Preparation and catalytic performance of quaternary ammonium base resin for methanolysis of natural phosphatidylcholine
-
Hong-Ya Li
,
Biao Yan
Abstract
Received 1 August 2015; Revised 23 November 2015; Accepted 26 November 2015
The most acceptable method for preparing glycerophosphocholine is to hydrolyse the natural phosphatidylcholine and use the quaternary ammonium base resin, as a promising heterogeneous catalyst can simplify the craft and minimise the problems existing in the homogeneous catalytic process. However, most of the resins reported in the literature are commercial trimethyl benzyl ammonium base resins and the application of other longer carbon-chain quaternary ammonium resins has not been reported. In the present work, a series of quaternary ammonium base resins were prepared from chloromethyl polystyrene microspheres and different tertiary amines and were used to prepare glycerophosphocholine from natural phosphatidylcholine. The factors affecting the exchange capacity and activity of the resin were investigated. The results showed that the resin possessed a better activity and stability under the following conditions: 1,4-dioxane as solvent, triethylamine as amination agent, reaction temperature of 60°C and amination time of 3 h; it was then used in the methanolysis of phosphatidylcholine by ultrasound-assisted reaction at ambient temperature, with the conversion of phosphatidylcholine attaining 97 % after 4 h. The catalyst was easy to separate from the reaction mixture and could also be readily available for repeat use; the activity and stability were largely consistent after six repeat uses.
5 References
Ali, S. W., Waqar, F., Malik, M. A., Yasin, T., & Muhammad, B. J. (2013). Study on the synthesis of a macroporous ethylacrylate-divinylbenzene copolymer, its conversion into a bi-functional cation exchange resin and applications for extraction of toxic heavy metals from wastewater. Journal of Applied Polymer Science, 129, 2234-2243. DOI: 10.1002/app. 38940.10.1002/app.38940Search in Google Scholar
Bariwal, J., & Van der Eycken, E. (2013). C-N bond forming cross-coupling reactions: an overview. Chemical Society Reviews, 42, 9283-9303. DOI: 10.1039/c3cs60228a.10.1039/c3cs60228aSearch in Google Scholar
Bialk, M., Prucker, O., & Ruhe, J. (2002). Grafting of polymers to solid surfaces by using immobilized methacrylates. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 198, 543-549. DOI: 10.1016/s0927-7757(01)00958-x.10.1016/S0927-7757(01)00958-XSearch in Google Scholar
Di Serio, M., Ledda, M., Cozzolino, M., Minutillo, G., Tesser, R., & Santacesaria, E. (2006). Transesterification of soybean oil to biodiesel by using heterogeneous basic catalysts. Industrial & Engineering Chemistry Research, 45, 3009-3014. DOI: 10.1021/ie051402o.10.1021/ie051402oSearch in Google Scholar
Feng, Y. H., He, B. Q., Cao, Y. H., Li, J. X., Liu, M., Yan, F. , & Liang, X. P. (2010). Biodiesel production using cationexchange resin as heterogeneous catalyst. Bioresource Technology, 101, 1518-1521. DOI: 10.1016/j.biortech.2009.07.084.10.1016/j.biortech.2009.07.084Search in Google Scholar PubMed
Fernandez-Murray, J. P., & McMaster, C. R. (2005). Glyc- erophosphocholine catabolism as a new route for choline formation for phosphatidylcholine synthesis by the Kennedy pathway. The Journal of Biological Chemistry, 280, 3829038296. DOI: 10.1074/jbc.m507700200.10.1074/jbc.M507700200Search in Google Scholar PubMed
Gey, C., & Seeger, K. (2013). Metabolic changes during cellular senescence investigated by proton NMR-spectroscopy. Mechanisms of Ageing and Development, 134, 130-138. DOI: 10.1016/j.mad.2013.02.002.10.1016/j.mad.2013.02.002Search in Google Scholar PubMed
Gomes, J. F., Puna, J. F., Bordado, J. C., & Correia, M. J. N.(2008) . Development of heterogeneous catalysts for transes- terification of triglycerides. Reaction Kinetics and Catalysis Letters, 95, 273-279. DOI: 10.1007/s11144-008-5372-9.10.1007/s11144-008-5372-9Search in Google Scholar
Ham, H. T., Choi, Y. S., & Chung, I. J. (2005). An explanation of dispersion states of single-walled carbon nanotubes in solvents and aqueous surfactant solutions using solubility parameters. Journal of Colloid and Interface Science, 286, 216-223. DOI: 10.1016/j.jcis. 2005.01.002.10.1016/j.jcis.2005.01.002Search in Google Scholar PubMed
Ichihara, K., Iwasaki, H., Ueda, K., Takizawa, R., Naito, H., & Tomosugi, M. (2005). Synthesis of phosphatidylcholine: An improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine. Chemistry and Physics of Lipids, 137, 94-99. DOI: 10.1016/j.chemphyslip.2005.06. 001.10.1016/j.chemphyslip.2005.06.001Search in Google Scholar PubMed
