff base derivatives containing 4(3H)-quinazolinone moiety
- Short Communication
- The aza-Pudovik reaction accelerated in external constant magnetic field
Articles in the same Issue
- Original Paper
- Fluorescence-enhanced optical sensor for detection of Al3+ in water based on functionalised nanoporous silica type SBA-15
- Original Paper
- 3′-O-(3-Chloropivaloyl)quercetin, α-glucosidase inhibitor with multi-targeted therapeutic potential in relation to diabetic complications
- Original Paper
- Production of high-content galacto-oligosaccharides mixture using β-galactosidase and Kluyveromyces marxianus entrapped in polyvinylalcohol gel
- Original Paper
- Efficient utilization of inulin and glycerol as fermentation substrates in erythritol and citric acid production using Yarrowia lipolytica expressing inulinase
- Original Paper
- Production and characterization of surfactant-stable fungal keratinase from Gibberella intermedia CA3-1 with application potential in detergent industry
- Original Paper
- Vapour-phase condensation of methyl propionate with trioxane over alumina-supported potassium catalyst
- Original Paper
- Slow pyrolysis of pre-dried sewage sludge
- Original Paper
- Synthesis, antioxidant, antibacterial, and DFT study on a coumarin based salen-type Schiff base and its copper complex
- Original Paper
- Identification of selective oxidation of TiC/SiC composite with X-ray diffraction and Raman spectroscopy
- Original Paper
- Toxicity of zinc oxide nanoparticles to the annelid Enchytraeus crypticus in agar-based exposure media
- Original Paper
- Synthesis and antibacterial evaluation of novel Schiff base derivatives containing 4(3H)-quinazolinone moiety
- Short Communication
- The aza-Pudovik reaction accelerated in external constant magnetic field