Synthesis of butyrate using a heterogeneous catalyst based on polyvinylpolypyrrolidone
-
Song Wang
,
Qian-Qian Chang
A heterogeneous polyvinylpolypyrrolidone supported Brønsted acidic catalyst ([PVPP-BS]HSO4) was used to synthesize butyrate in this paper. The prepared catalysts were characterized by FT-IR, TG, and FESEM and their catalytic activity in butyric acid esterification with benzyl alcohol was investigated. The influencing factors such as the amount of catalyst, reaction temperature, and reaction time were carefully studied. Under the optimized condition with the butyric acid to benzyl alcohol mole ratio of 1 : 1.2 and the reaction temperature of 130°C, the yield of benzyl butyrate reached 96.8 % within 4 h in the presence of 8 mass % of catalyst. Moreover, the catalyst could be reused six times without noticeable drop in activity. This catalyst was also used to synthesize other kinds of butyrates achieving the butyrate yield above 90 %.
Acknowledgements.
This work was financially supported by the Shenyang Science and Technology Project (No.F15-199-1-12) and by the Key Laboratory for Catalyst Synthesis of Polymer of the Liaoning Province (No. 2010-36), China.
References
Bates, E. D., Mayton, R. D., Ntai, I., & Davis, J. H., Jr. (2002). CO2 capture by a task-specific ionic liquid. Joural of the American Chemical Society, 124, 926–927. DOI: 10.1021/ja017593d.10.1021/ja017593dSuche in Google Scholar PubMed
Chowdhury, S., Mohan, R. S., & Scott, J. L. (2007). Reactivity of ionic liquids. Tetrahedron, 63, 2363–2389. DOI: 10.1016/j.tet.2006.11.001.10.1016/j.tet.2006.11.001Suche in Google Scholar
Dijs, I. J., van Ochten, H. L. F., van Walree, C. A., Geus, J. W., & Jenneskens, L. W. (2002). Alkyl sulphonic acid surface-functionalised silica as heterogeneous acid catalyst in the solvent-free liquid-phase addition of acetic acid to camphene. Journal of Molecular Catalysis A: Chemical, 188, 209–224. DOI: 10.1016/s1381-1169(02)00334-5.10.1016/s1381-1169(02)00334-5Suche in Google Scholar
Fahmy, H. M., Abo-Shosha, M. H., & Ibrahim, N. A. (2009). Finishing of cotton fabrics with poly (N-vinyl-2-pyrrolidone) to improve their performance and antibacterial properties. Carbohydrate Polymers, 77, 845–850. DOI: 10.1016/j.carbpol.2009.03.003.10.1016/j.carbpol.2009.03.003Suche in Google Scholar
Fang, D., Zhou, X. L., Ye, Z. W., & Liu, Z. L. (2006). Brønsted acidic ionic liquids and their use as dual solvent-catalysts for Fischer esterifications. Industrial & Engineering Chemistry Research, 45, 7982–7984. DOI: 10.1021/ie060365d.10.1021/ie060365dSuche in Google Scholar
Han, X. X., & Zhou, L. X. (2011). Optimization of process variables in the synthesis of butyl butyrate using acid ionic liquid as catalyst. Chemical Engineering Journal, 172, 459–466. DOI: 10.1016/j.cej.2011.06.025.10.1016/j.cej.2011.06.025Suche in Google Scholar
Huang, B. H., Wang, Y. F., Zhang, K., Fang, Y. X., & Zhou, B. L. (2007). Synthesis of pyrrolidonium acidic ionic liquids and their catalytic activity for esterification of acetic acid and butanol. Chinese Journal of Catalysis, 28, 743–748. DOI: 10.3321/j.issn:0253-9837(2007)08-0743-06.10.3321/j.issn:0253-9837(2007)08-0743-06Suche in Google Scholar
Kafuku, G., Lee, K. T., & Mbarawa, M. (2010). The use of sulfated tin oxide as solid super acid catalyst for heterogeneous transesterification of Jatropha curcas oil. Chemical Papers, 64, 734–740. DOI: 10.2478/s11696-010-0063-1.10.2478/s11696-010-0063-1Suche in Google Scholar
Laborde, B., Moine-Ledoux, V., Richard, T., Saucier, C., Dubourdieu, D., & Monti, J. P. (2006). PVPP-polyphenol complexes: A molecular approach. Journal of Agricultural and Food Chemistry, 54, 4383–4389. DOI: 10.1021/jf060427a.10.1021/jf060427aSuche in Google Scholar PubMed