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.10.2478/s11696-011-0125-zSearch in Google Scholar
Kawamura, T., Okubo, T., Sato, K., Fujita, S., Goto, K., Hamaoka, T., & Iemitsu, M. (2012). Glycerophosphocholine enhances growth hormone secretion and fat oxidation in young adults. Nutrition, 28, 1122-1126. DOI: 10.1016/j.nut.2012.02.011.10.1016/j.nut.2012.02.011Search in Google Scholar PubMed
Kidd, P. M. (2007). GPC (GlyceroPhosphoCholine) mind-body power for active living and healthy aging. St. George, UT, USA: Total Health Communications.Search in Google Scholar
Kim, M., Salley, S. O., & Ng, K. Y. S. (2008). Transesterification of glycerides using a heterogeneous resin catalyst combined with a homogeneous catalyst. Energy & Fuels, 22, 3594-3599. DOI: 10.1021/ef800443x.10.1021/ef800443xSearch in Google Scholar
Kralik, M. (2014). Adsorption, chemisorption, and catalysis. Chemical Papers, 68, 1625-1638. DOI: 10.2478/s11696-014- 0624-9.10.2478/s11696-014-0624-9Search in Google Scholar
Langer, R., Diskin-Posner, Y., Leitus, G., Shimon, L. J. W., Ben-David, Y., & Milstein, D. (2011). Low-pressure hydrogenation of carbon dioxide catalyzed by an iron pincer complex exhibiting noble metal activity. Angewandte Chemie International Edition, 50, 9948-9952. DOI: 10.1002/anie.2011 04542.10.1002/anie.201104542Search in Google Scholar PubMed
Li, H. Y., Zhang, X. L., Zhang, J. B., Zhang, T. T., & Zhao, B. X. (2014). Preparing L-a-glycerophosphocholine in a phase-transfer catalytic reaction: Kinetic study. International Journal of Chemical Kinetics, 46, 169-175. DOI: 10.1002/kin.20840.10.1002/kin.20840Search in Google Scholar
May, P., Khan, U., Hughes, J. M., & Coleman, J. N. (2012). Role of solubility parameters in understanding the steric stabilization of exfoliated two-dimensional nanosheets by adsorbed polymers. The Journal of Physical Chemistry C, 116, 11393-11400. DOI: 10.1021/jp302365w.10.1021/jp302365wSearch in Google Scholar
Mills, J. E., Maryanoff, C. A., Cosgrove, R. M., Scott, L., & Mc- Comsey, D. F. (1984). The reaction of amines with methylene chloride. A brief review. Organic Preparations and Procedures International: The New Journal for Organic Synthesis, 16, 97-114. DOI: 10.1080/00304948409356172.10.1080/00304948409356172Search in Google Scholar
Seo, D. W., Lim, Y. D., Hossain, M. A., Lee, S. H., Lee, H.C., Jang, H. H., Choi, S. Y., & Kim, W. G. (2013). Anion conductive poly(tetraphenyl phthalazine ether sulfone) containing tetra quaternary ammonium hydroxide for alkaline fuel cell application. International Journal of Hydrogen Energy, 38, 579-587. DOI: 10.1016/j.ijhydene.2012.07.044.10.1016/j.ijhydene.2012.07.044Search in Google Scholar
Tronconi, G. (1990). WO Patent No. 90/13552. Geneva, Switzerland: World Intellectual Property Organization.Search in Google Scholar
Tronconi, G., & Coccoli, C. (1991). WO Patent No. 91/15494. Geneva, Switzerland: World Intellectual Property Organization.Search in Google Scholar
Wang, F. (2003). The standard manual for ion exchange resin. Beijing, China: Standard Press of China. (in Chinese)Search in Google Scholar
Wu, Q. Y. (2011). Polymer physics. Beijing, China: Higher Education Press. (in Chinese)Search in Google Scholar
Yan, H. P., Yang, Y., Tong, D. M., Xiang, X., & Hu, C. W. (2009). Catalytic conversion of glucose to 5-hydroxymethyl- furfural over SO^-/ZrO2 and SO^-/ZrO2-ADO3 solid acid catalysts. Catalysis Communications, 10, 1558-1563. DOI: 10.1016/j.catcom.2009.04.020.10.1016/j.catcom.2009.04.020Search in Google Scholar
Yang, L., Lv, L., Zhang, S. J., Pan, B. C., & Zhang, W. M. (2011). Catalytic dechlorination of monochlorobenzene by Pd/Fe nanoparticles immobilized within a polymeric anion exchanger. Chemical Engineering Journal, 178, 161-167. DOI: 10.1016/j.cej.2011.10.039.10.1016/j.cej.2011.10.039Search in Google Scholar
Zhang, Y., Stanciulescu, M., & Ikura, M. (2009). Rapid transesterification of soybean oil with phase transfer catalysts. Applied Catalysis A: General, 366, 176-183. DOI: 10.1016/j.apcata. 2009.07.001.10.1016/j.apcata.2009.07.001Search in Google Scholar
Zhang, T. T., Zhang, X. L., Li, H. Y., Bai, W. L., & Zhao, B. X. (2013). Kinetic evaluation of the ethanolysis of phosphatidylcholine catalyzed by choline hydroxide. Reaction Kinetics, Mechanisms and Catalysis, 110, 31-39. DOI: 10.1007/s11144-013-0579-9.10.1007/s11144-013-0579-9Search in Google Scholar
© 2016 Institute of Chemistry, Slovak Academy of Sciences
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