Leng, Y., Wang, J., Zhu, D. R., Ren, X. Q., Ge, H. Q., & Shen, L. (2008). Heteropolyanion-based ionic liquids: Reactioninduced self-separation catalysts for esterification. Angewandte Chemie International Edition, 48, 168–171. DOI: 10.1002/anie.200803567.10.1002/anie.200803567Suche in Google Scholar PubMed
Liang, X. Z. (2013). Novel acidic ionic liquid polymer for biodiesel synthesis from waste oils. Applied Catalysis A: General, 455, 206–210. DOI: 10.1016/j.apcata.2013.01.036.10.1016/j.apcata.2013.01.036Suche in Google Scholar
Liu, X. M., Ma, H. Y., Wu, Y., Wang, C., Yang, M., Yan, P. F., & Welz-Biermann, U. (2011). Esterification of glycerol with acetic acid using double SO3H-functionalized ionic liquids as recoverable catalysts. Green Chemistry, 13, 697–701. DOI: 10.1039/c0gc00732c.10.1039/c0gc00732cSuche in Google Scholar
Miao, J. M., Wan, H., & Guan, G. F. (2011). Synthesis of immobilized Brønsted acidic ionic liquid on silica gel as heterogeneous catalyst for esterification. Catalysis Communications, 12, 353–356. DOI: 10.1016/j.catcom.2010.10.014.10.1016/j.catcom.2010.10.014Suche in Google Scholar
Mokhtary, M., & Langroudi, S. A. M. (2014). Polyvinylpolypyrrolidone-supported boron trifluoride: a mild and efficient catalyst for the synthesis of 1,8-dioxooctahydroxanthenes and 1,8-dioxodecahydroacridines. Monatshefte für Chemie, 145, 1489–1494. DOI: 10.1007/s00706-014-1206-9.10.1007/s00706-014-1206-9Suche in Google Scholar
Sahoo, S., Kumar, P., Lefebvre, F., & Halligudi, S. B. (2009). Oxidative kinetic resolution of alcohols using chiral Mn-salen complex immobilized onto ionic liquid modified silica. Applied Catalysis A: General, 354, 17–25. DOI: 10.1016/j.apcata.2008.10.039.10.1016/j.apcata.2008.10.039Suche in Google Scholar
Shah, K. A., Parikh, J. K., Dholakiya, B. Z., & Maheria, K. C. (2014). Fatty acid methyl ester production from acid oil using silica sulfuric acid: Process optimization and reaction kinetics. Chemical Papers, 68, 472–483. DOI: 10.2478/s11696-013-0488-4.10.2478/s11696-013-0488-4Suche in Google Scholar
Visser, A. E., Holbrey, J. D., & Rogers, R. D. (2001). Hydrophobic ionic liquids incorporating N-alkylisoquinolinium cations and their utilization in liquid–liquid separations. Chemical Communications, 2001, 2484–2485. DOI: 10.1039/b109340c.10.1039/b109340cSuche in Google Scholar PubMed
Wang, Q. H., Zhao, W. C., Sun, X. H., & Zhao, W. J. (2008). Preparation and characterization of a magnetic solid acid for esterification of ammonium lactate with n-butanol. Catalysis Letters, 121, 324–330. DOI: 10.1007/s10562-007-9342-z.10.1007/s10562-007-9342-zSuche in Google Scholar
Wasserscheid, P., & Keim, W. (2000). Ionic liquids: New “solutions” for transition metal catalysis. Angewandte Chemie International Edition, 39, 3772–3789. DOI: 10.1002/1521-3773(20001103)39:21<3772: AID-ANIE3772>3.0.CO; 2-5.10.1002/1521-3773(20001103)39:21<3772: AID-ANIE3772>3.0.CO; 2-5Suche in Google Scholar
Zhang, H. B., Xu, F., Zhou, X. H., Zhang, G. Y., & Wang, C. X. (2007). A Brønsted acidic ionic liquid as an efficient and reusable catalyst system for esterification. Green Chemistry, 9, 1208–1211. DOI: 10.1039/b705480g.10.1039/b705480gSuche in Google Scholar
Zhi, H. Z., Lü, C. X., Zhang, Q., & Luo, J. (2009). A new PEG-1000-based dicationic ionic liquid exhibiting temperature-dependent phase behavior with toluene and its application in one-pot synthesis of benzopyrans. Chemical Communications, 2009, 2878–2880. DOI: 10.1039/b822481a.10.1039/b822481aSuche in Google Scholar PubMed
Zhu, L. L., Liu, Y. H., & Chen, J. (2009). Synthesis of N-methylimidazolium functionalized strongly basic anion exchange resins for adsorption of Cr(VI). Industrial & Engineering Chemistry Research, 48, 3261–3267. DOI: 10.1021/ie801278f.10.1021/ie801278fSuche in Google Scholar
© 2015 Institute of Chemistry, Slovak Academy of Sciences
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